NCBI Taxonomy: 452338

Corticiales (ncbi_taxid: 452338)

found 78 associated metabolites at order taxonomy rank level.

Ancestor: Agaricomycetes incertae sedis

Child Taxonomies: Corticiaceae, Dendrominiaceae, Vuilleminiaceae, Punctulariaceae, environmental samples, unclassified Corticiales

4-Hydroxybenzoic acid

4-hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   
   

4-hydroxybenzoate

4-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

p-Hydroxybenzoic acid

p-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

   

Laetisaric acid

Laetisaric acid

C18H32O3 (296.2351322)


A C18, straight-chain, hydroxy fatty acid composed of linoleic acid having an (R)-hydroxy group at the 8-position.

   

(4as,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

(4as,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

C23H30O5 (386.209313)


   

(1r,3ar,5ar,7s,9ar,9br,11ar)-7-(dimethylamino)-9a,11a-dimethyl-1-[(2s,3e)-4-(3-methyl-1,2,5,6-tetrahydropyridin-4-yl)but-3-en-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

(1r,3ar,5ar,7s,9ar,9br,11ar)-7-(dimethylamino)-9a,11a-dimethyl-1-[(2s,3e)-4-(3-methyl-1,2,5,6-tetrahydropyridin-4-yl)but-3-en-2-yl]-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

C31H48N2O (464.37664379999995)


   

(2r,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

(2r,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

C15H24O3 (252.1725354)


   

(4r,9r,10r,12r,13r,14r)-10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

(4r,9r,10r,12r,13r,14r)-10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

C20H30O6 (366.204228)


   

(4s,4ar,5s,8ar)-3,4a,5-trimethyl-8-oxo-4h,5h,6h,7h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

(4s,4ar,5s,8ar)-3,4a,5-trimethyl-8-oxo-4h,5h,6h,7h,8ah,9h-naphtho[2,3-b]furan-4-yl 2-methylpropanoate

C19H26O4 (318.1830996)


   

(1r,3s)-4-(buta-1,3-diyn-1-yl)cyclopent-4-ene-1,3-diol

(1r,3s)-4-(buta-1,3-diyn-1-yl)cyclopent-4-ene-1,3-diol

C9H8O2 (148.0524268)


   

(4s,4ar,7as,7br)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

(4s,4ar,7as,7br)-4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

C15H22O3 (250.1568862)


   

(1r,2s,6r,7s,8r,11s,12s,13r)-1,4,4-trimethyl-10-oxatetracyclo[6.4.1.0²,⁶.0¹¹,¹³]tridecane-7,8,11,12-tetrol

(1r,2s,6r,7s,8r,11s,12s,13r)-1,4,4-trimethyl-10-oxatetracyclo[6.4.1.0²,⁶.0¹¹,¹³]tridecane-7,8,11,12-tetrol

C15H24O5 (284.1623654)


   

(3s,4s,4ar,7as,7br)-6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

(3s,4s,4ar,7as,7br)-6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

C14H22O2 (222.1619712)


   

1,4,4-trimethyl-9-oxatricyclo[6.3.1.0²,⁶]dodecane-7,8-diol

1,4,4-trimethyl-9-oxatricyclo[6.3.1.0²,⁶]dodecane-7,8-diol

C14H24O3 (240.1725354)


   

(1r,3ar,5ar,6r,7s,9ar,9br,11ar)-7-(dimethylamino)-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-ol

(1r,3ar,5ar,6r,7s,9ar,9br,11ar)-7-(dimethylamino)-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-ol

C31H50N2O (466.392293)


   

n-[(1r,3ar,5ar,6r,7s,9ar,9br,11ar)-6-hydroxy-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]ethanimidic acid

n-[(1r,3ar,5ar,6r,7s,9ar,9br,11ar)-6-hydroxy-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]ethanimidic acid

C31H48N2O2 (480.37155879999995)


   

(1s,4r,9r,10r,12r,13r,14r)-10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

(1s,4r,9r,10r,12r,13r,14r)-10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

C20H30O6 (366.204228)


   

6,6,8-trimethyl-3h,5h,7h-indeno[5,6-c]furan-1-one

6,6,8-trimethyl-3h,5h,7h-indeno[5,6-c]furan-1-one

C14H16O2 (216.1150236)


   

(4s)-3-(buta-1,3-diyn-1-yl)-4-hydroxycyclopent-2-en-1-one

(4s)-3-(buta-1,3-diyn-1-yl)-4-hydroxycyclopent-2-en-1-one

C9H6O2 (146.0367776)


   

2-hydroxy-1-[(1s,2r,5s,6s,7r)-6-hydroxy-2,9,9-trimethyltricyclo[5.3.0.0²,⁵]decan-5-yl]ethanone

2-hydroxy-1-[(1s,2r,5s,6s,7r)-6-hydroxy-2,9,9-trimethyltricyclo[5.3.0.0²,⁵]decan-5-yl]ethanone

C15H24O3 (252.1725354)


   
   

7-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

7-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

C33H54N2O2 (510.41850639999996)


   

(5z)-5-[(2r)-2-[(1r,3ar,5as,7r,9as,9br,11ar)-7-amino-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]propylidene]-4-isopropylpyrrol-2-ol

(5z)-5-[(2r)-2-[(1r,3ar,5as,7r,9as,9br,11ar)-7-amino-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]propylidene]-4-isopropylpyrrol-2-ol

C29H44N2O (436.3453454)


   

(5s)-5-ethyl-3-(4-methylphenyl)-5h-furan-2-one

(5s)-5-ethyl-3-(4-methylphenyl)-5h-furan-2-one

C13H14O2 (202.09937440000002)


   

(1r,3ar,5ar,6r,7r,9ar,9br,11ar)-1-[(2r,3e)-4-(1,3-dimethyl-5,6-dihydro-2h-pyridin-4-yl)but-3-en-2-yl]-9a,11a-dimethyl-7-(methylamino)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl acetate

(1r,3ar,5ar,6r,7r,9ar,9br,11ar)-1-[(2r,3e)-4-(1,3-dimethyl-5,6-dihydro-2h-pyridin-4-yl)but-3-en-2-yl]-9a,11a-dimethyl-7-(methylamino)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl acetate

C33H52N2O2 (508.40285719999997)


   

1,4,4-trimethyl-8,10-dioxatetracyclo[7.3.1.0²,⁶.0⁷,¹¹]tridecan-11-ol; 2-(7-hydroxy-2,2,4-trimethyl-6-oxo-hexahydroinden-4-yl)acetaldehyde

1,4,4-trimethyl-8,10-dioxatetracyclo[7.3.1.0²,⁶.0⁷,¹¹]tridecan-11-ol; 2-(7-hydroxy-2,2,4-trimethyl-6-oxo-hexahydroinden-4-yl)acetaldehyde

C28H44O6 (476.3137724)


   

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(3r)-3-isopropyl-4,5-dihydro-3h-pyrrol-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(3r)-3-isopropyl-4,5-dihydro-3h-pyrrol-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

C29H48N2 (424.38172879999996)


   

(1s,2ar,4as,7as,7br)-1-hydroxy-6,6,7b-trimethyl-2-oxo-1h,2ah,4ah,5h,7h,7ah-cyclobuta[e]indene-3-carbaldehyde

(1s,2ar,4as,7as,7br)-1-hydroxy-6,6,7b-trimethyl-2-oxo-1h,2ah,4ah,5h,7h,7ah-cyclobuta[e]indene-3-carbaldehyde

C15H20O3 (248.14123700000002)


   

(1s,4s,4ar,7as,7br)-1,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

(1s,4s,4ar,7as,7br)-1,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

C15H22O4 (266.1518012)


   

2-(3-methylbut-3-en-1-yn-1-yl)benzene-1,4-diol

2-(3-methylbut-3-en-1-yn-1-yl)benzene-1,4-diol

C11H10O2 (174.06807600000002)


   

1,4,4-trimethyl-10-oxatetracyclo[6.4.1.0²,⁶.0¹¹,¹³]tridecane-7,8,11,12-tetrol

1,4,4-trimethyl-10-oxatetracyclo[6.4.1.0²,⁶.0¹¹,¹³]tridecane-7,8,11,12-tetrol

C15H24O5 (284.1623654)


   

(1r,4r,9r,10r,12r,13r,14s)-10,12,13,14-tetrahydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

(1r,4r,9r,10r,12r,13r,14s)-10,12,13,14-tetrahydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

C20H32O6 (368.2198772)


   

1,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

1,4-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

C15H22O4 (266.1518012)


   

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(2r,3r)-3-isopropyl-1-methylpyrrolidin-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(2r,3r)-3-isopropyl-1-methylpyrrolidin-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

C30H52N2 (440.4130272)


   

7-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-6-one

7-(dimethylamino)-1-{4-[1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-6-one

C33H54N2O2 (510.41850639999996)


   

1-[1-(3-isopropylpyrrolidin-2-yl)propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

1-[1-(3-isopropylpyrrolidin-2-yl)propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

C29H50N2 (426.397378)


   

(2s,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

(2s,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

C15H24O3 (252.1725354)


   

7-(2-hydroxyethyl)-2,2,7-trimethyl-hexahydro-1h-indene-4,5-diol

7-(2-hydroxyethyl)-2,2,7-trimethyl-hexahydro-1h-indene-4,5-diol

C14H26O3 (242.1881846)


   

(2s)-2-({[(2s)-1-[(2s)-3-(4-bromophenyl)-2-{[(2s)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1r)-1-({12-[(4-bromophenyl)methyl]-15-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(c-hydroxycarbonimidoylmethyl)-9-(1-hydroxyethyl)-7,16,19-trimethyl-1-oxa-4,7,10,13,16-pentaazacyclononadecan-18-yl}-c-hydroxycarbonimidoyl)-2-sulfoethyl]-c-hydroxycarbonimidoyl}-4-carbamimidamidobutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-3,3-dimethylpentanimidic acid

(2s)-2-({[(2s)-1-[(2s)-3-(4-bromophenyl)-2-{[(2s)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1r)-1-({12-[(4-bromophenyl)methyl]-15-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(c-hydroxycarbonimidoylmethyl)-9-(1-hydroxyethyl)-7,16,19-trimethyl-1-oxa-4,7,10,13,16-pentaazacyclononadecan-18-yl}-c-hydroxycarbonimidoyl)-2-sulfoethyl]-c-hydroxycarbonimidoyl}-4-carbamimidamidobutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-3,3-dimethylpentanimidic acid

C80H124Br2N20O16S (1810.7591144)


   

(1r,7s,9as,11ar)-7-(dimethylamino)-1-[(2r)-4-[(3e)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-6-one

(1r,7s,9as,11ar)-7-(dimethylamino)-1-[(2r)-4-[(3e)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-6-one

C33H54N2O2 (510.41850639999996)


   

10,12,13,14-tetrahydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

10,12,13,14-tetrahydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-one

C20H32O6 (368.2198772)


   

(4s,4ar,7as,8r)-4,8-dihydroxy-6,6,8-trimethyl-4h,4ah,5h,7h,7ah-indeno[5,6-c]furan-1-carboxylic acid

(4s,4ar,7as,8r)-4,8-dihydroxy-6,6,8-trimethyl-4h,4ah,5h,7h,7ah-indeno[5,6-c]furan-1-carboxylic acid

C15H20O5 (280.13106700000003)


   

4-(buta-1,3-diyn-1-yl)cyclopent-4-ene-1,3-diol

4-(buta-1,3-diyn-1-yl)cyclopent-4-ene-1,3-diol

C9H8O2 (148.0524268)


   

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(2r,3r)-3-isopropylpyrrolidin-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

(1r,3ar,5as,7r,9as,9br,11ar)-1-[(2r)-1-[(2r,3r)-3-isopropylpyrrolidin-2-yl]propan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-amine

C29H50N2 (426.397378)


   

(1s,2r,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-1,2,4-triol

(1s,2r,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-1,2,4-triol

C15H24O4 (268.1674504)


   

(2s)-2-({[(2r)-1-[(2s)-3-(4-bromophenyl)-2-{[(2r)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-{[(1r)-1-{[(1r)-1-{[(1s)-1-{[(6s,9s,12r,15r,18s,19r)-12-[(4-bromophenyl)methyl]-5,11,14-trihydroxy-15-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(c-hydroxycarbonimidoylmethyl)-9-[(1s)-1-hydroxyethyl]-7,16,19-trimethyl-2,8,17-trioxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,10,13-trien-18-yl]-c-hydroxycarbonimidoyl}-2-sulfoethyl]-c-hydroxycarbonimidoyl}-4-carbamimidamidobutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-3,3-dimethylpentanimidic acid

(2s)-2-({[(2r)-1-[(2s)-3-(4-bromophenyl)-2-{[(2r)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-n-[(1s)-1-{[(1r)-1-{[(1r)-1-{[(1s)-1-{[(6s,9s,12r,15r,18s,19r)-12-[(4-bromophenyl)methyl]-5,11,14-trihydroxy-15-[2-(c-hydroxycarbonimidoyl)ethyl]-6-(c-hydroxycarbonimidoylmethyl)-9-[(1s)-1-hydroxyethyl]-7,16,19-trimethyl-2,8,17-trioxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,10,13-trien-18-yl]-c-hydroxycarbonimidoyl}-2-sulfoethyl]-c-hydroxycarbonimidoyl}-4-carbamimidamidobutyl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-3,3-dimethylpentanimidic acid

C80H112Br2N20O22S (1894.6347092)


   

1-hydroxy-6,6,7b-trimethyl-2-oxo-1h,2ah,4ah,5h,7h,7ah-cyclobuta[e]indene-3-carbaldehyde

1-hydroxy-6,6,7b-trimethyl-2-oxo-1h,2ah,4ah,5h,7h,7ah-cyclobuta[e]indene-3-carbaldehyde

C15H20O3 (248.14123700000002)


   

4-(buta-2,3-dien-1-yl)pyran-2-one

4-(buta-2,3-dien-1-yl)pyran-2-one

C9H8O2 (148.0524268)


   

10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

10,12,13,14-tetrahydroxy-5,5,9-trimethyl-11-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-14-carbaldehyde

C20H30O6 (366.204228)


   

5-ethyl-3-(4-methylphenyl)-5h-furan-2-one

5-ethyl-3-(4-methylphenyl)-5h-furan-2-one

C13H14O2 (202.09937440000002)


   

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-1,2,4-triol

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-1,2,4-triol

C15H24O4 (268.1674504)


   

n-[(1r,3ar,5as,6r,7s,9ar,9br,11ar)-6-hydroxy-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]ethanimidic acid

n-[(1r,3ar,5as,6r,7s,9ar,9br,11ar)-6-hydroxy-9a,11a-dimethyl-1-[(2r)-1-[3-(propan-2-ylidene)-4,5-dihydropyrrol-2-yl]propan-2-yl]-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]ethanimidic acid

C31H48N2O2 (480.37155879999995)


   

(4s,4ar,7as)-6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

(4s,4ar,7as)-6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

C14H22O2 (222.1619712)


   

6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

6,6,7b-trimethyl-1h,3h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

C14H22O2 (222.1619712)


   

3-hydroxy-6,10,20-triazapentacyclo[11.7.1.0²,⁷.0⁹,²¹.0¹⁴,¹⁹]henicosa-1(20),2,4,6,9,11,13(21),14(19),15,17-decaen-8-one

3-hydroxy-6,10,20-triazapentacyclo[11.7.1.0²,⁷.0⁹,²¹.0¹⁴,¹⁹]henicosa-1(20),2,4,6,9,11,13(21),14(19),15,17-decaen-8-one

C18H9N3O2 (299.0694734)


   

(4as)-6,6,8-trimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

(4as)-6,6,8-trimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

C15H18O3 (246.1255878)


   

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-one

C15H22O3 (250.1568862)


   

6,6,8-trimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

6,6,8-trimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

C15H18O3 (246.1255878)


   

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

C15H24O3 (252.1725354)


   

(1r,7s,9ar,11ar)-7-(dimethylamino)-1-[(2r)-4-[(3e)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

(1r,7s,9ar,11ar)-7-(dimethylamino)-1-[(2r)-4-[(3e)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

C33H54N2O2 (510.41850639999996)


   

(4as,6r)-6-(hydroxymethyl)-6,8-dimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

(4as,6r)-6-(hydroxymethyl)-6,8-dimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

C15H18O4 (262.1205028)


   

1-[4-(1,3-dimethyl-5,6-dihydro-2h-pyridin-4-yl)but-3-en-2-yl]-9a,11a-dimethyl-7-(methylamino)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl acetate

1-[4-(1,3-dimethyl-5,6-dihydro-2h-pyridin-4-yl)but-3-en-2-yl]-9a,11a-dimethyl-7-(methylamino)-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-yl acetate

C33H52N2O2 (508.40285719999997)


   

(3s,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

(3s,4s,4ar,7as,7br)-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-3,4-diol

C15H24O3 (252.1725354)


   

3-(2-carboxyethyl)-1,4-dimethylpyridin-1-ium

3-(2-carboxyethyl)-1,4-dimethylpyridin-1-ium

[C10H14NO2]+ (180.10244840000001)


   

3-(buta-1,3-diyn-1-yl)-4-hydroxycyclopent-2-en-1-one

3-(buta-1,3-diyn-1-yl)-4-hydroxycyclopent-2-en-1-one

C9H6O2 (146.0367776)


   

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4h,4ah,5h,7h,7ah-cyclobuta[e]indene-2,4-diol

C15H24O3 (252.1725354)


   

n-[(3r,6s,10r,13s)-10-[(5-bromo-1h-indol-3-yl)methyl]-2,5,9,12,13-pentahydroxy-3-(c-hydroxycarbonimidoylmethyl)-1,4,8,11-tetraazacyclotetradeca-1,4,8,11-tetraen-6-yl]-2-[(4,5-dichloro-1-methylpyrrol-2-yl)formamido]ethanimidic acid

n-[(3r,6s,10r,13s)-10-[(5-bromo-1h-indol-3-yl)methyl]-2,5,9,12,13-pentahydroxy-3-(c-hydroxycarbonimidoylmethyl)-1,4,8,11-tetraazacyclotetradeca-1,4,8,11-tetraen-6-yl]-2-[(4,5-dichloro-1-methylpyrrol-2-yl)formamido]ethanimidic acid

C29H32BrCl2N9O8 (783.0934152)


   

7-(dimethylamino)-1-{4-[(3z)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

7-(dimethylamino)-1-{4-[(3z)-1-(2-hydroxyethyl)-2,2-dimethylpyrrolidin-3-ylidene]butan-2-yl}-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-6-one

C33H54N2O2 (510.41850639999996)


   

2-hydroxy-1-{6-hydroxy-2,9,9-trimethyltricyclo[5.3.0.0²,⁵]decan-5-yl}ethanone

2-hydroxy-1-{6-hydroxy-2,9,9-trimethyltricyclo[5.3.0.0²,⁵]decan-5-yl}ethanone

C15H24O3 (252.1725354)


   

6-(hydroxymethyl)-6,8-dimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

6-(hydroxymethyl)-6,8-dimethyl-4h,4ah,5h,7h-indeno[5,6-c]furan-1-carboxylic acid

C15H18O4 (262.1205028)


   

4,8-dihydroxy-6,6,8-trimethyl-4h,4ah,5h,7h,7ah-indeno[5,6-c]furan-1-carboxylic acid

4,8-dihydroxy-6,6,8-trimethyl-4h,4ah,5h,7h,7ah-indeno[5,6-c]furan-1-carboxylic acid

C15H20O5 (280.13106700000003)