NCBI Taxonomy: 27334

Penicillium expansum (ncbi_taxid: 27334)

found 67 associated metabolites at species taxonomy rank level.

Ancestor: Penicillium

Child Taxonomies: Penicillium expansum T01, Penicillium expansum NRRL 62431, Penicillium expansum ATCC 24692

Gluconic acid

(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid

C6H12O7 (196.0583)


Gluconic acid, also known as D-gluconic acid, D-gluconate or (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid (also named dextronic acid), is the C1-oxidized form of D-glucose where the aldehyde group has become oxidized to the corresponding carboxylic acid. Gluconic acid belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone. Gluconic acid occurs naturally in fruit, honey, kombucha tea and wine. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Gluconic acid exists in all living species, ranging from bacteria to plants to humans. The metabolism of gluconate is well characterized in prokaryotes where it is known to be degraded following phosphorylation by gluconokinase. Glucokinase activity has also been detected in mammals, including humans (PMID: 24896608). Gluconic acid is produced in the gluconate shunt pathway. In the gluconate shunt, glucose is oxidized by glucose dehydrogenase (also called glucose oxidase) to furnish gluconate, the form in which D-gluconic acid is present at physiological pH. Subsequently, gluconate is phosphorylated by the action of gluconate kinase to produce 6-phosphogluconate, which is the second intermediate of the pentose phosphate pathway. This gluconate shunt is mainly found in plants, algae, cyanobacteria and some bacteria, which all use the Entner–Doudoroff pathway to degrade glucose or gluconate; this generates 2-keto-3-deoxygluconate-6-phosphate, which is then cleaved to generate pyruvate and glyceraldehyde 3-phosphate. Glucose dehydrogenase and gluconate kinase activities are also present in mammals, fission yeast, and flies. Gluconic acid has many industrial uses. It is used as a drug as part of electrolyte supplementation in total parenteral nutrition. It is also used in cleaning products where it helps cleaning up mineral deposits. Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). [Spectral] D-Gluconic acid (exact mass = 196.0583) and Guanine (exact mass = 151.04941) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement, acidity regulator approved in Japan. Component of bottle rinsing formulations Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G031

   

Patulin

(2,4-Dihydroxy-2H-pyran-3(6H)-ylidene)acetic acid, 3,4-lactone

C7H6O4 (154.0266)


Patulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins D009676 - Noxae > D009153 - Mutagens Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

   
   

gluconic acid

D-gluconic acid

C6H12O7 (196.0583)


   

Diorcinol

Diorcinol

C14H14O3 (230.0943)


An aromatic ether that is diphenyl ether in which both phenyl groups are substituted at position 3 by a hydroxy group and at position 5 by a methyl group.

   

3-hydroxy-4-(2-hydroxy-6-methylheptan-2-yl)benzoic acid

NCGC00180240-02!3-hydroxy-4-(2-hydroxy-6-methylheptan-2-yl)benzoic acid

C15H22O4 (266.1518)


   

3-hydroxy-4-(2-hydroxy-6-methylheptan-2-yl)benzoic acid

3-hydroxy-4-(2-hydroxy-6-methylheptan-2-yl)benzoic acid

C15H22O4 (266.1518)


   

patulin

patulin

C7H6O4 (154.0266)


D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE standard compound; INTERNAL_ID 5971 D009676 - Noxae > D009153 - Mutagens CONFIDENCE Reference Standard (Level 1) Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

   

(+)-(7S)-sydonic acid

(+)-(7S)-sydonic acid

C15H22O4 (266.1518)


A sesquiterpenoid that is benzoic acid substituted by a hydroxy group at position 3 and a (2S)-2-hydroxy-6-methylheptan-2-yl group at position 4. It has been isolated from the sea fan derived fungus Aspergillus sydowii.

   

Mycoin

4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one

C7H6O4 (154.0266)


A furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic. D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins D009676 - Noxae > D009153 - Mutagens Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

   

(6ar)-9-acetyl-3-[(1e,3e,5s)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

(6ar)-9-acetyl-3-[(1e,3e,5s)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C23H26O5 (382.178)


   
   

(2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

(2e,4e)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

C31H34N4O2 (494.2682)


   

(1s,4r)-4-benzyl-3,10-dihydroxy-1-(sec-butyl)-1h,4h-pyrazino[2,1-b]quinazolin-6-one

(1s,4r)-4-benzyl-3,10-dihydroxy-1-(sec-butyl)-1h,4h-pyrazino[2,1-b]quinazolin-6-one

C22H23N3O3 (377.1739)


   

9-hydroxy-9-({3-hydroxy-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl}methyl)-2-methyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one

9-hydroxy-9-({3-hydroxy-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl}methyl)-2-methyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one

C23H21N5O4 (431.1593)


   

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

C32H36N4O2 (508.2838)


   

2-({3-hydroxy-4-[(2s)-2-hydroxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

2-({3-hydroxy-4-[(2s)-2-hydroxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

C29H36O5 (464.2563)


   

(3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

(3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C12H16O3 (208.1099)


   

(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-3-[(2e,4e)-hexa-2,4-dienoyl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-3-[(2e,4e)-hexa-2,4-dienoyl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

C32H34N4O3 (522.2631)


   

(3s)-1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

(3s)-1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C14H20O4 (252.1362)


   

1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C14H20O4 (252.1362)


   

(2s,7as,11as,12s)-5,6,7a,8,11a,12-hexahydroxy-3-methoxy-2',6',6'-trimethyl-7,10-dioxo-11,12-dihydro-1h-spiro[cyclohexa[k]aceanthrylene-2,1'-cyclohexan]-2'-ene-9-carboximidic acid

(2s,7as,11as,12s)-5,6,7a,8,11a,12-hexahydroxy-3-methoxy-2',6',6'-trimethyl-7,10-dioxo-11,12-dihydro-1h-spiro[cyclohexa[k]aceanthrylene-2,1'-cyclohexan]-2'-ene-9-carboximidic acid

C30H31NO10 (565.1948)


   

(1s,3s)-1,8-dimethoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

(1s,3s)-1,8-dimethoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C13H18O4 (238.1205)


   

8-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-6-one

8-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-6-one

C12H14O3 (206.0943)


   

1-[25-(3,3-dimethyloxiran-2-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[25-(3,3-dimethyloxiran-2-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C27H30N4O2 (442.2369)


   

2-({3-hydroxy-4-[(2r)-2-methoxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

2-({3-hydroxy-4-[(2r)-2-methoxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

C30H38O5 (478.2719)


   

(2e,4e)-1-[(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

(2e,4e)-1-[(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]hexa-2,4-dien-1-one

C31H34N4O2 (494.2682)


   

(3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-6-one

(3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-6-one

C12H14O3 (206.0943)


   

1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C27H30N4O2 (442.2369)


   

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O2 (456.2525)


   

6-hydroxy-4-(1h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

6-hydroxy-4-(1h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

C22H23N5O2 (389.1852)


   

1-[15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O (440.2576)


   

(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-3-[(2e,4e)-hexa-2,4-dienoyl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-3-[(2e,4e)-hexa-2,4-dienoyl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

C32H34N4O3 (522.2631)


   

4''-methyl-2-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

4''-methyl-2-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

C17H22O5 (306.1467)


   

1-[(2s,6r,14r,22r,25r)-15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2s,6r,14r,22r,25r)-15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O (440.2576)


   

(4s)-4-hydroxy-4h,6h-furo[3,2-c]pyran-2-one

(4s)-4-hydroxy-4h,6h-furo[3,2-c]pyran-2-one

C7H6O4 (154.0266)


   

(4r)-4-hydroxy-4h,6h-furo[3,2-c]pyran-2-one

(4r)-4-hydroxy-4h,6h-furo[3,2-c]pyran-2-one

C7H6O4 (154.0266)


   

(2s,9r,9as)-9-hydroxy-9-{[(4s)-3-hydroxy-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one

(2s,9r,9as)-9-hydroxy-9-{[(4s)-3-hydroxy-6-oxo-1h,4h-pyrazino[2,1-b]quinazolin-4-yl]methyl}-2-methyl-1h,2h,9ah-imidazo[1,2-a]indol-3-one

C23H21N5O4 (431.1593)


   

3-hydroxy-4-(2-hydroxy-6-methylhept-6-en-2-yl)benzoic acid

3-hydroxy-4-(2-hydroxy-6-methylhept-6-en-2-yl)benzoic acid

C15H20O4 (264.1362)


   

2-({3-hydroxy-4-[(2s)-2-methoxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

2-({3-hydroxy-4-[(2s)-2-methoxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

C30H38O5 (478.2719)


   

4-[7-(acetyloxy)-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

4-[7-(acetyloxy)-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

C17H24O6 (324.1573)


   

1-[(2s,6r,14r,22r,25s)-25-[(2s)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2s,6r,14r,22r,25s)-25-[(2s)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O2 (456.2525)


   

(1s,2'r,3r,4''r,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

(1s,2'r,3r,4''r,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

C17H22O5 (306.1467)


   

8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C12H16O3 (208.1099)


   

8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

C12H16O4 (224.1049)


   

(1s,2'r,3r,4''r,5s,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

(1s,2'r,3r,4''r,5s,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

C17H22O5 (306.1467)


   

3-hydroxy-4-[(2s)-2-hydroxy-6-methylhept-6-en-2-yl]benzoic acid

3-hydroxy-4-[(2s)-2-hydroxy-6-methylhept-6-en-2-yl]benzoic acid

C15H20O4 (264.1362)


   

(1r,4z,7r,9s)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

(1r,4z,7r,9s)-6-hydroxy-4-(3h-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

C22H23N5O2 (389.1852)


   

1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O2 (456.2525)


   

4-benzyl-3,10-dihydroxy-1-(sec-butyl)-1h,4h-pyrazino[2,1-b]quinazolin-6-one

4-benzyl-3,10-dihydroxy-1-(sec-butyl)-1h,4h-pyrazino[2,1-b]quinazolin-6-one

C22H23N3O3 (377.1739)


   
   

(1s,3r)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

(1s,3r)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

C12H16O4 (224.1049)


   

1,8-dimethoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

1,8-dimethoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C13H18O4 (238.1205)


   

4-[(2s,6s)-7-(acetyloxy)-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

4-[(2s,6s)-7-(acetyloxy)-2-hydroxy-6-methylheptan-2-yl]-3-hydroxybenzoic acid

C17H24O6 (324.1573)


   

(1s,3s)-1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

(1s,3s)-1-ethoxy-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-6-ol

C14H20O4 (252.1362)


   

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]-3-hydroxyhexan-1-one

1-[25-(3,3-dimethyloxiran-2-yl)-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]-3-hydroxyhexan-1-one

C32H40N4O3 (528.31)


   

1-[(2r,6s,14s,22s,25s)-15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2r,6s,14s,22s,25s)-15-methyl-25-(2-methylprop-1-en-1-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C28H32N4O (440.2576)


   

1-[(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

1-[(2r,6s,14s,22s,25r)-25-[(2s)-3,3-dimethyloxiran-2-yl]-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]ethanone

C27H30N4O2 (442.2369)


   

25-(3,3-dimethyloxiran-2-yl)-3-(hexa-2,4-dienoyl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

25-(3,3-dimethyloxiran-2-yl)-3-(hexa-2,4-dienoyl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

C32H34N4O3 (522.2631)


   

(1r,3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

(1r,3s)-8-methoxy-3,5-dimethyl-3,4-dihydro-1h-2-benzopyran-1,6-diol

C12H16O4 (224.1049)


   

(9z)-9-[amino(hydroxy)methylidene]-5,6,7a,11a,12-pentahydroxy-3-methoxy-2',6',6'-trimethyl-11,12-dihydro-1h-spiro[cyclohexa[k]aceanthrylene-2,1'-cyclohexan]-2'-ene-7,8,10-trione

(9z)-9-[amino(hydroxy)methylidene]-5,6,7a,11a,12-pentahydroxy-3-methoxy-2',6',6'-trimethyl-11,12-dihydro-1h-spiro[cyclohexa[k]aceanthrylene-2,1'-cyclohexan]-2'-ene-7,8,10-trione

C30H31NO10 (565.1948)


   

(1s,2's,3r,4''r,5s,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

(1s,2's,3r,4''r,5s,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

C17H22O5 (306.1467)


   

(3s)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]-3-hydroxyhexan-1-one

(3s)-1-[(2s,6r,14r,22r,25s)-25-[(2r)-3,3-dimethyloxiran-2-yl]-15-methyl-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaen-3-yl]-3-hydroxyhexan-1-one

C32H40N4O3 (528.31)


   

2-({3-hydroxy-4-[(2r)-2-hydroxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

2-({3-hydroxy-4-[(2r)-2-hydroxy-6-methylheptan-2-yl]phenyl}methyl)-5-(3-hydroxy-5-methylphenoxy)-3-methylphenol

C29H36O5 (464.2563)


   

(6ar,9r,9ar)-9-acetyl-3-[(1e,3e,5s)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

(6ar,9r,9ar)-9-acetyl-3-[(1e,3e,5s)-3,5-dimethylhepta-1,3-dien-1-yl]-6a-methyl-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C23H26O5 (382.178)


   

(1s,2's,3r,4''r,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

(1s,2's,3r,4''r,6r)-4''-methyl-4-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl acetate

C17H22O5 (306.1467)


   

3-acetyl-25-(3,3-dimethyloxiran-2-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

3-acetyl-25-(3,3-dimethyloxiran-2-yl)-1,3,13,15-tetraazaheptacyclo[18.4.1.0²,⁶.0⁶,²².0⁷,¹².0¹⁴,²².0¹⁶,²¹]pentacosa-7,9,11,16,18,20-hexaene-15-carbaldehyde

C28H30N4O3 (470.2318)