NCBI Taxonomy: 60167

Penicillium cyclopium (ncbi_taxid: 60167)

found 110 associated metabolites at species taxonomy rank level.

Ancestor: Penicillium

Child Taxonomies: none taxonomy data.

Orsellinic_acid

6-Methyl-beta-resorcylic acid; Orcinolcarboxylic acid

C8H8O4 (168.0422568)


O-orsellinic acid is a dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group. It has a role as a metabolite, a marine metabolite and a fungal metabolite. It is a dihydroxybenzoic acid and a member of resorcinols. It is a conjugate acid of an o-orsellinate. 2,4-Dihydroxy-6-methylbenzoic acid is a natural product found in Nidularia pulvinata, Hypoxylon rubiginosum, and other organisms with data available. A dihydroxybenzoic acid that is 2,4-dihydroxybenzoic acid in which the hydrogen at position 6 is replaced by a methyl group. Orsellinic acid is a compound produced by Lecanoric acid treated with alcohols. Lecanoric acid is a lichen depside isolated from a Parmotrema tinctorum specimen[1].

   

penicillic acid

(2E)-3-methoxy-5-methyl-4-oxohexa-2,5-dienoic acid

C8H10O4 (170.057906)


D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE isolated standard

   

Compactin

2S-methyl-(1S,2,3,7S,8S,8aR)-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2-H-pyran-2-yl]ethyl]-1-naphthalenyl ester-butanoic acid

C23H34O5 (390.2406114)


A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor D009676 - Noxae > D000963 - Antimetabolites Mevastatin (Compactin) is a first HMG-CoA reductase inhibitor that belongs to the statins class. Mevastatin is a lipid-lowering agent, and induces apoptosis, arrests cancer cells in G0/G1 phase. Mevastatin also increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels. Mevastatin has antitumor activity and has the potential for cardiovascular diseases treatment[1][2][3]. Mevastatin (Compactin) is a first HMG-CoA reductase inhibitor that belongs to the statins class. Mevastatin is a lipid-lowering agent, and induces apoptosis, arrests cancer cells in G0/G1 phase. Mevastatin also increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels. Mevastatin has antitumor activity and has the potential for cardiovascular diseases treatment[1][2][3].

   

Patulin

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

C7H6O4 (154.0266076)


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].

   

CYCLOPIAZONIC ACID

.alpha.-Cyclopiazonic acid

C20H20N2O3 (336.147385)


D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D004791 - Enzyme Inhibitors Cyclopiazonic acid (CPA), a neurotoxic secondary metabolite (SM) made by Aspergillus flavus, is an inhibitor of endoplasmic reticulum calcium ATPase (Ca2+ATPase; SERCA) and a potent inducer of cell death in plants[1].

   

Citreorosein

1,3,8-trihydroxy-6-(hydroxymethyl)-9,10-dihydroanthracene-9,10-dione

C15H10O6 (286.047736)


Citreorosein is found in green vegetables. Citreorosein is found in roots of Polygonum cuspidatum (Japanese knotweed Found in roots of Polygonum cuspidatum (Japanese knotweed)

   

Mevastatin

8-[2-(4-Hydroxy-6-oxooxan-2-yl)ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoic acid

C23H34O5 (390.24061140000003)


   

Penicillic acid

3-Methoxy-5-methyl-4-oxo-2,5-hexadienoic acid

C8H10O4 (170.057906)


   

Emodic acid

2-Anthracenecarboxylic acid, 9,10-dihydro-4,5,7-trihydroxy-9,10-dioxo-

C15H8O7 (300.0270018)


Emodicacid is a member of anthracenes.

   

Orsellic acid

2,4-Dihydroxy-6-methylbenzoic acid

C8H8O4 (168.0422568)


Orsellinic acid is a compound produced by Lecanoric acid treated with alcohols. Lecanoric acid is a lichen depside isolated from a Parmotrema tinctorum specimen[1].

   

Viridicatol

3-hydroxy-4-(3-hydroxyphenyl)-1H-quinolin-2-one

C15H11NO3 (253.0738896)


CONFIDENCE Penicillium sp. Viridicatol, a quinolinone alkaloid, is isolated from the fermentation of an endophytic fungus Penicillium sp. R22 in Nerium indicum. Viridicatol has strong antifungal activity against Staphylococcus aureus with MIC value of 15.6 μg/mL[1].

   

conidiogenone

conidiogenone

C20H32O2 (304.24021719999996)


A diterpenoid with formula C20H32O2. It is isolated from Penicillium cyclopium and exhibits potent conidiation inducing activity.

   

conidiogenol

conidiogenol

C20H34O2 (306.2558664)


A diterpenoid with formula C20H34O2. It is isolated from Penicillium cyclopium and exhibits potent conidiation inducing activity.

   

Mevastatin

[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

C23H34O5 (390.24061140000003)


Mevastatin is a carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals. It has a role as a fungal metabolite, an EC 3.4.24.83 (anthrax lethal factor endopeptidase) inhibitor, an antifungal agent, a Penicillium metabolite and an apoptosis inducer. It is a carboxylic ester, a statin (naturally occurring), a member of hexahydronaphthalenes, a member of 2-pyranones and a polyketide. Mevastatin (Compactin) is a first HMG-CoA reductase inhibitor that belongs to the statins class. Mevastatin is a lipid-lowering agent, and induces apoptosis, arrests cancer cells in G0/G1 phase. Mevastatin also increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels. Mevastatin has antitumor activity and has the potential for cardiovascular diseases treatment. Mevastatin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=73573-88-3 (retrieved 2024-10-09) (CAS RN: 73573-88-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

patulin

patulin

C7H6O4 (154.0266076)


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].

   

orsellinic acid

orsellinic acid

C8H8O4 (168.0422568)


   

Citreorosein

9,10-Anthracenedione, 1,3,8-trihydroxy-6-(hydroxymethyl)-

C15H10O6 (286.047736)


   

1-(2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl)ethanone

1-(2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl)ethanone

C20H22N2O3 (338.16303419999997)


   

5-(1-aminoethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),11(18),12,14-tetraene-4,6-dione

5-(1-aminoethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),11(18),12,14-tetraene-4,6-dione

C20H21N3O2 (335.1633686)


   

2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

C20H34O2 (306.2558664)


   

2-hydroxy-4-methyl-3-(phenylmethylidene)-1,4-benzodiazepin-5-one

2-hydroxy-4-methyl-3-(phenylmethylidene)-1,4-benzodiazepin-5-one

C17H14N2O2 (278.1055224)


   

(1r,3as,7s,9as,9br,11ar)-1-[(2s,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(1r,3as,7s,9as,9br,11ar)-1-[(2s,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C28H44O (396.3391974)


   

(1r,2r,3r,6r,9s,10r,14r)-3-hydroxy-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecan-5-one

(1r,2r,3r,6r,9s,10r,14r)-3-hydroxy-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecan-5-one

C20H32O2 (304.24021719999996)


   

(3s,4s)-3-methoxy-4-(4-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-3h-quinoline-2,4,5-triol

(3s,4s)-3-methoxy-4-(4-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-3h-quinoline-2,4,5-triol

C22H25NO5 (383.173264)


   

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 (389.1851658)


   

4-phenylquinoline-2,3-diol

4-phenylquinoline-2,3-diol

C15H11NO2 (237.0789746)


   

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

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

C28H44O (396.3391974)


   

(5as,7r,8as,9ar)-9'-methoxy-5',5',8,8-tetramethyl-5a-nitro-1,2,3,5,6,8a,9,9a-octahydro-4'-azaspiro[cyclopenta[f]indolizine-7,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),8'(12'),9'-triene-3',7'-dione

(5as,7r,8as,9ar)-9'-methoxy-5',5',8,8-tetramethyl-5a-nitro-1,2,3,5,6,8a,9,9a-octahydro-4'-azaspiro[cyclopenta[f]indolizine-7,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),8'(12'),9'-triene-3',7'-dione

C26H33N3O5 (467.24200880000006)


   

1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone

1-[(5s)-2,4-dihydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1h-indol-3-yl]methyl}-5h-pyrrol-3-yl]ethanone

C20H22N2O3 (338.16303419999997)


   

5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one

5-acetyl-4-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),4,11(18),12,14-pentaen-6-one

C20H20N2O3 (336.147385)


   

(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 (154.0266076)


   

(3s,3's)-2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

(3s,3's)-2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

C17H14N2O3 (294.10043740000003)


   

(2s,3s,5e,9r)-5-(1-aminoethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),11(18),12,14-tetraene-4,6-dione

(2s,3s,5e,9r)-5-(1-aminoethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0²,⁹.0³,⁷.0¹⁵,¹⁸]octadeca-1(17),11(18),12,14-tetraene-4,6-dione

C20H21N3O2 (335.1633686)


   

9'-methoxy-5',5',8,8-tetramethyl-5a-nitro-1,2,3,5,6,8a,9,9a-octahydro-4'-azaspiro[cyclopenta[f]indolizine-7,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),8'(12'),9'-triene-3',7'-dione

9'-methoxy-5',5',8,8-tetramethyl-5a-nitro-1,2,3,5,6,8a,9,9a-octahydro-4'-azaspiro[cyclopenta[f]indolizine-7,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),8'(12'),9'-triene-3',7'-dione

C26H33N3O5 (467.24200880000006)


   

3-hydroxy-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecan-5-one

3-hydroxy-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecan-5-one

C20H32O2 (304.24021719999996)


   

(3r,3's)-2-hydroxy-3'-(3-hydroxyphenyl)-4-methylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

(3r,3's)-2-hydroxy-3'-(3-hydroxyphenyl)-4-methylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

C17H14N2O4 (310.0953524)


   

2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

C17H14N2O3 (294.10043740000003)


   

(3z)-2-hydroxy-4-methyl-3-(phenylmethylidene)-1,4-benzodiazepin-5-one

(3z)-2-hydroxy-4-methyl-3-(phenylmethylidene)-1,4-benzodiazepin-5-one

C17H14N2O2 (278.1055224)


   

(1r,2r,3r,5r,6r,9s,10r,14r)-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

(1r,2r,3r,5r,6r,9s,10r,14r)-2,6,11,11,14-pentamethyltetracyclo[7.6.0.0¹,⁶.0¹⁰,¹⁴]pentadecane-3,5-diol

C20H34O2 (306.2558664)


   

(3'r)-2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

(3'r)-2-hydroxy-4-methyl-3'-phenylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

C17H14N2O3 (294.10043740000003)


   

3-hydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,3,6,8,10,12(15)-hexaen-14-one

3-hydroxy-5,5,13-trimethyl-4,13-diazatetracyclo[6.6.1.0²,⁶.0¹²,¹⁵]pentadeca-1,3,6,8,10,12(15)-hexaen-14-one

C16H14N2O2 (266.1055224)


   

3-methoxy-4-(4-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-3h-quinoline-2,4,5-triol

3-methoxy-4-(4-methoxyphenyl)-6-(3-methylbut-2-en-1-yl)-3h-quinoline-2,4,5-triol

C22H25NO5 (383.173264)


   

4-(3-hydroxyphenyl)quinoline-2,3-diol

4-(3-hydroxyphenyl)quinoline-2,3-diol

C15H11NO3 (253.0738896)


   

(3'r)-2-hydroxy-3'-(3-hydroxyphenyl)-4-methylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

(3'r)-2-hydroxy-3'-(3-hydroxyphenyl)-4-methylspiro[1,4-benzodiazepine-3,2'-oxiran]-5-one

C17H14N2O4 (310.0953524)