variotin

ID: ALA486174

Chembl Id: CHEMBL486174

Cas Number: 19504-77-9

PubChem CID: 5282176

Max Phase: Phase

Molecular Formula: C17H25NO3

Molecular Weight: 291.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-291839 | Pecilocin|variotin|Leofungine|Supral|19504-77-9|Pecilocine [INN-French]|Pecilocinum [INN-Latin]|TSA7W27MF8|1-[(2E,4E,6E,8R)-8-hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one|CHEBI:32289|Pecilocin (INN)|Variotin (JAN)|NSC-291839|PECILOCIN [INN]|VARIOTIN [JAN]|1-[(2E,4E,6Z)-8-hydroxy-6-methyldodeca-2,4,6-trienoyl]pyrrolidin-2-one|Pecilocina|Pecilocine|Pecilocinum|Pecilocina [INN-Spanish]|Pecilocin [INN:BAN]|EINECS 243-116-9|UNII-TSA7W27MF8|NSC 291839|Leofungine; NSC 291839;SuprShow More⌵

Canonical SMILES:  CCCC[C@@H](O)/C=C(C)/C=C/C=C/C(=O)N1CCCC1=O

Standard InChI:  InChI=1S/C17H25NO3/c1-3-4-9-15(19)13-14(2)8-5-6-10-16(20)18-12-7-11-17(18)21/h5-6,8,10,13,15,19H,3-4,7,9,11-12H2,1-2H3/b8-5+,10-6+,14-13+/t15-/m1/s1

Standard InChI Key:  ZYPGADGCNXOUJP-CXVPHVKISA-N

Alternative Forms

1. Parent:

   

   ALA486174

   PECILOCIN

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 291.39

Molecular Weight (Monoisotopic): 291.1834

AlogP: 2.75

#Rotatable Bonds: 7

Polar Surface Area: 57.61

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.40

CX LogD: 2.40

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 1.14

References

1. Omolo JO, Anke H, Chhabra S, Sterner O..  (2000)  New variotin analogues from Aspergillus viridi-nutans.,  63  (7): [PMID:10924177] [10.1021/np990509b]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Mizushina Y, Suzuki-Fukudome H, Takeuchi T, Takemoto K, Kuriyama I, Yoshida H, Kamisuki S, Sugawara F..  (2014)  Formosusin A, a novel specific inhibitor of mammalian DNA polymerase β from the fungus Paecilomyces formosus.,  22  (3): [PMID:24411199] [10.1016/j.bmc.2013.12.038]

4. WHO Anatomical Therapeutic Chemical Classification, 

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification