Drophiobolin A; (3aR,6aR,7S,9aR,10aS)-7-hydroxy-7-((S)-6-hydroxy-6-methylheptan-2-yl)-1,9a-dimethyl-3-oxo-3,3a,6,6a,7,8,9,9a,10,10a-decahydrodicyclopenta[a,d][8]annulene-4-carbaldehyde

ID: ALA4755393

Chembl Id: CHEMBL4755393

PubChem CID: 162655768

Max Phase: Preclinical

Molecular Formula: C25H38O4

Molecular Weight: 402.58

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)[C@H]2/C(C=O)=C\C[C@@H]3[C@](C)(CC[C@]3(O)[C@@H](C)CCCC(C)(C)O)C[C@H]12

Standard InChI:  InChI=1S/C25H38O4/c1-16-13-20(27)22-18(15-26)8-9-21-24(5,14-19(16)22)11-12-25(21,29)17(2)7-6-10-23(3,4)28/h8,13,15,17,19,21-22,28-29H,6-7,9-12,14H2,1-5H3/b18-8-/t17-,19+,21+,22-,24+,25-/m0/s1

Standard InChI Key:  PQLLTQKWIQPVMI-ZSOFCWHRSA-N

Alternative Forms

1. Parent:

   

   ALA4755393

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 402.58

Molecular Weight (Monoisotopic): 402.2770

AlogP: 4.39

#Rotatable Bonds: 6

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 0.09

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: 0

Heavy Atoms: 29

QED Weighted: 0.65

Np Likeness Score: 2.89

References

1. Zatout R,Masi M,Sangermano F,Vurro M,Zonno MC,Santoro E,Calabrò V,Superchi S,Evidente A.  (2020)  Drophiobiolins A and B, Bioactive Ophiobolan Sestertepenoids Produced by Dreschslera gigantea.,  83  (11): [PMID:33074690] [10.1021/acs.jnatprod.0c00836]

Source

Source(1):

• Scientific Literature