Berkeleyone A

ID: ALA1911627

Chembl Id: CHEMBL1911627

PubChem CID: 57391090

Max Phase: Preclinical

Molecular Formula: C26H38O6

Molecular Weight: 446.58

Molecule Type: Small molecule

Representations

Synonyms: Berkeleyone A | Berkeleyone A|CHEMBL1911627|CHEBI:69024|maimone82|8TC|BDBM50355789|XG-I-186-1|Q27137366|rel-methyl (3R,4aS,6aS,7R,9S,11R,12aS,12bS)-3,9-dihydroxy-4,4,6a,9,11,12b-hexamethyl-13-methylidene-8,10-dioxotetradecahydro-7,11-methanocycloocta[a]naphthalene-7(2H)-carboxylate

Canonical SMILES:  C=C1[C@@]2(C)C[C@H]3[C@]4(C)CC[C@@H](O)C(C)(C)[C@H]4CC[C@]3(C)[C@]1(C(=O)OC)C(=O)[C@@](C)(O)C2=O

Standard InChI:  InChI=1S/C26H38O6/c1-14-23(5)13-16-22(4)11-10-17(27)21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-17,27,31H,1,9-13H2,2-8H3/t15-,16+,17-,22-,23-,24+,25+,26+/m1/s1

Standard InChI Key:  NNHHTFDBMMPBSL-JFPRQHOTSA-N

Alternative Forms

1. Parent:

   

   ALA1911627

   BERKELEYONE A

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 446.58

Molecular Weight (Monoisotopic): 446.2668

AlogP: 3.23

#Rotatable Bonds: 1

Polar Surface Area: 100.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.48

CX Basic pKa:

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 0

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: 2.77

References

1. Stierle DB, Stierle AA, Patacini B, McIntyre K, Girtsman T, Bolstad E..  (2011)  Berkeleyones and related meroterpenes from a deep water acid mine waste fungus that inhibit the production of interleukin 1-β from induced inflammasomes.,  74  (10): [PMID:21916432] [10.1021/np2003066]

Source

Source(1):

• Scientific Literature