Berkeleyone C

ID: ALA1911630

Chembl Id: CHEMBL1911630

Cas Number: 1334495-43-0

PubChem CID: 57401571

Max Phase: Preclinical

Molecular Formula: C26H34O7

Molecular Weight: 458.55

Molecule Type: Small molecule

Representations

Synonyms: Berkeleyone C | Berkeleyone C|CHEMBL1911630|CHEBI:69027|DTXSID401098395|BDBM50355792|Q27137369|1334495-43-0|5,9-Methanobenzocyclooctene-1-propanoic acid, 1,4,4a,5,6,7,8,9,10,10a-decahydro-7-hydroxy-5-(methoxycarbonyl)-1,4a,7,9-tetramethyl-11-methylene-2-(1-methylethenyl)-6,8-dioxo-, (1S,4aS,5R,7S,9R,10aS)-|rel-3-[(1S,4aS,5R,7S,9R,10aS)-7-hydroxy-5-(methoxycarbonyl)-1,4a,7,9-tetramethyl-11-methylidene-6,8-dioxo-2-(prop-1-en-2-yl)-1,4,4a,5,6,7,8,9,10,10a-decahydro-5,9-methanobenzo[8]annulen-1-yl]pShow More⌵

Canonical SMILES:  C=C(C)C1=CC[C@@]2(C)[C@@H](C[C@]3(C)C(=C)[C@@]2(C(=O)OC)C(=O)[C@@](C)(O)C3=O)[C@]1(C)CCC(=O)O

Standard InChI:  InChI=1S/C26H34O7/c1-14(2)16-9-12-24(6)17(22(16,4)11-10-18(27)28)13-23(5)15(3)26(24,21(31)33-8)20(30)25(7,32)19(23)29/h9,17,32H,1,3,10-13H2,2,4-8H3,(H,27,28)/t17-,22+,23+,24-,25-,26-/m0/s1

Standard InChI Key:  HBZLILHFZMWEGE-QFRJCEMRSA-N

Alternative Forms

1. Parent:

   

   ALA1911630

   BERKELEYONE C

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: 458.55

Molecular Weight (Monoisotopic): 458.2305

AlogP: 3.41

#Rotatable Bonds: 5

Polar Surface Area: 117.97

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.20

CX Basic pKa:

CX LogP: 3.72

CX LogD: 0.68

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 2.64

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