berkeleyone B

ID: ALA1911628

Chembl Id: CHEMBL1911628

Cas Number: 1334495-42-9

PubChem CID: 57398142

Max Phase: Preclinical

Molecular Formula: C26H34O7

Molecular Weight: 458.55

Molecule Type: Small molecule

Representations

Synonyms: Berkeleyone B | Berkeleyone B|CHEMBL1911628|CHEBI:69025|DTXSID301098223|BDBM50355790|Q27137367|1334495-42-9|8,12-Methanocycloocta[g][2]benzoxepin-8(5H)-carboxylic acid, 1,2,3,7,7a,9,10,11,12,13,13a,13b-dodecahydro-10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylene-3,9,11-trioxo-, methyl ester, (7aS,8R,10S,12R,13aS,13bS)-|rel-methyl (7aS,8R,10S,12R,13aS,13bS)-10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylidene-3,9,11-trioxo-1,2,3,7,7a,9,10,11,12,13,13a,13b-dodecahydro-8,12-methanocycloocta[3,4Show More⌵

Canonical SMILES:  C=C1[C@@]2(C)C[C@@H]3[C@](C)(CC=C4C(C)(C)OC(=O)CC[C@]43C)[C@]1(C(=O)OC)C(=O)[C@@](C)(O)C2=O

Standard InChI:  InChI=1S/C26H34O7/c1-14-23(5)13-16-22(4)11-10-17(27)33-21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h9,16,31H,1,10-13H2,2-8H3/t16-,22+,23+,24-,25-,26-/m0/s1

Standard InChI Key:  IWYHWTWGKBGNTO-GSISZECUSA-N

Alternative Forms

1. Parent:

   

   ALA1911628

   BERKELEYONE B

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: 3.09

#Rotatable Bonds: 1

Polar Surface Area: 106.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.48

CX Basic pKa:

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 0

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: 2.76

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]

2. Qi B, Liu X, Mo T, Zhu Z, Li J, Wang J, Shi X, Zeng K, Wang X, Tu P, Abe I, Shi S..  (2017)  3,5-Dimethylorsellinic Acid Derived Meroterpenoids from Penicillium chrysogenum MT-12, an Endophytic Fungus Isolated from Huperzia serrata.,  80  (10): [PMID:28960979] [10.1021/acs.jnatprod.7b00438]

Source

Source(1):

• Scientific Literature