((5R,5aS,6S,9aS,9bS)-5,9b-dihydroxy-6,9a-dimethyl-3-oxo-1,3,5,5a,6,7,8,9,9a,9b-decahydronaphtho[2,1-c]furan-6-yl)methyl 4-nitrobenzoate

ID: ALA3580705

Chembl Id: CHEMBL3580705

PubChem CID: 101891076

Max Phase: Preclinical

Molecular Formula: C22H25NO8

Molecular Weight: 431.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(COC(=O)c2ccc([N+](=O)[O-])cc2)CCC[C@@]2(C)[C@H]1[C@H](O)C=C1C(=O)OC[C@@]12O

Standard InChI:  InChI=1S/C22H25NO8/c1-20(11-30-18(25)13-4-6-14(7-5-13)23(28)29)8-3-9-21(2)17(20)16(24)10-15-19(26)31-12-22(15,21)27/h4-7,10,16-17,24,27H,3,8-9,11-12H2,1-2H3/t16-,17+,20-,21+,22-/m1/s1

Standard InChI Key:  SXOSXJVAEAFKDC-PNBTUHDLSA-N

Alternative Forms

1. Parent:

   

   ALA3580705

   6_,9_-Dihydroxy-14-p-nitrobenzoylcinnamolide

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 431.44

Molecular Weight (Monoisotopic): 431.1580

AlogP: 2.15

#Rotatable Bonds: 4

Polar Surface Area: 136.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.74

CX Basic pKa:

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: 1.83

References

1. Fang W, Lin X, Zhou X, Wan J, Lu X, Yang B, Ai W, Lin J, Zhang T, Tu Z, Liu Y.  (2014)  Cytotoxic and antiviral nitrobenzoyl sesquiterpenoids from the marine-derived fungus Aspergillus ochraceus Jcma1F17,  5  (6): [10.1039/C3MD00371J]

2. Tan Y, Yang B, Lin X, Luo X, Pang X, Tang L, Liu Y, Li X, Zhou X..  (2018)  Nitrobenzoyl Sesquiterpenoids with Cytotoxic Activities from a Marine-Derived Aspergillus ochraceus Fungus.,  81  (1): [PMID:29297688] [10.1021/acs.jnatprod.7b00698]

Source

Source(1):

• Scientific Literature