rel-(2aR,2a1S,2a2S,3S,3aS,4aS,7R,7aR)-3-(benzo[d][1,3]dioxol-5-ylmethyl)-2a1,2a2,3,3a,4,4a,7,7a-octahydro-2aH-cyclobuta[bc]acenaphthylene-7-carboxylic acid

ID: ALA1821986

PubChem CID: 54671629

Max Phase: Preclinical

Molecular Formula: C22H22O4

Molecular Weight: 350.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Tsangibeilin B | tsangibeilin B, rel-|CHEMBL1821986|CHEBI:69314|Tsangibeilin B|BDBM50353024|1,3-benzodioxol-5-ylmethyl[?]carboxylic acid|Q27137655

Canonical SMILES:  O=C(O)[C@@H]1C=C[C@@H]2C[C@H]3[C@H](Cc4ccc5c(c4)OCO5)[C@H]4C=C[C@@H]1[C@@H]2[C@H]43

Standard InChI:  InChI=1S/C22H22O4/c23-22(24)15-3-2-12-9-17-16(14-5-4-13(15)20(12)21(14)17)7-11-1-6-18-19(8-11)26-10-25-18/h1-6,8,12-17,20-21H,7,9-10H2,(H,23,24)/t12-,13+,14-,15-,16-,17+,20-,21-/m1/s1

Standard InChI Key:  DXINWPCQBUXMER-STJBOKOVSA-N

Molfile:  

     RDKit          2D

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    8.0754   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9010    1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125    1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3333    0.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0542   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -0.7667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8417    0.0750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4833   -2.0542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -1.1375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7688   -1.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6140    2.3217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851    2.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1821986

   TSANGIBEILIN 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

Calculated Properties

Molecular Weight: 350.41

Molecular Weight (Monoisotopic): 350.1518

AlogP: 3.53

#Rotatable Bonds: 3

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.36

CX Basic pKa: ┄

CX LogP: 3.43

CX LogD: 0.52

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: 2.12

References

1. Huang YT, Chang HS, Wang GJ, Cheng MJ, Chen CH, Yang YJ, Chen IS..  (2011)  Anti-inflammatory endiandric acid analogues from the roots of Beilschmiedia tsangii.,  74  (9): [PMID:21846089] [10.1021/np200279r]

2. Talontsi FM, Lamshöft M, Bauer JO, Razakarivony AA, Andriamihaja B, Strohmann C, Spiteller M..  (2013)  Antibacterial and antiplasmodial constituents of Beilschmiedia cryptocaryoides.,  76  (1): [PMID:23320609] [10.1021/np300773x]

Source

Source(1):

• Scientific Literature