(1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.0^{1,10}.0^{4,9}]heptadecane-5-carboxylic acid

ID: ALA470998

Chembl Id: CHEMBL470998

PubChem CID: 44590334

Max Phase: Preclinical

Molecular Formula: C20H30O4

Molecular Weight: 334.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CC[C@@H]3[C@@](CC[C@H]4[C@@]3(C)CCC[C@@]4(C)C(=O)O)(CC(=O)O1)C2

Standard InChI:  InChI=1S/C20H30O4/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(21)24-17/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18+,19+,20-/m0/s1

Standard InChI Key:  OLJRAFPOAGIZKX-XGBBNYNSSA-N

Alternative Forms

1. Parent:

   

   ALA470998

   (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-15-oxo-14-oxatetracyclo[11.3.1.01,10.04,9]heptadecane-5-carboxylic acid

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: 334.46

Molecular Weight (Monoisotopic): 334.2144

AlogP: 4.17

#Rotatable Bonds: 1

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.53

CX Basic pKa: ┄

CX LogP: 3.73

CX LogD: 0.95

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: 2.66

References

1. Wu Y, Yang JH, Dai GF, Liu CJ, Tian GQ, Ma WY, Tao JC..  (2009)  Stereoselective synthesis of bioactive isosteviol derivatives as alpha-glucosidase inhibitors.,  17  (4): [PMID:19167896] [10.1016/j.bmc.2009.01.017]

2. Chang SF, Chou BH, Yang LM, Hsu FL, Lin WK, Ho Y, Lin SJ..  (2009)  Microbial transformation of isosteviol oxime and the inhibitory effects on NF-kappaB and AP-1 activation in LPS-stimulated macrophages.,  17  (17): [PMID:19648015] [10.1016/j.bmc.2009.07.029]

3. Ye N, Ding Y, Wild C, Shen Q, Zhou J..  (2014)  Small molecule inhibitors targeting activator protein 1 (AP-1).,  57  (16): [PMID:24831826] [10.1021/jm5004733]

Source

Source(1):

• Scientific Literature