(4alpha,6'alpha,7alpha,17alpha,20S,23R,24E)-2',3',5',6'-Tetrahydro-7,23,26-trihydroxy-6'-p-methoxyphenyl-13,30-cyclo-29-nordammara-2,11,24-trieno[4,3-c]pyran-21-oic acid gamma-lactone

ID: ALA502745

Chembl Id: CHEMBL502745

Cas Number: 876610-29-6

PubChem CID: 11585309

Max Phase: Preclinical

Molecular Formula: C39H50O6

Molecular Weight: 614.82

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dichapetalin K | Dichapetalin K|876610-29-6|14,18-Cyclocholesta-2,11,24-trieno(4,3-c)pyran-21-oic acid, 2',4,5',6'-tetrahydro-7,23,26-trihydroxy-6'-(4-methoxyphenyl)-4,8-dimethyl-, gamma-lactone, (4alpha,5alpha,6'alpha,7alpha,13alpha,17alpha,20S,23R,24E)-|CHEMBL502745

Canonical SMILES:  COc1ccc([C@@H]2CC3=CC[C@]4(C)[C@H]5C=C[C@]67C[C@]6(CC[C@H]7[C@@H]6C[C@H](/C=C(\C)CO)OC6=O)[C@]5(C)[C@H](O)C[C@H]4[C@@]3(C)CO2)cc1

Standard InChI:  InChI=1S/C39H50O6/c1-23(20-40)16-27-18-28(34(42)45-27)29-11-15-39-21-38(29,39)14-12-31-35(2)13-10-25-17-30(24-6-8-26(43-5)9-7-24)44-22-36(25,3)32(35)19-33(41)37(31,39)4/h6-10,12,14,16,27-33,40-41H,11,13,15,17-22H2,1-5H3/b23-16+/t27-,28-,29-,30-,31+,32+,33+,35+,36-,37-,38+,39+/m0/s1

Standard InChI Key:  TUJRURFPAUTAHC-OJWYEGDGSA-N

Alternative Forms

1. Parent:

   

   ALA502745

   DICHAPETALIN K

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: 614.82

Molecular Weight (Monoisotopic): 614.3607

AlogP: 6.73

#Rotatable Bonds: 5

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.67

CX LogD: 4.67

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.28

Np Likeness Score: 3.15

References

1. Fang L, Ito A, Chai HB, Mi Q, Jones WP, Madulid DR, Oliveros MB, Gao Q, Orjala J, Farnsworth NR, Soejarto DD, Cordell GA, Swanson SM, Pezzuto JM, Kinghorn AD..  (2006)  Cytotoxic constituents from the stem bark of Dichapetalum gelonioides collected in the Philippines.,  69  (3): [PMID:16562829] [10.1021/np058083q]

2. Jing SX, Luo SH, Li CH, Hua J, Wang YL, Niu XM, Li XN, Liu Y, Huang CS, Wang Y, Li SH..  (2014)  Biologically active dichapetalins from Dichapetalum gelonioides.,  77  (4): [PMID:24597894] [10.1021/np400971r]

Source

Source(1):

• Scientific Literature