Dichapetalin A

ID: ALA453157

Chembl Id: CHEMBL453157

PubChem CID: 5469156

Max Phase: Preclinical

Molecular Formula: C38H48O5

Molecular Weight: 584.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=C\[C@H]1C[C@@H]([C@@H]2CC[C@]34C[C@]23C=C[C@@H]2[C@@]3(C)CC=C5C[C@@H](c6ccccc6)OC[C@]5(C)[C@@H]3C[C@@H](O)[C@]24C)C(=O)O1)CO

Standard InChI:  InChI=1S/C38H48O5/c1-23(20-39)16-26-18-27(33(41)43-26)28-11-15-38-21-37(28,38)14-12-30-34(2)13-10-25-17-29(24-8-6-5-7-9-24)42-22-35(25,3)31(34)19-32(40)36(30,38)4/h5-10,12,14,16,26-32,39-40H,11,13,15,17-22H2,1-4H3/b23-16+/t26-,27-,28-,29-,30+,31+,32+,34+,35-,36-,37+,38+/m0/s1

Standard InChI Key:  LRJFCTOUXFAGON-NNLSLSRSSA-N

Alternative Forms

1. Parent:

   

   ALA453157

   DICHAPETALIN A

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: 584.80

Molecular Weight (Monoisotopic): 584.3502

AlogP: 6.72

#Rotatable Bonds: 4

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.30

Np Likeness Score: 3.29

References

1. Tuchinda P, Kornsakulkarn J, Pohmakotr M, Kongsaeree P, Prabpai S, Yoosook C, Kasisit J, Napaswad C, Sophasan S, Reutrakul V..  (2008)  Dichapetalin-type triterpenoids and lignans from the aerial parts of Phyllanthus acutissima.,  71  (4): [PMID:18271551] [10.1021/np7007347]

2. 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]

3. PubChem BioAssay data set, 

4. 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]

5. Ren Y,Kinghorn AD.  (2020)  Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones.,  63  (24.0): [PMID:33289552] [10.1021/acs.jmedchem.0c01449]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays