(1S,2S,4S,5S,7R,8R,9S,11S,13R)-8,13-dihydroxy-1-methyl-7-(propan-2-yl)-3,6,10,16-tetraoxaheptacyclo[11.7.0.0^{2,4}.0^{2,9}.0^{5,7}.0^{9,11}.0^{14,18}]icos-14(18)-en-17-one

ID: ALA3358841

Chembl Id: CHEMBL3358841

Cas Number: 583028-68-6

PubChem CID: 10317383

Max Phase: Preclinical

Molecular Formula: C20H24O7

Molecular Weight: 376.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@]12O[C@H]1[C@@H]1O[C@]13[C@]1(O[C@H]1C[C@@]1(O)C4=C(CC[C@]31C)C(=O)OC4)[C@@H]2O

Standard InChI:  InChI=1S/C20H24O7/c1-8(2)18-12(26-18)13-20(27-13)16(3)5-4-9-10(7-24-14(9)21)17(16,23)6-11-19(20,25-11)15(18)22/h8,11-13,15,22-23H,4-7H2,1-3H3/t11-,12-,13-,15+,16-,17+,18-,19+,20+/m0/s1

Standard InChI Key:  OKRSVUYYCJPECG-LFGMFVMYSA-N

Alternative Forms

1. Parent:

   

   ALA3358841

   5alpha-Hydroxytriptolide

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: 376.41

Molecular Weight (Monoisotopic): 376.1522

AlogP: 0.22

#Rotatable Bonds: 1

Polar Surface Area: 104.35

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.07

CX Basic pKa:

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 0

Heavy Atoms: 27

QED Weighted: 0.50

Np Likeness Score: 3.40

References

1. Xu H, Chen Y, Tang H, Feng H, Li Y..  (2014)  Semisynthesis of triptolide analogues: effect of B-ring substituents on cytotoxic activities.,  24  (24): [PMID:25467158] [10.1016/j.bmcl.2014.10.069]

2. Hou W, Liu B, Xu H..  (2019)  Triptolide: Medicinal chemistry, chemical biology and clinical progress.,  176  [PMID:31121546] [10.1016/j.ejmech.2019.05.032]

Source

Source(1):

• Scientific Literature