3-Hydroxy-prop-1-yl(2alpha,3beta)2,3-dihydroxy-olean-12-en-28-oate

ID: ALA3086602

PubChem CID: 76331622

Max Phase: Preclinical

Molecular Formula: C33H54O5

Molecular Weight: 530.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC[C@]2(C(=O)OCCCO)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C33H54O5/c1-28(2)13-15-33(27(37)38-18-8-17-34)16-14-31(6)21(22(33)19-28)9-10-25-30(5)20-23(35)26(36)29(3,4)24(30)11-12-32(25,31)7/h9,22-26,34-36H,8,10-20H2,1-7H3/t22-,23+,24-,25+,26-,30-,31+,32+,33-/m0/s1

Standard InChI Key:  ZWXRKXDTNZNWAV-RBNDYAJOSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3086602

   3-hydroxypropyl (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

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: 530.79

Molecular Weight (Monoisotopic): 530.3971

AlogP: 6.05

#Rotatable Bonds: 4

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.62

CX Basic pKa: ┄

CX LogP: 5.04

CX LogD: 5.04

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.23

Np Likeness Score: 3.08

References

1. Siewert B, Pianowski E, Csuk R..  (2013)  Esters and amides of maslinic acid trigger apoptosis in human tumor cells and alter their mode of action with respect to the substitution pattern at C-28.,  70  [PMID:24161703] [10.1016/j.ejmech.2013.10.016]

2. Schwarz S, Loesche A, Lucas SD, Sommerwerk S, Serbian I, Siewert B, Pianowski E, Csuk R..  (2015)  Converting maslinic acid into an effective inhibitor of acylcholinesterases.,  103  [PMID:26383128] [10.1016/j.ejmech.2015.09.007]

Source

Source(1):

• Scientific Literature