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

ID: ALA3086608

PubChem CID: 76313534

Max Phase: Preclinical

Molecular Formula: C34H52O4

Molecular Weight: 524.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCCOC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2

Standard InChI:  InChI=1S/C34H52O4/c1-9-10-19-38-28(37)34-17-15-29(2,3)20-23(34)22-11-12-26-31(6)21-24(35)27(36)30(4,5)25(31)13-14-33(26,8)32(22,7)16-18-34/h1,11,23-27,35-36H,10,12-21H2,2-8H3/t23-,24+,25-,26+,27-,31-,32+,33+,34-/m0/s1

Standard InChI Key:  ODBCWOLAUHFTGZ-LULZRBEKSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3086608

   but-3-ynyl (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: 524.79

Molecular Weight (Monoisotopic): 524.3866

AlogP: 6.69

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.63

CX Basic pKa: ┄

CX LogP: 6.18

CX LogD: 6.18

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.19

Np Likeness Score: 2.86

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