(2S,4aS,6aR,6bS,8aR,12aS,14aR,14bS)-methyl 11-cyano-2,4a,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-2-carboxylate

ID: ALA260926

Chembl Id: CHEMBL260926

PubChem CID: 44450342

Max Phase: Preclinical

Molecular Formula: C32H43NO4

Molecular Weight: 505.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@@]1(C)CC[C@]2(C)CC[C@]3(C)[C@H](C(=O)C=C4[C@@]5(C)C=C(C#N)C(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Standard InChI:  InChI=1S/C32H43NO4/c1-27(2)22-9-10-31(6)23(30(22,5)16-19(18-33)25(27)35)15-21(34)24-20-17-29(4,26(36)37-8)12-11-28(20,3)13-14-32(24,31)7/h15-16,20,22,24H,9-14,17H2,1-8H3/t20-,22-,24-,28+,29-,30-,31+,32+/m0/s1

Standard InChI Key:  OXWDHTUXPNXTIF-YVJUSAHHSA-N

Alternative Forms

1. Parent:

   

   ALA260926

   (2S,4aS,6aR,6bS,8aR,12aS,14aR,14bS)-methyl 11-cyano-2,4a,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-2-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: 505.70

Molecular Weight (Monoisotopic): 505.3192

AlogP: 6.38

#Rotatable Bonds: 1

Polar Surface Area: 84.23

Molecular Species: NEUTRAL

HBA: 5

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 6.55

CX LogD: 6.55

Aromatic Rings: 0

Heavy Atoms: 37

QED Weighted: 0.39

Np Likeness Score: 2.14

References

1. Chadalapaka G, Jutooru I, McAlees A, Stefanac T, Safe S..  (2008)  Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives.,  18  (8): [PMID:18359628] [10.1016/j.bmcl.2008.03.031]

2. Salomatina OV, Markov AV, Logashenko EB, Korchagina DV, Zenkova MA, Salakhutdinov NF, Vlassov VV, Tolstikov GA..  (2014)  Synthesis of novel 2-cyano substituted glycyrrhetinic acid derivatives as inhibitors of cancer cells growth and NO production in LPS-activated J-774 cells.,  22  (1): [PMID:24268542] [10.1016/j.bmc.2013.10.049]

3. Popadyuk II, Markov AV, Babich VO, Salomatina OV, Logashenko EB, Zenkova MA, Salakhutdinov NF..  (2017)  Novel derivatives of deoxycholic acid bearing aliphatic or cyclic diamine moieties at the C-3 position: Synthesis and evaluation of anti-proliferative activity.,  27  (16): [PMID:28688958] [10.1016/j.bmcl.2017.06.072]

4. Alper P,Salomatina OV,Salakhutdinov NF,Ulukaya E,Ari F.  (2021)  Soloxolone methyl, as a 18βH-glycyrrhetinic acid derivate, may result in endoplasmic reticulum stress to induce apoptosis in breast cancer cells.,  30  [PMID:33383441] [10.1016/j.bmc.2020.115963]

5. Perevoshchikova KA, Eshtukova-Shcheglova EA, Markov OV, Markov AV, Chernikov IV, Maslov MA, Zenkova MA..  (2022)  Symmetric lipophilic polyamines exhibiting antitumor activity.,  76  [PMID:36399911] [10.1016/j.bmc.2022.117089]

Source

Source(1):

• Scientific Literature