Acetic acid (4aS,6S,6aS,7R,10bR)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydro-chrysen-6-yl ester

ID: ALA487005

Chembl Id: CHEMBL487005

Cas Number: 53527-28-9

PubChem CID: 21637538

Max Phase: Preclinical

Molecular Formula: C27H40O4

Molecular Weight: 428.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Scalaradial | Scalaradial|53527-28-9|CHEBI:67731|(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-6-yl acetate|CCRIS 1710|CHEMBL487005|BDBM50242184|12-(acetyloxy)-4,4,8-trimethylhomoandrost-16-ene-17,17a-dicarboxaldehyde|Q27136204|[(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate|1,2-Chrysenedicarboxaldehyde, 12-(acetyShow More⌵

Canonical SMILES:  CC(=O)O[C@H]1C[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]2(C)[C@@H]2CC=C(C=O)[C@H](C=O)[C@@]12C

Standard InChI:  InChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1

Standard InChI Key:  ADWFEADZGIHPDE-QGERINELSA-N

Alternative Forms

1. Parent:

   

   ALA487005

   SCALARADIAL

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: 428.61

Molecular Weight (Monoisotopic): 428.2927

AlogP: 5.54

#Rotatable Bonds: 3

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.34

CX LogD: 4.34

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: 3.09

References

1. Glaser KB, Sung M, Lock Y, Bauer J, Kubrak D, Kreft A.  (1994)  Analogs of the marine natural product scalaradial lacking the ,-unsaturated aldehyde: effects on human synovial fluid phospholipase A2 and macrophage lipid mediator production,  4  (15): [10.1016/S0960-894X(01)80388-7]

2. Gavagnin M, Mollo E, Docimo T, Guo YW, Cimino G..  (2004)  Scalarane metabolites of the nudibranch Glossodoris rufomarginata and Its dietary sponge from the South China Sea.,  67  (12): [PMID:15620263] [10.1021/np040087s]

3. De Rosa S, Puliti R, Crispino A, De Giulio A..  (1994)  A new scalarane sesterterpenoid from the marine sponge Cacospongia mollior.,  57  (2): [PMID:8176402] [10.1021/np50104a010]

4. Fontana A, Mollo E, Ortea J, Gavagnin M, Cimino G..  (2000)  Scalarane and homoscalarane compounds from the nudibranchs Glossodoris sedna and Glossodoris dalli: chemical and biological properties.,  63  (4): [PMID:10785432] [10.1021/np990506z]

5. Potts BC, Faulkner DJ, Jacobs RS..  (1992)  Phospholipase A2 inhibitors from marine organisms.,  55  (12): [PMID:1294693] [10.1021/np50090a001]

6. Starkus JG, Poerzgen P, Layugan K, Kawabata KG, Goto JI, Suzuki S, Myers G, Kelly M, Penner R, Fleig A, Horgen FD..  (2017)  Scalaradial Is a Potent Inhibitor of Transient Receptor Potential Melastatin 2 (TRPM2) Ion Channels.,  80  (10): [PMID:29019677] [10.1021/acs.jnatprod.7b00515]

7. Zhang H, Yu P, Lin H, Jin Z, Zhao S, Zhang Y, Xu Q, Jin H, Liu Z, Yang W, Zhang L..  (2021)  The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both In Vitro and In Vivo.,  64  (7.0): [PMID:33784097] [10.1021/acs.jmedchem.0c02129]

Source

Source(1):

• Scientific Literature