N-[(5R,8S,9S,10R,13S,14S,17S)-17-((S)-1-Dimethylamino-ethyl)-10,13-dimethyl-4-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-benzamide

ID: ALA335133

Chembl Id: CHEMBL335133

Cas Number: 128255-16-3

PubChem CID: 3004425

Max Phase: Preclinical

Molecular Formula: C30H42N2O2

Molecular Weight: 462.68

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (+)-Axillaridine A | Axillaridine A|128255-16-3|(+)-Axillaridine A|CHEMBL335133|N-[(5R,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]benzamide|NSC652122|HY-N2912|BDBM50135147|AKOS040761391|FS-10284|CS-0023513|N-(20-(Dimethylamino)-4-oxopregn-2-en-3-yl)benzamide|Benzamide, N-[(5alpha,20S)-20-(dimethylamino)-4-oxopregn-2-en-3-yl]-|14-(1-dimethylaminoethyl)-2,15-dimethyl-6-oxo-5-phenylcarboxamido-(Show More⌵

Canonical SMILES:  C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C(=O)C(NC(=O)c5ccccc5)=CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C

Standard InChI:  InChI=1S/C30H42N2O2/c1-19(32(4)5)22-13-14-23-21-11-12-25-27(33)26(31-28(34)20-9-7-6-8-10-20)16-18-30(25,3)24(21)15-17-29(22,23)2/h6-10,16,19,21-25H,11-15,17-18H2,1-5H3,(H,31,34)/t19-,21-,22+,23-,24-,25-,29+,30+/m0/s1

Standard InChI Key:  ZMAOKPMWBVUQPK-IWDJEAQTSA-N

Alternative Forms

1. Parent:

   

   ALA335133

   Axillaridine A

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: 462.68

Molecular Weight (Monoisotopic): 462.3246

AlogP: 5.70

#Rotatable Bonds: 4

Polar Surface Area: 49.41

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.36

CX Basic pKa: 9.60

CX LogP: 5.47

CX LogD: 3.28

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.62

Np Likeness Score: 1.66

References

1. Zaheer-ul-Haq, Wellenzohn B, Tonmunphean S, Khalid A, Choudhary MI, Rode BM..  (2003)  3D-QSAR studies on natural acetylcholinesterase inhibitors of Sarcococca saligna by comparative molecular field analysis (CoMFA).,  13  (24): [PMID:14643329] [10.1016/j.bmcl.2003.09.034]

2. Zaheer-Ul-Haq ZU, Wellenzohn B, Liedl KR, Rode BM..  (2003)  Molecular docking studies of natural cholinesterase-inhibiting steroidal alkaloids from Sarcococca saligna.,  46  (23): [PMID:14584959] [10.1021/jm0309194]

3. Chang LC, Bhat KP, Pisha E, Kennelly EJ, Fong HH, Pezzuto JM, Kinghorn AD..  (1998)  Activity-guided isolation of steroidal alkaloid antiestrogen-binding site inhibitors from Pachysandra procumbens.,  61  (10): [PMID:9784163] [10.1021/np980162x]

Source

Source(1):

• Scientific Literature