Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-allylamino-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl ester

ID: ALA109480

Chembl Id: CHEMBL109480

Max Phase: Phase

Molecular Formula: C31H43N3O8

Molecular Weight: 585.70

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 17aag | Tanespimycin | 17-AAG | BMS-722782 | CNF-1010 | CNF1010 | KOS-953 | NSC-330507

Canonical SMILES:  C=CCNC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O

Standard InChI:  InChI=1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1

Standard InChI Key:  AYUNIORJHRXIBJ-TXHRRWQRSA-N

Alternative Forms

1. Parent:

   

   ALA109480

   TANESPIMYCIN

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 585.70

Molecular Weight (Monoisotopic): 585.3050

AlogP: 2.54

#Rotatable Bonds: 6

Polar Surface Area: 166.28

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.78

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.57

Aromatic Rings: ┄

Heavy Atoms: 42

QED Weighted: 0.27

Np Likeness Score: 2.38

References

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Source

Source(8):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• PubChem BioAssays
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• Gene Expression Atlas Compounds
• SARS-CoV-2 Screening Data 2020-21
• Fraunhofer HDAC6