(S)-2-amino-3-hydroxy-N-(3-methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-yl)propanamide hydrochloride

ID: ALA3087397

Chembl Id: CHEMBL3087397

PubChem CID: 72735233

Max Phase: Preclinical

Molecular Formula: C24H31ClN2O6

Molecular Weight: 442.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1NC(=O)[C@@H](N)CO)CCCC=C2c1cc(OC)c(OC)c(OC)c1.Cl

Standard InChI:  InChI=1S/C24H30N2O6.ClH/c1-29-19-10-9-16-15(14-11-20(30-2)23(32-4)21(12-14)31-3)7-5-6-8-17(16)22(19)26-24(28)18(25)13-27;/h7,9-12,18,27H,5-6,8,13,25H2,1-4H3,(H,26,28);1H/t18-;/m0./s1

Standard InChI Key:  WOEGIMOPYQOHAC-FERBBOLQSA-N

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: 442.51

Molecular Weight (Monoisotopic): 442.2104

AlogP: 2.75

#Rotatable Bonds: 8

Polar Surface Area: 112.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.83

CX Basic pKa: 7.69

CX LogP: 2.23

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.58

Np Likeness Score: 0.46

References

1. Tanpure RP, George CS, Strecker TE, Devkota L, Tidmore JK, Lin CM, Herdman CA, Macdonough MT, Sriram M, Chaplin DJ, Trawick ML, Pinney KG..  (2013)  Synthesis of structurally diverse benzosuberene analogues and their biological evaluation as anti-cancer agents.,  21  (24): [PMID:24183586] [10.1016/j.bmc.2013.08.035]

2. Devkota L, Lin CM, Strecker TE, Wang Y, Tidmore JK, Chen Z, Guddneppanavar R, Jelinek CJ, Lopez R, Liu L, Hamel E, Mason RP, Chaplin DJ, Trawick ML, Pinney KG..  (2016)  Design, synthesis, and biological evaluation of water-soluble amino acid prodrug conjugates derived from combretastatin, dihydronaphthalene, and benzosuberene-based parent vascular disrupting agents.,  24  (5): [PMID:26852340] [10.1016/j.bmc.2016.01.007]

Source

Source(1):

• Scientific Literature