(2S,2'S)-N,N'-(3-Methoxy-6-((Z)-3,4,5-trimethoxystyryl)-1,2-phenylene)bis(2-amino-3-hydroxypropanamide) dihydrochloride

ID: ALA3765640

Chembl Id: CHEMBL3765640

PubChem CID: 127025065

Max Phase: Preclinical

Molecular Formula: C24H34Cl2N4O8

Molecular Weight: 504.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C\c2cc(OC)c(OC)c(OC)c2)c(NC(=O)[C@@H](N)CO)c1NC(=O)[C@@H](N)CO.Cl.Cl

Standard InChI:  InChI=1S/C24H32N4O8.2ClH/c1-33-17-8-7-14(6-5-13-9-18(34-2)22(36-4)19(10-13)35-3)20(27-23(31)15(25)11-29)21(17)28-24(32)16(26)12-30;;/h5-10,15-16,29-30H,11-12,25-26H2,1-4H3,(H,27,31)(H,28,32);2*1H/b6-5-;;/t15-,16-;;/m0../s1

Standard InChI Key:  OXBYAMBSWZTPCC-WXCMVKROSA-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: 504.54

Molecular Weight (Monoisotopic): 504.2220

AlogP: 0.41

#Rotatable Bonds: 12

Polar Surface Area: 187.62

Molecular Species: NEUTRAL

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.06

CX Basic pKa: 7.99

CX LogP: -0.65

CX LogD: -1.58

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: 0.18

References

1. 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