ID: ALA2048825

Max Phase: Preclinical

Molecular Formula: C32H41N9O10

Molecular Weight: 711.73

Molecule Type: Small molecule

Representations

Synonyms (1): Pacidamycin D
Synonyms from Alternative Forms(1):

Canonical SMILES:  C[C@H](N)C(=O)N(C)[C@@H](C)[C@H](NC(=O)[C@H](C)NC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O)C(=O)N/C=C1/C[C@@H](O)[C@H](n2ccc(=O)[nH]c2=O)O1

Standard InChI:  InChI=1S/C32H41N9O10/c1-15(33)28(46)40(4)17(3)25(27(45)35-14-19-12-23(42)29(51-19)41-10-9-24(43)38-32(41)50)39-26(44)16(2)36-31(49)37-22(30(47)48)11-18-13-34-21-8-6-5-7-20(18)21/h5-10,13-17,22-23,25,29,34,42H,11-12,33H2,1-4H3,(H,35,45)(H,39,44)(H,47,48)(H2,36,37,49)(H,38,43,50)/b19-14-/t15-,16-,17-,22-,23+,25-,29+/m0/s1

Standard InChI Key:  PBFVZISIBPPZNE-SYZWNRCCSA-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

Properties

Molecular Weight: 711.73

Molecular Weight (Monoisotopic): 711.2976

AlogP: -1.68

#Rotatable Bonds: 13

Polar Surface Area: 283.07

Molecular Species: ZWITTERION

HBA: 11

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.89

CX Basic pKa: 9.72

CX LogP: -4.98

CX LogD: -5.02

Aromatic Rings: 3

Heavy Atoms: 51

QED Weighted: 0.10

Np Likeness Score: -0.06

References

1. Okamoto K, Sakagami M, Feng F, Takahashi F, Uotani K, Togame H, Takemoto H, Ichikawa S, Matsuda A..  (2012)  Synthesis of pacidamycin analogues via an Ugi-multicomponent reaction.,  22  (14): [PMID:22677318] [10.1016/j.bmcl.2012.05.050]

2. Serpi M, Ferrari V, Pertusati F..  (2016)  Nucleoside Derived Antibiotics to Fight Microbial Drug Resistance: New Utilities for an Established Class of Drugs?,  59  (23): [PMID:27607900] [10.1021/acs.jmedchem.6b00325]

Source

Source(1):

• Scientific Literature