ID: ALA449780

Max Phase: Preclinical

Molecular Formula: C36H53N3O10

Molecular Weight: 687.83

Molecule Type: Small molecule

Representations

Synonyms (1): Lajollamycin
Synonyms from Alternative Forms(1):

Canonical SMILES:  COC(CC(C)C(O)/C=C/C=C/CNC(=O)C(C)(C)C(O)/C(C)=C\C=C/C=C/C(C)=C(\C)[N+](=O)[O-])C1(O)C(C)C(=O)N(C)C12C(=O)OC2C

Standard InChI:  InChI=1S/C36H53N3O10/c1-22(26(5)39(46)47)17-13-11-14-18-23(2)30(41)34(7,8)32(43)37-20-16-12-15-19-28(40)24(3)21-29(48-10)36(45)25(4)31(42)38(9)35(36)27(6)49-33(35)44/h11-19,24-25,27-30,40-41,45H,20-21H2,1-10H3,(H,37,43)/b14-11-,16-12+,17-13+,19-15+,23-18-,26-22+

Standard InChI Key:  NSTDWVVCICGULY-RLJWGYAPSA-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: 687.83

Molecular Weight (Monoisotopic): 687.3731

AlogP: 3.16

#Rotatable Bonds: 16

Polar Surface Area: 188.77

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.38

CX Basic pKa:

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: 0

Heavy Atoms: 49

QED Weighted: 0.08

Np Likeness Score: 1.96

References

1. Manam RR, Teisan S, White DJ, Nicholson B, Grodberg J, Neuteboom ST, Lam KS, Mosca DA, Lloyd GK, Potts BC..  (2005)  Lajollamycin, a nitro-tetraene spiro-beta-lactone-gamma-lactam antibiotic from the marine actinomycete Streptomyces nodosus.,  68  (2): [PMID:15730252] [10.1021/np049725x]

2. Ko K, Lee SH, Kim SH, Kim EH, Oh KB, Shin J, Oh DC..  (2014)  Lajollamycins, nitro group-bearing spiro-β-lactone-γ-lactams obtained from a marine-derived Streptomyces sp.,  77  (9): [PMID:25211234] [10.1021/np500500t]

Source

Source(1):

• Scientific Literature