ID: ALA503821

Max Phase: Preclinical

Molecular Formula: C31H33N3O9

Molecular Weight: 591.62

Molecule Type: Small molecule

Representations

Synonyms (1): Renieramycin O
Synonyms from Alternative Forms(1):

Canonical SMILES:  C/C=C(/C)C(=O)OC[C@H]1C2=C(C[C@H]3[C@H]4C5=C(C(=O)C(C)=C(OC)C5=O)[C@H](O)[C@@H]([C@H](C#N)N13)N4C)C(=O)C(C)=C(OC)C2=O

Standard InChI:  InChI=1S/C31H33N3O9/c1-8-12(2)31(40)43-11-18-19-15(24(35)13(3)29(41-6)27(19)38)9-16-22-20-21(25(36)14(4)30(42-7)28(20)39)26(37)23(33(22)5)17(10-32)34(16)18/h8,16-18,22-23,26,37H,9,11H2,1-7H3/b12-8-/t16-,17-,18-,22-,23+,26-/m0/s1

Standard InChI Key:  GBUWZFVJCKIAMH-TVNZNNQYSA-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: 591.62

Molecular Weight (Monoisotopic): 591.2217

AlogP: 0.63

#Rotatable Bonds: 5

Polar Surface Area: 163.54

Molecular Species: NEUTRAL

HBA: 12

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.64

CX Basic pKa: 1.88

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 0

Heavy Atoms: 43

QED Weighted: 0.27

Np Likeness Score: 2.15

References

1. Amnuoypol S, Suwanborirux K, Pummangura S, Kubo A, Tanaka C, Saito N..  (2004)  Chemistry of renieramycins. Part 5. Structure elucidation of renieramycin-type derivatives O, Q, R, and S from thai marine sponge Xestospongia species pretreated with potassium cyanide.,  67  (6): [PMID:15217287] [10.1021/np030534o]

2. Suwanborirux K, Amnuoypol S, Plubrukarn A, Pummangura S, Kubo A, Tanaka C, Saito N..  (2003)  Chemistry of renieramycins. Part 3.(1) isolation and structure of stabilized renieramycin type derivatives possessing antitumor activity from Thai sponge Xestospongia species, pretreated with potassium cyanide.,  66  (11): [PMID:14640515] [10.1021/np030262p]

3. Fang Y, Li H, Ji B, Cheng K, Wu B, Li Z, Zheng C, Hua H, Li D..  (2021)  Renieramycin-type alkaloids from marine-derived organisms: Synthetic chemistry, biological activity and structural modification.,  210  [PMID:33333398] [10.1016/j.ejmech.2020.113092]

Source

Source(1):

• Scientific Literature