ID: ALA468488

Max Phase: Preclinical

Molecular Formula: C30H31N3O8

Molecular Weight: 561.59

Molecule Type: Small molecule

Representations

Synonyms (1): Renieramycin S
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[C@@H]([C@H](C#N)N13)N4C)C(=O)C(C)=C(OC)C5=O)C(=O)C(C)=C(O)C2=O

Standard InChI:  InChI=1S/C30H31N3O8/c1-7-12(2)30(39)41-11-20-21-15(24(34)13(3)26(36)27(21)37)9-18-23-22-16(25(35)14(4)29(40-6)28(22)38)8-17(32(23)5)19(10-31)33(18)20/h7,17-20,23,36H,8-9,11H2,1-6H3/b12-7-/t17-,18-,19-,20-,23-/m0/s1

Standard InChI Key:  FSDHSSHYVUZGFT-INUIFXHSSA-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: 561.59

Molecular Weight (Monoisotopic): 561.2111

AlogP: 1.57

#Rotatable Bonds: 4

Polar Surface Area: 154.31

Molecular Species: ACID

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.59

CX Basic pKa: 2.24

CX LogP: 2.57

CX LogD: 0.77

Aromatic Rings: 0

Heavy Atoms: 41

QED Weighted: 0.30

Np Likeness Score: 2.18

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. 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]

3. Yokoya M, Yamazaki-Nakai M, Nakai K, Sirimangkalakitti N, Chamni S, Suwanborirux K, Saito N..  (2023)  Transformation of Renieramycin M into Renieramycins T and S by Intramolecular Photoredox Reaction of 7-Methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-5,8-dione Derivatives.,  86  (1.0): [PMID:36631738] [10.1021/acs.jnatprod.2c00974]

Source

Source(1):

• Scientific Literature