ID: ALA451147

Max Phase: Preclinical

Molecular Formula: C31H33N3O8

Molecular Weight: 575.62

Molecule Type: Small molecule

Representations

Synonyms (1): Renieramycin M
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(OC)C2=O

Standard InChI:  InChI=1S/C31H33N3O8/c1-8-13(2)31(39)42-12-21-22-16(25(35)14(3)29(40-6)27(22)37)10-19-24-23-17(26(36)15(4)30(41-7)28(23)38)9-18(33(24)5)20(11-32)34(19)21/h8,18-21,24H,9-10,12H2,1-7H3/b13-8-/t18-,19-,20-,21-,24-/m0/s1

Standard InChI Key:  QOGBZZDZYZICFV-NZDGDHNMSA-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: 575.62

Molecular Weight (Monoisotopic): 575.2268

AlogP: 1.65

#Rotatable Bonds: 5

Polar Surface Area: 143.31

Molecular Species: NEUTRAL

HBA: 11

HBD: 0

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 2.24

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 0

Heavy Atoms: 42

QED Weighted: 0.27

Np Likeness Score: 1.88

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. Charupant K, Daikuhara N, Saito E, Amnuoypol S, Suwanborirux K, Owa T, Saito N..  (2009)  Chemistry of renieramycins. Part 8: synthesis and cytotoxicity evaluation of renieramycin M-jorunnamycin A analogues.,  17  (13): [PMID:19457672] [10.1016/j.bmc.2009.05.009]

4. Cheun-Arom T, Chanvorachote P, Sirimangkalakitti N, Chuanasa T, Saito N, Abe I, Suwanborirux K..  (2013)  Replacement of a quinone by a 5-O-acetylhydroquinone abolishes the accidental necrosis inducing effect while preserving the apoptosis-inducing effect of renieramycin M on lung cancer cells.,  76  (8): [PMID:23876104] [10.1021/np400277m]

5. 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]

6. 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