1,11-dichloro-12-(3,4-dihydroxy-6-hydroxymethyl-5-methoxytetrahydro-2H-2-pyranyl)-6-methyl-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione

ID: ALA3350558

Chembl Id: CHEMBL3350558

PubChem CID: 10415905

Max Phase: Preclinical

Molecular Formula: C28H23Cl2N3O7

Molecular Weight: 584.41

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@H](O)[C@@H](O)[C@H](n2c3c(Cl)cccc3c3c4c(c5c6cccc(Cl)c6[nH]c5c32)C(=O)N(C)C4=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C28H23Cl2N3O7/c1-32-26(37)17-15-10-5-3-7-12(29)19(10)31-20(15)22-16(18(17)27(32)38)11-6-4-8-13(30)21(11)33(22)28-24(36)23(35)25(39-2)14(9-34)40-28/h3-8,14,23-25,28,31,34-36H,9H2,1-2H3/t14-,23-,24-,25-,28-/m1/s1

Standard InChI Key:  IDJBSIHZPGRCAI-BJIUMZSASA-N

Associated Targets(Human)

CEM-SS (2428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TOP1 Tclin DNA topoisomerase I (7553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCA Tchem Protein kinase C alpha (5923 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKD3 Tchem Protein kinase C (PKC) (1010 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

P388 (20296 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus cereus (7522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16 (5829 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P388CPT5 (17 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptomyces chartreusis (24 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 584.41Molecular Weight (Monoisotopic): 583.0913AlogP: 3.59#Rotatable Bonds: 3
Polar Surface Area: 137.25Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: 1HBA (Lipinski): 10HBD (Lipinski): 4#RO5 Violations (Lipinski): 1
CX Acidic pKa: 11.86CX Basic pKa: CX LogP: 2.81CX LogD: 2.81
Aromatic Rings: 5Heavy Atoms: 40QED Weighted: 0.24Np Likeness Score: 0.68

References

1. Moreau P, Anizon F, Sancelme M, Prudhomme M, Bailly C, Carrasco C, Ollier M, Sevère D, Riou JF, Fabbro D, Meyer T, Aubertin AM..  (1998)  Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle.,  41  (10): [PMID:9572888] [10.1021/jm970843+]
2. Moreau P, Anizon F, Sancelme M, Prudhomme M, Bailly C, Carrasco C, Ollier M, Sevère D, Riou JF, Fabbro D, Meyer T, Aubertin AM..  (1998)  Syntheses and biological evaluation of indolocarbazoles, analogues of rebeccamycin, modified at the imide heterocycle.,  41  (10): [PMID:9572888] [10.1021/jm970843+]
3. Moreau P, Anizon F, Sancelme M, Prudhomme M, Sevère D, Riou JF, Goossens JF, Hénichart JP, Bailly C, Labourier E, Tazzi J, Fabbro D, Meyer T, Aubertin AM..  (1999)  Synthesis, mode of action, and biological activities of rebeccamycin bromo derivatives.,  42  (10): [PMID:10346933] [10.1021/jm980702n]
4. Anizon F, Belin L, Moreau P, Sancelme M, Voldoire A, Prudhomme M, Ollier M, Sevère D, Riou JF, Bailly C, Fabbro D, Meyer T..  (1997)  Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group.,  40  (21): [PMID:9341921] [10.1021/jm9702084]

Source