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: ALA3350560

Chembl Id: CHEMBL3350560

PubChem CID: 10481621

Max Phase: Preclinical

Molecular Formula: C28H25N3O7

Molecular Weight: 515.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1[C@H](O)[C@@H](O)[C@H](n2c3ccccc3c3c4c(c5c6ccccc6[nH]c5c32)C(=O)N(C)C4=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C28H25N3O7/c1-30-26(35)19-17-12-7-3-5-9-14(12)29-21(17)22-18(20(19)27(30)36)13-8-4-6-10-15(13)31(22)28-24(34)23(33)25(37-2)16(11-32)38-28/h3-10,16,23-25,28-29,32-34H,11H2,1-2H3/t16-,23-,24-,25-,28-/m1/s1

Standard InChI Key:  DCJDTHHXEQWNBO-KWHOMZPESA-N

Alternative Forms

1. Parent:

   

   ALA3350560

   3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-13-methyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaene-12,14-dione

Molecule Features

Natural Product: Yes

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

Calculated Properties

Molecular Weight: 515.52

Molecular Weight (Monoisotopic): 515.1693

AlogP: 2.28

#Rotatable Bonds: 3

Polar Surface Area: 137.25

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 1.61

CX LogD: 1.61

Aromatic Rings: 5

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 0.88

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, 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]

3. 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]

4. Shaaban KA, Elshahawi SI, Wang X, Horn J, Kharel MK, Leggas M, Thorson JS..  (2015)  Cytotoxic Indolocarbazoles from Actinomadura melliaura ATCC 39691.,  78  (7): [PMID:26091285] [10.1021/acs.jnatprod.5b00429]

Source

Source(1):

• Scientific Literature