Catharanthine base

ID: ALA4170050

PubChem CID: 72315

Max Phase: Preclinical

Molecular Formula: C21H24N2O2

Molecular Weight: 336.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1=CC2CN3CCc4c([nH]c5ccccc45)[C@@](C(=O)OC)(C2)C13

Standard InChI:  InChI=1S/C21H24N2O2/c1-3-14-10-13-11-21(20(24)25-2)18-16(8-9-23(12-13)19(14)21)15-6-4-5-7-17(15)22-18/h4-7,10,13,19,22H,3,8-9,11-12H2,1-2H3/t13?,19?,21-/m0/s1

Standard InChI Key:  CMKFQVZJOWHHDV-BPLLPPDFSA-N

Molfile:  

     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    2.7811  -22.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5652  -23.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1455  -23.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773  -22.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7931  -21.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116  -20.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9379  -23.6687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1555  -22.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9173  -22.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4294  -24.3384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2591  -24.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6531  -22.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7996  -23.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3825  -22.5356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9799  -23.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6191  -23.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0814  -24.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9046  -24.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2632  -23.7258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7987  -23.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469  -21.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582  -21.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7148  -21.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8372  -20.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165  -22.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  3  1  0
  3  7  1  0
  8  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
  9 12  1  0
 10 11  1  0
 11 13  1  0
 12 13  2  0
 13 16  1  0
 15 14  1  0
 14 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  9 21  1  1
 21 22  2  0
 21 23  1  0
 23 24  1  0
  2 25  1  0
  9 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4170050

   methyl (1R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate

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: 336.44

Molecular Weight (Monoisotopic): 336.1838

AlogP: 3.18

#Rotatable Bonds: 2

Polar Surface Area: 45.33

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.49

CX LogP: 3.19

CX LogD: 2.84

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: 1.47

References

1. Karhu E, Isojärvi J, Vuorela P, Hanski L, Fallarero A..  (2017)  Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy.,  80  (10): [PMID:29043803] [10.1021/acs.jnatprod.6b01052]

Source

Source(1):

• Scientific Literature