Candimine

ID: ALA1651762

Cas Number: 24585-19-1

PubChem CID: 441588

Max Phase: Preclinical

Molecular Formula: C18H19NO6

Molecular Weight: 345.35

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Candimine | Candimine|24585-19-1|CHEBI:70240|(2S,3S,9S,10S)-9-hydroxy-14-methoxy-4-methyl-11,16,18-trioxa-4-azapentacyclo[11.7.0.02,10.03,7.015,19]icosa-1(20),7,13,15(19)-tetraen-12-one|C08520|CHEMBL1651762|DTXSID90331597|Q27104986

Canonical SMILES:  COc1c2c(cc3c1C(=O)O[C@H]1[C@@H]3[C@H]3C(=C[C@@H]1O)CCN3C)OCO2

Standard InChI:  InChI=1S/C18H19NO6/c1-19-4-3-8-5-10(20)15-12(14(8)19)9-6-11-16(24-7-23-11)17(22-2)13(9)18(21)25-15/h5-6,10,12,14-15,20H,3-4,7H2,1-2H3/t10-,12-,14+,15+/m0/s1

Standard InChI Key:  OLGJGNBIBXKMJN-OBCWZRDOSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.4772   -2.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754   -0.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1852   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1841   -1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6137   -1.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8978   -0.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -1.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8921   -2.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3154   -3.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -2.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5951   -3.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8833   -3.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2660   -3.7312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5962   -4.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4176   -4.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679   -1.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7692   -1.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -0.8676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5028   -1.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9854   -2.1984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4736    0.1037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    0.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8978    0.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665   -3.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0066   -2.6088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3178   -1.5338    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0289   -1.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  4  8  1  0
  7  5  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 16 17  2  0
  5  6  1  0
  7  8  1  0
  2 17  1  0
  3  4  1  0
 16  1  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  1  4  2  0
  2 21  1  0
  7 10  1  0
 21 22  1  0
  8 12  1  0
  6 23  2  0
 11  9  2  0
 13 24  1  0
  9 10  1  0
 12 25  1  6
 11 12  1  0
  8 26  1  1
  7 27  1  1
  3  2  2  0
 10 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1651762

   CANDIMINE

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: 345.35

Molecular Weight (Monoisotopic): 345.1212

AlogP: 1.05

#Rotatable Bonds: 1

Polar Surface Area: 77.46

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.76

CX Basic pKa: 7.39

CX LogP: 0.58

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: 2.46

References

1. Giordani RB, Vieira Pde B, Weizenmann M, Rosemberg DB, Souza AP, Bonorino C, De Carli GA, Bogo MR, Zuanazzi JA, Tasca T..  (2010)  Candimine-induced cell death of the amitochondriate parasite Trichomonas vaginalis.,  73  (12): [PMID:21105684] [10.1021/np100449g]

2. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature