Nitidine

ID: ALA176008

Cas Number: 6872-57-7

PubChem CID: 4501

Product Number: N693349, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H18NO4+

Molecular Weight: 348.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): NSC-146397

Canonical SMILES:  COc1cc2c[n+](C)c3c4cc5c(cc4ccc3c2cc1OC)OCO5

Standard InChI:  InChI=1S/C21H18NO4/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22/h4-10H,11H2,1-3H3/q+1

Standard InChI Key:  KKMPSGJPCCJYRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    8.0295  -14.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7384  -14.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996  -14.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0295  -13.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4590  -14.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7384  -15.5616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996  -15.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839  -14.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7384  -13.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4590  -13.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1653  -14.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0295  -15.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4494  -15.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5839  -15.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8610  -14.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1653  -13.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9071  -14.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8610  -15.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569  -14.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9071  -13.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6773  -14.5671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569  -15.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1569  -13.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6773  -13.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1591  -13.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578  -15.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  3  1  0
  1  4  1  0
  2  5  1  0
  2  6  1  0
  3  7  2  0
  3  8  1  0
  4  9  2  0
  5 10  2  0
  5 11  1  0
  6 12  2  0
  6 13  1  0
  7 14  1  0
  8 15  2  0
 10 16  1  0
 11 17  2  0
 14 18  2  0
 15 19  1  0
 16 20  2  0
 17 21  1  0
 18 22  1  0
 19 23  1  0
 20 24  1  0
 21 25  1  0
 22 26  1  0
  7 12  1  0
  9 10  1  0
 15 18  1  0
 17 20  1  0
 24 25  1  0
M  CHG  1   6   1
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA176008

   Nitidine chloride

2. Parent:

   

   ALA176008

   Nitidine Chloride

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: 348.38

Molecular Weight (Monoisotopic): 348.1230

AlogP: 3.72

#Rotatable Bonds: 2

Polar Surface Area: 40.80

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -0.88

CX LogD: -0.88

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 0.87

References

1. Cheng P, Zhou J, Qing Z, Kang W, Liu S, Liu W, Xie H, Zeng J..  (2014)  Synthesis of 5-methyl phenanthridium derivatives: a new class of human DOPA decarboxylase inhibitors.,  24  (12): [PMID:24794108] [10.1016/j.bmcl.2014.04.047]

2. Swain SS, Pati S, Hussain T..  (2022)  Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation.,  232  [PMID:35168150] [10.1016/j.ejmech.2022.114173]

3. Mishra SK, Tripathi G, Kishore N, Singh RK, Singh A, Tiwari VK..  (2017)  Drug development against tuberculosis: Impact of alkaloids.,  137  [PMID:28628823] [10.1016/j.ejmech.2017.06.005]

Source

Source(1):

• Scientific Literature