rhinacanthin-C

ID: ALA462962

Cas Number: 159278-74-7

PubChem CID: 6474554

Max Phase: Preclinical

Molecular Formula: C25H30O5

Molecular Weight: 410.51

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rhinacanthin-C | Rhinacanthin C|Rhinacanthin-C|T5Z47BVF6Z|CHEBI:66303|159278-74-7|2,6-Octadienoic acid, 2,6-dimethyl-, 3-(1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthalenyl)-2,2-dimethylpropyl ester, (2E,6E)-|(3-(1-Hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl) (2E,6E)-2,6-dimethylocta-2,6-dienoate|[3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl] (2E,6E)-2,6-dimethylocta-2,6-dienoate|2,6-Octadienoic acid, 2,6-dimethyl-, 3-(1,4-dihydro-3-hydroxy-1,4-dioxo-2-naphthalenyl)-2,2-dimethyShow More⌵

Canonical SMILES:  C/C=C(\C)CC/C=C(\C)C(=O)OCC(C)(C)CC1=C(O)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C25H30O5/c1-6-16(2)10-9-11-17(3)24(29)30-15-25(4,5)14-20-21(26)18-12-7-8-13-19(18)22(27)23(20)28/h6-8,11-13,28H,9-10,14-15H2,1-5H3/b16-6+,17-11+

Standard InChI Key:  HBWJZSWEQJLURT-QIGLBIQCSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
    1.0917    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3772   -0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5206    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6640   -0.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9496    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3785    0.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3431    1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3443    0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6294    0.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312    1.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159    1.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9124    0.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1933    0.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729    0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4763    1.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2001    1.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046    2.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910   -0.5240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7631    1.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    1.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3375    1.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    0.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573    0.3076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 17 16  2  0
 16 13  1  0
 17 18  1  0
  8  9  1  0
  3  5  2  0
  9 10  2  0
  1  3  1  0
  9 11  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  1  6  1  0
 22 23  2  0
 10 12  1  0
 19 24  2  0
  1  2  2  0
 21 25  1  0
  2  7  1  0
 25 26  1  0
 13 14  2  0
 26 27  1  0
  3  4  1  0
 26 28  1  0
 14 15  1  0
 26 29  1  0
 27  4  1  0
 15 18  2  0
 20 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA462962

   RHINACANTHIN C

Molecule Features

Natural Product: No

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: 410.51

Molecular Weight (Monoisotopic): 410.2093

AlogP: 5.53

#Rotatable Bonds: 8

Polar Surface Area: 80.67

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.70

CX Basic pKa: ┄

CX LogP: 5.44

CX LogD: 3.74

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.35

Np Likeness Score: 1.79

References

1. Sendl A, Chen JL, Jolad SD, Stoddart C, Rozhon E, Kernan M, Nanakorn W, Balick M..  (1996)  Two new naphthoquinones with antiviral activity from Rhinacanthus nasutus.,  59  (8): [PMID:8792629] [10.1021/np9601871]

2. Awai N, Kuwahara S, Kodama O, Santisopasri V.  (1995)  Synthesis of an Antifungal Naphthoquinone Isolated fromRhinacanthus nasutus(Acanthaceae),  59  (10): [10.1271/bbb.59.1999]

Source

Source(1):

• Scientific Literature