rhinacanthin-D

ID: ALA462963

Cas Number: 179461-46-2

PubChem CID: 465430

Max Phase: Preclinical

Molecular Formula: C23H20O7

Molecular Weight: 408.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rhinacanthin-D | Rhinacanthin D|Rhinacanthin-D|179461-46-2|CHEBI:66304|[3-(1-hydroxy-3,4-dioxonaphthalen-2-yl)-2,2-dimethylpropyl] 1,3-benzodioxole-5-carboxylate|3-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl 1,3-benzodioxole-5-carboxylate|CHEMBL462963|DTXSID60939226|Q27134847|[3-(3-hydroxy-1,4-dioxo-2-naphthyl)-2,2-dimethyl-propyl] 1,3-benzodioxole-5-carboxylate|3-(1-Hydroxy-3,4-dioxo-3,4-dihydronaphthalen-2-yl)-2,2-dimethylpropyl 2H-1,3-benzodioxole-5-carboxylate

Canonical SMILES:  CC(C)(COC(=O)c1ccc2c(c1)OCO2)CC1=C(O)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C23H20O7/c1-23(2,11-28-22(27)13-7-8-17-18(9-13)30-12-29-17)10-16-19(24)14-5-3-4-6-15(14)20(25)21(16)26/h3-9,26H,10-12H2,1-2H3

Standard InChI Key:  QWHPVCGUVBLEQF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   13.4189    0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7044    0.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4189   -0.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986    1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6974    0.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4122    0.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4104    2.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1258    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1292    0.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8484    0.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5688    0.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5654    1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8416    2.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8370    3.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8507   -0.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2786    2.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9943    1.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7042    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4057    2.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5876    1.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2844    0.5284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1333    1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1308    0.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8412    0.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8423    1.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5533    1.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5549    0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3406    0.2885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8247    0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3381    1.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 10 15  2  0
  7  4  1  0
 12 16  1  0
  8  9  1  0
 16 17  1  0
 17 18  1  0
  1  2  1  0
 17 19  1  0
  4  5  2  0
 17 20  1  0
 18  2  1  0
 23  1  1  0
 11 21  1  0
  5  6  1  0
  6  9  2  0
 22 23  2  0
  8 13  1  0
 23 24  1  0
 24 27  2  0
  9 10  1  0
 26 25  2  0
 25 22  1  0
 26 27  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  1  3  2  0
 13 14  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA462963

   Rhinacanthin D

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: 408.41

Molecular Weight (Monoisotopic): 408.1209

AlogP: 3.88

#Rotatable Bonds: 5

Polar Surface Area: 99.13

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.40

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 1.69

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.75

Np Likeness Score: 0.61

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]

Source

Source(1):

• Scientific Literature