alpha-toxicarol

ID: ALA508992

Cas Number: 82-09-7

PubChem CID: 442826

Max Phase: Preclinical

Molecular Formula: C23H22O7

Molecular Weight: 410.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Alpha-Toxicarol | Toxicarol | alpha-Toxicarol|TOXICAROL|82-09-7|CHEBI:9643|(1S,14S)-11-hydroxy-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.03,12.04,9.015,20]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one|CHEMBL508992|SCHEMBL4742046|HY-N7563|LMPK12060027|AKOS032949012|CS-0133854|Q27108457

Canonical SMILES:  COc1cc2c(cc1OC)[C@@H]1C(=O)c3c(O)cc4c(c3O[C@@H]1CO2)C=CC(C)(C)O4

Standard InChI:  InChI=1S/C23H22O7/c1-23(2)6-5-11-15(30-23)8-13(24)20-21(25)19-12-7-16(26-3)17(27-4)9-14(12)28-10-18(19)29-22(11)20/h5-9,18-19,24H,10H2,1-4H3/t18-,19+/m1/s1

Standard InChI Key:  JLTNCZQNGBLBGO-MOPGFXCFSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    7.4710  -11.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1865  -12.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9008  -11.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8996  -11.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3337  -11.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3302  -11.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631  -11.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0479  -10.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7597  -11.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0416  -12.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0328  -13.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7413  -13.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4602  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4655  -12.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1822  -10.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1829   -9.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7653   -9.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7629  -10.7420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3263  -10.3179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3221  -12.7952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6123  -13.2126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5478   -9.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9638  -10.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1725  -13.6331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1669  -14.4588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7339  -14.4494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0151  -14.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1882  -13.2150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0
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 15 16  2  0
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  7  8  1  0
  3 18  2  0
  3  4  1  0
 17  1  2  0
  7 10  1  0
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 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
  8 12  1  0
  7 23  1  1
 11  9  1  0
  8 24  1  1
  9 10  1  0
  5 25  2  0
  1  2  1  0
 21 26  1  0
  2  4  2  0
 21 27  1  0
 11 12  2  0
 15 28  1  0
  3  6  1  0
 28 29  1  0
 12 13  1  0
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  4  5  1  0
 30 31  1  0
 13 14  2  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA508992

   TOXICAROL

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: 410.42

Molecular Weight (Monoisotopic): 410.1366

AlogP: 3.71

#Rotatable Bonds: 2

Polar Surface Area: 83.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.64

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.81

Np Likeness Score: 2.60

References

1. Jang DS, Park EJ, Kang YH, Hawthorne ME, Vigo JS, Graham JG, Cabieses F, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD..  (2003)  Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.,  66  (9): [PMID:14510590] [10.1021/np0302100]

2. Takashima J, Chiba N, Yoneda K, Ohsaki A..  (2002)  Derrisin, a new rotenoid from Derris malaccensis plain and anti-Helicobacter pylori activity of its related constituents.,  65  (4): [PMID:11975515] [10.1021/np010126p]

3. Belmain SR, Amoah BA, Nyirenda SP, Kamanula JF, Stevenson PC..  (2012)  Highly variable insect control efficacy of Tephrosia vogelii chemotypes.,  60  (40): [PMID:22970736] [10.1021/jf3032217]

4. Muharini R, Díaz A, Ebrahim W, Mándi A, Kurtán T, Rehberg N, Kalscheuer R, Hartmann R, Orfali RS, Lin W, Liu Z, Proksch P..  (2017)  Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa.,  80  (1): [PMID:28075580] [10.1021/acs.jnatprod.6b00809]

Source

Source(1):

• Scientific Literature