9-O-demethyltrigonostemone

ID: ALA1078686

PubChem CID: 44557096

Max Phase: Preclinical

Molecular Formula: C19H20O4

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 9-O-Demethyltrigonostemone | 9-O-demethyltrigonostemone|CHEMBL1078686|1,1,7-Trimethyl-3,6-dimethoxy-9-hydroxyphenanthrene-2(1H)-one

Canonical SMILES:  COC1=Cc2c(cc(O)c3cc(C)c(OC)cc23)C(C)(C)C1=O

Standard InChI:  InChI=1S/C19H20O4/c1-10-6-13-11(7-16(10)22-4)12-8-17(23-5)18(21)19(2,3)14(12)9-15(13)20/h6-9,20H,1-5H3

Standard InChI Key:  LPMUQQPZLWUZEQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.0187    1.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0176    1.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7313    0.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7295    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4439    1.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4446    1.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8681    1.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1532    2.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8728    1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1578    0.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1639   -0.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8832   -0.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5982   -0.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5938    0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8880   -1.3376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1771   -1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3141   -0.5015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9976    1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3013    0.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    2.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3039    0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907    1.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1488    3.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  5  6  1  0
  6 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
  3  6  2  0
 12 15  1  0
  9  7  1  0
 15 16  1  0
  1  2  2  0
 13 17  2  0
  7  8  2  0
 14 18  1  0
  8  5  1  0
 14 19  1  0
  9 10  2  0
  1 20  1  0
  5  4  2  0
  2 21  1  0
  4  1  1  0
 21 22  1  0
  8 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1078686

   1,1,7-Trimethyl-3,6-dimethoxy-9-hydroxyphenanthrene-2(1H)-one

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: 312.37

Molecular Weight (Monoisotopic): 312.1362

AlogP: 3.71

#Rotatable Bonds: 2

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.03

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 1.84

References

1. Seephonkai P, Sangdee A, Bunchalee P, Pyne SG..  (2009)  Cytotoxic and antiplasmodial compounds from the roots of Strophioblachia fimbricalyx.,  72  (10): [PMID:19778068] [10.1021/np900352n]

Source

Source(1):

• Scientific Literature