6-carboxy-2-hydroxy-1-methyl-8-vinyl-9,10-dihydrophenanthrene

ID: ALA4582456

PubChem CID: 155561820

Max Phase: Preclinical

Molecular Formula: C18H16O3

Molecular Weight: 280.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=Cc1cc(C(=O)O)cc2c1CCc1c-2ccc(O)c1C

Standard InChI:  InChI=1S/C18H16O3/c1-3-11-8-12(18(20)21)9-16-14(11)5-4-13-10(2)17(19)7-6-15(13)16/h3,6-9,19H,1,4-5H2,2H3,(H,20,21)

Standard InChI Key:  QCLRWEPKGXPRKB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   16.6478   -4.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6467   -4.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3547   -5.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3529   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9386   -5.3919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3545   -6.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0616   -4.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0604   -4.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7666   -5.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4785   -4.9834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7689   -3.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4786   -4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1907   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1943   -2.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4799   -2.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7707   -2.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8967   -4.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8931   -4.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4801   -1.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1880   -1.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7725   -1.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  8  2  0
  7  4  2  0
  4  1  1  0
  2  5  1  0
  3  6  1  0
  7  8  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
 17 18  2  0
 15 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582456

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 280.32

Molecular Weight (Monoisotopic): 280.1099

AlogP: 3.81

#Rotatable Bonds: 2

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.12

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 1.70

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.88

Np Likeness Score: 1.15

References

1. Li X, Qiao Y, Wang X, Ma R, Li T, Zhang Y, Borris RP..  (2019)  Dihydrophenanthrenes from Juncus effusus as Inhibitors of OAT1 and OAT3.,  82  (4): [PMID:30892891] [10.1021/acs.jnatprod.8b00888]

Source

Source(1):

• Scientific Literature