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

ID: ALA4519013

PubChem CID: 155541607

Max Phase: Preclinical

Molecular Formula: C18H16O3

Molecular Weight: 280.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=Cc1c(C(=O)O)ccc2c1CCc1c-2ccc(O)c1C

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

Standard InChI Key:  TXFNKGVIAHRGBI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    8.8515   -4.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8503   -5.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5584   -5.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5566   -3.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1423   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5582   -6.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2652   -4.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2641   -5.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9703   -5.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6821   -5.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9726   -3.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6823   -4.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3944   -3.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3980   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6835   -2.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9744   -2.9563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1067   -2.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8134   -2.9634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1088   -1.7359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1003   -4.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0968   -5.0106    0.0000 C   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
 14 17  1  0
 17 18  1  0
 17 19  2  0
 13 20  1  0
 20 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519013

   ---

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: 3.81

CX Basic pKa: ┄

CX LogP: 4.79

CX LogD: 1.53

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.88

Np Likeness Score: 0.98

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]

2. Takeda, Michio M, Babu, Ellappan E, Narikawa, Shinichi S and Endou, Hitoshi H.  2002-03-08  Interaction of human organic anion transporters with various cephalosporin antibiotics.  [PMID:11909604]

Source

Source(1):

• Scientific Literature