(2S,4aS,6aS,6bR,10S,12aS,14bR)-10-Hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-2-carboxylic acid

ID: ALA109757

PubChem CID: 5702287

Max Phase: Preclinical

Molecular Formula: C30H46O4

Molecular Weight: 470.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)C2CC[C@]3(C)C(C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O

Standard InChI:  InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21?,22-,23?,26+,27-,28-,29+,30+/m0/s1

Standard InChI Key:  MPDGHEJMBKOTSU-VOPRYAMFSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  1  0  0  0  0  0999 V2000
    3.4917   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042    1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -0.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9250   -1.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042    2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7792   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917    1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000   -3.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -0.0542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  7  1  0
  6  1  2  0
  7  6  1  0
  8  4  1  0
  9  1  1  0
 10  8  1  0
 11 12  1  0
 12  9  1  0
 13  9  1  0
 14  2  1  0
 11 15  1  1
 16  4  1  0
 17  3  1  0
 18 14  1  0
 19 25  1  0
 20  7  2  0
 21 13  1  0
 22 23  1  0
 23 13  1  0
 24 15  2  0
 25 16  1  0
  2 26  1  1
  4 27  1  1
  3 28  1  6
 29 15  1  0
 30 10  1  0
 31 10  1  0
 19 32  1  1
 11 33  1  6
 13 34  1  1
  9 35  1  1
 21 17  1  0
  5  2  1  0
 22 11  1  0
 18  8  1  0
 19 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA109757

   (18beta-Glycyrrhetinic acid)

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: 470.69

Molecular Weight (Monoisotopic): 470.3396

AlogP: 6.41

#Rotatable Bonds: 1

Polar Surface Area: 74.60

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.44

CX Basic pKa: ┄

CX LogP: 6.03

CX LogD: 3.18

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: 3.18

References

1. Vicker N, Su X, Lawrence H, Cruttenden A, Purohit A, Reed MJ, Potter BV..  (2004)  A novel 18 beta-glycyrrhetinic acid analogue as a potent and selective inhibitor of 11 beta-hydroxysteroid dehydrogenase 2.,  14  (12): [PMID:15149687] [10.1016/s0960-894x(04)00488-3]

2. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(2):

• Scientific Literature
• Fraunhofer HDAC6