Sodium (3R,5S,7R,8R,10S,13R,14S,17R)-3-Methoxy-10,13-dimethyl-17-((R)-5-oxo-5-(pyrrolidin-1-yl)pentan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl sulfate

ID: ALA4521043

PubChem CID: 155542354

Max Phase: Preclinical

Molecular Formula: C29H48NNaO6S

Molecular Weight: 539.78

Molecule Type: Unknown

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  CO[C@@H]1CC[C@@]2(C)[C@@H](C1)C[C@@H](OS(=O)(=O)[O-])[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(=O)N3CCCC3)CC[C@@H]12.[Na+]

Standard InChI:  InChI=1S/C29H49NO6S.Na/c1-19(7-10-26(31)30-15-5-6-16-30)22-8-9-23-27-24(12-14-29(22,23)3)28(2)13-11-21(35-4)17-20(28)18-25(27)36-37(32,33)34;/h19-25,27H,5-18H2,1-4H3,(H,32,33,34);/q;+1/p-1/t19-,20+,21-,22-,23+,24+,25-,27+,28+,29-;/m1./s1

Standard InChI Key:  UBORLHXTUNPGGO-RKDIHDQDSA-M

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
   21.2387   -7.5776    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   19.0719   -8.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2865   -7.9367    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.4965   -8.1449    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7454   -5.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7454   -6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4507   -7.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4507   -5.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1601   -5.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1566   -6.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8628   -7.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5769   -6.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8697   -5.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5766   -5.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5933   -4.2509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8750   -4.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3001   -4.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2913   -5.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0666   -5.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5522   -5.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0809   -4.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3419   -3.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1471   -3.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6914   -4.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8714   -4.2056    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7976   -3.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2948   -3.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1528   -5.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1486   -7.5198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8626   -6.2899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2865   -6.3064    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5684   -5.0682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0341   -7.1122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2874   -7.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4920   -3.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3269   -6.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9942   -8.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0345   -4.5446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.7500   -3.1581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8551   -5.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5599   -5.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1711   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8439   -4.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  1  0
  9 13  1  0
 10 11  1  0
 11 12  1  0
 12 14  1  0
 13 14  1  0
 13 16  1  0
 14 18  1  0
 17 15  1  0
 15 16  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 21 25  1  6
 22 26  1  6
 17 27  1  1
  9 28  1  1
 10 29  1  1
 13 30  1  6
 18 31  1  6
 14 32  1  1
  6 33  1  6
 12 34  1  6
 24 35  1  0
 34  3  1  0
 33 36  1  0
  3 37  1  0
 35 38  1  0
 35 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 38  1  0
M  CHG  2   1   1  37  -1
M  END

Associated Targets(Human)

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 539.78Molecular Weight (Monoisotopic): 539.3281AlogP: 5.50#Rotatable Bonds: 7
Polar Surface Area: 93.14Molecular Species: ACIDHBA: 5HBD: 1
#RO5 Violations: 2HBA (Lipinski): 7HBD (Lipinski): 1#RO5 Violations (Lipinski): 2
CX Acidic pKa: -1.22CX Basic pKa: CX LogP: 3.28CX LogD: 2.08
Aromatic Rings: Heavy Atoms: 37QED Weighted: 0.43Np Likeness Score: 1.47

References

1. Nakhi A, McDermott CM, Stoltz KL, John K, Hawkinson JE, Ambrose EA, Khoruts A, Sadowsky MJ, Dosa PI..  (2019)  7-Methylation of Chenodeoxycholic Acid Derivatives Yields a Substantial Increase in TGR5 Receptor Potency.,  62  (14): [PMID:31268316] [10.1021/acs.jmedchem.9b00770]

Source