ID: ALA1743263

Max Phase: Unknown

Molecular Formula: C32H43N5O5

Molecular Weight: 577.73

Molecule Type: Small molecule

Representations

Synonyms (1): Alpha-Dihydroergocriptine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(C)C[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C[C@@H]4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12

Standard InChI:  InChI=1S/C32H43N5O5/c1-17(2)12-25-29(39)36-11-7-10-26(36)32(41)37(25)30(40)31(42-32,18(3)4)34-28(38)20-13-22-21-8-6-9-23-27(21)19(15-33-23)14-24(22)35(5)16-20/h6,8-9,15,17-18,20,22,24-26,33,41H,7,10-14,16H2,1-5H3,(H,34,38)/t20-,22-,24-,25+,26+,31-,32+/m1/s1

Standard InChI Key:  PBUNVLRHZGSROC-VTIMJTGVSA-N

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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 577.73

Molecular Weight (Monoisotopic): 577.3264

AlogP: 2.52

#Rotatable Bonds: 5

Polar Surface Area: 118.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.69

CX Basic pKa: 8.39

CX LogP: 3.43

CX LogD: 2.55

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.50

Np Likeness Score: 1.17

References

1.  (2008)  Casarett and Doull's Toxicology The Basic Science of Poisons, 7th edition, 

2. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG..  (2002)  Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.,  303  (1): [PMID:12235267] [10.1124/jpet.102.037549]

3. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA..  (2002)  Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein.,  61  (1): [PMID:11961113] [10.1124/mol.61.5.964]

4. PubChem BioAssay data set, 

5. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database