5-Bromo-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (10a-hydroxy-2,5-diisopropyl-6-oxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide (Bromocryptine)

ID: ALA311816

Chembl Id: CHEMBL311816

PubChem CID: 44312438

Max Phase: Preclinical

Molecular Formula: C31H40BrN5O4

Molecular Weight: 626.60

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bromocryptine | CHEMBL311816|BDBM50113315|5-Bromo-7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (10a-hydroxy-2,5-diisopropyl-6-oxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide (Bromocryptine)

Canonical SMILES:  CC(C)C1C(=O)N2CCCC2(O)C2OC(NC(=O)C3C=C4c5cccc6[nH]c(Br)c(c56)CC4N(C)C3)(C(C)C)CN12

Standard InChI:  InChI=1S/C31H40BrN5O4/c1-16(2)25-28(39)37-11-7-10-31(37,40)29-36(25)15-30(41-29,17(3)4)34-27(38)18-12-20-19-8-6-9-22-24(19)21(26(32)33-22)13-23(20)35(5)14-18/h6,8-9,12,16-18,23,25,29,33,40H,7,10-11,13-15H2,1-5H3,(H,34,38)

Standard InChI Key:  SXABZWSEWJTRJP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA311816

   BROMOCRYPTINE

Molecule Features

Natural Product: No

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: 626.60

Molecular Weight (Monoisotopic): 625.2264

AlogP: 3.28

#Rotatable Bonds: 4

Polar Surface Area: 101.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.52

CX Basic pKa: 6.69

CX LogP: 4.08

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.48

Np Likeness Score: 1.03

References

1. Carrigan CN, Bartlett RD, Esslinger CS, Cybulski KA, Tongcharoensirikul P, Bridges RJ, Thompson CM..  (2002)  Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport.,  45  (11): [PMID:12014964] [10.1021/jm010261z]

2. Carrigan CN, Patel SA, Cox HD, Bolstad ES, Gerdes JM, Smith WE, Bridges RJ, Thompson CM..  (2014)  The development of benzo- and naphtho-fused quinoline-2,4-dicarboxylic acids as vesicular glutamate transporter (VGLUT) inhibitors reveals a possible role for neuroactive steroids.,  24  (3): [PMID:24424130] [10.1016/j.bmcl.2013.12.086]

Source

Source(1):

• Scientific Literature