SID856021

ID: ALA1385840

Chembl Id: CHEMBL1385840

Cas Number: 564-36-3

PubChem CID: 73453

Product Number: E113769

Max Phase: Preclinical

Molecular Formula: C31H39N5O5

Molecular Weight: 561.68

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ergocornine | Ergocornine|564-36-3|MLS000069342|SMR000058938|CHEBI:4820|7W36B25464|Ergotaman-3',6',18-trione, 12'-hydroxy-2',5'-bis(1-methylethyl)-, (5'-alpha)-|12'-hydroxy-2',5'alpha-bis(1-methylethyl)ergotaman-3',6',18-trione|12'-hydroxy-3',6',18-trioxo-2',5'alpha-di(propan-2-yl)ergotaman|EINECS 209-272-7|NSC 407316|BRN 0078784|NSC-407316|UNII-7W36B25464|ERGOCORNINE [MI]|regid856021|Opera_ID_1715|12'-Hydroxy-2',5'-alpha-bis(1-methylethyl)ergotaman-3',6',18-trione|Biomol-NT_000006|Ergocornine, Show More⌵

Canonical SMILES:  CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12

Standard InChI:  InChI=1S/C31H39N5O5/c1-16(2)26-28(38)35-11-7-10-24(35)31(40)36(26)29(39)30(41-31,17(3)4)33-27(37)19-12-21-20-8-6-9-22-25(20)18(14-32-22)13-23(21)34(5)15-19/h6,8-9,12,14,16-17,19,23-24,26,32,40H,7,10-11,13,15H2,1-5H3,(H,33,37)/t19-,23-,24+,26+,30-,31+/m1/s1

Standard InChI Key:  UJYGDMFEEDNVBF-OGGGUQDZSA-N

Alternative Forms

1. Parent:

   

   ALA1385840

   ERGOCORNINE

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: 561.68

Molecular Weight (Monoisotopic): 561.2951

AlogP: 2.04

#Rotatable Bonds: 4

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: 7.78

CX LogP: 2.95

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.53

Np Likeness Score: 1.43

References

1. PubChem BioAssay data set, 

2. Engel JC, Ang KK, Chen S, Arkin MR, McKerrow JH, Doyle PS..  (2010)  Image-based high-throughput drug screening targeting the intracellular stage of Trypanosoma cruzi, the agent of Chagas' disease.,  54  (8): [PMID:20547819] [10.1128/aac.01777-09]

3. PubChem BioAssay data set, 

4. Scott S. Auerbach, DrugMatrix¨ and ToxFX¨ Coordinator National Toxicology Program. DrugMatrix in vitro pharmacology data, 

5. 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]

6. 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]

7. Crider AM, Lu CK, Floss HG, Cassady JM, Clemens JA..  (1979)  Ergot alkaloids. Synthesis of nitrosourea derivatives of ergolines as potential anticancer agents.,  22  (1): [PMID:423180] [10.1021/jm00187a008]

8. Bach NJ, Kornfeld EC, Dorman DE..  (1977)  Synthesis and biological activity of 8-arylergolines.,  20  (8): [PMID:561190] [10.1021/jm00218a025]

9. Rusterholz DB, Barfknecht CF, Clemens JA..  (1976)  Ergoline congeners as potential inhibitors of prolactin release. 2.,  19  (1): [PMID:1246056] [10.1021/jm00223a016]

Source

Source(4):

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