7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((2R,5S,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide

ID: ALA1732

Chembl Id: CHEMBL1732

Cas Number: 511-12-6

PubChem CID: 10531

Max Phase: Approved

First Approval: 1946

Molecular Formula: C33H37N5O5

Molecular Weight: 583.69

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 9,10-dihydroergotamine | Dihydroergotamine | Neomigran | MAP-0004 | MAP0004 | dihydroergotamine|9,10-Dihydroergotamine|511-12-6|Levadex|Dehydroergotamine|Dihidroergotamina|Dihydroergotaminum|Neomigran|Diidroergotamina|Dihydroergotaminum [INN-Latin]|Dihidroergotamina [INN-Spanish]|MAP0004|Ergotamine, 9,10-dihydro-|MAP-0004|EINECS 208-123-3|UNII-436O5HM03C|BRN 5720196|CHEBI:4562|DTXSID6045614|436O5HM03C|Dihydroergotamine (INN)|Dihydroergotamine [INN]|MAP 0004|CHEMBL1732|DTXCID4025614|5'-Benzyl-12'Show More⌵

Synonyms from Alternative Forms(11): Dihydroergotamine mesilate | Dihydroergotamine methanesulfonate | Dihydroergotamine mesylate | Migranal | DHE-45 | NSC-759848 | D.h.e. 45 | Diergo | Dihydergot | Tonopan | Trudhesa

Canonical SMILES:  CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]21

Standard InChI:  InChI=1S/C33H37N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1

Standard InChI Key:  LUZRJRNZXALNLM-JGRZULCMSA-N

Alternative Forms

1. Parent:

   

   ALA1732

   DIHYDROERGOTAMINE

2. Alternative Forms:

   

   ALA1732

   Dihydro Ergotamine Mesylate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: Yes

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 583.69

Molecular Weight (Monoisotopic): 583.2795

AlogP: 2.08

#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: 8.39

CX LogP: 2.71

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.43

Np Likeness Score: 0.83

References

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24. Unpublished dataset, 

25. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

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Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• DrugMatrix
• TP-search Transporter Database
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6