Dihydroergotamine

Details

• Internal ID: 2151ffb6-0a00-4a1d-8646-b7d05dcfef08
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines > Ergotamines, dihydroergotamines, and derivatives
• IUPAC Name: (6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 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
• InChI Key: LUZRJRNZXALNLM-JGRZULCMSA-N
• Popularity: 2,001 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₇N₅O₅
• Molecular Weight: 583.70 g/mol
• Exact Mass: 583.27946930 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 9,10-Dihydroergotamine
• 511-12-6
• Dehydroergotamine
• Dihidroergotamina
• Dihydroergotaminum
• Neomigran
• Levadex
• 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'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
• 9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
• NCGC00017400-05
• Diidroergotamina [DCIT]
• (10alphaH)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
• Ergotaman-3',6',18-trione, 9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'alpha,10alpha)-
• Dihydroergotaminum (INN-Latin)
• Dihidroergotamina (INN-Spanish)
• DIHYDROERGOTAMINE (MART.)
• DIHYDROERGOTAMINE [MART.]
• 9,10-dihydro-ergotamine
• DHE
• Neomigran (TN)
• (2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• (6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
• CAS-511-12-6
• Dihydroergotamine [INN:BAN]
• Dihydroergotamin
• NCGC00017400-10
• (2R,4R,7R)-N-((1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• (2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• Spectrum_001057
• Spectrum2_001188
• Spectrum3_000395
• Spectrum4_000958
• Spectrum5_000905
• Lopac0_000357
• SCHEMBL44931
• BSPBio_002209
• GTPL121
• KBioGR_001576
• KBioSS_001537
• BIDD:GT0120
• DIHYDROERGOTAMINE [MI]
• DivK1c_000592
• SPBio_001235
• DIHYDROERGOTAMINE [VANDF]
• KBio1_000592
• KBio2_001537
• KBio2_004105
• KBio2_006673
• KBio3_001429
• N02CA01
• LUZRJRNZXALNLM-JGRZULCMSA-N
• NINDS_000592
• DIHYDROERGOTAMINE [WHO-DD]
• 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
• Tox21_110821
• BDBM50295557
• Tox21_110821_1
• CCG-204452
• DB00320
• SDCCGSBI-0050345.P005
• IDI1_000592
• NCGC00017400-06
• NCGC00017400-07
• NCGC00017400-08
• SBI-0050345.P004
• C07798
• D07837
• AB00053458_03
• EN300-26508628
• Q421336
• BRD-K72166146-066-02-1
• BRD-K72166146-066-03-9
• CODERGOCRINE MESILATE IMPURITY D [EP IMPURITY]
• (10alpha)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
• (2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),9,12(16),13-tetraene-4-carboxamide
• (5'alpha,10alpha)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotaman-3',6',18-trione
• (5alpha,5'beta,10alpha)-5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
• (6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
• (6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 2GM
• 7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (5-benzyl-10b-hydroxy-2-methyl-3,6-dioxo-octahydro-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-amide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7081	70.81%
Caco-2	-	0.8370	83.70%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Lysosomes	0.3335	33.35%
OATP2B1 inhibitior	+	0.5651	56.51%
OATP1B1 inhibitior	-	0.7121	71.21%
OATP1B3 inhibitior	+	0.8982	89.82%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9578	95.78%
P-glycoprotein inhibitior	+	0.9109	91.09%
P-glycoprotein substrate	+	0.8037	80.37%
CYP3A4 substrate	+	0.7981	79.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7174	71.74%
CYP3A4 inhibition	+	0.7120	71.20%
CYP2C9 inhibition	+	0.8950	89.50%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.8931	89.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.6796	67.96%
CYP inhibitory promiscuity	-	0.5910	59.10%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6097	60.97%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9567	95.67%
Skin irritation	-	0.7733	77.33%
Skin corrosion	-	0.9395	93.95%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7934	79.34%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	-	0.9679	96.79%
skin sensitisation	-	0.8919	89.19%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8027	80.27%
Acute Oral Toxicity (c)	III	0.6054	60.54%
Estrogen receptor binding	+	0.8365	83.65%
Androgen receptor binding	+	0.8695	86.95%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7756	77.56%
Aromatase binding	+	0.6449	64.49%
PPAR gamma	+	0.8179	81.79%
Honey bee toxicity	-	0.7859	78.59%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9516	95.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.75%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.13%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	95.33%	95.89%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.99%	97.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.79%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.03%	93.03%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.67%	94.45%
CHEMBL217	P14416	Dopamine D2 receptor	92.15%	95.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.92%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.72%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.63%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.73%	97.09%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	89.60%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.57%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.57%	89.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	86.14%	96.25%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.93%	85.83%
CHEMBL1951	P21397	Monoamine oxidase A	85.36%	91.49%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.08%	92.67%
CHEMBL2327	P21452	Neurokinin 2 receptor	83.31%	98.89%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.09%	88.56%
CHEMBL1902	P62942	FK506-binding protein 1A	82.95%	97.05%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.63%	82.69%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	82.51%	95.00%
CHEMBL238	Q01959	Dopamine transporter	81.40%	95.88%
CHEMBL340	P08684	Cytochrome P450 3A4	81.21%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.80%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10531
• LOTUS: LTS0083989
• wikiData: Q421336