Ergocristine

Details

• Internal ID: 30a00f75-cc1a-4573-afe9-c623ce03e766
• Taxonomy: Alkaloids and derivatives > Ergoline and derivatives > Lysergic acids and derivatives > Ergopeptines > Ergotamines, dihydroergotamines, and derivatives
• IUPAC Name: (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• InChI: InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1
• InChI Key: HEFIYUQVAZFDEE-MKTPKCENSA-N
• Popularity: 399 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₃₉N₅O₅
• Molecular Weight: 609.70 g/mol
• Exact Mass: 609.29511936 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 511-08-0
• Ergocrystine
• 3E58HO2T0U
• CHEBI:4821
• DTXSID40891858
• 5'alpha-benzyl-12'-hydroxy-3',6',18-trioxo-2'-(propan-2-yl)ergotaman
• NSC-93743
• (5'alpha)-12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)ergotaman-3',6',18-trione
• (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 12'-hydroxy-2'-(1-methyl)-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'alpha)-
• ergocrystin
• ergokrystin
• (6aR,9R)-N-((1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide
• RefChem:137504
• DTXCID901031279
• 208-120-7
• N-(7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-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),2,9,12,14-pentaene-4-carboxamide
• NSC 93743
• MLS000069350
• SMR000058447
• Ergotaman-3',6',18-trione,12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'a)-
• Ergocristin
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'.alpha.)-
• UNII-3E58HO2T0U
• NSC93743
• EINECS 208-120-7
• BRN 0079046
• ERGOCRISTINE [MI]
• Lopac0_000514
• 4-25-00-00966 (Beilstein Handbook Reference)
• cid_31116
• ERGOCRISTINE [WHO-DD]
• SCHEMBL177877
• CHEMBL446315
• SCHEMBL30957132
• BDBM30702
• HSDB 8380
• HEFIYUQVAZFDEE-MKTPKCENSA-N
• C35H39N5O5
• MFCD00215848
• CCG-204605
• Ergotamine EP Impurity D (Free Base)
• FE22781
• Ergotaman-3',6',18-trione, 12'-hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)-, (5'-alpha)-
• E-140
• EU-0100514
• NS00007974
• C09164
• SR-01000075383
• ERGOTAMINE TARTRATE IMPURITY D [EP IMPURITY]
• Q5385810
• SR-01000075383-1
• 491D4F3D-1B0B-4E0A-8AB0-0C759A3E8E26
• 2-Hydroxy-2-[1-methylethyl]-5-[phenylmethyl]ergotaman-3,6,18-trione
• (5'a)-12'-Hydroxy-2'-(1-methylethyl)-5'-(phenylmethyl)ergotaman-3',6',18-trione
• 12'-Hydroxy-2'-(1-methyl-ethyl)-5'-(phenylmethyl)ergotaman-3'6'18-trione
• Dihydroergocristine Mesilate EP Impurity K; Ergotamine Tartrate EP Impurity D
• (6aR,9R)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
• (6AR,9R)-N-((2R,5S,10AS,10BS)-5-BENZYL-10B-HYDROXY-3,6-DIOXO-2-(PROPAN-2-YL)OCTAHYDRO-8H-(1,3)OXAZOLO(3,2-A)PYRROLO(2,1-C)PYRAZIN-2-YL)-7-METHYL-4,6,6A,7,8,9-HEXAHYDROINDOLO(4,3-FG)QUINOLINE-9-CARBOXAMIDE
• (6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• N-[(2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-isopropyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-methyl-[?]carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9592	95.92%
Caco-2	-	0.8272	82.72%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.9429	94.29%
Subcellular localzation	Nucleus	0.3901	39.01%
OATP2B1 inhibitior	+	0.7067	70.67%
OATP1B1 inhibitior	+	0.8238	82.38%
OATP1B3 inhibitior	+	0.9050	90.50%
MATE1 inhibitior	+	0.9967	99.67%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9848	98.48%
P-glycoprotein inhibitior	+	0.9512	95.12%
P-glycoprotein substrate	+	0.7031	70.31%
CYP3A4 substrate	+	0.7953	79.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	+	0.8487	84.87%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.7688	76.88%
CYP2D6 inhibition	-	0.9340	93.40%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.6411	64.11%
CYP inhibitory promiscuity	-	0.6627	66.27%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4969	49.69%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9500	95.00%
Skin irritation	-	0.7415	74.15%
Skin corrosion	-	0.9258	92.58%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7797	77.97%
Micronuclear	+	0.8700	87.00%
Hepatotoxicity	-	0.8477	84.77%
skin sensitisation	-	0.8673	86.73%
Respiratory toxicity	+	1.0000	100.00%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.7973	79.73%
Acute Oral Toxicity (c)	III	0.6051	60.51%
Estrogen receptor binding	+	0.8507	85.07%
Androgen receptor binding	+	0.8577	85.77%
Thyroid receptor binding	+	0.5631	56.31%
Glucocorticoid receptor binding	+	0.7885	78.85%
Aromatase binding	+	0.6939	69.39%
PPAR gamma	+	0.8598	85.98%
Honey bee toxicity	-	0.7594	75.94%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9882	98.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.93%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.67%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	96.43%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.30%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.28%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	95.97%	91.49%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	94.98%	97.64%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.95%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.38%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.44%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.63%	96.47%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.41%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.35%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.29%	89.00%
CHEMBL217	P14416	Dopamine D2 receptor	87.84%	95.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.78%	97.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.52%	90.08%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	87.06%	95.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.83%	94.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	86.71%	98.33%
CHEMBL3524	P56524	Histone deacetylase 4	86.59%	92.97%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.94%	92.67%
CHEMBL221	P23219	Cyclooxygenase-1	85.71%	90.17%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	84.91%	97.50%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.44%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.35%	86.33%
CHEMBL5747	Q92793	CREB-binding protein	81.74%	95.12%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.29%	91.43%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.81%	85.83%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.79%	99.18%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.25%	85.11%

Plants that contains it

• Calamagrostis arundinacea

Cross-Links

• PubChem: 31116
• LOTUS: LTS0198051
• wikiData: Q5385810