Dihydroergocristine (CED0014077)

Record Information

Version

1.0

Creation Date

2016-05-22 05:40:24 UTC

Update Date

2026-08-22 11:45:22 UTC

Accession Number

CHEM018924

Identification

Common Name

Dihydroergocristine

Class

Small Molecule

Description

Dihydroergocristine is an organic compound with the chemical formula C35H41N5O5. Dihydroergocristine belongs to the lysergic acids and derivatives, a subclass of ergoline and derivatives within the organic compounds. With an average molecular weight of 611.74 g/mol, Dihydroergocristine is a heavy molecule. This compound is identified as a peripheral vasodilator and is found in healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this substance is oral. Dihydroergocristine interacts with 27 recorded protein targets. It acts as an agonist, antagonist, or modulator of 5-hydroxytryptamine receptor 1A (HTR1A), 5-hydroxytryptamine receptor 1B (HTR1B), 5-hydroxytryptamine receptor 1D (HTR1D), and 5-hydroxytryptamine receptor 3E (HTR3E), in addition to 23 other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9,10-Dihydroergocristine	ChEBI
DHEC	ChEBI
Diertine	MeSH
Enirant	MeSH
Dihydroergocristine monomesylate	MeSH
Ergodavur	MeSH
Mesylate, dihydroergocristine	MeSH
Monomesylate, dihydroergocristine	MeSH
Dihydroergocristine mesylate	MeSH
Desitin brand OF dihydroergocristine monomesylate	MeSH
Yamanouchi brand OF dihydroergocristine monomesylate	MeSH
Davur brand OF dihydroergocristine monomesylate	MeSH

Chemical Formula

C₃₅H₄₁N₅O₅

Average Molecular Mass

611.743 g/mol

Monoisotopic Mass

611.311 g/mol

CAS Registry Number

17479-19-5

IUPAC Name

(2R,4R,7R)-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]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene-4-carboximidic acid

Traditional Name

mesylate, dihydroergocristine

SMILES

[H][C@@]12CCCN1C(=O)[C@]([H])(CC1=CC=CC=C1)N1C(=O)[C@@](O[C@@]21O)(N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1)C(C)C

InChI Identifier

InChI=1S/C35H41N5O5/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/h4-7,9-12,18,20,23,25,27-29,36,44H,8,13-17,19H2,1-3H3,(H,37,41)/t23-,25-,27-,28+,29+,34-,35+/m1/s1

InChI Key

DEQITUUQPICUMR-HJPBWRTMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
Phenoxy compound
Phenol ether
Alkyl aryl ether
Hydroxamic acid
Carboxylic acid derivative
Ether
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:31317 )
hydroxamic acid (CHEBI:31317 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	3.58	ALOGPS
logP	2.16	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	168.8 m³·mol⁻¹	ChemAxon
Polarizability	67.82 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0012029000-899c5e486627044efded	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zi3-3192021000-04eb9b120e7966c07bc2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-7491000000-4fcbaae2466b9a69fcf4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-02t9-0029024000-d8d19045a17a52b30261	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3279061000-85b3b420535d42097fcc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0gl1-9730000000-b7853817d93fb99152c3	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
826.0	Log mg/kg	[460:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
291	Peripheral vasodilators	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Dihydroergocristine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	4.82665
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	8.95266
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	5.44945
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	1.94623
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	12.4559
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	1.47914
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	2.33548
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	2.10193
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	11.7552
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	8.09632
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	13.3122
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28564	Rattus norvegicus	Predicted (SEA)	1.63483
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	5.68299
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	2.88042
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	2.72472
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	0.700643
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	73.1004
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	3.81461
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	11.1324
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	27.1694
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	113.193
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	85.0114
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	88.0475
Click to view 3D structure	Beta-2 adrenergic receptor	P07550	Humans	Predicted (SEA)	21.2528
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	139.895