Human Metabolome Database: Showing metabocard for Apomorphine (HMDB0014852)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

enzymes (15) Show 15 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2020-02-26 21:40:27 UTC

HMDB ID

HMDB0014852

Secondary Accession Numbers

HMDB14852

Metabolite Identification

Common Name

Apomorphine

Description

Apomorphine, also known as uprima or apomorfin, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Apomorphine is a drug which is used for the acute, intermittent treatment of hypomobility, off episodes (end-of-dose wearing off and unpredictable on/off episodes) associated with advanced parkinson's disease. Apomorphine is a very strong basic compound (based on its pKa). Apomorphine is a potentially toxic compound. In particular, apomorphine attenuates the motor deficits induced by lesions in the ascending nigrostriatal dopaminergic pathway with the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in primates. Apomorphine has been shown to improve motor function in an animal model of Parkinson's disease. It is a powerful emetic and has been used for that effect in acute poisoning. In higher doses it is a highly effective emetic.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-10,11-Dihydroxyaporphine	ChEBI
(6AR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol	ChEBI
(R)-5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol	ChEBI
Apomorphin	ChEBI
R-(-)-Apomorphine	ChEBI
Uprima	Kegg
Apomorfin	HMDB
Apomorphine hydrochloride hemihydrate	HMDB
Apomorphinium chloride hemihydrate	HMDB
Apormorphine	HMDB
L-Apomorphine	HMDB
VR-040	HMDB
VR-400	HMDB
VR004	HMDB
Anhydrous apomorphine hydrochloride	HMDB
Apomorphin-teclapharm	HMDB
Britannia brand OF apomorphine hydrochloride	HMDB
Hemihydrate apomorphine hydrochloride	HMDB
Apomorphine hydrochloride, hemihydrate	HMDB
Britaject	HMDB
Chloride, apomorphine	HMDB
Hydrochloride, apomorphine	HMDB
Aguettant brand OF apomorphine hydrochloride	HMDB
Apokinon	HMDB
Apomorphine hydrochloride, anhydrous	HMDB
Hydrochloride, anhydrous apomorphine	HMDB
Teclapharm brand OF apomorphine hydrochloride	HMDB
Anhydrous, apomorphine hydrochloride	HMDB
Apomorphin teclapharm	HMDB
ApomorphinTeclapharm	HMDB
Apomorphine chloride	HMDB
Apomorphine hydrochloride	HMDB
Apomorphine hydrochloride anhydrous	HMDB
Hydrochloride anhydrous, apomorphine	HMDB
Hydrochloride, hemihydrate apomorphine	HMDB

Chemical Formula

C₁₇H₁₇NO₂

Average Molecular Weight

267.3224

Monoisotopic Molecular Weight

267.125928793

IUPAC Name

(9R)-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-3,4-diol

Traditional Name

apomorphine

CAS Registry Number

41372-20-7

SMILES

[H][C@]12CC3=C(C(O)=C(O)C=C3)C3=CC=CC(CCN1C)=C23

InChI Identifier

InChI=1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m1/s1

InChI Key

VMWNQDUVQKEIOC-CYBMUJFWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
2-naphthol
1-naphthol
Naphthalene
Quinoline
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:48538 )
isoquinolines (CHEBI:48538 )

Ontology

Disposition

Route of exposure:

Parenteral:

Intradermal

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.51 g/L	Not Available
LogP	3.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.87	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	13.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.99 m³·mol⁻¹	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gb9-0190000000-4a508d96ec3f544ad0a5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01vt-1119000000-110790047aaa5266ec7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014r-0090000000-29608efdadd8efd375a6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0090000000-052772c02bbf103a3ef5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00kr-0290000000-1e831a8078d43cfbdb51	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-49baaafc781fbd1a40ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-b2abd157ce4880c73d0b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-b747e9bb748f801c3f50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-0090000000-1a55345a571167f3fca6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0090000000-0329e43d2073db5426bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0190000000-4dc4f5ea615d9b0a78e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05xu-1950000000-298a2d8a85a241732677	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-8dcf24a32f1f7baba7c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-734acff31070eb2a5a84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-2190000000-5a6e0c712dad2d12eaa9	Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00714	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00714	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00714

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Apomorphine

METLIN ID

Not Available

PubChem Compound

6005

PDB ID

Not Available

ChEBI ID

48538

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Corsini GU, Del Zompo M, Gessa GL, Mangoni A: Therapeutic efficacy of apomorphine combined with an extracerebral inhibitor of dopamine receptors in Parkinson's disease. Lancet. 1979 May 5;1(8123):954-6. [PubMed:87620 ]
Cotzias GC, Papavasiliou PS, Fehling C, Kaufman B, Mena I: Similarities between neurologic effects of L-dopa and of apomorphine. N Engl J Med. 1970 Jan 1;282(1):31-3. [PubMed:4901383 ]
Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. [PubMed:9522772 ]
SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. [PubMed:14913646 ]
Matsumoto K, Yoshida M, Andersson KE, Hedlund P: Effects in vitro and in vivo by apomorphine in the rat corpus cavernosum. Br J Pharmacol. 2005 Sep;146(2):259-67. [PubMed:16025145 ]

Only showing the first 10 proteins. There are 15 proteins in total.

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Enzymes

Enzyme Details

1. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Enzyme Details

2. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Enzyme Details

3. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Enzyme Details

4. 5-hydroxytryptamine receptor 2B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2B
Uniprot ID:: P41595
Molecular weight:: 54297.4

References

Enzyme Details

5. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Enzyme Details

6. D(4) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Enzyme Details

7. 5-hydroxytryptamine receptor 1A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Enzyme Details

8. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Enzyme Details

9. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Enzyme Details

10. 5-hydroxytryptamine receptor 1D

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1D
Uniprot ID:: P28221
Molecular weight:: 41906.4

References

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for Apomorphine (HMDB0014852)

Structure for HMDB0014852 (Apomorphine)

Enzymes

References

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