Livestock Metabolome Database: Showing metabocard for Hydroxyurea (LMDB00648)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:54:36 UTC

Update Date

2016-07-20 21:02:24 UTC

Lmdb

LMDB00648

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydroxyurea

Description

Hydroxyurea, also known as hydroxycarbamide or hydrea, belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2. Hydroxyurea is a drug which is used for management of melanoma, resistant chronic myelocytic leukemia, and recurrent, metastatic, or inoperable carcinoma of the ovary and sickle-cell anemia. Hydroxyurea is an extremely weak basic (essentially neutral) compound (based on its pKa). Due to its chemical properties hydroxyurea was explored as an antisickling agent in the treatment of hematological conditions. Hydroxyurea is a potentially toxic compound. It has been found to be superior to anagrelide for the control of ET.Sickle-cell disease (increases production of fetal hemoglobin that then interferes with the hemoglobin polymerisation as well as by reducing white blood cells that contribute to the general inflammatory state in sickle cell patients.)Second line treatment for psoriasis (slows down the rapid division of skin cells)PsoriasisSystemic mastocytosisChronic myelogenous leukemia (largely replaced by imatinib, but still in use for its cost-effectiveness)Reported side-effects are: neurological reactions (e.g., headache, dizziness, drowsiness, disorientation, hallucinations, and convulsions), nausea, vomiting, diarrhea, constipation, mucositis, anorexia, stomatitis, bone marrow toxicity (dose-limiting toxicity; may take 7–21 days to recover after the drug has been discontinued), megaloblastic anemia, thrombocytopenia, bleeding, hemorrhage, gastrointestinal ulceration and perforation, immunosuppression, leukopenia, alopecia (hair loss), skin rashes (e.g., maculopapular rash), erythema, pruritus, vesication or irritation of the skin and mucous membranes, pulmonary edema, abnormal liver enzymes, creatinine and blood urea nitrogen. It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system. Hydroxyurea has many pharmacological applications under the Medical Subject Headings classification system:Antineoplastic Agents – Substances that inhibit or prevent the proliferation of neoplasms.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Carbamohydroxamic acid	ChEBI
Carbamohydroximic acid	ChEBI
Carbamoyl oxime	ChEBI
Carbamyl hydroxamate	ChEBI
Hidroxicarbamida	ChEBI
Hydrea	ChEBI
Hydroxycarbamid	ChEBI
Hydroxycarbamide	ChEBI
Hydroxycarbamidum	ChEBI
Hydroxyharnstoff	ChEBI
N-Carbamoylhydroxylamine	ChEBI
N-HYDROXYUREA	ChEBI
Oxyurea	ChEBI
Droxia	Kegg
Carbamohydroxamate	Generator
Carbamohydroximate	Generator
Carbamyl hydroxamic acid	Generator
Carbamohydroxyamic acid	HMDB
HU	HMDB
Hydroxicarbamidum	HMDB
Hydroxycarbamine	HMDB
Hydroxylurea	HMDB
Idrossicarbamide	HMDB
Oncocarbide	HMDB

Chemical Formula

CH₄N₂O₂

Average Molecular Weight

76.0547

Monoisotopic Molecular Weight

76.027277382

IUPAC Name

hydroxyurea

Traditional Name

hydroxyurea

CAS Registry Number

127-07-1

SMILES

NC(=O)NO

InChI Identifier

InChI=1S/CH4N2O2/c2-1(4)3-5/h5H,(H3,2,3,4)

InChI Key

VSNHCAURESNICA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboximidic acids and derivatives. Carboximidic acids and derivatives are compounds containing a carboximidic group, with the general formula R-C(=NR1)OR2.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Not Available

Direct Parent

Carboximidic acids and derivatives

Alternative Parents

Substituents

Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:44423 )
ureas (CHEBI:44423 )
a small molecule (HYDROXY-UREA )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-1.4	ChemAxon
logS	0.55	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	14.91 m³·mol⁻¹	ChemAxon
Polarizability	5.94 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0059-3950000000-0418fbb00ea645e9e0ce	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-3950000000-0418fbb00ea645e9e0ce	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0920000000-be691e1a11d76d687cc5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-725178d2fb4e3ae0a710	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9000000000-15e079ef519fdae75dab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9000000000-f39d1396b2b03d5846c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-01ox-9000000000-b5fb6577ca88b375ebea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-6093ebde62cb84552dd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-5f85466dc663205c60f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-9000000000-fb233b42b45077d2475d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06tf-9000000000-868a329446e04867fc56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-6245f3456e3558782716	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-722afb6d05d2ca0794f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f6792fcc64ed7bdb2466	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-fbd92a2a1457de08f558	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01r6-9000000000-ff7708ba70751a23d1eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-fd9f25340762315b4515	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum