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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:54 UTC

HMDB ID

HMDB0000528

Secondary Accession Numbers

HMDB0011746
HMDB00528
HMDB11746

Metabolite Identification

Common Name

4,5-Dihydroorotic acid

Description

4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076 ). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-Dihydro-orotic acid	ChEBI
DL-Dihydroortotic acid	ChEBI
Hydroorotic acid	ChEBI
5,6-Dihydro-orotate	Generator
DL-Dihydroortotate	Generator
Hydroorotate	Generator
4,5-Dihydroorotate	Generator
4,5-Dihydroorotic acid, (D)-isomer	MeSH
4,5-Dihydroorotic acid, (DL)-isomer	MeSH
4,5-Dihydroorotic acid, (L)-isomer	MeSH
5,6-Dihydroorotate	MeSH
L-Dihydroorotate	MeSH
Dihydroorotate	MeSH
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylate	HMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acid	HMDB
L-Hydroorotate	HMDB
L-Hydroorotic acid	HMDB
R,S-Hydroorotate	HMDB

Chemical Formula

C₅H₆N₂O₄

Average Molecular Weight

158.1121

Monoisotopic Molecular Weight

158.03275669

IUPAC Name

2,6-dioxo-1,3-diazinane-4-carboxylic acid

Traditional Name

dihydroorotic acid

CAS Registry Number

155-54-4

SMILES

OC(=O)C1CC(=O)NC(=O)N1

InChI Identifier

InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)

InChI Key

UFIVEPVSAGBUSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
N-acyl urea
Pyrimidone
Ureide
1,3-diazinane
Pyrimidine
Dicarboximide
Urea
Carbonic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30865 )
N-acylurea (CHEBI:30865 )
secondary amide (CHEBI:30865 )
pyrimidinemonocarboxylic acid (CHEBI:30865 )

Ontology

Not Available

Prostate (HMDB: HMDB0000528)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000528)

Source

Exogenous

Exogenous (HMDB: HMDB0000528)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000528)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyrimidine Metabolism (PathBank: SMP0121324)
Pyrimidine Metabolism (PathBank: SMP0002370)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.7 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-1.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.28	ChemAxon
pKa (Strongest Basic)	-8.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	31.58 m³·mol⁻¹	ChemAxon
Polarizability	13.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.159	31661259
DarkChem	[M-H]-	128.823	31661259
AllCCS	[M+H]+	133.844	32859911
AllCCS	[M-H]-	126.046	32859911
DeepCCS	[M+H]+	130.745	30932474
DeepCCS	[M-H]-	127.684	30932474
DeepCCS	[M-2H]-	164.713	30932474
DeepCCS	[M+Na]+	139.786	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	138.0	32859911
AllCCS	[M+Na]+	139.2	32859911
AllCCS	[M-H]-	126.0	32859911
AllCCS	[M+Na-2H]-	127.3	32859911
AllCCS	[M+HCOO]-	128.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	1.35 minutes	32390414
Predicted by Siyang on May 30, 2022	9.796 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	238.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	821.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	56.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	270.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	277.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	656.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	626.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	70.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	895.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	261.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	703.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	290.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	339.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dihydroorotic acid	OC(=O)C1CC(=O)NC(=O)N1	3123.6	Standard polar	33892256
4,5-Dihydroorotic acid	OC(=O)C1CC(=O)NC(=O)N1	1588.4	Standard non polar	33892256
4,5-Dihydroorotic acid	OC(=O)C1CC(=O)NC(=O)N1	1859.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4,5-Dihydroorotic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1	1660.6	Semi standard non polar	33892256
4,5-Dihydroorotic acid,1TMS,isomer #2	C[Si](C)(C)N1C(=O)CC(C(=O)O)NC1=O	1676.6	Semi standard non polar	33892256
4,5-Dihydroorotic acid,1TMS,isomer #3	C[Si](C)(C)N1C(=O)NC(=O)CC1C(=O)O	1672.5	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1	1708.7	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1	1803.2	Standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1	2846.9	Standard polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C	1682.0	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C	1807.4	Standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C	2875.1	Standard polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #3	C[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C)C1=O	1671.8	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #3	C[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C)C1=O	1748.6	Standard non polar	33892256
4,5-Dihydroorotic acid,2TMS,isomer #3	C[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C)C1=O	2485.0	Standard polar	33892256
4,5-Dihydroorotic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	1699.5	Semi standard non polar	33892256
4,5-Dihydroorotic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	1812.4	Standard non polar	33892256
4,5-Dihydroorotic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C)C(=O)N1[Si](C)(C)C	2209.8	Standard polar	33892256
4,5-Dihydroorotic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1	1942.6	Semi standard non polar	33892256
4,5-Dihydroorotic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=O)CC(C(=O)O)NC1=O	1964.9	Semi standard non polar	33892256
4,5-Dihydroorotic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)CC1C(=O)O	1969.8	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1	2157.1	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1	2239.9	Standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1	2802.5	Standard polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C	2180.9	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C	2254.4	Standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)NC(=O)N1[Si](C)(C)C(C)(C)C	2908.0	Standard polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O	2183.1	Semi standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O	2208.1	Standard non polar	33892256
4,5-Dihydroorotic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)CC(C(=O)O)N([Si](C)(C)C(C)(C)C)C1=O	2559.5	Standard polar	33892256
4,5-Dihydroorotic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2385.0	Semi standard non polar	33892256
4,5-Dihydroorotic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2467.5	Standard non polar	33892256
4,5-Dihydroorotic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)N1[Si](C)(C)C(C)(C)C	2480.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9400000000-248b8d6d703ba73c2058	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (1 TMS) - 70eV, Positive	splash10-03di-3900000000-b0776f22820e6e570a09	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4,5-Dihydroorotic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4,5-Dihydroorotic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-059i-9700000000-c8ce0433c02db41880b9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4,5-Dihydroorotic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-9000000000-56601203ef19b09212fe	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4,5-Dihydroorotic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-006x-9000000000-b6342346ce51dd871eaa	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 10V, Positive-QTOF	splash10-0a4i-0900000000-2ddb498acc970a567f6b	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 20V, Positive-QTOF	splash10-03dl-5900000000-4b73ae512e57466dd4e6	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 40V, Positive-QTOF	splash10-0006-9100000000-d6c31a36d6fe5c68d9e1	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 10V, Negative-QTOF	splash10-0a4i-1900000000-c84801951eaa1da750f7	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 20V, Negative-QTOF	splash10-0006-9000000000-4ae1d11ab20f903606c3	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 40V, Negative-QTOF	splash10-0006-9000000000-aec3a40befb20e60f21b	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 10V, Positive-QTOF	splash10-06r6-0900000000-86736ae769db7bc83c23	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 20V, Positive-QTOF	splash10-03di-5900000000-f6e9e0cbdc2adf67aa89	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 40V, Positive-QTOF	splash10-00dl-9000000000-aac58a007ab745825d74	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-b0c5e687f246809cdae9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 20V, Negative-QTOF	splash10-01ox-6900000000-cb60b796898e6ca4336d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4,5-Dihydroorotic acid 40V, Negative-QTOF	splash10-0006-9000000000-fccf5d7216b23cffed7a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022096

KNApSAcK ID

Not Available

Chemspider ID

628

KEGG Compound ID

C00337

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4,5-Dihydroorotic_acid

METLIN ID

5513

PubChem Compound

648

PDB ID

Not Available

ChEBI ID

30865

Food Biomarker Ontology

Not Available

VMH ID

DHOR_S

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Burger, Klaus; Neuhauser, Horst; Rudolph, Martin. A new, preparatively simple way to dihydroorotic acid, 1-methyl-4,5-dihydroorotic acid and their derivatives. Chemiker-Zeitung (1990), 114(7-8), 251-5.

Material Safety Data Sheet (MSDS)

Not Available

General References

Ng SB, Buckingham KJ, Lee C, Bigham AW, Tabor HK, Dent KM, Huff CD, Shannon PT, Jabs EW, Nickerson DA, Shendure J, Bamshad MJ: Exome sequencing identifies the cause of a mendelian disorder. Nat Genet. 2010 Jan;42(1):30-5. doi: 10.1038/ng.499. Epub 2009 Nov 13. [PubMed:19915526 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
LIEBERMAN I, KORNBERG A: Enzymatic synthesis and breakdown of a pyrimidine, orotic acid. I. Dihydroortic acid, ureidosuccinic acid, and 5-carboxymethylhydantoin. J Biol Chem. 1954 Apr;207(2):911-24. [PubMed:13163076 ]

Enzymes

Enzyme Details

1. Dihydroorotate dehydrogenase (quinone), mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:: DHODH
Uniprot ID:: Q02127
Molecular weight:: 42866.93

Enzyme Details

2. CAD protein

General function:: Involved in hydrolase activity
Specific function:: This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:: CAD
Uniprot ID:: P27708
Molecular weight:: 242981.73

Showing metabocard for 4,5-Dihydroorotic acid (HMDB0000528)

MOL for HMDB0000528 (4,5-Dihydroorotic acid)

3D MOL for HMDB0000528 (4,5-Dihydroorotic acid)

3D SDF for HMDB0000528 (4,5-Dihydroorotic acid)

3D-SDF for HMDB0000528 (4,5-Dihydroorotic acid)

PDB for HMDB0000528 (4,5-Dihydroorotic acid)

3D PDB for HMDB0000528 (4,5-Dihydroorotic acid)

SMILES for HMDB0000528 (4,5-Dihydroorotic acid)

INCHI for HMDB0000528 (4,5-Dihydroorotic acid)

Structure for HMDB0000528 (4,5-Dihydroorotic acid)

3D Structure for HMDB0000528 (4,5-Dihydroorotic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes