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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2023-02-21 17:18:29 UTC

HMDB ID

HMDB0015400

Secondary Accession Numbers

HMDB15400

Metabolite Identification

Common Name

Hydralazine

Description

Hydralazine is only found in individuals that have used or taken this drug. It is a direct-acting vasodilator that is used as an antihypertensive agent. [PubChem]Although the precise mechanism of action of hydralazine is not fully understood, the major effects are on the cardiovascular system. Hydralazine apparently lowers blood pressure by exerting a peripheral vasodilating effect through a direct relaxation of vascular smooth muscle. It has also been suggested that cyclic 3',5'-adenosine monophosphate (cyclic AMP) mediates, at least partly, the relaxation of arterial smooth muscle by altering cellular calcium metabolism, which interferes with the calcium movements within the vascular smooth muscle that are responsible for initiating or maintaining the contractile state. In hypertensive patients, the hydralazine-induced decrease in blood pressure is accompanied by increased heart rate, cardiac output, and stroke volume, probably because of a reflex response to decreased peripheral resistance. The drug has no direct effect on the heart. Hydralazine may increase pulmonary arterial pressure, as well as coronary, splanchnic, cerebral, and renal blood flow. The preferential dilatation of arterioles, as compared to veins, minimizes postural hypotension and promotes the increase in cardiac output. Hydralazine usually increases renin activity in plasma, presumably as a result of increased secretion of renin by the renal juxtaglomerular cells in response to reflex sympathetic discharge. This increase in renin activity leads to the production of angiotensin II, which then causes stimulation of aldosterone and consequent sodium reabsorption. Tolerance to the antihypertensive effect of the drug develops during prolonged therapy, especially if a diuretic is not administered concurrently. In patients with CHF, hydralazine decreases systemic vascular resistance and increases cardiac output.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1275                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.031  -1.415   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       3.751   0.802   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.751   2.281   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.751  -2.155   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.312   0.802   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.312   2.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.031   0.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.633   0.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.633   3.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.973   0.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.031   3.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.973   2.312   0.000  0.00  0.00           C+0
CONECT    1    4    7                                                       
CONECT    2    3    7                                                       
CONECT    3    2   11                                                       
CONECT    4    1                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9   11                                                  
CONECT    7    1    2    5                                                  
CONECT    8    5   10                                                       
CONECT    9    6   12                                                       
CONECT   10    8   12                                                       
CONECT   11    3    6                                                       
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1Z)-1(2H)-Phthalazinone hydrazone	ChEBI
(2H)-Phthalazinone hydrazone	ChEBI
1-Hydrazinophthalazine	ChEBI
1-Phthalazinylhydrazine	ChEBI
6-Hydralazine	ChEBI
Hidralazina	ChEBI
Hydralazin	ChEBI
Hydralazinum	ChEBI
Hydrallazine	ChEBI
Hydrazinophthalazine	ChEBI
Hydrazone 1(2H)-phthalazinone	ChEBI
Hypophthalin	ChEBI
Idralazina	ChEBI
Phthalazin-1-ylhydrazine	ChEBI
Hidral	Kegg
Hydralazine hydrochloride	HMDB
Nepresol	HMDB
Apressin	HMDB
Apressoline	HMDB
Hydralazine mono hydrochloride	HMDB
Hydralazine mono-hydrochloride	HMDB
Hydrallazin	HMDB
Hydrochloride, hydralazine	HMDB
mono-Hydrochloride, hydralazine	HMDB
Apresoline	HMDB

Chemical Formula

C₈H₈N₄

Average Molecular Weight

160.1759

Monoisotopic Molecular Weight

160.074896276

IUPAC Name

1-hydrazinylphthalazine

Traditional Name

hydralazine

CAS Registry Number

86-54-4

SMILES

NNC1=NN=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C8H8N4/c9-11-8-7-4-2-1-3-6(7)5-10-12-8/h1-5H,9H2,(H,11,12)

InChI Key

RPTUSVTUFVMDQK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalazines. Phthalazines are compounds containing a phthalazine moiety, which consists of a benzene ring fused to a pyridazine, forming a 2,3-benzodiazine skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Phthalazines

Alternative Parents

Substituents

Phthalazine
Imidolactam
Benzenoid
Pyridazine
Heteroaromatic compound
Carboxylic acid amidrazone
Azacycle
Hydrazone
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydrazines (CHEBI:5775 )
phthalazines (CHEBI:5775 )
azaarene (CHEBI:5775 )
ortho-fused heteroarene (CHEBI:5775 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015400)

Source

Exogenous

Exogenous (HMDB: HMDB0015400)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.61 g/L	Not Available
LogP	0.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.61 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.75	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	17.69	ChemAxon
pKa (Strongest Basic)	6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.23 m³·mol⁻¹	ChemAxon
Polarizability	16.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	132.746	31661259
DarkChem	[M-H]-	132.627	31661259
DeepCCS	[M-2H]-	165.488	30932474
DeepCCS	[M+Na]+	140.853	30932474
AllCCS	[M+H]+	135.5	32859911
AllCCS	[M+H-H2O]+	130.9	32859911
AllCCS	[M+NH4]+	139.8	32859911
AllCCS	[M+Na]+	141.0	32859911
AllCCS	[M-H]-	132.7	32859911
AllCCS	[M+Na-2H]-	133.4	32859911
AllCCS	[M+HCOO]-	134.1	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. Predicted by Afia on May 17, 2022.	2.34 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8245 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	55.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1353.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	391.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	261.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	382.8 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	582.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	814.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	310.8 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	1187.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	460.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	606.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	248.1 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	113.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydralazine	NNC1=NN=CC2=CC=CC=C12	2763.4	Standard polar	33892256
Hydralazine	NNC1=NN=CC2=CC=CC=C12	1591.5	Standard non polar	33892256
Hydralazine	NNC1=NN=CC2=CC=CC=C12	1911.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydralazine,1TMS,isomer #1	C[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	1839.2	Semi standard non polar	33892256
Hydralazine,1TMS,isomer #1	C[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	1769.0	Standard non polar	33892256
Hydralazine,1TMS,isomer #1	C[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	2866.3	Standard polar	33892256
Hydralazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	1734.8	Semi standard non polar	33892256
Hydralazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	1782.8	Standard non polar	33892256
Hydralazine,1TMS,isomer #2	C[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	2910.1	Standard polar	33892256
Hydralazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1892.9	Semi standard non polar	33892256
Hydralazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1934.1	Standard non polar	33892256
Hydralazine,2TMS,isomer #1	C[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C	2703.0	Standard polar	33892256
Hydralazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1821.0	Semi standard non polar	33892256
Hydralazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1851.3	Standard non polar	33892256
Hydralazine,2TMS,isomer #2	C[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	2422.0	Standard polar	33892256
Hydralazine,3TMS,isomer #1	C[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	1910.3	Semi standard non polar	33892256
Hydralazine,3TMS,isomer #1	C[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2016.7	Standard non polar	33892256
Hydralazine,3TMS,isomer #1	C[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C)[Si](C)(C)C	2313.2	Standard polar	33892256
Hydralazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	2092.9	Semi standard non polar	33892256
Hydralazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	1945.9	Standard non polar	33892256
Hydralazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNC1=NN=CC2=CC=CC=C12	2970.6	Standard polar	33892256
Hydralazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	1974.4	Semi standard non polar	33892256
Hydralazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	1969.3	Standard non polar	33892256
Hydralazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)C1=NN=CC2=CC=CC=C12	2972.1	Standard polar	33892256
Hydralazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2311.5	Semi standard non polar	33892256
Hydralazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2305.0	Standard non polar	33892256
Hydralazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NC1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2868.7	Standard polar	33892256
Hydralazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2235.5	Semi standard non polar	33892256
Hydralazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2288.5	Standard non polar	33892256
Hydralazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2627.6	Standard polar	33892256
Hydralazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2479.2	Semi standard non polar	33892256
Hydralazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2664.4	Standard non polar	33892256
Hydralazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NN=CC2=CC=CC=C12)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2610.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydralazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-1900000000-f91e3313037f100cda4a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydralazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 10V, Positive-QTOF	splash10-03di-0900000000-8b7f181371fbed1e004c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 20V, Positive-QTOF	splash10-03e9-0900000000-8e1028367f84d64f9c73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 40V, Positive-QTOF	splash10-0f89-3900000000-324287ae696d06b87174	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 10V, Negative-QTOF	splash10-0a4i-0900000000-a3afccefb2246e5901f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 20V, Negative-QTOF	splash10-0560-0900000000-7b01083726dab57d5322	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 40V, Negative-QTOF	splash10-0a59-1900000000-15fc53aed0fa9d04b4d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 10V, Positive-QTOF	splash10-03di-0900000000-86317c6fb29f228114ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 20V, Positive-QTOF	splash10-03xu-4900000000-7990b6c5790e6ba5beae	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 40V, Positive-QTOF	splash10-000i-9000000000-c0eb36379ffd59449206	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 10V, Negative-QTOF	splash10-0a4i-0900000000-ac294195ce6174807530	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 20V, Negative-QTOF	splash10-004i-0900000000-1ead11198d84b2fa9185	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine 40V, Negative-QTOF	splash10-0ufr-4900000000-48281db360c4a9ee1de6	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	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 DB01275	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01275	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01275

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3511

KEGG Compound ID

C07040

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydralazine

METLIN ID

Not Available

PubChem Compound

3637

PDB ID

Not Available

ChEBI ID

5775

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kandler MR, Mah GT, Tejani AM, Stabler SN: Hydralazine for essential hypertension. Cochrane Database Syst Rev. 2010 Aug 4;(8):CD004934. doi: 10.1002/14651858.CD004934.pub3. [PubMed:20687078 ]

Enzymes

Enzyme Details

1. Prolyl 4-hydroxylase subunit alpha-1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the post-translational formation of 4-hydroxyproline in -Xaa-Pro-Gly- sequences in collagens and other proteins.
Gene Name:: P4HA1
Uniprot ID:: P13674
Molecular weight:: 60966.645

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Knowles HJ, Tian YM, Mole DR, Harris AL: Novel mechanism of action for hydralazine: induction of hypoxia-inducible factor-1alpha, vascular endothelial growth factor, and angiogenesis by inhibition of prolyl hydroxylases. Circ Res. 2004 Jul 23;95(2):162-9. Epub 2004 Jun 10. [PubMed:15192023 ]
Murad S, Tajima S, Pinnell SR: A paradoxical effect of hydralazine on prolyl and lysyl hydroxylase activities in cultured human skin fibroblasts. Arch Biochem Biophys. 1985 Sep;241(2):356-63. [PubMed:2994564 ]
Chen KH, Paz MA, Gallop PM: Collagen prolyl hydroxylation in WI-38 fibroblast cultures: action of hydralazine. In Vitro. 1977 Jan;13(1):49-54. [PubMed:856725 ]

Enzyme Details

2. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

References

Claud P, Padovani P, Guichard JP, Artur Y, Laine R: Involvement of semicarbazide-sensitive amine oxidase in tresperimus metabolism in human and in rat. Drug Metab Dispos. 2001 May;29(5):735-41. [PubMed:11302941 ]
Vidrio H, Medina M, Gonzalez-Romo P, Lorenzana-Jimenez M, Diaz-Arista P, Baeza A: Semicarbazide-sensitive amine oxidase substrates potentiate hydralazine hypotension: possible role of hydrogen peroxide. J Pharmacol Exp Ther. 2003 Nov;307(2):497-504. Epub 2003 Sep 11. [PubMed:12970383 ]
Vidrio H: Semicarbazide-sensitive amine oxidase: role in the vasculature and vasodilation after in situ inhibition. Auton Autacoid Pharmacol. 2003 Oct-Dec;23(5-6):275-83. [PubMed:15255812 ]
Vidrio H, Medina M: 2-bromoethylamine, a suicide inhibitor of semicarbazide-sensitive amine oxidase, increases hydralazine hypotension in rats. J Cardiovasc Pharmacol. 2005 Sep;46(3):316-24. [PubMed:16116337 ]
Vidrio H, Medina M: Hypotensive effect of hydroxylamine, an endogenous nitric oxide donor and SSAO inhibitor. J Neural Transm (Vienna). 2007;114(6):863-5. Epub 2007 Mar 26. [PubMed:17385063 ]
Gronvall JL, Garpenstrand H, Oreland L, Ekblom J: An autoradiographic method of visualising semicarbazide-sensitive amine oxidase activity in mouse tissue sections. Neurobiology (Bp). 2000;8(2):167-77. [PubMed:11061213 ]
Gronvall JL, Garpenstrand H, Oreland L, Ekblom J: Autoradiographic imaging of formaldehyde adducts in mice: possible relevance for vascular damage in diabetes. Life Sci. 1998;63(9):759-68. [PubMed:9740313 ]
Lizcano JM, Fernandez de Arriba A, Tipton KF, Unzeta M: Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives. Biochem Pharmacol. 1996 Jul 26;52(2):187-95. [PubMed:8694842 ]
Lyles GA, McDougall SA: The enhanced daily excretion of urinary methylamine in rats treated with semicarbazide or hydralazine may be related to the inhibition of semicarbazide-sensitive amine oxidase activities. J Pharm Pharmacol. 1989 Feb;41(2):97-100. [PubMed:2568436 ]
Barrand MA, Callingham BA: The interaction of hydralazine with a semicarbazide-sensitive amine oxidase in brown adipose tissue of the rat. Its use as a radioactive ligand for the enzyme. Biochem J. 1985 Dec 1;232(2):415-23. [PubMed:4091799 ]
Barrand MA, Fox SA: Amine oxidase activities in brown adipose tissue of the rat: identification of semicarbazide-sensitive (clorgyline-resistant) activity at the fat cell membrane. J Pharm Pharmacol. 1984 Oct;36(10):652-8. [PubMed:6150080 ]

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Hydralazine (HMDB0015400)

MOL for HMDB0015400 (Hydralazine)

3D MOL for HMDB0015400 (Hydralazine)

3D SDF for HMDB0015400 (Hydralazine)

3D-SDF for HMDB0015400 (Hydralazine)

PDB for HMDB0015400 (Hydralazine)

3D PDB for HMDB0015400 (Hydralazine)

SMILES for HMDB0015400 (Hydralazine)

INCHI for HMDB0015400 (Hydralazine)

Structure for HMDB0015400 (Hydralazine)

3D Structure for HMDB0015400 (Hydralazine)

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

References

References

References