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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 17:50:42 UTC

Update Date

2023-02-21 17:30:05 UTC

HMDB ID

HMDB0060606

Secondary Accession Numbers

HMDB60606

Metabolite Identification

Common Name

Hydralazine acetone hydrazone

Description

Hydralazine acetone hydrazone is a metabolite of hydralazine. Hydralazine (apresoline) is a direct-acting smooth muscle relaxant used to treat hypertension by acting as a vasodilator primarily in arteries and arterioles. By relaxing vascular smooth muscle, vasodilators act to decrease peripheral resistance, thereby lowering blood pressure and decreasing afterload. (Wikipedia)

Structure

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


  Mrv0541 06151310502D          

 15 16  0  0  0  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060606

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=NNC1=NN=CC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N4/c1-8(2)13-15-11-10-6-4-3-5-9(10)7-12-14-11/h3-7H,1-2H3,(H,14,15)

> <INCHI_KEY>
AKFJXINWDQGPHO-UHFFFAOYSA-N

> <FORMULA>
C11H12N4

> <MOLECULAR_WEIGHT>
200.2398

> <EXACT_MASS>
200.106196404

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.690908308759234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[2-(propan-2-ylidene)hydrazin-1-yl]phthalazine

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.6076363076666669

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.41864089635126

> <JCHEM_PKA_STRONGEST_BASIC>
4.641321836999758

> <JCHEM_POLAR_SURFACE_AREA>
50.17

> <JCHEM_REFRACTIVITY>
62.40260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[2-(propan-2-ylidene)hydrazin-1-yl]phthalazine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0060606
HETATM    1  C1  UNL     1      -3.844   1.054   0.830  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.832   0.047   0.367  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.161  -0.752  -0.831  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.725  -0.133   0.962  1.00  0.00           N  
HETATM    5  N2  UNL     1      -0.809  -1.059   0.528  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.229  -0.780  -0.407  1.00  0.00           C  
HETATM    7  N3  UNL     1       0.101  -1.035  -1.720  1.00  0.00           N  
HETATM    8  N4  UNL     1       1.071  -0.767  -2.579  1.00  0.00           N  
HETATM    9  C5  UNL     1       2.244  -0.225  -2.208  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.461   0.069  -0.883  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.640   0.627  -0.441  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.808   0.905   0.895  1.00  0.00           C  
HETATM   13  C9  UNL     1       2.767   0.609   1.764  1.00  0.00           C  
HETATM   14  C10 UNL     1       1.578   0.051   1.351  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.422  -0.223   0.006  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.684   0.501   1.259  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.179   1.583  -0.069  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.361   1.702   1.590  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.613  -0.410  -1.743  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.261  -0.710  -1.002  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.878  -1.814  -0.632  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.818  -2.066   0.875  1.00  0.00           H  
HETATM   23  H8  UNL     1       3.032  -0.006  -2.911  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.443   0.849  -1.124  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.734   1.349   1.276  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.870   0.816   2.817  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.764  -0.182   2.032  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    4
CONECT    3   19   20   21
CONECT    4    5
CONECT    5    6   22
CONECT    6    7    7   15
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   23
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hydralazine acetonide	HMDB

Chemical Formula

C₁₁H₁₂N₄

Average Molecular Weight

200.2398

Monoisotopic Molecular Weight

200.106196404

IUPAC Name

1-[2-(propan-2-ylidene)hydrazin-1-yl]phthalazine

Traditional Name

1-[2-(propan-2-ylidene)hydrazin-1-yl]phthalazine

CAS Registry Number

56173-18-3

SMILES

CC(C)=NNC1=NN=CC2=C1C=CC=C2

InChI Identifier

InChI=1S/C11H12N4/c1-8(2)13-15-11-10-6-4-3-5-9(10)7-12-14-11/h3-7H,1-2H3,(H,14,15)

InChI Key

AKFJXINWDQGPHO-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
Azacycle
Hydrazone
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0060606)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060606)

Organ

Kidney (HMDB: HMDB0060606)
Liver (HMDB: HMDB0060606)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060606)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	0.11 g/L	ALOGPS
logP	2.12	ALOGPS
logP	1.61	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.17 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.4 m³·mol⁻¹	ChemAxon
Polarizability	21.69 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
DeepCCS	[M+H]+	141.594	30932474
DeepCCS	[M-H]-	139.171	30932474
DeepCCS	[M-2H]-	174.523	30932474
DeepCCS	[M+Na]+	150.062	30932474
AllCCS	[M+H]+	145.1	32859911
AllCCS	[M+H-H2O]+	141.0	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.1	32859911
AllCCS	[M-H]-	148.0	32859911
AllCCS	[M+Na-2H]-	148.2	32859911
AllCCS	[M+HCOO]-	148.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydralazine acetone hydrazone	CC(C)=NNC1=NN=CC2=C1C=CC=C2	2513.0	Standard polar	33892256
Hydralazine acetone hydrazone	CC(C)=NNC1=NN=CC2=C1C=CC=C2	1856.5	Standard non polar	33892256
Hydralazine acetone hydrazone	CC(C)=NNC1=NN=CC2=C1C=CC=C2	2016.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydralazine acetone hydrazone,1TMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1867.7	Semi standard non polar	33892256
Hydralazine acetone hydrazone,1TMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	1855.5	Standard non polar	33892256
Hydralazine acetone hydrazone,1TMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C	2848.4	Standard polar	33892256
Hydralazine acetone hydrazone,1TBDMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2069.5	Semi standard non polar	33892256
Hydralazine acetone hydrazone,1TBDMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2057.4	Standard non polar	33892256
Hydralazine acetone hydrazone,1TBDMS,isomer #1	CC(C)=NN(C1=NN=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2908.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydralazine acetone hydrazone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-3900000000-bdc2b1f25dc7fe4c560f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydralazine acetone hydrazone 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 acetone hydrazone 10V, Positive-QTOF	splash10-0pb9-0960000000-ac5ebdf3553e1c5d698f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 20V, Positive-QTOF	splash10-08fr-0910000000-6aa3fffc40cef2048385	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 40V, Positive-QTOF	splash10-0a4i-2900000000-8cc9f6a211e442e72e51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 10V, Negative-QTOF	splash10-0002-0900000000-3773a740d0de4999d2fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 20V, Negative-QTOF	splash10-0aba-0900000000-7870c15ae658fc79d54e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 40V, Negative-QTOF	splash10-0a4i-1900000000-75698158a2c8c8722f04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 10V, Positive-QTOF	splash10-0udi-0090000000-3fedaf27067b946e1ef5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 20V, Positive-QTOF	splash10-0udi-1390000000-ec57d4d3df71b0a1d7e6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 40V, Positive-QTOF	splash10-0zg3-9600000000-4d4fe9c9d98486a1248b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 10V, Negative-QTOF	splash10-0002-0900000000-56b61dcdf2f52aa7fe3b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 20V, Negative-QTOF	splash10-004i-0900000000-a4b475208afdf0b7af36	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydralazine acetone hydrazone 40V, Negative-QTOF	splash10-004i-0900000000-ccc84e40c2b026a7adb0	2021-10-12	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

41772

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Hydralazine acetone hydrazone (HMDB0060606)

MOL for HMDB0060606 (Hydralazine acetone hydrazone)

3D MOL for HMDB0060606 (Hydralazine acetone hydrazone)

3D SDF for HMDB0060606 (Hydralazine acetone hydrazone)

3D-SDF for HMDB0060606 (Hydralazine acetone hydrazone)

PDB for HMDB0060606 (Hydralazine acetone hydrazone)

3D PDB for HMDB0060606 (Hydralazine acetone hydrazone)

SMILES for HMDB0060606 (Hydralazine acetone hydrazone)

INCHI for HMDB0060606 (Hydralazine acetone hydrazone)

Structure for HMDB0060606 (Hydralazine acetone hydrazone)

3D Structure for HMDB0060606 (Hydralazine acetone hydrazone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra