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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:24:41 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062443

Secondary Accession Numbers

HMDB62443

Metabolite Identification

Common Name

alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol

Description

4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. 4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol is a strong basic compound (based on its pKa).

Structure

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

  Mrv1652303211707242D          

 14 14  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062443

> <DATABASE_NAME>
hmdb

> <SMILES>
ON=NCCCC(O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O2/c13-9(4-2-6-11-12-14)8-3-1-5-10-7-8/h1,3,5,7,9,13H,2,4,6H2,(H,11,14)

> <INCHI_KEY>
QCCXEQGBFPINIY-UHFFFAOYSA-N

> <FORMULA>
C9H13N3O2

> <MOLECULAR_WEIGHT>
195.222

> <EXACT_MASS>
195.100776671

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.49885184847722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.8562633753333333

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.231964117678373

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.177825648944982

> <JCHEM_PKA_STRONGEST_BASIC>
4.704627805099485

> <JCHEM_POLAR_SURFACE_AREA>
78.07000000000001

> <JCHEM_REFRACTIVITY>
53.6037

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAR-17         0                                  
HETATM    1  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       9.336  -5.390   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0062443
HETATM    1  O1  UNL     1       4.032   0.738   0.748  1.00  0.00           O  
HETATM    2  N1  UNL     1       4.155  -0.051  -0.362  1.00  0.00           N  
HETATM    3  N2  UNL     1       3.442  -1.051  -0.587  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.383  -1.534   0.274  1.00  0.00           C  
HETATM    5  C2  UNL     1       1.075  -1.279  -0.490  1.00  0.00           C  
HETATM    6  C3  UNL     1       0.954   0.204  -0.747  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.263   0.625  -1.464  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.208   2.029  -1.675  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.553   0.436  -0.756  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.739   0.033   0.517  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.003  -0.121   1.026  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.119   0.125   0.277  1.00  0.00           C  
HETATM   13  N3  UNL     1      -3.924   0.526  -0.985  1.00  0.00           N  
HETATM   14  C9  UNL     1      -2.705   0.687  -1.516  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.465   1.653   0.779  1.00  0.00           H  
HETATM   16  H2  UNL     1       2.426  -2.610   0.452  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.343  -1.012   1.247  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.263  -1.757   0.023  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.187  -1.838  -1.470  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.887   0.523  -1.300  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.082   0.686   0.251  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.374   0.182  -2.474  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.078   2.409  -0.764  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.906  -0.152   1.144  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.109  -0.447   2.051  1.00  0.00           H  
HETATM   26  H12 UNL     1      -5.083  -0.014   0.731  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.629   1.012  -2.538  1.00  0.00           H  
CONECT    1    2   15
CONECT    2    3    3
CONECT    3    4
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23
CONECT    9   10   10   14
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14
CONECT   14   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-[3-(nitrosoamino)Propyl]-3-pyridinemethanol	Generator
α-[3-(nitrosoamino)propyl]-3-pyridinemethanol	Generator

Chemical Formula

C₉H₁₃N₃O₂

Average Molecular Weight

195.222

Monoisotopic Molecular Weight

195.100776671

IUPAC Name

4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol

Traditional Name

4-(2-hydroxydiazen-1-yl)-1-(pyridin-3-yl)butan-1-ol

CAS Registry Number

Not Available

SMILES

ON=NCCCC(O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C9H13N3O2/c13-9(4-2-6-11-12-14)8-3-1-5-10-7-8/h1,3,5,7,9,13H,2,4,6H2,(H,11,14)

InChI Key

QCCXEQGBFPINIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
Heteroaromatic compound
Secondary alcohol
Organic n-nitroso compound
Azacycle
Organic nitroso compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:82575 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062443)

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	1.37 g/l	ALOGPS
LogP	0.13	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.68	ALOGPS
logP	0.86	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	53.6 m³·mol⁻¹	ChemAxon
Polarizability	20.5 Å³	ChemAxon
Number of Rings	1	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]+	144.779	31661259
DarkChem	[M-H]-	141.896	31661259
DeepCCS	[M+H]+	142.152	30932474
DeepCCS	[M-H]-	139.28	30932474
DeepCCS	[M-2H]-	176.119	30932474
DeepCCS	[M+Na]+	151.657	30932474
AllCCS	[M+H]+	143.6	32859911
AllCCS	[M+H-H2O]+	139.5	32859911
AllCCS	[M+NH4]+	147.3	32859911
AllCCS	[M+Na]+	148.4	32859911
AllCCS	[M-H]-	145.2	32859911
AllCCS	[M+Na-2H]-	145.9	32859911
AllCCS	[M+HCOO]-	146.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol	ON=NCCCC(O)C1=CN=CC=C1	2644.2	Standard polar	33892256
alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol	ON=NCCCC(O)C1=CN=CC=C1	1770.3	Standard non polar	33892256
alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol	ON=NCCCC(O)C1=CN=CC=C1	1983.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol,1TMS,isomer #1	C[Si](C)(C)OC(CCCN=NO)C1=CC=CN=C1	1852.3	Semi standard non polar	33892256
alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CCCN=NO)C1=CC=CN=C1	2065.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-0fac8697f12f3f8152c0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9520000000-649436784ea689f80e40	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 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 - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 10V, Positive-QTOF	splash10-00mk-0900000000-9931ab7986b2c40ca805	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 20V, Positive-QTOF	splash10-0f89-2900000000-59d830a8477691eb3e3a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 40V, Positive-QTOF	splash10-0a5c-9800000000-edaac4f83d74038db8c0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 10V, Negative-QTOF	splash10-0006-2900000000-de7f4d741591f59995ed	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 20V, Negative-QTOF	splash10-004i-6900000000-2953197c779f9c6b4160	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 40V, Negative-QTOF	splash10-002b-9300000000-fdbda21e8b0636040f96	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 10V, Negative-QTOF	splash10-0006-2900000000-33ae4e7383a7e90da539	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 20V, Negative-QTOF	splash10-004i-4900000000-a44a146d23d5458919d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 40V, Negative-QTOF	splash10-004j-9600000000-226c3581096a77d1048f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 10V, Positive-QTOF	splash10-00l2-0900000000-d0acffc6721a4daa94d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 20V, Positive-QTOF	splash10-0f89-1900000000-8c68c27cb02d05a51e17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol 40V, Positive-QTOF	splash10-001i-9600000000-4f47133c2ca7325be1da	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

C19581

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53297442

PDB ID

Not Available

ChEBI ID

82575

Food Biomarker Ontology

Not Available

VMH ID

M01319

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 alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol (HMDB0062443)

MOL for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

3D MOL for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

3D SDF for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

3D-SDF for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

PDB for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

3D PDB for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

SMILES for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

INCHI for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

Structure for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

3D Structure for HMDB0062443 (alpha-[3-(Nitrosoamino)propyl]-3-pyridinemethanol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra