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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:46:58 UTC

Update Date

2021-09-26 22:54:21 UTC

HMDB ID

HMDB0245728

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

Description

5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. Based on a literature review very few articles have been published on 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0245728
     RDKit          3D
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
 44 44  0  0  0  0  0  0  0  0999 V2000
    4.9651   -0.4614   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1777   -0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.0041   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -0.7793   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -0.9694   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3684   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002   -0.5016    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7326    0.1304    1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.6019    2.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    0.1076   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    1.5457   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1291    2.5300   -0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929    2.4908    0.2143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191   -1.9553    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.5439    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -2.8436   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    0.4247    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152    0.6133    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.4024    1.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    2.0765    2.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -0.2327   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0289   -0.1403   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.5713   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7626   -1.2747   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4008   -1.5991   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4346   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -0.0841   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.8002   -2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    1.7215   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4413    2.4946    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.5775   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1035    2.9300   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105    2.9251    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -1.8858    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -3.6349    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317   -2.2093    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882   -2.0991    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.3973   -1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835   -3.4869   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -3.6279   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    0.9110    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189    2.5049    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    1.3087    3.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    2.8223    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

  Mrv0541 09051314502D          

 20 20  0  0  0  0            999 V2000
    2.3645   -2.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2686    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    0.4273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8561    1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 19  1  0  0  0  0
  2 18  1  0  0  0  0
  2 20  1  0  0  0  0
  3 10  1  0  0  0  0
  4 13  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  5 13  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 14  2  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245728

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(C=C1)C(CCCN)(C#N)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O2/c1-12(2)16(11-18,8-5-9-17)13-6-7-14(19-3)15(10-13)20-4/h6-7,10,12H,5,8-9,17H2,1-4H3

> <INCHI_KEY>
UCWOSFAANAZHKR-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O2

> <MOLECULAR_WEIGHT>
276.374

> <EXACT_MASS>
276.183778022

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.84775720997505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-amino-2-(3,4-dimethoxyphenyl)-2-(propan-2-yl)pentanenitrile

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.5297656989999986

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.20347648139716

> <JCHEM_POLAR_SURFACE_AREA>
68.27000000000001

> <JCHEM_REFRACTIVITY>
80.28459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245728
     RDKit          3D
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
 44 44  0  0  0  0  0  0  0  0999 V2000
    4.9651   -0.4614   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1777   -0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.0041   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -0.7793   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -0.9694   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3684   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002   -0.5016    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7326    0.1304    1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.6019    2.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    0.1076   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    1.5457   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1291    2.5300   -0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929    2.4908    0.2143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191   -1.9553    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.5439    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -2.8436   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    0.4247    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152    0.6133    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.4024    1.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    2.0765    2.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -0.2327   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0289   -0.1403   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.5713   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7626   -1.2747   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4008   -1.5991   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4346   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -0.0841   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.8002   -2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    1.7215   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4413    2.4946    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.5775   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1035    2.9300   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105    2.9251    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -1.8858    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -3.6349    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317   -2.2093    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882   -2.0991    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.3973   -1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835   -3.4869   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -3.6279   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    0.9110    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189    2.5049    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    1.3087    3.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    2.8223    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 05-SEP-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-13         0                                  
HETATM    1  O   UNK     0       4.414  -3.823   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081  -5.362   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      11.701   3.465   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.001   0.798   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.081   0.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   2.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621   0.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.391   2.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -0.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.931   2.131   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   3.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   3.108   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.541   0.798   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -1.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -1.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -3.053   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -3.053   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -3.823   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -3.053   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -6.133   0.000  0.00  0.00           C+0
CONECT    1   16   19                                                       
CONECT    2   18   20                                                       
CONECT    3   10                                                            
CONECT    4   13                                                            
CONECT    5    6    7    9   13                                             
CONECT    6    5   11   12                                                  
CONECT    7    5    8                                                       
CONECT    8    7   10                                                       
CONECT    9    5   14   15                                                  
CONECT   10    3    8                                                       
CONECT   11    6                                                            
CONECT   12    6                                                            
CONECT   13    4    5                                                       
CONECT   14    9   16                                                       
CONECT   15    9   17                                                       
CONECT   16    1   14   18                                                  
CONECT   17   15   18                                                       
CONECT   18    2   16   17                                                  
CONECT   19    1                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0245728
HETATM    1  C1  UNL     1       4.965  -0.461  -1.513  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.280   0.178  -0.458  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.916   0.004  -0.337  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.232  -0.779  -1.229  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.857  -0.969  -1.125  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.151  -0.368  -0.118  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.300  -0.502   0.065  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.733   0.130   1.328  1.00  0.00           C  
HETATM    9  N1  UNL     1      -2.078   0.602   2.357  1.00  0.00           N  
HETATM   10  C8  UNL     1      -2.077   0.108  -1.062  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.858   1.546  -1.348  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.129   2.530  -0.267  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.493   2.491   0.214  1.00  0.00           N  
HETATM   14  C11 UNL     1      -1.719  -1.955   0.244  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.034  -2.544   1.465  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.601  -2.844  -0.921  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.872   0.425   0.778  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.215   0.613   0.681  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.901   1.402   1.581  1.00  0.00           O  
HETATM   20  C16 UNL     1       2.298   2.077   2.664  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.446  -0.233  -2.450  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.029  -0.140  -1.513  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.986  -1.571  -1.357  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.763  -1.275  -2.044  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.401  -1.599  -1.872  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.813  -0.435  -2.025  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.173  -0.084  -0.962  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.600   1.800  -2.180  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.876   1.722  -1.855  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.441   2.495   0.594  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.056   3.578  -0.743  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.104   2.930  -0.494  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.611   2.925   1.137  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.805  -1.886   0.543  1.00  0.00           H  
HETATM   35  H15 UNL     1      -1.126  -3.635   1.480  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.032  -2.209   1.466  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.488  -2.099   2.375  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.835  -2.397  -1.901  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.683  -3.487  -0.922  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.430  -3.628  -0.809  1.00  0.00           H  
HETATM   41  H21 UNL     1       0.339   0.911   1.588  1.00  0.00           H  
HETATM   42  H22 UNL     1       1.319   2.505   2.369  1.00  0.00           H  
HETATM   43  H23 UNL     1       2.089   1.309   3.450  1.00  0.00           H  
HETATM   44  H24 UNL     1       2.975   2.822   3.127  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   18
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   17
CONECT    7    8   10   14
CONECT    8    9    9    9
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   32   33
CONECT   14   15   16   34
CONECT   15   35   36   37
CONECT   16   38   39   40
CONECT   17   18   18   41
CONECT   18   19
CONECT   19   20
CONECT   20   42   43   44
END

HMDB0245728
     RDKit          3D
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
 44 44  0  0  0  0  0  0  0  0999 V2000
    4.9651   -0.4614   -1.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    0.1777   -0.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    0.0041   -0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -0.7793   -1.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570   -0.9694   -1.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -0.3684   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002   -0.5016    0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7326    0.1304    1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.6019    2.3565 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    0.1076   -1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8576    1.5457   -1.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1291    2.5300   -0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929    2.4908    0.2143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7191   -1.9553    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338   -2.5439    1.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6013   -2.8436   -0.9212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8718    0.4247    0.7776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152    0.6133    0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.4024    1.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2979    2.0765    2.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4458   -0.2327   -2.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0289   -0.1403   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9857   -1.5713   -1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7626   -1.2747   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4008   -1.5991   -1.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130   -0.4346   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -0.0841   -0.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004    1.8002   -2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8760    1.7215   -1.8550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4413    2.4946    0.5945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    3.5775   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1035    2.9300   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6105    2.9251    1.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8053   -1.8858    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -3.6349    1.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0317   -2.2093    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4882   -2.0991    2.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -2.3973   -1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6835   -3.4869   -0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -3.6279   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3388    0.9110    1.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189    2.5049    2.3693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0890    1.3087    3.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749    2.8223    3.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  3  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  1  0
 14 16  1  0
  6 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 18  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-(3-Aminopropyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile	HMDB

Chemical Formula

C₁₆H₂₄N₂O₂

Average Molecular Weight

276.374

Monoisotopic Molecular Weight

276.183778022

IUPAC Name

5-amino-2-(3,4-dimethoxyphenyl)-2-(propan-2-yl)pentanenitrile

Traditional Name

5-amino-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(C=C1)C(CCCN)(C#N)C(C)C

InChI Identifier

InChI=1S/C16H24N2O2/c1-12(2)16(11-18,8-5-9-17)13-6-7-14(19-3)15(10-13)20-4/h6-7,10,12H,5,8-9,17H2,1-4H3

InChI Key

UCWOSFAANAZHKR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Dimethoxybenzene
O-dimethoxybenzene
Phenylpropane
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Aralkylamine
Nitrile
Carbonitrile
Ether
Organopnictogen compound
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Primary amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	2.57	ALOGPS
logP	2.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.27 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	80.28 m³·mol⁻¹	ChemAxon
Polarizability	31.85 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
DeepCCS	[M+H]+	168.458	30932474
DeepCCS	[M-H]-	166.1	30932474
DeepCCS	[M-2H]-	199.072	30932474
DeepCCS	[M+Na]+	174.551	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.1	32859911
AllCCS	[M+Na]+	171.0	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.9	32859911
AllCCS	[M+HCOO]-	172.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile	COC1=C(OC)C=C(C=C1)C(CCCN)(C#N)C(C)C	2722.0	Standard polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile	COC1=C(OC)C=C(C=C1)C(CCCN)(C#N)C(C)C	2238.5	Standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile	COC1=C(OC)C=C(C=C1)C(CCCN)(C#N)C(C)C	2154.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C)C(C)C)C=C1OC	2215.8	Semi standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C)C(C)C)C=C1OC	2443.5	Standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C)C(C)C)C=C1OC	3043.1	Standard polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C)[Si](C)(C)C)C(C)C)C=C1OC	2374.0	Semi standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C)[Si](C)(C)C)C(C)C)C=C1OC	2611.6	Standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C)[Si](C)(C)C)C(C)C)C=C1OC	2936.0	Standard polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	2442.4	Semi standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	2640.4	Standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,1TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	3088.6	Standard polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	2801.4	Semi standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	2940.0	Standard non polar	33892256
5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile,2TBDMS,isomer #1	COC1=CC=C(C(C#N)(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C)C)C=C1OC	3034.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9150000000-88826015d4ec99e49b42	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 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 - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 10V, Positive-QTOF	splash10-004i-0090000000-40b9947b4b91d9767adf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 20V, Positive-QTOF	splash10-059x-2490000000-ecb7f5403a6db09621e2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 40V, Positive-QTOF	splash10-05mo-8490000000-d4823be25ccc6e9ff600	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 10V, Negative-QTOF	splash10-004i-0090000000-c3f0d9ea217aec5395bc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 20V, Negative-QTOF	splash10-0pc3-0290000000-00f72ccfaa23426cd676	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile 40V, Negative-QTOF	splash10-0089-2490000000-a0ef31318c88f7df7e4f	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

141913

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161569

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile (HMDB0245728)

MOL for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

3D MOL for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

3D SDF for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

3D-SDF for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

PDB for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

3D PDB for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

SMILES for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

INCHI for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

Structure for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

3D Structure for HMDB0245728 (5-Amino-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra