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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:33:06 UTC

Update Date

2022-11-23 22:13:43 UTC

HMDB ID

HMDB0253715

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isoxsuprine

Description

isoxsuprine, also known as dilator or duvadilan, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a significant number of articles have been published on isoxsuprine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isoxsuprine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isoxsuprine 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

HMDB0253715
     RDKit          3D
isoxsuprine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -1.2720   -2.2819    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587   -1.2371   -1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -0.0590   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2943   -0.5718   -0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3701    0.1879    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344    1.5540    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    2.1979    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405    1.5376    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6754    0.1649    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -0.4776    0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -0.9455   -1.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770   -0.3571   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683   -1.1394    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.1893   -1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.5126   -1.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684    0.3730   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048    1.2085    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3805    1.6900    1.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763    1.3542    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182    1.8565    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    0.5171   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.0414   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425   -1.8845    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -2.6547    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627   -3.1576   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -1.6895   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    0.6191   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.5438    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166    2.0886    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563    3.2797    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5390    2.0539    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953   -0.3774    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -1.5684    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463   -1.3483   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033    0.7012   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346   -2.2217    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -1.0674    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -0.7819    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907    0.3524   -2.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -1.9047   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2905    1.4821    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541    2.3481    2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567    1.6151    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974    0.2710   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908   -0.6109   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END


  Mrv0541 05261414302D          

 22 23  0  0  0  0            999 V2000
    0.7144    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    3.7125    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
    2.8578    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    2.4750    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
   -3.5723    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8578    0.8250    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
    0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    2.4750    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
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 13  1  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17  6  2  0  0  0  0
 17  7  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 18  1  0  0  0  0
 22 12  1  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253715

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(COC1=CC=CC=C1)NC(C)C(O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H23NO3/c1-13(12-22-17-6-4-3-5-7-17)19-14(2)18(21)15-8-10-16(20)11-9-15/h3-11,13-14,18-21H,12H2,1-2H3

> <INCHI_KEY>
BMUKKTUHUDJSNZ-UHFFFAOYSA-N

> <FORMULA>
C18H23NO3

> <MOLECULAR_WEIGHT>
301.3801

> <EXACT_MASS>
301.167793607

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.32084919628475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{1-hydroxy-2-[(1-phenoxypropan-2-yl)amino]propyl}phenol

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.564600513061784

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.029563160093545

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.651482674333462

> <JCHEM_PKA_STRONGEST_BASIC>
8.997586357485336

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
86.6392

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoxsuprine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253715
     RDKit          3D
isoxsuprine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -1.2720   -2.2819    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587   -1.2371   -1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -0.0590   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2943   -0.5718   -0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3701    0.1879    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344    1.5540    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    2.1979    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405    1.5376    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6754    0.1649    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -0.4776    0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -0.9455   -1.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770   -0.3571   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683   -1.1394    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.1893   -1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.5126   -1.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684    0.3730   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048    1.2085    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3805    1.6900    1.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763    1.3542    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182    1.8565    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    0.5171   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.0414   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425   -1.8845    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -2.6547    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627   -3.1576   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -1.6895   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    0.6191   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.5438    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166    2.0886    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563    3.2797    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5390    2.0539    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953   -0.3774    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -1.5684    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463   -1.3483   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033    0.7012   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346   -2.2217    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -1.0674    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -0.7819    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907    0.3524   -2.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -1.9047   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2905    1.4821    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541    2.3481    2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567    1.6151    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974    0.2710   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908   -0.6109   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

HEADER    PROTEIN                                 26-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-14         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   17                                                       
CONECT    7    5   17                                                       
CONECT    8   10   15                                                       
CONECT    9   11   15                                                       
CONECT   10    8   16                                                       
CONECT   11    9   16                                                       
CONECT   12   13   22                                                       
CONECT   13    1   12   19                                                  
CONECT   14    2   18   19                                                  
CONECT   15    8    9   18                                                  
CONECT   16   10   11   20                                                  
CONECT   17    6    7   22                                                  
CONECT   18   14   15   21                                                  
CONECT   19   13   14                                                       
CONECT   20   16                                                            
CONECT   21   18                                                            
CONECT   22   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0253715
HETATM    1  C1  UNL     1      -1.272  -2.282   0.031  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.159  -1.237  -1.046  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.025  -0.059  -0.665  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.294  -0.572  -0.317  1.00  0.00           O  
HETATM    5  C4  UNL     1      -4.370   0.188   0.107  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.334   1.554   0.242  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.473   2.198   0.674  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.640   1.538   0.978  1.00  0.00           C  
HETATM    9  C8  UNL     1      -6.675   0.165   0.843  1.00  0.00           C  
HETATM   10  C9  UNL     1      -5.536  -0.478   0.410  1.00  0.00           C  
HETATM   11  N1  UNL     1       0.145  -0.946  -1.401  1.00  0.00           N  
HETATM   12  C10 UNL     1       1.077  -0.357  -0.542  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.468  -1.139   0.667  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.381  -0.189  -1.362  1.00  0.00           C  
HETATM   15  O2  UNL     1       2.723  -1.513  -1.703  1.00  0.00           O  
HETATM   16  C13 UNL     1       3.468   0.373  -0.545  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.305   1.209   0.539  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.381   1.690   1.271  1.00  0.00           C  
HETATM   19  C16 UNL     1       5.676   1.354   0.949  1.00  0.00           C  
HETATM   20  O3  UNL     1       6.718   1.857   1.706  1.00  0.00           O  
HETATM   21  C17 UNL     1       5.857   0.517  -0.136  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.788   0.041  -0.861  1.00  0.00           C  
HETATM   23  H1  UNL     1      -0.942  -1.885   0.998  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.333  -2.655   0.117  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.663  -3.158  -0.274  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.681  -1.689  -1.950  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.191   0.619  -1.535  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.664   0.544   0.161  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.417   2.089   0.005  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.456   3.280   0.785  1.00  0.00           H  
HETATM   31  H9  UNL     1      -7.539   2.054   1.320  1.00  0.00           H  
HETATM   32  H10 UNL     1      -7.595  -0.377   1.081  1.00  0.00           H  
HETATM   33  H11 UNL     1      -5.613  -1.568   0.319  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.546  -1.348  -2.262  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.803   0.701  -0.304  1.00  0.00           H  
HETATM   36  H14 UNL     1       1.335  -2.222   0.482  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.591  -1.067   0.866  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.037  -0.782   1.623  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.191   0.352  -2.291  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.394  -1.905  -1.107  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.290   1.482   0.805  1.00  0.00           H  
HETATM   42  H20 UNL     1       4.154   2.348   2.116  1.00  0.00           H  
HETATM   43  H21 UNL     1       7.657   1.615   1.476  1.00  0.00           H  
HETATM   44  H22 UNL     1       6.897   0.271  -0.363  1.00  0.00           H  
HETATM   45  H23 UNL     1       4.991  -0.611  -1.702  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   11   26
CONECT    3    4   27   28
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   33
CONECT   11   12   34
CONECT   12   13   14   35
CONECT   13   36   37   38
CONECT   14   15   16   39
CONECT   15   40
CONECT   16   17   17   22
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   21
CONECT   20   43
CONECT   21   22   22   44
CONECT   22   45
END

HMDB0253715
     RDKit          3D
isoxsuprine
 45 46  0  0  0  0  0  0  0  0999 V2000
   -1.2720   -2.2819    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1587   -1.2371   -1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -0.0590   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2943   -0.5718   -0.3169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3701    0.1879    0.1074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344    1.5540    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4727    2.1979    0.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6405    1.5376    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6754    0.1649    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361   -0.4776    0.4098 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453   -0.9455   -1.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0770   -0.3571   -0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683   -1.1394    0.6672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -0.1893   -1.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.5126   -1.7027 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4684    0.3730   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048    1.2085    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3805    1.6900    1.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6763    1.3542    0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182    1.8565    1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8566    0.5171   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.0414   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425   -1.8845    0.9977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3333   -2.6547    0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6627   -3.1576   -0.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809   -1.6895   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1912    0.6191   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640    0.5438    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4166    2.0886    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563    3.2797    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5390    2.0539    1.3201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5953   -0.3774    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6127   -1.5684    0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5463   -1.3483   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8033    0.7012   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346   -2.2217    0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909   -1.0674    0.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -0.7819    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1907    0.3524   -2.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -1.9047   -1.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2905    1.4821    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541    2.3481    2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6567    1.6151    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8974    0.2710   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9908   -0.6109   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 10  5  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dilator	Kegg
Duvadilan	MeSH
Hydrochloride, isoxsuprine	MeSH
Isoxsuprine hydrochloride	MeSH

Chemical Formula

C₁₈H₂₃NO₃

Average Molecular Weight

301.3801

Monoisotopic Molecular Weight

301.167793607

IUPAC Name

4-{1-hydroxy-2-[(1-phenoxypropan-2-yl)amino]propyl}phenol

Traditional Name

isoxsuprine

CAS Registry Number

Not Available

SMILES

CC(COC1=CC=CC=C1)NC(C)C(O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H23NO3/c1-13(12-22-17-6-4-3-5-7-17)19-14(2)18(21)15-8-10-16(20)11-9-15/h3-11,13-14,18-21H,12H2,1-2H3

InChI Key

BMUKKTUHUDJSNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Ether
Secondary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic nitrogen compound
Amine
Hydrocarbon derivative
Aromatic alcohol
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)

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	2.06	ALOGPS
logP	2.56	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.64 m³·mol⁻¹	ChemAxon
Polarizability	33.32 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]+	176.542	30932474
DeepCCS	[M-H]-	174.184	30932474
DeepCCS	[M-2H]-	207.07	30932474
DeepCCS	[M+Na]+	182.635	30932474
AllCCS	[M+H]+	177.0	32859911
AllCCS	[M+H-H2O]+	173.6	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	176.7	32859911
AllCCS	[M+Na-2H]-	176.9	32859911
AllCCS	[M+HCOO]-	177.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
isoxsuprine	CC(COC1=CC=CC=C1)NC(C)C(O)C1=CC=C(O)C=C1	3472.9	Standard polar	33892256
isoxsuprine	CC(COC1=CC=CC=C1)NC(C)C(O)C1=CC=C(O)C=C1	2502.7	Standard non polar	33892256
isoxsuprine	CC(COC1=CC=CC=C1)NC(C)C(O)C1=CC=C(O)C=C1	2620.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
isoxsuprine,3TMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2609.3	Semi standard non polar	33892256
isoxsuprine,3TMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2422.4	Standard non polar	33892256
isoxsuprine,3TMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2868.7	Standard polar	33892256
isoxsuprine,3TBDMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3274.3	Semi standard non polar	33892256
isoxsuprine,3TBDMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3023.0	Standard non polar	33892256
isoxsuprine,3TBDMS,isomer #1	CC(COC1=CC=CC=C1)N(C(C)C(O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3128.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-5910000000-ffc79183515c370e5242	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoxsuprine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 10V, Positive-QTOF	splash10-0udi-0029000000-cb172e8986ecd8060795	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 20V, Positive-QTOF	splash10-001i-0590000000-6139a4cea70d37915aea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 40V, Positive-QTOF	splash10-0a4i-3900000000-c7c2326d44c34b92d455	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 30V, Positive-QTOF	splash10-0a4i-1900000000-3f8993d6227fb966f431	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 50V, Positive-QTOF	splash10-056r-7900000000-4fbb8e4efd83a3a10022	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 50V, Positive-QTOF	splash10-056r-7900000000-c4de5913bea355139432	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoxsuprine 30V, Positive-QTOF	splash10-0a4i-1900000000-860f3fc642e9bf250c53	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 10V, Positive-QTOF	splash10-0f89-0196000000-bfa4807368a6620164e5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 20V, Positive-QTOF	splash10-001i-1951000000-8758e206e0e9b2179fba	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 40V, Positive-QTOF	splash10-0pc3-9400000000-1c46b8ddc7edb185a11f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 10V, Negative-QTOF	splash10-0udi-3019000000-6e05ff9353b0d2a22ea0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 20V, Negative-QTOF	splash10-0006-9111000000-c3a9626855aae5a1510f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 40V, Negative-QTOF	splash10-0006-9000000000-9abedd05e1a1770b3826	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 10V, Positive-QTOF	splash10-0ue9-0559000000-36fd3b1112b31ef3a6d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 20V, Positive-QTOF	splash10-004i-0910000000-b2728bccdde6eb381ed6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 40V, Positive-QTOF	splash10-004i-9810000000-3c5b0a4cb07138e5ae14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 10V, Negative-QTOF	splash10-0zfr-3498000000-54182365114f3bfb0bc9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 20V, Negative-QTOF	splash10-0006-9441000000-575b23deb86d993628cd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoxsuprine 40V, Negative-QTOF	splash10-0006-9110000000-3f6db56416bad92731c2	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

3651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Isoxsuprine

METLIN ID

Not Available

PubChem Compound

3783

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 Isoxsuprine (HMDB0253715)

MOL for HMDB0253715 (Isoxsuprine)

3D MOL for HMDB0253715 (Isoxsuprine)

3D SDF for HMDB0253715 (Isoxsuprine)

3D-SDF for HMDB0253715 (Isoxsuprine)

PDB for HMDB0253715 (Isoxsuprine)

3D PDB for HMDB0253715 (Isoxsuprine)

SMILES for HMDB0253715 (Isoxsuprine)

INCHI for HMDB0253715 (Isoxsuprine)

Structure for HMDB0253715 (Isoxsuprine)

3D Structure for HMDB0253715 (Isoxsuprine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra