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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:09:43 UTC

Update Date

2021-09-14 15:48:01 UTC

HMDB ID

HMDB0060962

Secondary Accession Numbers

HMDB60962

Metabolite Identification

Common Name

3-hydroxyropivacaine

Description

3-hydroxyropivacaine belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 3-hydroxyropivacaine is a very strong basic compound (based on its pKa). The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin. Ropivacaine is a local anaesthetic drug belonging to the amino amide group. 3-hydroxyropivacaine is a metabolite of ropivacaine.

Structure

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

HMDB0060962
     RDKit          3D
3-hydroxyropivacaine
 47 48  0  0  0  0  0  0  0  0999 V2000
    3.5073    1.9663   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    1.9552   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.4360    0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9919    0.1180    1.2270 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -0.2831    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -1.6457    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.9243   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367   -1.5640   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -0.9164    0.9052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3245   -0.5331    0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -0.0485    2.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -0.6455   -0.0722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.3270   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850   -1.2894   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -2.6946    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.9803   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934    0.3118   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.3175   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    2.6073   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.9724   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    2.0455   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    0.9755   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    2.6119   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143    2.4593    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182    1.4846   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    3.0347   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    1.6068    1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827    2.1102    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.4663    2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    0.4207    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -1.6515    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.4595    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3760   -1.3491   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626   -2.9896   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -0.8730   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -2.4904   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.7224    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528   -0.6778    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -2.7324    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -3.1376   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622   -3.2904    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -1.7271   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1470    0.5639   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    3.3766   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.7278   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    1.6534   -0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7387    2.6632    0.3668 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 13 14  2  0
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 18 20  2  0
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  9  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
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  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 11 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
M  END


  Mrv0541 07091309092D          

 21 22  0  0  0  0            999 V2000
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 13  3  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 14 17  1  6  0  0  0
 18 16  1  4  0  0  0
 18 17  2  0  0  0  0
 19 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060962

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C17H26N2O2/c1-4-10-19-11-6-5-7-14(19)17(21)18-16-12(2)8-9-15(20)13(16)3/h8-9,14,20H,4-7,10-11H2,1-3H3,(H,18,21)/t14-/m1/s1

> <INCHI_KEY>
IXOVDWXTIIYVOJ-CQSZACIVSA-N

> <FORMULA>
C17H26N2O2

> <MOLECULAR_WEIGHT>
290.4005

> <EXACT_MASS>
290.199428086

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.4845024330977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.4341756808487647

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
10.276279530391717

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590445608020404

> <JCHEM_PKA_STRONGEST_BASIC>
8.515635019251688

> <JCHEM_POLAR_SURFACE_AREA>
56.06

> <JCHEM_REFRACTIVITY>
88.3283

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060962
     RDKit          3D
3-hydroxyropivacaine
 47 48  0  0  0  0  0  0  0  0999 V2000
    3.5073    1.9663   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    1.9552   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.4360    0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9919    0.1180    1.2270 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -0.2831    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -1.6457    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.9243   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367   -1.5640   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -0.9164    0.9052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3245   -0.5331    0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -0.0485    2.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -0.6455   -0.0722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.3270   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850   -1.2894   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -2.6946    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.9803   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934    0.3118   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.3175   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    2.6073   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.9724   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    2.0455   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    0.9755   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    2.6119   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143    2.4593    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182    1.4846   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    3.0347   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    1.6068    1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827    2.1102    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.4663    2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    0.4207    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -1.6515    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.4595    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3760   -1.3491   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626   -2.9896   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -0.8730   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -2.4904   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.7224    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528   -0.6778    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -2.7324    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -3.1376   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622   -3.2904    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -1.7271   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1470    0.5639   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    3.3766   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.7278   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    1.6534   -0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7387    2.6632    0.3668 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  3
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  9  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 11 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.000  10.780   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.667   9.240   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    1   10                                                       
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   14                                                       
CONECT    8    9   12                                                       
CONECT    9    8   15                                                       
CONECT   10    4   19                                                       
CONECT   11    6   19                                                       
CONECT   12    2    8   16                                                  
CONECT   13    3   15   16                                                  
CONECT   14    7   17   19                                                  
CONECT   15    9   13   20                                                  
CONECT   16   12   13   18                                                  
CONECT   17   14   18   21                                                  
CONECT   18   16   17                                                       
CONECT   19   10   11   14                                                  
CONECT   20   15                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0060962
HETATM    1  C1  UNL     1       3.507   1.966  -0.793  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.060   1.955  -0.448  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.687   1.436   0.883  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.992   0.118   1.227  1.00  0.00           N  
HETATM    5  C4  UNL     1       3.326  -0.283   1.432  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.633  -1.646   0.825  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.884  -1.924  -0.435  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.437  -1.564  -0.415  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.079  -0.916   0.905  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.325  -0.533   0.969  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.862  -0.048   2.146  1.00  0.00           O  
HETATM   12  N2  UNL     1      -1.069  -0.646  -0.072  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.422  -0.327  -0.178  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.385  -1.289  -0.059  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.984  -2.695   0.176  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.722  -0.980  -0.156  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.093   0.312  -0.375  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.156   1.317  -0.501  1.00  0.00           C  
HETATM   19  O2  UNL     1      -4.604   2.607  -0.721  1.00  0.00           O  
HETATM   20  C16 UNL     1      -2.818   0.972  -0.399  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.815   2.046  -0.545  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.909   0.976  -1.089  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.710   2.612  -1.702  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.114   2.459   0.003  1.00  0.00           H  
HETATM   25  H4  UNL     1       1.518   1.485  -1.295  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.720   3.035  -0.484  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.585   1.607   1.079  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.183   2.110   1.655  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.430  -0.466   2.553  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.123   0.421   1.205  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.714  -1.651   0.584  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.369  -2.460   1.544  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.376  -1.349  -1.268  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.063  -2.990  -0.693  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.120  -0.873  -1.220  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.829  -2.490  -0.570  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.218  -1.722   1.693  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.353  -0.678   2.762  1.00  0.00           H  
HETATM   39  H18 UNL     1      -2.071  -2.732   0.810  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.788  -3.138  -0.832  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.762  -3.290   0.661  1.00  0.00           H  
HETATM   42  H21 UNL     1      -5.493  -1.727  -0.066  1.00  0.00           H  
HETATM   43  H22 UNL     1      -6.147   0.564  -0.453  1.00  0.00           H  
HETATM   44  H23 UNL     1      -3.992   3.377  -0.817  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.168   2.728  -1.363  1.00  0.00           H  
HETATM   46  H25 UNL     1      -0.818   1.653  -0.838  1.00  0.00           H  
HETATM   47  H26 UNL     1      -1.739   2.663   0.367  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5    9
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37
CONECT   10   11   12   12
CONECT   11   38
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   16
CONECT   15   39   40   41
CONECT   16   17   17   42
CONECT   17   18   43
CONECT   18   19   20   20
CONECT   19   44
CONECT   20   21
CONECT   21   45   46   47
END

HMDB0060962
     RDKit          3D
3-hydroxyropivacaine
 47 48  0  0  0  0  0  0  0  0999 V2000
    3.5073    1.9663   -0.7932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0596    1.9552   -0.4484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6865    1.4360    0.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9919    0.1180    1.2270 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3261   -0.2831    1.4318 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -1.6457    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842   -1.9243   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367   -1.5640   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -0.9164    0.9052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3245   -0.5331    0.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8620   -0.0485    2.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694   -0.6455   -0.0722 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4221   -0.3270   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850   -1.2894   -0.0593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9838   -2.6946    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.9803   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0934    0.3118   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.3175   -0.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6038    2.6073   -0.7210 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8182    0.9724   -0.3990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    2.0455   -0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087    0.9755   -1.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099    2.6119   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1143    2.4593    0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5182    1.4846   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    3.0347   -0.4840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853    1.6068    1.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827    2.1102    1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305   -0.4663    2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1231    0.4207    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -1.6515    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3686   -2.4595    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3760   -1.3491   -1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626   -2.9896   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -0.8730   -1.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -2.4904   -0.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2175   -1.7224    1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3528   -0.6778    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708   -2.7324    0.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7883   -3.1376   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7622   -3.2904    0.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4930   -1.7271   -0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1470    0.5639   -0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9922    3.3766   -0.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.7278   -1.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8176    1.6534   -0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7387    2.6632    0.3668 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  3
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  9  4  1  0
 20 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 11 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 19 44  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₆N₂O₂

Average Molecular Weight

290.4005

Monoisotopic Molecular Weight

290.199428086

IUPAC Name

(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid

Traditional Name

(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C

InChI Identifier

InChI=1S/C17H26N2O2/c1-4-10-19-11-6-5-7-14(19)17(21)18-16-12(2)8-9-15(20)13(16)3/h8-9,14,20H,4-7,10-11H2,1-3H3,(H,18,21)/t14-/m1/s1

InChI Key

IXOVDWXTIIYVOJ-CQSZACIVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
2-piperidinecarboxamide
Piperidinecarboxamide
Anilide
Xylenol
M-xylene
Xylene
P-cresol
N-arylamide
O-cresol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Piperidine
Benzenoid
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060962)
Liver (HMDB: HMDB0060962)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060962)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060962)

Cellular substructure

Cytoplasm (HMDB: HMDB0060962)
Membrane (HMDB: HMDB0060962)

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	0.23 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.43	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	8.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.33 m³·mol⁻¹	ChemAxon
Polarizability	33.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.813	31661259
DarkChem	[M-H]-	170.192	31661259
DeepCCS	[M+H]+	172.295	30932474
DeepCCS	[M-H]-	169.937	30932474
DeepCCS	[M-2H]-	202.834	30932474
DeepCCS	[M+Na]+	178.388	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.8	32859911
AllCCS	[M+NH4]+	174.2	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	174.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-hydroxyropivacaine	CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C	3067.4	Standard polar	33892256
3-hydroxyropivacaine	CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C	2422.5	Standard non polar	33892256
3-hydroxyropivacaine	CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C	2408.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-hydroxyropivacaine,1TMS,isomer #1	CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O)=C1C)O[Si](C)(C)C	2235.1	Semi standard non polar	33892256
3-hydroxyropivacaine,1TMS,isomer #2	CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O[Si](C)(C)C)=C1C	2266.9	Semi standard non polar	33892256
3-hydroxyropivacaine,2TMS,isomer #1	CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O[Si](C)(C)C)=C1C)O[Si](C)(C)C	2298.5	Semi standard non polar	33892256
3-hydroxyropivacaine,1TBDMS,isomer #1	CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O)=C1C)O[Si](C)(C)C(C)(C)C	2424.5	Semi standard non polar	33892256
3-hydroxyropivacaine,1TBDMS,isomer #2	CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C	2471.7	Semi standard non polar	33892256
3-hydroxyropivacaine,2TBDMS,isomer #1	CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)O[Si](C)(C)C(C)(C)C	2690.1	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 - 3-hydroxyropivacaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-9810000000-7acf0f53478a7519055e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-hydroxyropivacaine GC-MS (2 TMS) - 70eV, Positive	splash10-05bb-9331300000-19c714aa941ae4a57167	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-hydroxyropivacaine 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 - 3-hydroxyropivacaine 10V, Positive-QTOF	splash10-000f-0970000000-54ae3bdef9ba245c7389	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Positive-QTOF	splash10-004r-2900000000-87e117fede1bb2be7a8a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Positive-QTOF	splash10-000x-9300000000-8dc96f8f7acca723ad63	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Negative-QTOF	splash10-000i-0190000000-44e36d2dfbc547648366	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Negative-QTOF	splash10-000i-0960000000-1fd4fefe9f449f37afa6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Negative-QTOF	splash10-0a5i-7900000000-bee7afe3c30b774e2ba6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Positive-QTOF	splash10-0006-0490000000-2116bdfdf05c5f6e7f79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Positive-QTOF	splash10-004i-1920000000-51d5b249484b24038424	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Positive-QTOF	splash10-004j-4900000000-1eaa9f83312df113715e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Negative-QTOF	splash10-000i-0090000000-3f77951545ee2559c16a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Negative-QTOF	splash10-000i-1890000000-06bd65d148e83e1e45ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Negative-QTOF	splash10-001i-2920000000-d609ce666238ccb26169	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

93486072

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 3-hydroxyropivacaine (HMDB0060962)

MOL for HMDB0060962 (3-hydroxyropivacaine)

3D MOL for HMDB0060962 (3-hydroxyropivacaine)

3D SDF for HMDB0060962 (3-hydroxyropivacaine)

3D-SDF for HMDB0060962 (3-hydroxyropivacaine)

PDB for HMDB0060962 (3-hydroxyropivacaine)

3D PDB for HMDB0060962 (3-hydroxyropivacaine)

SMILES for HMDB0060962 (3-hydroxyropivacaine)

INCHI for HMDB0060962 (3-hydroxyropivacaine)

Structure for HMDB0060962 (3-hydroxyropivacaine)

3D Structure for HMDB0060962 (3-hydroxyropivacaine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra