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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 00:36:42 UTC

Update Date

2021-09-24 00:36:42 UTC

HMDB ID

HMDB0303264

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-Monomenthyl glutarate

Description

5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoic acid belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review very few articles have been published on 5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoic acid.

Structure

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

HMDB0303264
     RDKit          3D
L-Monomenthyl glutarate
 45 45  0  0  0  0  0  0  0  0999 V2000
   -1.2683   -1.7801   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.6698   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -2.3578   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875   -0.2313    0.3079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8532    0.5789   -0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957    1.9294    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    2.6295    0.3233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    3.8847    1.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372    1.7380    1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676    0.4864    0.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3698   -0.2897    0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528   -0.5533    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730   -0.0792   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518   -1.3699    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147   -1.6271    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.3732   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.7431   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312   -1.5343   -0.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -0.2024   -2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -2.6627   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.0038   -2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -0.8350   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -2.1673    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -3.4323   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6048   -2.3470    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -1.9131   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -0.1986    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.1165   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    0.7707   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.8036    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    2.5375   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    2.9009   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    3.5909    2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    4.6374    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614    4.3405    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6360    1.4454    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.2612    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    0.7978   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.3692    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.9053    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -2.1645   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672   -2.2625    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    0.2996   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    0.1668    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.8433   -2.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END


  Mrv1533007151515362D          

 22 22  0  0  1  0            999 V2000
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    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
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  1  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  6  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 13 19  1  1  0  0  0
 19 15  1  0  0  0  0
 11 20  1  6  0  0  0
 12 21  1  1  0  0  0
 13 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303264

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@@]([H])(C1)OC(=O)CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O4/c1-10(2)12-8-7-11(3)9-13(12)19-15(18)6-4-5-14(16)17/h10-13H,4-9H2,1-3H3,(H,16,17)/t11-,12+,13-/m1/s1

> <INCHI_KEY>
CTMTYSVTTGVYAW-FRRDWIJNSA-N

> <FORMULA>
C15H26O4

> <MOLECULAR_WEIGHT>
270.369

> <EXACT_MASS>
270.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
31.093961485085998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoic acid

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.3748299693333337

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0736904408033325

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042305123627909

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
72.0911

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303264
     RDKit          3D
L-Monomenthyl glutarate
 45 45  0  0  0  0  0  0  0  0999 V2000
   -1.2683   -1.7801   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.6698   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -2.3578   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875   -0.2313    0.3079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8532    0.5789   -0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957    1.9294    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    2.6295    0.3233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    3.8847    1.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372    1.7380    1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676    0.4864    0.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3698   -0.2897    0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528   -0.5533    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730   -0.0792   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518   -1.3699    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147   -1.6271    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.3732   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.7431   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312   -1.5343   -0.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -0.2024   -2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -2.6627   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.0038   -2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -0.8350   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -2.1673    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -3.4323   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6048   -2.3470    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -1.9131   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -0.1986    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.1165   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    0.7707   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.8036    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    2.5375   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    2.9009   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    3.5909    2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    4.6374    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614    4.3405    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6360    1.4454    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.2612    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    0.7978   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.3692    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.9053    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -2.1645   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672   -2.2625    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    0.2996   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    0.1668    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.8433   -2.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 15-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUL-15         0                                  
HETATM    1  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       4.001   3.850   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       9.336   3.850   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       8.002   6.160   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4   14                                                       
CONECT    6    4   15                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   11   13                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3    7    9   20                                             
CONECT   12    8   10   13   21                                             
CONECT   13    9   12   19   22                                             
CONECT   14    5   16   17                                                  
CONECT   15    6   18   19                                                  
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   13   15                                                       
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0303264
HETATM    1  C1  UNL     1      -1.268  -1.780  -1.475  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.866  -1.670  -0.110  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.194  -2.358  -0.053  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.987  -0.231   0.308  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.853   0.579  -0.627  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.096   1.929   0.033  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.800   2.629   0.323  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.114   3.885   1.107  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.937   1.738   1.230  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.668   0.486   0.421  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.370  -0.290   0.967  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.553  -0.553   0.275  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.673  -0.079  -0.866  1.00  0.00           O  
HETATM   14  C12 UNL     1       2.552  -1.370   0.959  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.815  -1.627   0.203  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.554  -0.373  -0.155  1.00  0.00           C  
HETATM   17  C15 UNL     1       5.795  -0.743  -0.877  1.00  0.00           C  
HETATM   18  O3  UNL     1       6.631  -1.534  -0.337  1.00  0.00           O  
HETATM   19  O4  UNL     1       6.003  -0.202  -2.144  1.00  0.00           O  
HETATM   20  H1  UNL     1      -0.580  -2.663  -1.487  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.121  -2.004  -2.181  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.780  -0.835  -1.777  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.199  -2.167   0.636  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.041  -3.432  -0.319  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.605  -2.347   0.987  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.902  -1.913  -0.767  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.498  -0.199   1.314  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.798   0.116  -0.895  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.243   0.771  -1.535  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.648   1.804   0.964  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.669   2.538  -0.700  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.256   2.901  -0.600  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.255   3.591   2.159  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.293   4.637   1.040  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.061   4.341   0.713  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.636   1.445   2.058  1.00  0.00           H  
HETATM   37  H18 UNL     1      -0.047   2.261   1.567  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.358   0.798  -0.597  1.00  0.00           H  
HETATM   39  H20 UNL     1       2.100  -2.369   1.218  1.00  0.00           H  
HETATM   40  H21 UNL     1       2.809  -0.905   1.958  1.00  0.00           H  
HETATM   41  H22 UNL     1       3.536  -2.164  -0.737  1.00  0.00           H  
HETATM   42  H23 UNL     1       4.467  -2.263   0.825  1.00  0.00           H  
HETATM   43  H24 UNL     1       3.936   0.300  -0.760  1.00  0.00           H  
HETATM   44  H25 UNL     1       4.831   0.167   0.799  1.00  0.00           H  
HETATM   45  H26 UNL     1       6.146  -0.843  -2.935  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4   23
CONECT    3   24   25   26
CONECT    4    5   10   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    9   32
CONECT    8   33   34   35
CONECT    9   10   36   37
CONECT   10   11   38
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   18   19
CONECT   19   45
END

HMDB0303264
     RDKit          3D
L-Monomenthyl glutarate
 45 45  0  0  0  0  0  0  0  0999 V2000
   -1.2683   -1.7801   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8658   -1.6698   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936   -2.3578   -0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875   -0.2313    0.3079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8532    0.5789   -0.6275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0957    1.9294    0.0329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    2.6295    0.3233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    3.8847    1.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372    1.7380    1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6676    0.4864    0.4213 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3698   -0.2897    0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528   -0.5533    0.2746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730   -0.0792   -0.8660 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518   -1.3699    0.9591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147   -1.6271    0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541   -0.3732   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7951   -0.7431   -0.8774 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6312   -1.5343   -0.3373 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0033   -0.2024   -2.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -2.6627   -1.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1210   -2.0038   -2.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -0.8350   -1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1986   -2.1673    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0413   -3.4323   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6048   -2.3470    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9017   -1.9131   -0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4977   -0.1986    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7980    0.1165   -0.8951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2427    0.7707   -1.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    1.8036    0.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687    2.5375   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    2.9009   -0.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    3.5909    2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2929    4.6374    1.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0614    4.3405    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6360    1.4454    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.2612    1.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    0.7978   -0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -2.3692    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.9053    1.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -2.1645   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4672   -2.2625    0.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362    0.2996   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8314    0.1668    0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1459   -0.8433   -2.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 10  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  6
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoate	Generator
L-Monomenthyl glutaric acid	Generator
Monomenthyl glutarate	MeSH

Chemical Formula

C₁₅H₂₆O₄

Average Molecular Weight

270.369

Monoisotopic Molecular Weight

270.183109317

IUPAC Name

5-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}-5-oxopentanoic acid

Traditional Name

5-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl]oxy}-5-oxopentanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@@]([H])(C1)OC(=O)CCCC(O)=O

InChI Identifier

InChI=1S/C15H26O4/c1-10(2)12-8-7-11(3)9-13(12)19-15(18)6-4-5-14(16)17/h10-13H,4-9H2,1-3H3,(H,16,17)/t11-,12+,13-/m1/s1

InChI Key

CTMTYSVTTGVYAW-FRRDWIJNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

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	3.14	ALOGPS
logP	3.37	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.09 m³·mol⁻¹	ChemAxon
Polarizability	31.09 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
AllCCS	[M+H]+	167.446	32859911
AllCCS	[M+H-H2O]+	164.318	32859911
AllCCS	[M+Na]+	171.175	32859911
AllCCS	[M+NH4]+	170.343	32859911
AllCCS	[M-H]-	168.136	32859911
AllCCS	[M+Na-2H]-	168.876	32859911
AllCCS	[M+HCOO]-	169.807	32859911
DeepCCS	[M+H]+	175.939	30932474
DeepCCS	[M-H]-	173.58	30932474
DeepCCS	[M-2H]-	207.064	30932474
DeepCCS	[M+Na]+	182.132	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 10V, Positive-QTOF	splash10-0fki-2590000000-0c9d72f2695da63d5b3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 20V, Positive-QTOF	splash10-0ap0-9830000000-52a3999dce2a88f4d504	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 40V, Positive-QTOF	splash10-066r-9300000000-d9d145576dc7361353e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 10V, Negative-QTOF	splash10-014i-0690000000-1853d4de0b9a323aada9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 20V, Negative-QTOF	splash10-0a4i-2930000000-105276534ae9916edcd0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 40V, Negative-QTOF	splash10-0a4r-4900000000-34cc686979d4923c2fc0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 10V, Negative-QTOF	splash10-014i-0190000000-b865834c86ab4ed69af5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 20V, Negative-QTOF	splash10-0a4l-9700000000-e277199a35e5d5531a95	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 40V, Negative-QTOF	splash10-0007-9100000000-5ee3c93d09c571328c8b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 10V, Positive-QTOF	splash10-000b-9420000000-fcaed007ab3bf64e7163	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 20V, Positive-QTOF	splash10-00kb-9310000000-af6ce82d1fae5182012e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Monomenthyl glutarate 40V, Positive-QTOF	splash10-00kf-9100000000-2c9cce399c71df58aa44	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009910

KNApSAcK ID

Not Available

Chemspider ID

23350365

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24752885

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 L-Monomenthyl glutarate (HMDB0303264)

MOL for HMDB0303264 (L-Monomenthyl glutarate)

3D MOL for HMDB0303264 (L-Monomenthyl glutarate)

3D SDF for HMDB0303264 (L-Monomenthyl glutarate)

3D-SDF for HMDB0303264 (L-Monomenthyl glutarate)

PDB for HMDB0303264 (L-Monomenthyl glutarate)

3D PDB for HMDB0303264 (L-Monomenthyl glutarate)

SMILES for HMDB0303264 (L-Monomenthyl glutarate)

INCHI for HMDB0303264 (L-Monomenthyl glutarate)

Structure for HMDB0303264 (L-Monomenthyl glutarate)

3D Structure for HMDB0303264 (L-Monomenthyl glutarate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra