NP-MRD: Showing NP-Card for (1S,2S,5R)-(+)-Neomenthol (NP0002762)

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Record Information

Version

1.0

Created at

2020-11-23 19:39:46 UTC

Updated at

2021-08-19 23:59:19 UTC

NP-MRD ID

NP0002762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,2S,5R)-(+)-Neomenthol

Provided By

BMRB

Description

(+)-Neomenthol, also known as fema 2666, 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. Thus, (+)-neomenthol is considered to be an isoprenoid (+)-Neomenthol exists in all living organisms, ranging from bacteria to humans (+)-Neomenthol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (1S,2S,5R)-(+)-Neomenthol is found in Agathosma betulina, Clinopodium brownei, Clinopodium serpyllifolium, Mentha piperita, Mentha canadensis, Mentha verticillata, Minthostachys mollis, Pycnanthemum floridanum and Rhanterium epapposum. It was first documented in 2000 (PMID: 11413487). Based on a literature review a small amount of articles have been published on (+)-Neomenthol (PMID: 16902246) (PMID: 17374880) (PMID: 20044567) (PMID: 17984079).

Structure

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


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.5847   -1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031    0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857    0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -2.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7956   -1.7932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662   -2.4188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    1.1988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042    2.3108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    0.1596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7684    1.5097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0489   -1.1210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605    1.3786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    2.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    3.0051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402    2.5775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    1.9121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -1.3734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2099    1.4525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0110   -0.5117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -1.0669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006   -2.2994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -2.5887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274   -3.6493    0.0000 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
 10  4  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  6
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  1
  5 21  1  0
  6 22  1  6
  6 23  1  0
  7 24  1  6
  8 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  6
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

NP0002762
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7914    1.1216   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -0.1466   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437   -1.0505    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    0.1955    0.4044 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1021    1.1233   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.4732   -1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.2933   -0.4024 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5009    0.4287   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -0.5633    0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651   -1.0016    0.8150 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0463   -2.0898    0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.8134    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.6357   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    0.8694   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294   -0.6012   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.4153    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -0.4753    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1410   -1.9117    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    0.7860    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    1.5448   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    2.0000    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    1.3099   -1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.1197   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141   -1.3085   -0.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9299    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.1990   -1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -0.2690   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -1.3476    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.4007    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648   -1.3094    1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -1.9281   -0.9305 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
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END


     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.5847   -1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031    0.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857    0.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6204   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1453    1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456    0.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9130   -0.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4800   -1.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -2.1611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7956   -1.7932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4369   -0.7948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662   -2.4188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    1.1988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042    2.3108    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8261    0.1596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7684    1.5097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0489   -1.1210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605    1.3786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4754    2.7158    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    3.0051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402    2.5775    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0585    1.9121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -1.3734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2099    1.4525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0110   -0.5117    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -1.0669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1006   -2.2994    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653   -2.5887    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5274   -3.6493    0.0000 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
 10  4  1  0
  1 12  1  6
  1 13  1  0
  1 14  1  0
  2 15  1  6
  3 16  1  6
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  1
  5 21  1  0
  6 22  1  6
  6 23  1  0
  7 24  1  6
  8 25  1  1
  8 26  1  0
  8 27  1  0
  9 28  1  6
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END
> <DATABASE_ID>
NP0002762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10+/m1/s1

> <INCHI_KEY>
NOOLISFMXDJSKH-UTLUCORTSA-N

> <FORMULA>
C10H20O

> <MOLECULAR_WEIGHT>
156.2652

> <EXACT_MASS>
156.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
19.399617166020654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.6642731470000007

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.54964736878105

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8087842408951696

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.4453

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-neomenthol

> <JCHEM_VEBER_RULE>
1

$$$$

NP0002762
     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7914    1.1216   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -0.1466   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437   -1.0505    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    0.1955    0.4044 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1021    1.1233   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.4732   -1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.2933   -0.4024 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5009    0.4287   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -0.5633    0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651   -1.0016    0.8150 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0463   -2.0898    0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.8134    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.6357   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    0.8694   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294   -0.6012   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.4153    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -0.4753    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1410   -1.9117    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    0.7860    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    1.5448   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    2.0000    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    1.3099   -1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.1197   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141   -1.3085   -0.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9299    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.1990   -1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -0.2690   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -1.3476    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.4007    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648   -1.3094    1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -1.9281   -0.9305 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
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

COMPND    NP0002762
HETATM    1  C1  UNL     1      -2.791   1.122  -0.313  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.990  -0.147  -0.154  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.744  -1.051   0.781  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.624   0.196   0.404  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.102   1.123  -0.521  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.230   0.473  -1.269  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.174  -0.293  -0.402  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.501   0.429  -0.218  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.616  -0.563   0.978  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.165  -1.002   0.815  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.046  -2.090   0.002  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.602   1.813   0.545  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.633   1.636  -1.260  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.891   0.869  -0.274  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.829  -0.601  -1.148  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.649  -1.415   0.215  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.058  -0.475   1.655  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.141  -1.912   1.112  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.832   0.786   1.346  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.596   1.545  -1.269  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.548   2.000   0.030  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.823   1.310  -1.737  1.00  0.00           H  
HETATM   23  H12 UNL     1       0.860  -0.120  -2.148  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.414  -1.308  -0.834  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.537   0.930   0.765  1.00  0.00           H  
HETATM   26  H15 UNL     1       3.546   1.199  -1.036  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.347  -0.269  -0.271  1.00  0.00           H  
HETATM   28  H17 UNL     1       2.181  -1.348   1.488  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.598   0.401   1.534  1.00  0.00           H  
HETATM   30  H19 UNL     1      -0.165  -1.309   1.845  1.00  0.00           H  
HETATM   31  H20 UNL     1      -0.144  -1.928  -0.931  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5   10   19
CONECT    5    6   20   21
CONECT    6    7   22   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30
CONECT   11   31
END

NP0002762
     RDKit          3D

31 31  0  0  0  0  0  0  0  0999 V2000
   -2.7914    1.1216   -0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -0.1466   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7437   -1.0505    0.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    0.1955    0.4044 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1021    1.1233   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    0.4732   -1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.2933   -0.4024 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5009    0.4287   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155   -0.5633    0.9777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651   -1.0016    0.8150 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0463   -2.0898    0.0024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    1.8134    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6334    1.6357   -1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907    0.8694   -0.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294   -0.6012   -1.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6488   -1.4153    0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0581   -0.4753    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1410   -1.9117    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8323    0.7860    1.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957    1.5448   -1.2692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5485    2.0000    0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8233    1.3099   -1.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8598   -0.1197   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141   -1.3085   -0.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5373    0.9299    0.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    1.1990   -1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3474   -0.2690   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811   -1.3476    1.4881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.4007    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648   -1.3094    1.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -1.9281   -0.9305 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
 10  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  1
  5 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  1
 11 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,2S,5R)-(+)-Neomenthol	HMDB
(1S,2S,5R)-2-Isopropyl-5-methylcyclohexanol	HMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexan-1-ol	HMDB
(1S,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanol	HMDB
D-Neomenthol	HMDB
FEMA 2666	HMDB

Chemical Formula

C₁₀H₂₀O

Average Mass

156.2652 Da

Monoisotopic Mass

156.15142 Da

IUPAC Name

(1S,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

Traditional Name

(+)-neomenthol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O

InChI Identifier

InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10+/m1/s1

InChI Key

NOOLISFMXDJSKH-UTLUCORTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agathosma betulina	LOTUS Database	35616633
Calamintha nepeta	KNApSAcK Database	22123792
Cannabis sativa	CannabisDB	Not Available
Clinopodium brownei	LOTUS Database	35616633
Clinopodium serpyllifolium	LOTUS Database	35616633
Cunila angustifolia	KNApSAcK Database	22123792
Mentha piperita	LOTUS Database	35616633
Mentha sachalinensis	LOTUS Database	35616633
Mentha verticillata	LOTUS Database	35616633
Minthostachys mollis	LOTUS Database	35616633
Pycnanthemum floridanum	LOTUS Database	35616633
Rhanterium epapposum	LOTUS Database	35616633

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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	-22.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	95.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	434.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.216 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.68	ALOGPS
logP	2.66	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.45 m³·mol⁻¹	ChemAxon
Polarizability	19.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035763

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439263

PDB ID

Not Available

ChEBI ID

15402

Good Scents ID

rw1060561

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]

Showing NP-Card for (1S,2S,5R)-(+)-Neomenthol (NP0002762)

MOL for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

3D MOL for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

3D SDF for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

3D-SDF for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

PDB for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

3D PDB for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

SMILES for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

INCHI for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

Structure for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)

3D Structure for NP0002762 ((1S,2S,5R)-(+)-Neomenthol)