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Showing NP-Card for (1R,2R,4R)-Dihydrocarveol (NP0002778)

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Record Information
Version1.0
Created at2020-11-23 19:40:12 UTC
Updated at2021-08-19 23:59:21 UTC
NP-MRD IDNP0002778
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1R,2R,4R)-Dihydrocarveol
Provided ByBMRBBMRB logo
DescriptionDihydroisocarveol 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, dihydroisocarveol is considered to be an isoprenoid. Dihydroisocarveol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (1R,2R,4R)-Dihydrocarveol is found in Calamintha nepeta , Ceratocystis coerulescens, Heracleum candicans , Houttuynia cordata , Houttuynia emeiensis, Lavandula angustifolia , Mentha spp. and Piper longum . It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on Dihydroisocarveol (PMID: 18640226).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002778 ((1R,2R,4R)-Dihydrocarveol)


     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.3356   -1.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8620    1.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8865   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8733    0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246    0.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995    0.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121   -2.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4059   -1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8105   -1.2656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350   -2.9530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.5149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    1.5034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626    2.4295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119   -2.0769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6680    0.8906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978    2.2925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.7240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    2.7071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    2.2101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079   -0.9655    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730    2.0066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6744    0.2582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100   -0.6295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -2.3822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -2.5908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684   -2.5739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  6
  5 19  1  0
  6 20  1  1
  6 21  1  0
  7 22  1  6
  8 23  1  6
  8 24  1  0
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  6
 11 29  1  0
M  END
Download

3D MOL for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

NP0002778
     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.1892   -1.2580    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663   -0.3391    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.0423   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185   -0.6622    0.0872 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1835   -0.5627   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.9491   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424    0.2548   -0.4440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2068   -0.2450    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    0.9771    0.5008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5111    2.1484   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459    0.1339    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.2804    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -0.9973    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    1.6922    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7539    1.0660   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    1.4546   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120   -1.7482    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -1.1875   -2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    0.4964   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -1.1998   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -1.8511   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.9282   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8815    0.6124    0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612   -1.0862   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8970   -0.5626    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6816    1.3226    1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    2.4895   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -0.5097    1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    0.8206    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0002778 ((1R,2R,4R)-Dihydrocarveol)


     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.3356   -1.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8620    1.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8865   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8733    0.8280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    1.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246    0.8051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995    0.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7114   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2121   -2.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4059   -1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8105   -1.2656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8350   -2.9530    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2760    0.5149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834    1.5034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3626    2.4295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4119   -2.0769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6680    0.8906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1978    2.2925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.7240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4065    2.7071    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    2.2101    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1079   -0.9655    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4730    2.0066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6744    0.2582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100   -0.6295    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -2.3822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3599   -2.5908    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684   -2.5739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  6
  5 19  1  0
  6 20  1  1
  6 21  1  0
  7 22  1  6
  8 23  1  6
  8 24  1  0
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  6
 11 29  1  0
M  END
> <DATABASE_ID>
NP0002778

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10-/m1/s1

> <INCHI_KEY>
KRCZYMFUWVJCLI-OPRDCNLKSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.99882465297455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.316627336

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.994600424312566

> <JCHEM_PKA_STRONGEST_BASIC>
-1.051561774405684

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.22279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-dihydrocarveol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

NP0002778
     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.1892   -1.2580    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663   -0.3391    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.0423   -0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8185   -0.6622    0.0872 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1835   -0.5627   -1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.9491   -1.0916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9424    0.2548   -0.4440 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2068   -0.2450    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0410    0.9771    0.5008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5111    2.1484   -0.0487 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459    0.1339    1.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462   -2.2804    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2302   -0.9973    0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    1.6922    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7539    1.0660   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0665    1.4546   -1.0924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120   -1.7482    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -1.1875   -2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1851    0.4964   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585   -1.1998   -2.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3552   -1.8511   -0.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    0.9282   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8815    0.6124    0.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612   -1.0862   -0.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8970   -0.5626    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6816    1.3226    1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    2.4895   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -0.5097    1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    0.8206    1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  9 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  1
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

PDB for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.485   4.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.485   2.800   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.849   2.030   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.849   0.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.485  -0.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.819   0.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.819   2.030   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.152   2.800   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.485  -1.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.849  -2.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.819  -2.590   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

COMPND    NP0002778
HETATM    1  C1  UNL     1       3.189  -1.258   0.309  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.266  -0.339   0.052  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.674   1.042  -0.278  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.819  -0.662   0.087  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.184  -0.563  -1.293  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.288  -0.949  -1.092  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.942   0.255  -0.444  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.207  -0.245   0.256  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.041   0.977   0.501  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.511   2.148  -0.049  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.046   0.134   1.081  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.846  -2.280   0.552  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.230  -0.997   0.276  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.627   1.692   0.629  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.754   1.066  -0.605  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.066   1.455  -1.092  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.712  -1.748   0.377  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.682  -1.188  -2.030  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.185   0.496  -1.648  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.759  -1.200  -2.063  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.355  -1.851  -0.430  1.00  0.00           H  
HETATM   22  H11 UNL     1      -2.239   0.928  -1.301  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.882   0.612   0.350  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.661  -1.086  -0.321  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.897  -0.563   1.273  1.00  0.00           H  
HETATM   26  H15 UNL     1      -1.682   1.323   1.365  1.00  0.00           H  
HETATM   27  H16 UNL     1      -1.113   2.490  -0.759  1.00  0.00           H  
HETATM   28  H17 UNL     1      -0.427  -0.510   1.878  1.00  0.00           H  
HETATM   29  H18 UNL     1       0.723   0.821   1.656  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8    9   22
CONECT    8   23   24   25
CONECT    9   10   11   26
CONECT   10   27
CONECT   11   28   29
END
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SMILES for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

C[C@@H]1CC[C@H](C[C@H]1O)C(C)=C
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INCHI for NP0002778 ((1R,2R,4R)-Dihydrocarveol)

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(1R,2R,4R)-DihydrocarveolChEBI
(1R,2R,5R)-5-Isopropenyl-2-methylcyclohexanolChEBI
(-)-DihydrocarveolKegg
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1R,2R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol
Traditional Name(-)-dihydrocarveol
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@H](C[C@H]1O)C(C)=C
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3/t8-,9-,10-/m1/s1
InChI KeyKRCZYMFUWVJCLI-OPRDCNLKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calamintha nepetaPlant
Ceratocystis coerulescensFungi
Heracleum candicansPlant
Houttuynia cordataPlant
Houttuynia emeiensisPlant
Lavandula angustifoliaPlant
Mentha spp.Plant
Piper longumPlant
Triticum aestivumKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Cyclohexanol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point225.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility426.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.915 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP2.7ALOGPS
logP2.32ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)18.99ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.22 m³·mol⁻¹ChemAxon
Polarizability19 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0302262
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003930
KNApSAcK IDC00052451
Chemspider ID391435
KEGG Compound IDC11396
BioCyc IDCPD-10027
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound443163
PDB IDNot Available
ChEBI ID149
Good Scents IDrw1106561
References
General References
  1. 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 ]
  2. Bhatia SP, Letizia CS, Api AM: Fragrance material review on dihydrocarveol (R,R,R). Food Chem Toxicol. 2008 Nov;46 Suppl 11:S121-2. doi: 10.1016/j.fct.2008.06.041. Epub 2008 Jul 2. [PubMed:18640226 ]