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Showing NP-Card for cis-p-Menth-1-en-3-ol (NP0046838)

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Record Information
Version2.0
Created at2022-03-17 20:30:21 UTC
Updated at2022-03-17 20:30:21 UTC
NP-MRD IDNP0046838
Secondary Accession NumbersNone
Natural Product Identification
Common Namecis-p-Menth-1-en-3-ol
DescriptionCis-p-Menth-1-en-3-ol 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. cis-p-Menth-1-en-3-ol is found in Achillea abrotanoides, Alpinia zerumbet, Andropogon sp., Aster scaber, Bellis perennis, Cryptomeria japonica, Cymbopogon martinii, Eucalyptus behriana, Eucalyptus camaldulensis, Eucalyptus delegatensis, Eucalyptus paliformis, Liquidambar styraciflua, Melaleuca linariifolia, Myrtus communis, Origanum minutiflorum, Persea americana, Pimenta racemosa, Pinus mugo subsp. Mugo , Satureja cuneifolia, Vitex agnus-castus, Xylopia sericea and Zanthoxylum bungeanum. Cis-p-Menth-1-en-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046838 (cis-p-Menth-1-en-3-ol)


  Mrv0541 02241222492D          

 11 11  0  0  0  0            999 V2000
   -0.1882    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.1946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1882   -0.6071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5263   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -0.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -1.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  3  8  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for NP0046838 (cis-p-Menth-1-en-3-ol)

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3D SDF for NP0046838 (cis-p-Menth-1-en-3-ol)

  Mrv0541 02241222492D          

 11 11  0  0  0  0            999 V2000
   -0.1882    1.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -0.1946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1882   -0.6071    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5263   -0.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263    0.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6171   -0.6071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1882   -1.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5263   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9026   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  3  8  1  1  0  0  0
  4  9  1  1  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046838

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3/t9-,10-/m0/s1

> <INCHI_KEY>
HPOHAUWWDDPHRS-UWVGGRQHSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.05327095684219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.4146011256666675

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.763486870542224

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1526508428248317

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.141299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,6S)-6-isopropyl-3-methylcyclohex-2-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046838 (cis-p-Menth-1-en-3-ol)
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PDB for NP0046838 (cis-p-Menth-1-en-3-ol)
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      -0.351   1.947   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.685   1.177   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.685  -0.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.351  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.982  -0.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.982   1.177   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.351   3.487   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.019  -1.133   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.351  -2.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.982  -3.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.685  -3.443   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1                                                            
CONECT    8    3                                                            
CONECT    9    4   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 NP0046838 (cis-p-Menth-1-en-3-ol)
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SMILES for NP0046838 (cis-p-Menth-1-en-3-ol)
CC(C)[C@@H]1CCC(C)=C[C@@H]1O
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INCHI for NP0046838 (cis-p-Menth-1-en-3-ol)
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3/t9-,10-/m0/s1
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SynonymsNot Available
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(1R,6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-ol
Traditional Name(1R,6S)-6-isopropyl-3-methylcyclohex-2-en-1-ol
CAS Registry Number16721-38-3
SMILES
CC(C)[C@@H]1CCC(C)=C[C@@H]1O
InChI Identifier
InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9-11H,4-5H2,1-3H3/t9-,10-/m0/s1
InChI KeyHPOHAUWWDDPHRS-UWVGGRQHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea abrotanoidesLOTUS Database
Alpinia zerumbetLOTUS Database
Andropogon sp.Plant
Aster scaberLOTUS Database
Bellis perennisLOTUS Database
Cryptomeria japonicaLOTUS Database
Cymbopogon martiniiLOTUS Database
Eucalyptus behrianaLOTUS Database
Eucalyptus camaldulensisLOTUS Database
Eucalyptus delegatensisLOTUS Database
Eucalyptus paliformisLOTUS Database
Liquidambar styracifluaLOTUS Database
Melaleuca linariifoliaLOTUS Database
Mentha x piperitaFooDB
Myristica fragransFooDB
Myrtus communisLOTUS Database
Origanum majoranaFooDB
Origanum minutiflorumLOTUS Database
Origanum vulgareFooDB
Persea americanaLOTUS Database
Pimenta racemosaLOTUS Database
Pinus mugo subsp. MugoPlant
Salvia rosmarinusFooDB
Satureja cuneifoliaLOTUS Database
Vitex agnus-castusLOTUS Database
Xylopia sericeaPlant
Zanthoxylum bungeanumLOTUS 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
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.64ALOGPS
logP2.41ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)18.76ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.14 m³·mol⁻¹ChemAxon
Polarizability19.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006161  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85567  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available