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Showing NP-Card for (2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid (NP0261920)

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Record Information
Version2.0
Created at2022-09-08 04:30:30 UTC
Updated at2022-09-08 04:30:30 UTC
NP-MRD IDNP0261920
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid
Description(2E,6R)-8-hydroxy-2,6-dimethyl-2-octenoic acid belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. (2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid is found in Cistanche salsa. (2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid was first documented in 1999 (PMID: 10361686). Based on a literature review very few articles have been published on (2E,6R)-8-hydroxy-2,6-dimethyl-2-octenoic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)


  Mrv1652309082206302D          

 13 12  0  0  1  0            999 V2000
    1.0461   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
    3.1931    1.2299    0.5674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155   -0.0579   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5894   -0.5038    0.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    0.2710    1.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5977    0.6648    0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3695   -0.5447   -0.2017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7978   -1.4466    0.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5102   -0.1102   -1.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5728    0.6389   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183   -0.1370    0.6615 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752   -0.8070   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3975   -1.9100   -1.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447   -0.3761   -1.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    2.0378    0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3152    1.1102    1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1949    1.5153    0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3055   -1.4518   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0838    1.1489    1.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191   -0.4073    1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    1.2395   -0.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235    1.3275    0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6555   -1.1025   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0080   -2.2272    1.0818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8990   -0.8839    1.8772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233   -2.0122    0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9383   -1.0565   -1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231    0.4774   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0996    1.5665    0.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3250    0.9744   -1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.3077    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800    0.5248   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 11  1  0
 11 13  1  0
 11 12  2  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  6 22  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
  5 20  1  0
  5 21  1  0
  4 18  1  0
  4 19  1  0
  3 17  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
 13 31  1  0
M  END
Download

3D SDF for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)


  Mrv1652309082206302D          

 13 12  0  0  1  0            999 V2000
    1.0461   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316   -2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261920

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCO)CC\C=C(/C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O3/c1-8(6-7-11)4-3-5-9(2)10(12)13/h5,8,11H,3-4,6-7H2,1-2H3,(H,12,13)/b9-5+/t8-/m1/s1

> <INCHI_KEY>
CDAJACJYYZHNJA-CBVZUMJXSA-N

> <FORMULA>
C10H18O3

> <MOLECULAR_WEIGHT>
186.251

> <EXACT_MASS>
186.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
21.442669158650336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6R)-8-hydroxy-2,6-dimethyloct-2-enoic acid

> <JCHEM_LOGP>
1.943747916333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.109791816071453

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.003130550519207

> <JCHEM_PKA_STRONGEST_BASIC>
-1.875977125988892

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
52.203300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6R)-8-hydroxy-2,6-dimethyloct-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)

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PDB for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)
HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.953  -1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.953  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.287  -1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288  -3.437   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.619  -3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.619  -4.977   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.715  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

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3D PDB for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)
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SMILES for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)
C[C@@H](CCO)CC\C=C(/C)C(O)=O
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INCHI for NP0261920 ((2e,6r)-8-hydroxy-2,6-dimethyloct-2-enoic acid)
InChI=1S/C10H18O3/c1-8(6-7-11)4-3-5-9(2)10(12)13/h5,8,11H,3-4,6-7H2,1-2H3,(H,12,13)/b9-5+/t8-/m1/s1
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View in JSmol
Synonyms
ValueSource
(2E,6R)-8-Hydroxy-2,6-dimethyl-2-octenoateGenerator
Chemical FormulaC10H18O3
Average Mass186.2510 Da
Monoisotopic Mass186.12559 Da
IUPAC Name(2E,6R)-8-hydroxy-2,6-dimethyloct-2-enoic acid
Traditional Name(2E,6R)-8-hydroxy-2,6-dimethyloct-2-enoic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](CCO)CC\C=C(/C)C(O)=O
InChI Identifier
InChI=1S/C10H18O3/c1-8(6-7-11)4-3-5-9(2)10(12)13/h5,8,11H,3-4,6-7H2,1-2H3,(H,12,13)/b9-5+/t8-/m1/s1
InChI KeyCDAJACJYYZHNJA-CBVZUMJXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cistanche salsaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAcyclic monoterpenoids  
Alternative Parents
Substituents
  • Acyclic monoterpenoid
    • 

  • Medium-chain hydroxy acid
    • 

  • Medium-chain fatty acid
    • 

  • Branched fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP1.94ChemAxon
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity52.2 m³·mol⁻¹ChemAxon
Polarizability21.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8527866  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10352414  
PDB IDNot Available
ChEBI ID66026  
Good Scents IDNot Available
References
General References
  1. Yamaguchi K, Shinohara C, Kojima S, Sodeoka M, Tsuji T: (2E,6R)-8-hydroxy-2,6-dimethyl-2-octenoic acid, a novel anti-osteoporotic monoterpene, isolated from Cistanche salsa. Biosci Biotechnol Biochem. 1999 Apr;63(4):731-5. doi: 10.1271/bbb.63.731. [PubMed:10361686  ] 
  2. LOTUS database [Link]