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Showing NP-Card for (2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol (NP0311589)

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Record Information
Version2.0
Created at2022-09-11 07:40:58 UTC
Updated at2022-09-11 07:40:58 UTC
NP-MRD IDNP0311589
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol
DescriptionTrans-Sabinene hydrate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol is found in Artemisia dubia, Artemisia herba-alba and Thymus broussonetii. (2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol was first documented in 2021 (PMID: 34299420). Based on a literature review a small amount of articles have been published on trans-Sabinene hydrate (PMID: 35958807) (PMID: 35684205) (PMID: 33959421).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)


  Mrv1652309112209402D          

 11 12  0  0  1  0            999 V2000
    0.3019    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9570   -1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
Download

3D MOL for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.7145   -0.1948    1.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7886   -0.4790   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3017    0.4321   -1.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3779   -0.1123    0.2246 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1403    1.2117   -0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    0.8479   -1.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9474   -0.2718   -0.4006 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7027    0.2751    0.7628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -1.0009   -1.2073 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7317   -1.0953    0.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1929   -0.8334    1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3639   -0.6672    1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7989    0.8851    1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7029   -0.6389    0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8960   -1.5351   -0.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5884    1.3964   -0.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2523   -0.0218   -1.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    0.5330   -2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4774    1.8724    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5852    1.7845   -0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9383    1.6867   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7999    0.3892   -2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151    1.2052    1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7439    0.5097    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8361   -0.4449    1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1439   -1.7680   -0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5070   -2.0286   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8187   -0.2896    2.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -1.6473    1.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  6
  4 11  1  0
 11 10  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  6
  7  6  1  0
  6  5  1  0
 10  4  1  0
  5  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
 11 28  1  0
 11 29  1  0
 10 27  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
M  END
Download

3D SDF for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)


  Mrv1652309112209402D          

 11 12  0  0  1  0            999 V2000
    0.3019    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9570   -1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12CC1[C@@](C)(O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8?,9-,10+/m0/s1

> <INCHI_KEY>
KXSDPILWMGFJMM-CBMCFHRWSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.609859823574542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

> <JCHEM_LOGP>
1.8920337026666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.131154204711283

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9918331508592838

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.554399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

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PDB for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       0.563   2.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.095   2.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.000   3.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.721   0.656   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.186   1.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.091  -0.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.186  -1.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.520  -2.130   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.560  -2.767   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.721  -0.884   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.388  -0.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7    4   11                                                  
CONECT   11   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)
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SMILES for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)
CC(C)[C@@]12CC1[C@@](C)(O)CC2
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INCHI for NP0311589 ((2s,5r)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8?,9-,10+/m0/s1
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View in JSmol
Synonyms
ValueSource
trans-Sabinene hydric acidGenerator
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC(C)[C@@]12CC1[C@@](C)(O)CC2
InChI Identifier
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8?,9-,10+/m0/s1
InChI KeyKXSDPILWMGFJMM-CBMCFHRWSA-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
Artemisia dubiaLOTUS Database
Artemisia herba-albaLOTUS Database
Thymus broussonetiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000821  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12315151  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Zouirech O, Alyousef AA, El Barnossi A, El Moussaoui A, Bourhia M, Salamatullah AM, Ouahmane L, Giesy JP, Aboul-Soud MAM, Lyoussi B, Derwich E: Phytochemical Analysis and Antioxidant, Antibacterial, and Antifungal Effects of Essential Oil of Black Caraway (Nigella sativa L.) Seeds against Drug-Resistant Clinically Pathogenic Microorganisms. Biomed Res Int. 2022 Jul 26;2022:5218950. doi: 10.1155/2022/5218950. eCollection  2022. [PubMed:35958807  ] 
  2. Ghazal TSA, Schelz Z, Vidacs L, Szemeredi N, Veres K, Spengler G, Hohmann J: Antimicrobial, Multidrug Resistance Reversal and Biofilm Formation Inhibitory Effect of Origanum majorana Extracts, Essential Oil and Monoterpenes. Plants (Basel). 2022 May 27;11(11):1432. doi: 10.3390/plants11111432. [PubMed:35684205  ] 
  3. Farouk A, Mohsen M, Ali H, Shaaban H, Albaridi N: Antioxidant Activity and Molecular Docking Study of Volatile Constituents from Different Aromatic Lamiaceous Plants Cultivated in Madinah Monawara, Saudi Arabia. Molecules. 2021 Jul 7;26(14):4145. doi: 10.3390/molecules26144145. [PubMed:34299420  ] 
  4. Khruengsai S, Pripdeevech P, Tanapichatsakul C, Srisuwannapa C, D'Souza PE, Panuwet P: Antifungal properties of volatile organic compounds produced by Daldinia eschscholtzii MFLUCC 19-0493 isolated from Barleria prionitis leaves against Colletotrichum acutatum and its post-harvest infections on strawberry fruits. PeerJ. 2021 Apr 16;9:e11242. doi: 10.7717/peerj.11242. eCollection 2021. [PubMed:33959421  ] 
  5. LOTUS database [Link]