Showing NP-Card for Sabinene (NP0044875)

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Record Information
Version2.0
Created at2022-03-10 18:37:02 UTC
Updated at2022-03-10 22:22:19 UTC
NP-MRD IDNP0044875
Secondary Accession NumbersNone
Natural Product Identification
Common NameSabinene
DescriptionSabinene or 4(10)-thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids which contain 2 rings fused to each other. Thus, sabinene is an isoprenoid lipid molecule. It is very hydrophobic, practically insoluble in water and relatively neutral. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Sabinene has a citrus, pepper, and pine taste and is responsible for the spiciness of pepper. Sabinene is found in the essential oils of a variety of plants/trees including the holm oak, Norway spruce, bay laurel (Laurus nobilis). Common sage, and true nutmeg (Myristica fragrans tree; PMID: 5615546 ). Sabinene is also found in trace amounts in cannabis plants (PMID: 6991645 ). Sabinene is found in highest concentrations in nutmegs, tarragons, and sweet bay and in lower concentrations in common sages, caraway, and star anises. Sabinene has also been detected in saffrons, sunflowers, yellow bell peppers, summer savories, and pepper (C. Annuum). Sabinene can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. The microbial biosynthesis of sabinene has been well studied to facilitate the industrial production of this important compound (PMID: 29264773 ). Sabinene has some medicinal properties as it induced recovery of myotube shrinkage in fasting rats, suggesting that it may reverse muscle atrophy (PMID: 31597276 ).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0044875 (Sabinene)

  Mrv1652309272007422D          

 10 11  0  0  0  0            999 V2000
10004.9476 9995.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8310 9996.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0501 9997.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3827 9997.0867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6376 9996.3021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.4626 9996.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.7175 9997.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8304 9997.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0235 9997.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0849 9998.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  1  2  0  0  0  0
  4  2  1  1  0  0  0
  5  2  1  1  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0044875 (Sabinene)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.4303   -0.2652   -0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1971    0.0034   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736    0.4887    1.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3394    0.0740    1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -0.2333   -0.0967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5478    0.2865   -0.4452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5531   -0.8112   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9177    1.5454    0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645   -1.4255   -0.8601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9685   -0.1212   -0.9944 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6787   -0.6227   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2430   -0.1317    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    1.6102    1.1250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3762    0.0742    1.9834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -0.7723    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224    0.9411    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118    0.5057   -1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6987   -1.0186    0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274   -1.7378   -0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5617   -0.5282   -0.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8119    1.9735   -0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1131    2.2977    0.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1792    1.4068    1.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7722   -2.2800   -0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299   -1.7505   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8661    0.4912   -1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  5  6  1  0
  5  9  1  1
  9 10  1  0
 10  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 10  5  1  0
  4  5  1  0
  7 18  1  0
  7 19  1  0
  7 20  1  0
  6 17  1  6
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
Download

3D SDF for NP0044875 (Sabinene)

  Mrv1652309272007422D          

 10 11  0  0  0  0            999 V2000
10004.9476 9995.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8310 9996.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.0501 9997.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3827 9997.0867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6376 9996.3021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.4626 9996.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.7175 9997.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8304 9997.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.0235 9997.5276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0849 9998.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  1  2  0  0  0  0
  4  2  1  1  0  0  0
  5  2  1  1  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12C[C@@H]1C(=C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1

> <INCHI_KEY>
NDVASEGYNIMXJL-NXEZZACHSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.24278988407945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.859595116666666

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-sabinene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0044875 (Sabinene)

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PDB for NP0044875 (Sabinene)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8675.9028658.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.9518660.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8674.2278662.134   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8672.9818661.229   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8673.4578659.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.9978659.764   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.4738661.229   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.9508662.372   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8670.4448662.052   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8672.4258663.837   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    4    5                                                       
CONECT    3    4    7                                                       
CONECT    4    3    5    2    8                                             
CONECT    5    4    6    2                                                  
CONECT    6    5    7    1                                                  
CONECT    7    3    6                                                       
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0044875 (Sabinene)
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SMILES for NP0044875 (Sabinene)
CC(C)[C@@]12C[C@@H]1C(=C)CC2
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INCHI for NP0044875 (Sabinene)
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(1R,5R)-1-Isopropyl-4-methylenebicyclo[3.1.0]hexaneChEBI
(1R,5R)-SabineneChEBI
(+)-SabineneHMDB
(1R,5R)-(+)-4(10)-ThujeneHMDB
(1R,5R)-(+)-SabineneHMDB
(1R,5R)-4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexaneHMDB
1-Isopropyl-4-methylenebicyclo[3.1.0]hexaneHMDB
4(10)-ThujeneHMDB
4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexaneHMDB
SabeneneHMDB
SabinenHMDB
SabineneHMDB
(+)-4(10)-ThujeneHMDB
d-4(10)-ThujenePhytoBank
d-SabinenePhytoBank
Chemical FormulaC10H16
Average Mass136.2380 Da
Monoisotopic Mass136.12520 Da
IUPAC Name(1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane
Traditional Name(+)-sabinene
CAS Registry Number2009-00-9
SMILES
CC(C)[C@@]12C[C@@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1
InChI KeyNDVASEGYNIMXJL-NXEZZACHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
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
    • 

  • Branched unsaturated hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Cyclic olefin
    • 

  • Unsaturated aliphatic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Olefin
    • 

  • Hydrocarbon
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.04ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability17.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036076  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014908  
KNApSAcK IDC00000857  
Chemspider ID9063235  
KEGG Compound IDC20230  
BioCyc IDCPD-14013  
BiGG IDNot Available
Wikipedia LinkSabinene  
METLIN IDNot Available
PubChem Compound10887971  
PDB IDNot Available
ChEBI ID50029  
Good Scents IDNot Available
References
General References
  1. Cao Y, Zhang H, Liu H, Liu W, Zhang R, Xian M, Liu H: Biosynthesis and production of sabinene: current state and perspectives. Appl Microbiol Biotechnol. 2018 Feb;102(4):1535-1544. doi: 10.1007/s00253-017-8695-5. Epub 2017 Dec 20. [PubMed:29264773  ] 
  2. Ryu Y, Lee D, Jung SH, Lee KJ, Jin H, Kim SJ, Lee HM, Kim B, Won KJ: Sabinene Prevents Skeletal Muscle Atrophy by Inhibiting the MAPK-MuRF-1 Pathway in Rats. Int J Mol Sci. 2019 Oct 8;20(19). pii: ijms20194955. doi: 10.3390/ijms20194955. [PubMed:31597276  ]