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Showing NP-Card for (S)-cis-Verbenol (NP0333535)

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Record Information
Version2.0
Created at2024-06-27 17:48:07 UTC
Updated at2024-09-03 04:22:49 UTC
NP-MRD IDNP0333535
Natural Product DOIhttps://doi.org/10.57994/2992
Secondary Accession NumbersNone
Natural Product Identification
Common Name(S)-cis-Verbenol
Description(S)-cis-Verbenol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (S)-cis-Verbenol was first documented in 2019 (PMID: 31867219). Based on a literature review a small amount of articles have been published on (S)-cis-Verbenol (PMID: 36013945) (PMID: 38673947).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0333535 ((S)-cis-Verbenol)


  Mrv2104 03112320222D          

 11 12  0  0  1  0            999 V2000
    2.5423    1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.5580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017    0.8745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8862    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.2742    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
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  1  0  0  0
  7  2  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  6  0  0  0
M  END
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3D MOL for NP0333535 ((S)-cis-Verbenol)

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3D SDF for NP0333535 ((S)-cis-Verbenol)

  Mrv2104 03112320222D          

 11 12  0  0  1  0            999 V2000
    2.5423    1.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1267    0.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5362    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1206   -0.5580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2957   -0.5544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2326    0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3017    0.8745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8862    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594    0.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -0.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.2742    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
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  6  1  1  0  0  0
  7  2  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@H](O)[C@H]2C[C@@H]1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1

> <INCHI_KEY>
WONIGEXYPVIKFS-YIZRAAEISA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.03373214160772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol

> <JCHEM_LOGP>
1.648804109333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.58834245842004

> <JCHEM_PKA_STRONGEST_BASIC>
-1.229259008687073

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
46.160799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(S)-cis-verbenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0333535 ((S)-cis-Verbenol)
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PDB for NP0333535 ((S)-cis-Verbenol)
HEADER    PROTEIN                                 11-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAR-23         0                                  
HETATM    1  C   UNK     0       4.746   2.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.970   1.626   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.734   0.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.959  -1.042   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.419  -1.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.301   0.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.430   1.632   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.654   0.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.298   1.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.291  -0.415   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.723  -2.378   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    5    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

Download
3D PDB for NP0333535 ((S)-cis-Verbenol)
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SMILES for NP0333535 ((S)-cis-Verbenol)
CC1=C[C@H](O)[C@H]2C[C@@H]1C2(C)C
Download
INCHI for NP0333535 ((S)-cis-Verbenol)
InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1S,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
Traditional Name(S)-cis-verbenol
CAS Registry NumberNot Available
SMILES
CC1=C[C@H](O)[C@H]2C[C@@H]1C2(C)C
InChI Identifier
InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1
InChI KeyWONIGEXYPVIKFS-YIZRAAEISA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-27View Spectrum
Species
Species of OriginNot Available
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
  • Pinane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Secondary 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
logP1.65ChemAxon
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.16 m³·mol⁻¹ChemAxon
Polarizability18.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID79247  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound87839  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Salinas C, Florentin G, Rodriguez F, Alvarenga N, Guillen R: Terpenes Combinations Inhibit Biofilm Formation in Staphyloccocus aureus by Interfering with Initial Adhesion. Microorganisms. 2022 Jul 28;10(8):1527. doi: 10.3390/microorganisms10081527. [PubMed:36013945  ] 
  2. Xu Z, Chen P, Yan R, Chen G, Qian J, Zhu G, Chen M, Guo Y: Antenna-Biased Odorant Receptor PstrOR17 Mediates Attraction of Phyllotreta striolata to (S)-Cis-Verbenol and (-)-Verbenone. Int J Mol Sci. 2024 Apr 15;25(8):4362. doi: 10.3390/ijms25084362. [PubMed:38673947  ] 
  3. Lulekal E, Tesfaye S, Gebrechristos S, Dires K, Zenebe T, Zegeye N, Feleke G, Kassahun A, Shiferaw Y, Mekonnen A: Phytochemical analysis and evaluation of skin irritation, acute and sub-acute toxicity of Cymbopogon citratus essential oil in mice and rabbits. Toxicol Rep. 2019 Nov 4;6:1289-1294. doi: 10.1016/j.toxrep.2019.11.002.  eCollection 2019. [PubMed:31867219  ]