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Showing NP-Card for 14-hydroxycaryophyllene 4,5-oxide (NP0331646)

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Record Information
Version2.0
Created at2023-05-26 16:00:25 UTC
Updated at2024-09-03 04:16:22 UTC
NP-MRD IDNP0331646
Natural Product DOIhttps://doi.org/10.57994/0635
Secondary Accession NumbersNone
Natural Product Identification
Common Name14-hydroxycaryophyllene 4,5-oxide
Description14-Hydroxy-4,5-epoxy-.Beta.-Caryophyllene (.Beta.Beta.) Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 14-Hydroxy-4,5-epoxy-.Beta.-Caryophyllene (.Beta.Beta.).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)


  Mrv1652305262318002D          

 17 19  0  0  1  0            999 V2000
    5.8458    0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972    0.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666    1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    2.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291    1.2386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7241    0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441   -0.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509    1.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773    2.0495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3822    2.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    3.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562    3.4222    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
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3D MOL for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)

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3D SDF for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)

  Mrv1652305262318002D          

 17 19  0  0  1  0            999 V2000
    5.8458    0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972    0.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666    1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    2.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291    1.2386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7241    0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441   -0.1902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509    1.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773    2.0495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3822    2.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    3.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562    3.4222    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331646

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2C1CC[C@@]1(CO)O[C@H]1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10-4-5-13-15(9-16,17-13)7-6-12-11(10)8-14(12,2)3/h11-13,16H,1,4-9H2,2-3H3/t11?,12?,13-,15-/m0/s1

> <INCHI_KEY>
PUIHQHPNBOICHY-DVTFPSANSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.63578560178732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(4S,6S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methanol

> <JCHEM_LOGP>
2.571617916666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.28539388542666

> <JCHEM_PKA_STRONGEST_BASIC>
-3.111368714514377

> <JCHEM_POLAR_SURFACE_AREA>
32.76

> <JCHEM_REFRACTIVITY>
67.7566

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(4S,6S)-12,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecan-4-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)
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PDB for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      10.912   1.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.393   2.102   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.141   0.582   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.644   3.621   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.125   3.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.873   2.353   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.704   1.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.164   1.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.974   2.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.218   0.970   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.002  -0.355   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.522   2.824   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.691   3.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.447   5.168   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.888   5.709   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.341   5.198   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.318   6.388   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12   13                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13    9   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

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3D PDB for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)
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SMILES for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)
CC1(C)CC2C1CC[C@@]1(CO)O[C@H]1CCC2=C
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INCHI for NP0331646 (14-hydroxycaryophyllene 4,5-oxide)
InChI=1S/C15H24O2/c1-10-4-5-13-15(9-16,17-13)7-6-12-11(10)8-14(12,2)3/h11-13,16H,1,4-9H2,2-3H3/t11?,12?,13-,15-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O2
Average Mass236.3550 Da
Monoisotopic Mass236.17763 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CC1(C)CC2C1CC[C@@]1(CO)O[C@H]1CCC2=C
InChI Identifier
InChI=1S/C15H24O2/c1-10-4-5-13-15(9-16,17-13)7-6-12-11(10)8-14(12,2)3/h11-13,16H,1,4-9H2,2-3H3/t11?,12?,13-,15-/m0/s1
InChI KeyPUIHQHPNBOICHY-DVTFPSANSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CDCl3, simulated)570075670@qq.com黑龙江中医药大学Pan juan2024-05-14View Spectrum
Species
Species of Origin
Species NameSourceReference
stramonium
      Not Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Caryophyllane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91748779  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pan J, Liu Y, Wang AF, Wu JT, Yang R, Guan W, Algradi AM, Kuang HX, Yang BY: Cytotoxicity sesquiterpenoids from the leaves of Datura stramonium L. Nat Prod Res. 2024 May;38(10):1639-1646. doi: 10.1080/14786419.2023.2214292. Epub  2023 May 17. [PubMed:37198914  ]