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

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Record Information

Version

2.0

Created at

2023-05-26 16:00:25 UTC

Updated at

2024-09-03 04:16:22 UTC

NP-MRD ID

NP0331646

Natural Product DOI

https://doi.org/10.57994/0635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxycaryophyllene 4,5-oxide

Description

14-Hydroxycaryophyllene 4,5-oxide belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 14-hydroxycaryophyllene 4,5-oxide was first documented in 2024 (PMID: 37198914). Based on a literature review very few articles have been published on 14-hydroxycaryophyllene 4,5-oxide.

Structure

MOL SDF PDB SMILES InChI


  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

$$$$

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not 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 Key

PUIHQHPNBOICHY-DVTFPSANSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CDCl₃, simulated)	570075670@qq.com	黑龙江中医药大学	Pan juan	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
stramonium		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

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 Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.57	ChemAxon
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.76 m³·mol⁻¹	ChemAxon
Polarizability	27.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91748779

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

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

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

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

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

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

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

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

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

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

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

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