NP-MRD: Showing NP-Card for Isocaryophyllene-4S,5R-oxide (NP0331814)

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Record Information

Version

2.0

Created at

2023-09-13 16:01:38 UTC

Updated at

2024-09-03 04:17:02 UTC

NP-MRD ID

NP0331814

Natural Product DOI

https://doi.org/10.57994/0902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isocaryophyllene-4S,5R-oxide

Description

CHEMBL479134 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 CHEMBL479134.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    0.6264   -3.2341   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1008   -2.1451    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3693   -2.0696    0.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -1.2309   -0.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722   -0.1874   -0.0154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1799    0.2426    1.2492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4117    1.1288    0.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4198    2.2023    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    1.5691   -0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566    1.3122    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8414    0.2079   -0.3729 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9514   -1.0303    0.4887 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3674   -1.1426   -0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388    0.3997   -0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    1.0363   -1.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250    0.8809    1.3170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6946   -3.3008   -0.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0518   -4.1005   -0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8299   -3.0917    0.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5128   -1.6684    1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448   -0.8459   -1.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8358   -1.8853   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9013   -0.4480    0.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851    2.6978   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899    2.8652    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2526    1.7384    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0505    1.1519   -1.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2383    2.6779   -0.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6412    2.2385    0.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2889    0.9802    1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643    0.0518   -1.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9251   -0.7254    1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1136   -1.5727    0.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -1.4800   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0076    1.5126   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5168    1.8965   -1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3425    0.3423   -2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0846    0.0902    1.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3516    1.7111    1.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7257    1.2243    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 12  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  6  7  1  0
 14 11  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  6
 12 32  1  1
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  1
M  END


  Mrv1652309032221432D          

 16 18  0  0  1  0            999 V2000
    2.1423    0.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6659    0.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4441    0.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2163    0.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -0.4770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2476   -1.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4694   -1.2879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8744   -2.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319   -1.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069   -1.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3806   -1.2659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2459   -0.4519    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4319   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5666   -1.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066   -1.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5076   -2.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m1/s1

> <INCHI_KEY>
NVEQFIOZRFFVFW-BHPKHCPMSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.888224450244653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

> <JCHEM_LOGP>
3.6185278833333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224447799898045

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
66.2129

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.999   1.672   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.976   0.482   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.429   0.993   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.870   0.451   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.626  -0.890   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.796  -1.893   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.343  -2.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.099  -3.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.153  -3.381   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.613  -3.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.444  -2.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.192  -0.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.673  -1.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.924  -2.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.506  -3.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.814  -4.150   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   11   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(1R,4S,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

Traditional Name

(1R,4S,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0^{4,6}]dodecane

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2

InChI Identifier

InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15+/m1/s1

InChI Key

NVEQFIOZRFFVFW-BHPKHCPMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	LIOS	Georgijs Stakanovs	2024-05-08	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2024-05-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	Not Available	Not Available	Georgijs Stakanovs	2024-05-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.57, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101, CDCl₃, simulated)	st_george@inbox.lv	Latvian Institute of Organic Synthesis	Georgijs Stakanovs	2024-05-08	View Spectrum

Species

Species of Origin

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
Organooxygen compound
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	3.62	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.21 m³·mol⁻¹	ChemAxon
Polarizability	26.89 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

8166619

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9991037

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isocaryophyllene-4S,5R-oxide (NP0331814)

MOL for NP0331814 (Isocaryophyllene-4S,5R-oxide)

3D MOL for NP0331814 (Isocaryophyllene-4S,5R-oxide)

3D SDF for NP0331814 (Isocaryophyllene-4S,5R-oxide)

3D-SDF for NP0331814 (Isocaryophyllene-4S,5R-oxide)

PDB for NP0331814 (Isocaryophyllene-4S,5R-oxide)

3D PDB for NP0331814 (Isocaryophyllene-4S,5R-oxide)

SMILES for NP0331814 (Isocaryophyllene-4S,5R-oxide)

INCHI for NP0331814 (Isocaryophyllene-4S,5R-oxide)

Structure for NP0331814 (Isocaryophyllene-4S,5R-oxide)

3D Structure for NP0331814 (Isocaryophyllene-4S,5R-oxide)