NP-MRD: Showing NP-Card for Œ≤-Cadinene (NP0137128)

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Record Information

Version

1.0

Created at

2022-05-30 16:42:30 UTC

Updated at

2022-05-30 16:42:30 UTC

NP-MRD ID

NP0137128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Œ≤-Cadinene

Description

Beta-cadinene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, beta-cadinene is considered to be an isoprenoid lipid molecule. Œ≤-Cadinene is found in Achillea abrotanoides, Ageratum conyzoides, Aloysia gratissima, Angelica sinensis, Artemisia annua, Artemisia judaica, Chromolaena odorata, Helichrysum italicum, Helichrysum nudifolium, Helichrysum reflexum, Humulus lupulus, Larix gmelinii, Larix sibirica, Lavandula angustifolia, Melissa officinalis, Nelumbo lutea, Ocimum americanum, Ocimum basilicum, Pimenta racemosa, Populus alba, Rhododendron mucronulatum, Santolina insularis, Sassafras randaiense, Satureja thymbra, Tanacetum vulgare, Thymus vulgaris, Valeriana officinalis, Xanthium strumarium and Zingiber officinale. Beta-cadinene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.1458   -2.1083   -1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3715   -1.0387   -0.4265 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9531    0.0274    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2252    1.0854    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7613    1.0858    0.6585 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1585    2.3647    0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8834    3.6615    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865    2.3494   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735    1.1662   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2793   -0.0882    0.1899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0910   -1.2662   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6447   -2.5953    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208   -1.0819    0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356    0.0025   -0.2035 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8973   -1.2588   -0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5424   -2.7921   -0.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085   -2.6881   -1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485   -1.6831   -1.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0541    0.1458   -0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.0462    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.9762    1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3037    0.9320    1.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6706    3.7224    0.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3929    3.7801   -0.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1607    4.5245    0.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5148    3.2846   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2186    0.9927   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8504    1.3355    0.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3120   -0.0610    1.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1609   -1.3208   -1.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531   -3.2835    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -3.1816   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2968   -2.4944    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451   -2.0588    0.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159   -0.8475    1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0845   -0.3625   -0.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1534    0.4240   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8237   -1.9156    0.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972   -1.7805   -1.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  1  0
 15  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  5 14  1  0
 10 14  1  0
 14 37  1  6
 15 38  1  0
 15 39  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  1
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
M  END


  Mrv1652309272007472D          

 17 18  0  0  0  0            999 V2000
 9998.914110001.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.198710001.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.629510001.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9141 9998.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.771210000.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6275 9998.5263    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627510001.0119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.913710000.5944    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.199210000.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1992 9999.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9137 9998.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6282 9999.3568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.628210000.1819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.340910000.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3409 9998.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0554 9999.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055410000.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17  5  1  0  0  0  0
  8  1  1  1  0  0  0
 11  4  1  0  0  0  0
 14 13  1  0  0  0  0
 13  7  1  1  0  0  0
 12 15  1  0  0  0  0
 12  6  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0137128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(C)=CC[C@@]1([H])C(C)=CC[C@H]2C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-6,10,13-15H,7-9H2,1-4H3/t13-,14-,15-/m0/s1

> <INCHI_KEY>
USDOQCCMRDNVAH-KKUMJFAQSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.502309259648833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene

> <ALOGPS_LOGP>
5.29

> <JCHEM_LOGP>
4.448347697666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5984

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-cadinene

> <JCHEM_VEBER_RULE>
1

$$$$

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    8664.6408669.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3048670.101   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.9758670.101   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8664.6408663.139   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.9738667.785   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0    8665.9718663.916   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8665.9718668.556   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8664.6398667.776   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8663.3058667.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3058665.466   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6398664.696   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9738665.466   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9738667.006   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3038667.776   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8667.3038664.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.6378665.466   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8668.6378667.006   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   11                                                            
CONECT    5   17                                                            
CONECT    6   12                                                            
CONECT    7   13                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    4                                                  
CONECT   12   11   13   15    6                                             
CONECT   13    8   12   14    7                                             
CONECT   14   17   13                                                       
CONECT   15   16   12                                                       
CONECT   16   15   17                                                       
CONECT   17   14   16    5                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
(-)-beta-Cadinene	ChEBI
(1S,4AR,8as)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene	ChEBI
(-)-b-Cadinene	Generator
(-)-Β-cadinene	Generator
b-Cadinene	Generator
Β-cadinene	Generator
Cadina-3,9-diene	PhytoBank
beta-Cadinene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,4aR,8aS)-4,7-dimethyl-1-(propan-2-yl)-1,2,4a,5,8,8a-hexahydronaphthalene

Traditional Name

β-cadinene

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(C)=CC[C@@]1([H])C(C)=CC[C@H]2C(C)C

InChI Identifier

InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-6,10,13-15H,7-9H2,1-4H3/t13-,14-,15-/m0/s1

InChI Key

USDOQCCMRDNVAH-KKUMJFAQSA-N

Experimental Spectra

Not Available

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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea abrotanoides	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Aloysia gratissima	LOTUS Database	35616633
Angelica sinensis	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Helichrysum nudifolium	LOTUS Database	35616633
Helichrysum reflexum	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Lavandula angustifolia	LOTUS Database	35616633
Melissa officinalis	LOTUS Database	35616633
Nelumbo lutea	LOTUS Database	35616633
Ocimum americanum	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Pimenta racemosa	LOTUS Database	35616633
Populus alba	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633
Santolina insularis	LOTUS Database	35616633
Sassafras randaiense	LOTUS Database	35616633
Satureja thymbra	LOTUS Database	35616633
Tanacetum vulgare	LOTUS Database	35616633
Thymus vulgaris	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633

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

Sesquiterpenoid
Cadinane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cadinene (CHEBI:27723 )
Cadinane sesquiterpenoids (C09625 )
Cadinanes (C09625 )
Cadinane sesquiterpenoids (LMPR0103330003 )

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	5.29	ALOGPS
logP	4.45	ChemAxon
logS	-4.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.6 m³·mol⁻¹	ChemAxon
Polarizability	26.5 Å³	ChemAxon
Number of Rings	2	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

C00003106

Chemspider ID

Not Available

KEGG Compound ID

C09625

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10657

PDB ID

Not Available

ChEBI ID

27723

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Œ≤-Cadinene (NP0137128)

MOL for NP0137128 (Œ≤-Cadinene)

3D MOL for NP0137128 (Œ≤-Cadinene)

3D SDF for NP0137128 (Œ≤-Cadinene)

3D-SDF for NP0137128 (Œ≤-Cadinene)

PDB for NP0137128 (Œ≤-Cadinene)

3D PDB for NP0137128 (Œ≤-Cadinene)

SMILES for NP0137128 (Œ≤-Cadinene)

INCHI for NP0137128 (Œ≤-Cadinene)

Structure for NP0137128 (Œ≤-Cadinene)

3D Structure for NP0137128 (Œ≤-Cadinene)