NP-MRD: Showing NP-Card for (Z)-alpha-trans-Bergamotol (NP0070683)

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Record Information

Version

2.0

Created at

2022-04-28 16:08:40 UTC

Updated at

2022-04-28 16:08:40 UTC

NP-MRD ID

NP0070683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z)-alpha-trans-Bergamotol

Description

Bergamotol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (Z)-alpha-trans-Bergamotol is found in Artemisia annua, Artemisia annua L.cultivar Jwarharti , Curcuma phaeocaulis , Curcuma wenyujin , Mesosphaerum suaveolens, Mosla chinensis, Santalum album and Xylopia sericea . (Z)-alpha-trans-Bergamotol was first documented in 2011 (PMID: 21112592). Based on a literature review a small amount of articles have been published on Bergamotol (PMID: 24324844) (PMID: 26410184) (PMID: 26991058).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.2251    2.1158   -0.7114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8889    0.7106   -0.4129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5843    0.0721    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0967   -1.2626    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465   -1.6978    0.1875 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3222   -1.4690   -1.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8139   -0.0537   -1.0975 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8988   -0.5904   -0.0088 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7516    0.3310    1.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3548   -1.2170   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529   -0.3528   -0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0211    0.6304   -0.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2435    0.5811    0.4023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7183    1.6768    1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062   -0.4814    0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053    0.1644   -0.5398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2834    2.1316   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2533    2.7375    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5185    2.5374   -1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4984    0.4612    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9454   -1.2826    2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9335   -1.9844    0.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -2.6833    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276   -2.0027   -2.0173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4340   -1.5027   -1.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355    0.4104   -1.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1861    0.1812    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8188    1.3962    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5612    0.1886    1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -1.8666    0.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1535   -2.0042   -1.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2396   -0.9668   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278    0.2325   -1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4293    1.5053    0.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043    1.3473    2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937    2.6308    1.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7858    1.8513    1.1146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6827   -0.8910    1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018   -1.2671   -0.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1450   -0.3176   -0.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
  8 10  1  6
  8  9  1  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  7  8  1  0
  4  5  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 12 34  1  0
 11 32  1  0
 11 33  1  0
 10 30  1  0
 10 31  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  5 23  1  6
  6 24  1  0
  6 25  1  0
  7 26  1  6
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
M  END


  Mrv1652304282218082D          

 16 17  0  0  1  0            999 V2000
   -0.0474    0.1770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3651    0.8915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1901    0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -0.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -0.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5437    0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    1.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759    0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2039    0.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9036    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320    0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8748   -0.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1463   -1.1345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7759   -0.2103    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  2  7  1  1  0  0  0
  3  8  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C\CC[C@]1(C)[C@@H]2C[C@H]1C(C)=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)13-7-6-12(2)14(15)9-13/h5-6,13-14,16H,4,7-10H2,1-3H3/b11-5-/t13-,14-,15+/m0/s1

> <INCHI_KEY>
JGINTSAQGRHGMG-NLJYZETGSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.388249916519563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-5-[(1S,5S,6R)-2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl]-2-methylpent-2-en-1-ol

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
3.180604564666668

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.64402351692704

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797041136961134

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
70.2996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-5-[(1S,5S,6R)-2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl]-2-methylpent-2-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.089   0.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.681   1.664   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.221   1.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.991   0.330   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.221  -1.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.681  -1.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.015   0.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.991   2.998   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.448   1.053   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.754   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.114   0.960   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.420   0.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.780   0.867   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.366  -1.395   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.007  -2.118   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.448  -0.393   0.000  0.00  0.00           C+0
CONECT    1    2    6    9   16                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    2                                                       
CONECT    8    3                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    1                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(2Z)-5-[(1S,5S,6R)-2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl]-2-methylpent-2-en-1-ol

Traditional Name

(2Z)-5-[(1S,5S,6R)-2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl]-2-methylpent-2-en-1-ol

CAS Registry Number

Not Available

SMILES

C\C(CO)=C\CC[C@]1(C)[C@@H]2C[C@H]1C(C)=CC2

InChI Identifier

InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)13-7-6-12(2)14(15)9-13/h5-6,13-14,16H,4,7-10H2,1-3H3/b11-5-/t13-,14-,15+/m0/s1

InChI Key

JGINTSAQGRHGMG-NLJYZETGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Artemisia annua	LOTUS Database	35616633
Artemisia annua L.cultivar Jwarharti	Plant	KNApSAcK
Curcuma phaeocaulis	Plant	KNApSAcK
Curcuma wenyujin	Plant	KNApSAcK
Hyptis suaveolens	LOTUS Database	35616633
Mosla chinensis	LOTUS Database	35616633
Santalum album	Plant	KNApSAcK
Xylopia sericea	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.73	ALOGPS
logP	3.18	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.3 m³·mol⁻¹	ChemAxon
Polarizability	27.39 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

C00021903

Chemspider ID

103884960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73555482

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Diaz-Chavez ML, Moniodis J, Madilao LL, Jancsik S, Keeling CI, Barbour EL, Ghisalberti EL, Plummer JA, Jones CG, Bohlmann J: Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol. PLoS One. 2013 Sep 18;8(9):e75053. doi: 10.1371/journal.pone.0075053. eCollection 2013. [PubMed:24324844 ]
Panto S, Sciarrone D, Maimone M, Ragonese C, Giofre S, Donato P, Farnetti S, Mondello L: Performance evaluation of a versatile multidimensional chromatographic preparative system based on three-dimensional gas chromatography and liquid chromatography-two-dimensional gas chromatography for the collection of volatile constituents. J Chromatogr A. 2015 Oct 23;1417:96-103. doi: 10.1016/j.chroma.2015.09.039. Epub 2015 Sep 16. [PubMed:26410184 ]
Sciarrone D, Costa R, Ragonese C, Tranchida PQ, Tedone L, Santi L, Dugo P, Dugo G, Mondello L: Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil. J Chromatogr A. 2011 Jan 7;1218(1):137-42. doi: 10.1016/j.chroma.2010.10.117. Epub 2010 Nov 2. [PubMed:21112592 ]
Celedon JM, Chiang A, Yuen MM, Diaz-Chavez ML, Madilao LL, Finnegan PM, Barbour EL, Bohlmann J: Heartwood-specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)-santalol fragrance biosynthesis. Plant J. 2016 May;86(4):289-99. doi: 10.1111/tpj.13162. Epub 2016 Apr 15. [PubMed:26991058 ]

Showing NP-Card for (Z)-alpha-trans-Bergamotol (NP0070683)

MOL for NP0070683 ((Z)-alpha-trans-Bergamotol)

3D MOL for NP0070683 ((Z)-alpha-trans-Bergamotol)

3D SDF for NP0070683 ((Z)-alpha-trans-Bergamotol)

3D-SDF for NP0070683 ((Z)-alpha-trans-Bergamotol)

PDB for NP0070683 ((Z)-alpha-trans-Bergamotol)

3D PDB for NP0070683 ((Z)-alpha-trans-Bergamotol)

SMILES for NP0070683 ((Z)-alpha-trans-Bergamotol)

INCHI for NP0070683 ((Z)-alpha-trans-Bergamotol)

Structure for NP0070683 ((Z)-alpha-trans-Bergamotol)

3D Structure for NP0070683 ((Z)-alpha-trans-Bergamotol)