NP-MRD: Showing NP-Card for Bergamotene A (NP0333695)

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Record Information

Version

2.0

Created at

2024-08-06 07:45:19 UTC

Updated at

2026-02-28 01:56:32 UTC

NP-MRD ID

NP0333695

Natural Product DOI

https://doi.org/10.57994/3174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bergamotene A

Description

Bergamotene A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Bergamotene A was first documented in 2024 (PMID: 39623525). Based on a literature review very few articles have been published on Bergamotene A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04202310182D          

 19 20  0  0  1  0            999 V2000
    2.3732   -0.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979    0.1690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7729    0.1690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3604    0.8835    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2715    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2715    1.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0468    1.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6788    1.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5355    2.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7603    2.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1675    3.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    3.8171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428    2.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    1.5979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9516    0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5979    1.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547   -0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0104    0.8835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8354    0.8835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  6  0  0  0
  3 15  1  6  0  0  0
 14 16  1  0  0  0  0
  2 17  1  0  0  0  0
  2 18  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0333695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/CC[C@]1(C)[C@@H]2C[C@H]1[C@@](C)(O)C(=O)C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-9(13(17)18)5-4-6-14(2)10-7-11(14)15(3,19)12(16)8-10/h5,10-11,19H,4,6-8H2,1-3H3,(H,17,18)/b9-5+/t10-,11-,14-,15-/m1/s1

> <INCHI_KEY>
JJUMDTHJZDPESH-MEAPBICDSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.133941528677287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-[(1R,2R,5R,6R)-2-hydroxy-2,6-dimethyl-3-oxobicyclo[3.1.1]heptan-6-yl]-2-methylpent-2-enoic acid

> <JCHEM_LOGP>
2.2320646753333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.035859297534454

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.469638715817455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.65791512467105

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
71.6134

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(1R,2R,5R,6R)-2-hydroxy-2,6-dimethyl-3-oxobicyclo[3.1.1]heptan-6-yl]-2-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-23         0                                  
HETATM    1  O   UNK     0       4.430  -0.211   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.983   0.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.443   0.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.673   1.649   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.507   0.659   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.507   2.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.954   2.112   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.134   3.102   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.866   4.619   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.419   5.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.046   5.609   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.779   7.125   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.493   5.082   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.443   2.983   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.776   1.649   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.983   2.983   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.715  -1.201   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.753   1.649   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.293   1.649   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   18                                             
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6   14                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    4   15   16                                                  
CONECT   15   14    3                                                       
CONECT   16   14   18                                                       
CONECT   17    2                                                            
CONECT   18    2   16   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(2E)-5-[(1R,2R,5R,6R)-2-hydroxy-2,6-dimethyl-3-oxobicyclo[3.1.1]heptan-6-yl]-2-methylpent-2-enoic acid

Traditional Name

(2E)-5-[(1R,2R,5R,6R)-2-hydroxy-2,6-dimethyl-3-oxobicyclo[3.1.1]heptan-6-yl]-2-methylpent-2-enoic acid

CAS Registry Number

Not Available

SMILES

C\C(=C/CC[C@]1(C)[C@@H]2C[C@H]1[C@@](C)(O)C(=O)C2)C(O)=O

InChI Identifier

InChI=1S/C15H22O4/c1-9(13(17)18)5-4-6-14(2)10-7-11(14)15(3,19)12(16)8-10/h5,10-11,19H,4,6-8H2,1-3H3,(H,17,18)/b9-5+/t10-,11-,14-,15-/m1/s1

InChI Key

JJUMDTHJZDPESH-MEAPBICDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.132470967 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-28	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-28	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.132470967, CD₃OD, simulated)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aspergillus nidulans LO8030 expressing bgtABCD		Not Available
Aspergillus nidulans LO8030 expressing bgtABCD		Not Available

Chemical Taxonomy

Description

This compound 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

Farsesane sesquiterpenoid
Bergamotane sesquiterpenoid
Sesquiterpenoid
Methyl-branched fatty acid
Hydroxy fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Acyloin
Tertiary alcohol
Cyclic alcohol
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	2.23	ChemAxon
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.61 m³·mol⁻¹	ChemAxon
Polarizability	29.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Bergamotene A (NP0333695)

MOL for NP0333695 (Bergamotene A)

3D MOL for NP0333695 (Bergamotene A)

3D SDF for NP0333695 (Bergamotene A)

3D-SDF for NP0333695 (Bergamotene A)

PDB for NP0333695 (Bergamotene A)

3D PDB for NP0333695 (Bergamotene A)

SMILES for NP0333695 (Bergamotene A)

INCHI for NP0333695 (Bergamotene A)

Structure for NP0333695 (Bergamotene A)

3D Structure for NP0333695 (Bergamotene A)