NP-MRD: Showing NP-Card for Bergamotene G (NP0333701)

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Record Information

Version

2.0

Created at

2024-08-06 08:05:27 UTC

Updated at

2026-02-06 08:00:46 UTC

NP-MRD ID

NP0333701

Natural Product DOI

https://doi.org/10.57994/3180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bergamotene G

Description

Bergamotene G belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Bergamotene G was first documented in 2024 (PMID: 39623525). Based on a literature review very few articles have been published on Bergamotene G.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04202310382D          

 27 29  0  0  1  0            999 V2000
   -0.6794    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    0.1770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6794   -0.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5362   -1.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9434   -1.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0867   -0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -1.9442    0.0000 C   0  0  0  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    1.6060    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  1  0  0  0  0  0  0  0  0  0
    1.6026   -1.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -1.9664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6026   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -3.3953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6026   -4.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -4.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -3.3953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -4.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474   -2.6809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8724   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -1.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -1.2519    0.0000 O   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
  2  1  1  6  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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 17  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 15  1  0  0  0  0
 24 25  1  1  0  0  0
 26 13  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
  9 27  1  1  0  0  0
M  END


  Mrv2104 04202310382D          

 27 29  0  0  1  0            999 V2000
   -0.6794    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    0.1770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6794   -0.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5362   -1.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9434   -1.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0867   -0.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5754   -1.9442    0.0000 C   0  0  0  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    1.6060    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  1  0  0  0  0  0  0  0  0  0
    1.6026   -1.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -1.9664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6026   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901   -3.3953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6026   -4.1098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -4.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -3.3953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -4.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474   -2.6809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8724   -2.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3651   -1.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0474   -1.2519    0.0000 O   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
  2  1  1  6  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  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  1  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 20 17  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 15  1  0  0  0  0
 24 25  1  1  0  0  0
 26 13  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
  9 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@]1(C)[C@@H]2C[C@H]1C(C)=C[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O6/c1-11(2)6-5-7-21(4)13-9-14(21)15(8-12(13)3)26-20-19(25)18(24)17(23)16(10-22)27-20/h6,8,13-20,22-25H,5,7,9-10H2,1-4H3/t13-,14+,15+,16+,17+,18-,19+,20+,21-/m0/s1

> <INCHI_KEY>
CQQBRCTYCYTMKV-FBGPIUOESA-N

> <FORMULA>
C21H34O6

> <MOLECULAR_WEIGHT>
382.497

> <EXACT_MASS>
382.235538815

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.41139967660986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,6S)-4,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.5376827386666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199908000501177

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21009514225778

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083684482683

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
102.37670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,6S)-4,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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  C   UNK     0      -1.268   1.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.089   0.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.268  -0.659   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.001  -2.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.181  -3.166   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.628  -2.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.895  -1.123   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.807  -3.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.681   1.664   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.221   1.664   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.991   2.998   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.991   0.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.221  -1.003   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.991  -2.337   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.221  -3.671   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.991  -5.004   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.221  -6.338   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.991  -7.672   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.531  -7.672   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.681  -6.338   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.089  -7.672   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.089  -5.004   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.629  -5.004   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.681  -3.671   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.089  -2.337   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.681  -1.003   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.015   0.330   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24                                                            
CONECT   26   13    2   27                                                  
CONECT   27   26    9                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₆

Average Mass

382.4970 Da

Monoisotopic Mass

382.23554 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,6S)-4,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1S,2R,5S,6S)-4,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@]1(C)[C@@H]2C[C@H]1C(C)=C[C@H]2O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C21H34O6/c1-11(2)6-5-7-21(4)13-9-14(21)15(8-12(13)3)26-20-19(25)18(24)17(23)16(10-22)27-20/h6,8,13-20,22-25H,5,7,9-10H2,1-4H3/t13-,14+,15+,16+,17+,18-,19+,20+,21-/m0/s1

InChI Key

CQQBRCTYCYTMKV-FBGPIUOESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	Sun Yat-sen university	Wencong Yang	2024-08-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 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, 400.132470802 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	2026-02-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400.132470802, 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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Farsesane sesquiterpenoid
Bergamotane sesquiterpenoid
Sesquiterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Fatty alcohol
Fatty acyl
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
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	1.54	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	102.38 m³·mol⁻¹	ChemAxon
Polarizability	43.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Yang W, Tian S, Du YF, Zeng XL, Liang JJ, Lan WJ, Li H: Genome Mining of the Marine-Derived Fungus Trichoderma erinaceum F1-1 Unearths Bergamotene-Type Sesquiterpenoids. J Nat Prod. 2024 Dec 27;87(12):2746-2756. doi: 10.1021/acs.jnatprod.4c00905. Epub 2024 Dec 2. [PubMed:39623525 ]
DOI: 10.1021/acs.jnatprod.4c00905
PMID: 39623525

Showing NP-Card for Bergamotene G (NP0333701)

MOL for NP0333701 (Bergamotene G)

3D MOL for NP0333701 (Bergamotene G)

3D SDF for NP0333701 (Bergamotene G)

3D-SDF for NP0333701 (Bergamotene G)

PDB for NP0333701 (Bergamotene G)

3D PDB for NP0333701 (Bergamotene G)

SMILES for NP0333701 (Bergamotene G)

INCHI for NP0333701 (Bergamotene G)

Structure for NP0333701 (Bergamotene G)

3D Structure for NP0333701 (Bergamotene G)