NP-MRD: Showing NP-Card for Geranylgeraniol (NP0045609)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:42 UTC

Updated at

2022-03-17 19:32:42 UTC

NP-MRD ID

NP0045609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranylgeraniol

Description

Geranylgeraniol belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeraniol is considered to be an isoprenoid lipid molecule. Geranylgeraniol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Geranylgeraniol has been detected, but not quantified in, flaxseeds. This could make geranylgeraniol a potential biomarker for the consumption of these foods. Geranylgeraniol is found in Bellardia trixago, Bifurcaria bifurcata, Bixa orellana, Blepharispermum zanguebaricum, Cystoseira brachycarpa, Ectatomma ruidum, Pellia epiphylla, Pinus koraiensis , Pinus sibirica, Toona ciliata , Neofinetia falcata and Xylopia brasiliensis. A geranylgeraniol in which all four double bonds have E- (trans-) geometry.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309272007312D          

 21 20  0  0  0  0            999 V2000
10001.346710000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.631610000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.916110000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.201810000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.487210000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.772910000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.058510000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.344210000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.629610000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.915310000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.629610001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.487210001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.061910000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.775010000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.490210000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.205410000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.918510000.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.633710000.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.346810000.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.205410001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.346710001.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  1 21  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

> <INCHI_KEY>
OJISWRZIEWCUBN-QIRCYJPOSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.4834

> <EXACT_MASS>
290.26096571

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.17957192246918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

> <ALOGPS_LOGP>
6.06

> <JCHEM_LOGP>
5.821811845999999

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.33002421872553

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2170474067294528

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
98.78729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.43e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geranylgeraniol

> <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    8669.1818667.514   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.8468666.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8666.5108667.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8665.1778666.747   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.8438667.514   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.5098666.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8661.1768667.514   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.8428666.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8658.5098667.514   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8657.1758666.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8658.5098669.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.8438669.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.5158666.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.8478667.514   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8673.1828666.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8674.5178667.514   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8675.8488666.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8677.1838667.514   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8678.5148666.747   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8674.5178669.055   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.1818669.055   0.000  0.00  0.00           C+0
CONECT    1    2   13   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    5                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   16                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2E,6E,10E)-Geranylgeraniol	ChEBI
Geranylgeraniol, (e,e,e)-isomer	MeSH
Geranylgeraniol, (Z,Z,Z)-isomer	MeSH
Tetraprenol	MeSH
(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol	PhytoBank
(E,E,E)-Geranylgeraniol	PhytoBank
(E,E,E)-Geranylgeranyl alcohol	PhytoBank
All-trans-Geranylgeraniol	PhytoBank
Geranylgeraniol	PhytoBank
Geranylgeranyl alcohol	PhytoBank
trans,trans,trans-Geranylgeraniol	PhytoBank
trans-Geranylgeraniol	PhytoBank

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4834 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

Traditional Name

geranylgeraniol

CAS Registry Number

24034-73-9

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO

InChI Identifier

InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

InChI Key

OJISWRZIEWCUBN-QIRCYJPOSA-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
Bartsia trixago	LOTUS Database	35616633
Bifurcaria bifurcata	LOTUS Database	35616633
Bixa orellana	LOTUS Database	35616633
Blepharispermum zanguebaricum	LOTUS Database	35616633
Cystoseira brachycarpa	LOTUS Database	35616633
Ectatomma ruidum	LOTUS Database	35616633
Linum usitatissimum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pellia epiphylla	Plant	KNApSAcK
Pinus koraiensis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Toona ciliata	Plant	KNApSAcK
Vanda falcata	LOTUS Database	35616633
Xylopia brasiliensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

geranylgeraniol (CHEBI:46762 )
Acyclic diterpenoids (C09094 )
Linear diterpenes (C09094 )
Acyclic diterpenoids (LMPR0104010009 )

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	6.06	ALOGPS
logP	5.82	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	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	10	ChemAxon
Refractivity	98.79 m³·mol⁻¹	ChemAxon
Polarizability	38.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon