NP-MRD: Showing NP-Card for Euphol (NP0136979)

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Record Information

Version

2.0

Created at

2022-05-30 16:37:58 UTC

Updated at

2022-05-30 16:37:58 UTC

NP-MRD ID

NP0136979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euphol

Description

Euphol, also known as alpha-euphol or eupha-8,24-dienol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, euphol is considered to be an isoprenoid lipid molecule. Euphol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Euphol has been detected, but not quantified in, several different foods, such as cucumbers, muskmelons, shea tree, soy beans, and tea. Euphol is found in Camellia oleifera, Camellia sasanqua, Cicer arietinum, Clusia columnaris, Clusia multiflora, Cucumis sativus, Dacryodes hopkinsii, Euphorbia abyssinica, Euphorbia aleppica, Euphorbia antiquorum, Euphorbia boetica, Euphorbia caducifolia, Euphorbia drupifera, Euphorbia jolkinii, Euphorbia kansui, Euphorbia lathyris, Euphorbia neriifolia, Euphorbia nicaeensis, Euphorbia oxyphylla, Euphorbia portulacoides, Euphorbia resinifera, Euphorbia retusa, Euphorbia sapinii, Euphorbia tirucalli, Euphorbia trigona, Monocyclanthus vignei, Tripetalum cymosum and Vitellaria paradoxa. This could make euphol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241221102D          

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M  END

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  Mrv0541 02241221102D          

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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
  7 10  2  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
  3 18  1  1  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  5 21  1  6  0  0  0
  6 22  1  1  0  0  0
 15 23  1  1  0  0  0
 14 24  1  6  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 25 32  1  6  0  0  0
 13 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0136979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC[C@]2(C)C3=C(CC[C@@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1

> <INCHI_KEY>
CAHGCLMLTWQZNJ-WZLOIPHISA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
54.56681946585081

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol

> <ALOGPS_LOGP>
7.72

> <JCHEM_LOGP>
7.706672521

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.553786825962863

> <JCHEM_PKA_STRONGEST_BASIC>
-0.806973642323843

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
134.5447

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
euphol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.320   0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.014   0.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.014  -1.430   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.320  -2.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.654  -1.430   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.654   0.110   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.987   0.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.987  -2.200   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.321  -1.430   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.321   0.110   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.321   3.190   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.987   2.420   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.119   2.896   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.655   2.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.655   0.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.119   0.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.024   1.650   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.347  -2.200   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.320  -3.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.014  -2.970   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       2.654  -2.970   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       2.654   1.650   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.655  -0.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.655   3.960   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.119   4.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.453   5.206   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.787   4.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.120   5.206   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.454   4.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.788   5.206   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.454   2.896   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.786   5.206   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       9.607   3.294   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   18                                                  
CONECT    4    3    5   19   20                                             
CONECT    5    4    6    8   21                                             
CONECT    6    1    7    5   22                                             
CONECT    7    6   10   12                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   15    7                                                  
CONECT   11   12   14                                                       
CONECT   12    7   11                                                       
CONECT   13   14   17   25   33                                             
CONECT   14   11   13   15   24                                             
CONECT   15   10   16   14   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18    3                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    6                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25   13   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   25                                                            
CONECT   33   13                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(+)-alpha-Euphol	HMDB
(3beta,13alpha,14beta,17alpha)-Lanosta-8,24-dien-3-ol	HMDB
13alpha,14beta,17BetaH-lanosta-8,24-dien-3beta-ol (8ci)	HMDB
5alpha-Eupha-8,24-dien-3beta-ol	HMDB
alpha-Euphol	HMDB
Eupha-8,24-dienol	HMDB
Euphadienol	HMDB
Euphol (6ci)	HMDB
Euphol	MeSH
8,24-Euphadien-3 beta-ol	MeSH

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7174 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

(2S,5S,7R,11S,14S,15S)-2,6,6,11,15-pentamethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol

Traditional Name

euphol

CAS Registry Number

Not Available

SMILES

[H][C@]1(CC[C@]2(C)C3=C(CC[C@@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C

InChI Identifier

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22+,25+,26+,28-,29+,30-/m1/s1

InChI Key

CAHGCLMLTWQZNJ-WZLOIPHISA-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
Camellia oleifera	LOTUS Database	35616633
Camellia sasanqua	LOTUS Database	35616633
Cicer arietinum	LOTUS Database	35616633
Clusia columnaris	LOTUS Database	35616633
Clusia multiflora	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Dacryodes hopkinsii	LOTUS Database	35616633
Euphorbia abyssinica	LOTUS Database	35616633
Euphorbia aleppica	LOTUS Database	35616633
Euphorbia antiquorum	LOTUS Database	35616633
Euphorbia boetica	LOTUS Database	35616633
Euphorbia caducifolia	LOTUS Database	35616633
Euphorbia drupifera	LOTUS Database	35616633
Euphorbia jolkini	LOTUS Database	35616633
Euphorbia kansui	LOTUS Database	35616633
Euphorbia lathyris	LOTUS Database	35616633
Euphorbia neriifolia	LOTUS Database	35616633
Euphorbia nicaeensis	LOTUS Database	35616633
Euphorbia oxyphylla	LOTUS Database	35616633
Euphorbia portulacoides	LOTUS Database	35616633
Euphorbia resinifera	LOTUS Database	35616633
Euphorbia retusa	LOTUS Database	35616633
Euphorbia sapinii	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Euphorbia trigona	LOTUS Database	35616633
Monocyclanthus vignei	LOTUS Database	35616633
Tripetalum cymosum	LOTUS Database	35616633
Vitellaria paradoxa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:4940 )
Tirucallane/euphane triterpenoids (C08624 )
Dammarenes (C08624 )
Tirucallane/euphane triterpenoids (LMPR0106090002 )

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	7.72	ALOGPS
logP	7.71	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	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	134.54 m³·mol⁻¹	ChemAxon
Polarizability	54.57 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031438

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Euphol (NP0136979)

MOL for NP0136979 (Euphol)

3D MOL for NP0136979 (Euphol)

3D SDF for NP0136979 (Euphol)

3D-SDF for NP0136979 (Euphol)

PDB for NP0136979 (Euphol)

3D PDB for NP0136979 (Euphol)

SMILES for NP0136979 (Euphol)

INCHI for NP0136979 (Euphol)

Structure for NP0136979 (Euphol)

3D Structure for NP0136979 (Euphol)