NP-MRD: Showing NP-Card for Tirucallol (NP0137072)

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Record Information

Version

2.0

Created at

2022-05-30 16:40:51 UTC

Updated at

2022-05-30 16:40:51 UTC

NP-MRD ID

NP0137072

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tirucallol

Description

Tirucallol, also known as 20-epi-euphol or kanzuiol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, tirucallol is considered to be an isoprenoid lipid molecule. Tirucallol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Tirucallol has been detected, but not quantified in, several different foods, such as cucumbers, muskmelons, nuts, soy beans, and tea. Tirucallol is found in Cucumis melo, Dacryodes hopkinsii, Euphorbia caducifolia, Euphorbia ingens, Euphorbia jaxartica, Euphorbia oxyphylla, Euphorbia tirucalli and Euphorbia wallichii. This could make tirucallol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02241216202D          

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M  END

     RDKit          3D

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M  END

  Mrv0541 02241216202D          

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  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  1  0  0  0
  3 14  1  1  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  1  0  0  0  0
  8 22  1  6  0  0  0
 17 23  1  6  0  0  0
 18 24  1  1  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 21 32  1  1  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137072

> <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+/m0/s1

> <INCHI_KEY>
CAHGCLMLTWQZNJ-HGKXYCPESA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.7174

> <EXACT_MASS>
426.386166222

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
55.174086177399076

> <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-[(2S)-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>
134.54469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.76e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-tirucallol

> <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       4.169  -2.908   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.835  -2.138   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.501  -2.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.168  -2.138   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.166  -2.908   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.166  -4.448   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.168  -5.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.501  -4.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.835  -5.218   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.169  -4.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.555  -6.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.891  -6.578   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.500  -5.218   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.501  -1.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.835  -0.598   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.169   0.172   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.502  -0.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.502  -2.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.967  -2.614   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.872  -1.368   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.967  -0.122   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       1.501  -5.988   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       5.502   0.942   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.502  -3.678   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.967   1.418   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.633   2.188   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.301   2.188   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.634   1.418   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.968   2.188   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.302   1.418   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.635   2.188   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.455   0.277   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      12.302  -0.122   0.000  0.00  0.00           C+0
CONECT    1    2   10   18                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4    8   14                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11   12                                             
CONECT    8    7    3    9   22                                             
CONECT    9    8   10                                                       
CONECT   10    9    1                                                       
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    6                                                            
CONECT   14    3                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21   23                                             
CONECT   18   17    1   19   24                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   25   32                                             
CONECT   22    8                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   21   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30                                                            
CONECT   32   21                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3beta,13alpha,14beta,17alpha,20S)-Lanosta-8,24-dien-3-ol	HMDB
20-Epi-euphol	HMDB
Kanzuiol	HMDB
Tirucalladienol	HMDB
Lanostan-8,24-dien-3-ol	HMDB
Tirucallol	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-[(2S)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol

Traditional Name

(+)-tirucallol

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+/m0/s1

InChI Key

CAHGCLMLTWQZNJ-HGKXYCPESA-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
Cucumis melo	LOTUS Database	35616633
Dacryodes hopkinsii	LOTUS Database	35616633
Euphorbia caducifolia	LOTUS Database	35616633
Euphorbia ingens	LOTUS Database	35616633
Euphorbia jaxartica	LOTUS Database	35616633
Euphorbia oxyphylla	LOTUS Database	35616633
Euphorbia tirucalli	LOTUS Database	35616633
Euphorbia wallichii	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

Tirucallane/euphane triterpenoids (LMPR0106090001 )

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	55.17 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

HMDB0037032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016013

KNApSAcK ID

Not Available

Chemspider ID

91492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101257

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Tirucallol (NP0137072)

MOL for NP0137072 (Tirucallol)

3D MOL for NP0137072 (Tirucallol)

3D SDF for NP0137072 (Tirucallol)

3D-SDF for NP0137072 (Tirucallol)

PDB for NP0137072 (Tirucallol)

3D PDB for NP0137072 (Tirucallol)

SMILES for NP0137072 (Tirucallol)

INCHI for NP0137072 (Tirucallol)

Structure for NP0137072 (Tirucallol)

3D Structure for NP0137072 (Tirucallol)