NP-MRD: Showing NP-Card for α-elemolic acid (NP0272966)

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Record Information

Version

2.0

Created at

2022-09-08 19:49:25 UTC

Updated at

2022-09-08 19:49:26 UTC

NP-MRD ID

NP0272966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-elemolic acid

Description

Alpha-Elemolic acid, also known as a-elemolate or α-elemolic acid, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Alpha-Elemolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, alpha-elemolic acid has been detected, but not quantified in, herbs and spices. α-elemolic acid is found in Fomitopsis pinicola and Trattinnickia burserifolia. This could make alpha-elemolic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241219152D          

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M  END

     RDKit          3D

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  Mrv0541 02241219152D          

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  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
  7 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 24 31  1  1  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 21 34  1  6  0  0  0
  1 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0272966

> <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](CCC=C(C)C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24-25,31H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,25+,28+,29-,30+/m0/s1

> <INCHI_KEY>
NBSBUIQBEPROBM-IMJUUJEHSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.62187873935494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(2S,5R,7R,11S,14S,15S)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]-6-methylhept-5-enoic acid

> <ALOGPS_LOGP>
6.62

> <JCHEM_LOGP>
6.642397938

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.553786825962863

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851684068156024

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8069745953988422

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
136.23600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-elemolic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       8.212   2.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.118   1.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.212   0.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.748   0.737   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.909  -0.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.414  -0.033   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.080   0.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.080   2.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.414   3.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.748   2.277   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.909   3.808   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.747  -0.033   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.747   1.507   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.413   0.737   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.079  -0.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.079  -1.573   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.254  -2.343   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.413  -2.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.423  -3.523   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.593  -3.633   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.747  -1.573   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.080  -2.343   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.414  -1.573   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.688   4.217   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.195   4.537   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.670   6.002   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.177   6.322   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.653   7.787   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.159   8.107   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.622   8.931   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.658   5.362   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.134   6.826   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.151   5.041   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0       2.747  -3.113   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       9.752   2.753   0.000  0.00  0.00           H+0
CONECT    1    2   10   24   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   10                                             
CONECT    5    4                                                            
CONECT    6    4    7   23                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1    4   11                                             
CONECT   11   10                                                            
CONECT   12    7   13   14   21                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   12   22   34                                             
CONECT   22   21   23                                                       
CONECT   23   22    6                                                       
CONECT   24    1   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   24   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   21                                                            
CONECT   35    1                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
a-Elemolate	Generator
a-Elemolic acid	Generator
alpha-Elemolate	Generator
Α-elemolate	Generator
Α-elemolic acid	Generator
alpha-Elemenadienolic acid	HMDB
Elemadienolic acid	HMDB

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7003 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

(2S)-2-[(2S,5R,7R,11S,14S,15S)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]-6-methylhept-5-enoic acid

Traditional Name

α-elemolic acid

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](CCC=C(C)C)C(O)=O

InChI Identifier

InChI=1S/C30H48O3/c1-19(2)9-8-10-20(26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h9,20-21,24-25,31H,8,10-18H2,1-7H3,(H,32,33)/t20-,21-,24-,25+,28+,29-,30+/m0/s1

InChI Key

NBSBUIQBEPROBM-IMJUUJEHSA-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
Fomitopsis pinicola	LOTUS Database	35616633
Trattinnickia burserifolia	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
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

triterpenoid (CHEBI:10274 )
Dammarenes (C08623 )

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	6.62	ALOGPS
logP	6.64	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.24 m³·mol⁻¹	ChemAxon
Polarizability	55.62 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon