NP-MRD: Showing NP-Card for neotigogenin (NP0321569)

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Record Information

Version

2.0

Created at

2022-09-11 23:50:26 UTC

Updated at

2022-09-11 23:50:26 UTC

NP-MRD ID

NP0321569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

neotigogenin

Description

Neogrifolin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Neogrifolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Neogrifolin has been detected, but not quantified in, mushrooms. neotigogenin is found in Agave sisalana, Agave striata, Chlorogalum pomeridianum, Cordyline australis, Tristagma uniflorum, Tribulus cistoides, Trigonella foenum-graecum and Yucca schottii. This could make neogrifolin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217052D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241217052D          

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 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20  1  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  1  0  0  0
 23 30  1  0  0  0  0
  1 30  1  0  0  0  0
  7 31  1  6  0  0  0
 15 32  1  6  0  0  0
  4 33  1  1  0  0  0
  3 34  1  6  0  0  0
 20 35  1  6  0  0  0
  1 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0321569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
GMBQZIIUCVWOCD-PUHUBZITSA-N

> <FORMULA>
C27H44O3

> <MOLECULAR_WEIGHT>
416.6365

> <EXACT_MASS>
416.329045274

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.86637214686008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
5.332884935333334

> <ALOGPS_LOGS>
-7.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2963963211217

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3560752133131748

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
119.41590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.28e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

> <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      19.068  -3.410   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.163  -4.655   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.698  -4.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.365  -4.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.365  -6.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.031  -7.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.697  -6.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.364  -7.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.030  -6.490   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.696  -7.260   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.030  -4.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.364  -4.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.697  -4.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.697  -3.410   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.031  -4.180   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.031  -2.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.365  -1.870   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.698  -2.640   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.859  -1.108   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.163  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.068  -0.918   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.592   0.547   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.533  -1.394   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.372   0.138   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      21.618   1.043   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.024   0.417   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.270   1.322   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      23.185  -1.115   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.939  -2.020   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      20.533  -2.934   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      12.697  -8.030   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      14.031  -5.720   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      15.365  -3.410   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      16.698  -5.720   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      17.764  -3.651   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      20.157  -4.499   0.000  0.00  0.00           H+0
CONECT    1    2   20   30   36                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   18   34                                             
CONECT    4    3    5   15   33                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13   31                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    4   16   32                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    3   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    1   21   35                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29   30                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23                                                       
CONECT   30   23    1                                                       
CONECT   31    7                                                            
CONECT   32   15                                                            
CONECT   33    4                                                            
CONECT   34    3                                                            
CONECT   35   20                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
5-Methyl-6-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
e,e,5-Methyl-4-(3,7,11-trimethyl-2,6,10-dodecatrienyl)-1,3-benzenediol	HMDB
4-Farnesyl-5-methylresorcinol	MeSH
4-trans,trans-Farnesyl-5-methylresorcinol	MeSH
(25S)-5alpha-Spirostan-3beta-ol	HMDB
(3beta,5alpha,25S)-Spirostan-3-ol	HMDB
25S-Tigogenin	HMDB

Chemical Formula

C₂₇H₄₄O₃

Average Mass

416.6365 Da

Monoisotopic Mass

416.32905 Da

IUPAC Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

Traditional Name

(1'R,2R,2'S,4'S,5S,7'S,8'R,9'S,12'S,13'S,16'S,18'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-16'-ol

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]1(CC[C@H](C)CO1)O2

InChI Identifier

InChI=1S/C27H44O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI Key

GMBQZIIUCVWOCD-PUHUBZITSA-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
Agave sisalana	LOTUS Database	35616633
Agave striata Zucc.	LOTUS Database	35616633
Chlorogalum pomeridianum	LOTUS Database	35616633
Cordyline australis	LOTUS Database	35616633
Ipheion uniflorum	LOTUS Database	35616633
Tribulus cistoides	LOTUS Database	35616633
Trigonella foenum-graecum	LOTUS Database	35616633
Yucca schottii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Resorcinol
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.52	ALOGPS
logP	5.33	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	119.42 m³·mol⁻¹	ChemAxon
Polarizability	50.87 Å³	ChemAxon
Number of Rings	6	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

HMDB0030053

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001359

KNApSAcK ID

C00023938

Chemspider ID

8050115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9874426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for neotigogenin (NP0321569)

MOL for NP0321569 (neotigogenin)

3D MOL for NP0321569 (neotigogenin)

3D SDF for NP0321569 (neotigogenin)

3D-SDF for NP0321569 (neotigogenin)

PDB for NP0321569 (neotigogenin)

3D PDB for NP0321569 (neotigogenin)

SMILES for NP0321569 (neotigogenin)

INCHI for NP0321569 (neotigogenin)

Structure for NP0321569 (neotigogenin)

3D Structure for NP0321569 (neotigogenin)