NP-MRD: Showing NP-Card for Erinacine A (NP0049607)

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Record Information

Version

2.0

Created at

2022-03-17 21:15:11 UTC

Updated at

2024-09-03 04:17:08 UTC

NP-MRD ID

NP0049607

Natural Product DOI

https://doi.org/10.57994/0932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erinacine A

Description

Erinacine A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Erinacine A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Erinacine A has been detected, but not quantified in, mushrooms. Erinacine A is found in Hericium erinaceus. Erinacine A was first documented in 2023 (PMID: 37888275). This could make erinacine a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061311442D          

 31 34  0  0  0  0            999 V2000
    3.5076   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -1.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6603   -0.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141    1.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    0.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278   -1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298    1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    4.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    2.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    1.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    4.4210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    4.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    3.7394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208    2.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330    2.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  5  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  6  2  0  0  0  0
 18 13  1  0  0  0  0
 19 11  1  0  0  0  0
 20 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24  3  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 24 20  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
 26 12  2  0  0  0  0
 27 18  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30 13  1  0  0  0  0
 30 23  1  0  0  0  0
 31 19  1  0  0  0  0
 31 23  1  0  0  0  0
M  END


  Mrv0541 05061311442D          

 31 34  0  0  0  0            999 V2000
    3.5076   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -1.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6603   -0.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141    1.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    0.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7304   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4162    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278   -1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    0.4281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2195    3.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298    1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4272    4.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317    3.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    2.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    1.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4196    0.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8149    4.4210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2305    4.8814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0395    3.7394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208    2.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4330    2.1370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 15  5  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  6  2  0  0  0  0
 18 13  1  0  0  0  0
 19 11  1  0  0  0  0
 20 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24  3  1  0  0  0  0
 24  8  1  0  0  0  0
 24  9  1  0  0  0  0
 24 20  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 17  1  0  0  0  0
 25 19  1  0  0  0  0
 26 12  2  0  0  0  0
 27 18  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30 13  1  0  0  0  0
 30 23  1  0  0  0  0
 31 19  1  0  0  0  0
 31 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C3=CC=C(CC(OC4OCC(O)C(O)C4O)C3(C)CCC2(C)CC1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O6/c1-14(2)16-7-8-24(3)9-10-25(4)17(20(16)24)6-5-15(12-26)11-19(25)31-23-22(29)21(28)18(27)13-30-23/h5-6,12,14,18-19,21-23,27-29H,7-11,13H2,1-4H3

> <INCHI_KEY>
LPPCHLAEVDUIIW-UHFFFAOYSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.5497

> <EXACT_MASS>
432.251188884

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.104179423552694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,5a-dimethyl-1-(propan-2-yl)-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
1.9733997313333345

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.403212287166475

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.246231746121753

> <JCHEM_PKA_STRONGEST_BASIC>
-3.52658062854581

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
118.83849999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-isopropyl-3a,5a-dimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,4H,5H,6H,7H-cyclohepta[e]indene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.548  -3.074   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.975  -2.368   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.734   3.187   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.096   3.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.233  -0.966   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.728  -0.599   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.314   0.050   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.242   1.588   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.066   3.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.529   3.462   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.013   1.514   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.363  -0.717   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.510   5.691   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.465  -1.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.013  -0.026   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.873  -0.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.373   0.799   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.143   7.187   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.176   2.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.911   0.709   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.664   7.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.553   6.551   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.920   5.055   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.757   1.996   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.682   2.175   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.650   0.129   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.254   8.253   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.297   9.112   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.074   6.980   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.399   4.625   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.808   3.989   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5    6   15                                                       
CONECT    6    5   17                                                       
CONECT    7    8   16                                                       
CONECT    8    7   24                                                       
CONECT    9   10   24                                                       
CONECT   10    9   25                                                       
CONECT   11   15   19                                                       
CONECT   12   15   26                                                       
CONECT   13   18   30                                                       
CONECT   14    1    2   16                                                  
CONECT   15    5   11   12                                                  
CONECT   16    7   14   20                                                  
CONECT   17    6   20   25                                                  
CONECT   18   13   21   27                                                  
CONECT   19   11   25   31                                                  
CONECT   20   16   17   24                                                  
CONECT   21   18   22   28                                                  
CONECT   22   21   23   29                                                  
CONECT   23   22   30   31                                                  
CONECT   24    3    8    9   20                                             
CONECT   25    4   10   17   19                                             
CONECT   26   12                                                            
CONECT   27   18                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30   13   23                                                       
CONECT   31   19   23                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
Erinacine a	MeSH

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5497 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

3a,5a-dimethyl-1-(propan-2-yl)-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,3aH,4H,5H,5aH,6H,7H-cyclohepta[e]indene-8-carbaldehyde

Traditional Name

1-isopropyl-3a,5a-dimethyl-6-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2H,3H,4H,5H,6H,7H-cyclohepta[e]indene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2C3=CC=C(CC(OC4OCC(O)C(O)C4O)C3(C)CCC2(C)CC1)C=O

InChI Identifier

InChI=1S/C25H36O6/c1-14(2)16-7-8-24(3)9-10-25(4)17(20(16)24)6-5-15(12-26)11-19(25)31-23-22(29)21(28)18(27)13-30-23/h5-6,12,14,18-19,21-23,27-29H,7-11,13H2,1-4H3

InChI Key

LPPCHLAEVDUIIW-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2024-05-08	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	qjz@nwafu.edu.cn	Not Available	Not Available	2023-09-19	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Hericium erinaceus	LOTUS Database	35616633
Hericium rajendrae NPCB A08		Not Available
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aldehyde
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.98	ALOGPS
logP	1.97	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	118.84 m³·mol⁻¹	ChemAxon
Polarizability	48.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040291

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020012

KNApSAcK ID

Not Available

Chemspider ID

8043168

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9867477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei J, Cheng M, Zhu JF, Zhang Y, Cui K, Wang X, Qi J: Comparative Genomic Analysis and Metabolic Potential Profiling of a Novel Culinary-Medicinal Mushroom, Hericium rajendrae (Basidiomycota). J Fungi (Basel). 2023 Oct 15;9(10):1018. doi: 10.3390/jof9101018. [PubMed:37888275 ]
DOI: 10.3390/jof9101018

Showing NP-Card for Erinacine A (NP0049607)

MOL for NP0049607 (Erinacine A)

3D MOL for NP0049607 (Erinacine A)

3D SDF for NP0049607 (Erinacine A)

3D-SDF for NP0049607 (Erinacine A)

PDB for NP0049607 (Erinacine A)

3D PDB for NP0049607 (Erinacine A)

SMILES for NP0049607 (Erinacine A)

INCHI for NP0049607 (Erinacine A)

Structure for NP0049607 (Erinacine A)

3D Structure for NP0049607 (Erinacine A)