NP-MRD: Showing NP-Card for Erinacine E (NP0045438)

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Record Information

Version

2.0

Created at

2022-03-17 19:19:58 UTC

Updated at

2026-02-26 02:52:20 UTC

NP-MRD ID

NP0045438

Natural Product DOI

https://doi.org/10.57994/0931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erinacine E

Description

Erinacine E belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Erinacine E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, erinacine e has been detected, but not quantified in, mushrooms. Erinacine E is found in Hericium coralloides and Hericium erinaceus. Erinacine E was first documented in 2008 (PMID: 18181632). This could make erinacine e a potential biomarker for the consumption of these foods (PMID: 37888275).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241218142D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 02241218142D          

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M  END
> <DATABASE_ID>
NP0045438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C3CC=C4C5C(OC6OCC(O)(C4O)C(O)C56O)C3(C)CCC2(C)CC1

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

> <INCHI_KEY>
YUCYEVHMFBEBSC-UHFFFAOYSA-N

> <FORMULA>
C25H36O6

> <MOLECULAR_WEIGHT>
432.5497

> <EXACT_MASS>
432.251188884

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
47.49986820118179

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,12-dimethyl-6-(propan-2-yl)-14,16-dioxahexacyclo[16.3.1.0⁴,¹².0⁵,⁹.0¹³,²¹.0¹⁵,²⁰]docosa-1,5-diene-18,19,20,22-tetrol

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
1.289339268666666

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.275155864529122

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.511551549157836

> <JCHEM_PKA_STRONGEST_BASIC>
-3.550272184927371

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
114.49199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-isopropyl-9,12-dimethyl-14,16-dioxahexacyclo[16.3.1.0⁴,¹².0⁵,⁹.0¹³,²¹.0¹⁵,²⁰]docosa-1,5-diene-18,19,20,22-tetrol

> <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      -4.666   0.829   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.666  -0.718   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.331  -1.491   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.996  -0.718   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.996   0.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.331   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.790  -1.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.707  -1.331   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.365   0.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.707   1.429   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.790   1.751   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.880  -0.068   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.738   1.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.083   2.548   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.568   2.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.442   3.885   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.963   3.259   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.011   5.462   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.008   3.457   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.008   0.055   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.996   2.375   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.833   0.087   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.540  -1.465   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.094   1.143   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.905   3.859   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.817  -1.751   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.199  -3.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.676  -3.006   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.527  -3.916   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.527  -5.462   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.037  -3.514   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20   26                                             
CONECT    3    2    4   28                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   11   21                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11   15                                                  
CONECT   11    5   10   17                                                  
CONECT   12    9   13   23                                                  
CONECT   13   12   14   19   22                                             
CONECT   14   13   15   25                                                  
CONECT   15   10   14   16   24                                             
CONECT   16   15   17   18                                                  
CONECT   17   11   16                                                       
CONECT   18   16   19                                                       
CONECT   19   13   18                                                       
CONECT   20    2                                                            
CONECT   21    5                                                            
CONECT   22   13                                                            
CONECT   23   12                                                            
CONECT   24   15                                                            
CONECT   25   14                                                            
CONECT   26    2   27                                                       
CONECT   27   26   28                                                       
CONECT   28    3   27   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
(-)-Erinacine e	HMDB
Erinacine e	MeSH
Erinacine-e	MeSH

Chemical Formula

C₂₅H₃₆O₆

Average Mass

432.5497 Da

Monoisotopic Mass

432.25119 Da

IUPAC Name

9,12-dimethyl-6-(propan-2-yl)-14,16-dioxahexacyclo[16.3.1.0⁴,¹².0⁵,⁹.0¹³,²¹.0¹⁵,²⁰]docosa-1,5-diene-18,19,20,22-tetrol

Traditional Name

6-isopropyl-9,12-dimethyl-14,16-dioxahexacyclo[16.3.1.0⁴,¹².0⁵,⁹.0¹³,²¹.0¹⁵,²⁰]docosa-1,5-diene-18,19,20,22-tetrol

CAS Registry Number

178120-47-3

SMILES

CC(C)C1=C2C3CC=C4C5C(OC6OCC(O)(C4O)C(O)C56O)C3(C)CCC2(C)CC1

InChI Identifier

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

InChI Key

YUCYEVHMFBEBSC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2023-09-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	[email protected]	Not Available	Not Available	2023-09-19	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-26	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.0, Methanol-d4, simulated)	[email protected]	Not Available	Not Available	2026-02-26	View Spectrum

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 coralloides	LOTUS Database	35616633
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
Furopyran
Monosaccharide
Oxane
Pyran
Tertiary alcohol
Furan
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.69	ALOGPS
logP	1.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.51	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.49 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	6	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

HMDB0029656

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000830

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73082498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Watanabe H, Nakada M: Biomimetic total synthesis of (-)-erinacine E. J Am Chem Soc. 2008 Jan 30;130(4):1150-1. doi: 10.1021/ja7102795. Epub 2008 Jan 9. [PubMed:18181632 ]
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
PMID: 37888275

Showing NP-Card for Erinacine E (NP0045438)

MOL for NP0045438 (Erinacine E)

3D MOL for NP0045438 (Erinacine E)

3D SDF for NP0045438 (Erinacine E)

3D-SDF for NP0045438 (Erinacine E)

PDB for NP0045438 (Erinacine E)

3D PDB for NP0045438 (Erinacine E)

SMILES for NP0045438 (Erinacine E)

INCHI for NP0045438 (Erinacine E)

Structure for NP0045438 (Erinacine E)

3D Structure for NP0045438 (Erinacine E)