NP-MRD: Showing NP-Card for Hericerin (NP0049165)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:08 UTC

Updated at

2022-03-17 21:08:08 UTC

NP-MRD ID

NP0049165

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hericerin

Description

Hericerin belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Hericerin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hericerin has been detected, but not quantified in, mushrooms. Hericerin is found in Hericium erinaceus. This could make hericerin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310322D          

 31 33  0  0  0  0            999 V2000
    8.3536   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 14 13  1  0  0  0  0
 16 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19  9  2  0  0  0  0
 20  3  1  0  0  0  0
 20 10  1  0  0  0  0
 20 13  2  0  0  0  0
 21 11  2  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
 22 17  2  0  0  0  0
 22 18  1  0  0  0  0
 23 14  1  0  0  0  0
 24 17  1  0  0  0  0
 24 23  2  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  2  0  0  0  0
 27 25  1  0  0  0  0
 28 16  1  0  0  0  0
 28 18  1  0  0  0  0
 28 27  1  0  0  0  0
 29 26  1  0  0  0  0
 30 27  2  0  0  0  0
 31  4  1  0  0  0  0
 31 24  1  0  0  0  0
M  END


  Mrv0541 05061310322D          

 31 33  0  0  0  0            999 V2000
    8.3536   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0587   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 14 13  1  0  0  0  0
 16 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19  9  2  0  0  0  0
 20  3  1  0  0  0  0
 20 10  1  0  0  0  0
 20 13  2  0  0  0  0
 21 11  2  0  0  0  0
 21 12  1  0  0  0  0
 21 15  1  0  0  0  0
 22 17  2  0  0  0  0
 22 18  1  0  0  0  0
 23 14  1  0  0  0  0
 24 17  1  0  0  0  0
 24 23  2  0  0  0  0
 25 22  1  0  0  0  0
 26 23  1  0  0  0  0
 26 25  2  0  0  0  0
 27 25  1  0  0  0  0
 28 16  1  0  0  0  0
 28 18  1  0  0  0  0
 28 27  1  0  0  0  0
 29 26  1  0  0  0  0
 30 27  2  0  0  0  0
 31  4  1  0  0  0  0
 31 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049165

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C\C=C(\C)CCC=C(C)C)C(O)=C2C(=O)N(CCC3=CC=CC=C3)CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO3/c1-19(2)9-8-10-20(3)13-14-23-24(31-4)17-22-18-28(27(30)25(22)26(23)29)16-15-21-11-6-5-7-12-21/h5-7,9,11-13,17,29H,8,10,14-16,18H2,1-4H3/b20-13-

> <INCHI_KEY>
ULSKNVPXNYBAQZ-MOSHPQCFSA-N

> <FORMULA>
C27H33NO3

> <MOLECULAR_WEIGHT>
419.5558

> <EXACT_MASS>
419.246043927

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.049665209949275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
6.612644552333334

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.566942796276688

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804896863322638

> <JCHEM_PKA_STRONGEST_BASIC>
-1.114512169590399

> <JCHEM_POLAR_SURFACE_AREA>
49.769999999999996

> <JCHEM_REFRACTIVITY>
129.34149999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3H-isoindol-1-one

> <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      15.593  -4.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.260  -6.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.710  -2.636   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.940  -3.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.940  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592  -5.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.926  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.400  -3.970   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.400  -1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090  -2.636   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.260  -5.153   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.630  -2.636   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       1.220  -1.303   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3   20                                                            
CONECT    4   31                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   10                                                       
CONECT    9    8   19                                                       
CONECT   10    8   20                                                       
CONECT   11    6   21                                                       
CONECT   12    7   21                                                       
CONECT   13   14   20                                                       
CONECT   14   13   23                                                       
CONECT   15   16   21                                                       
CONECT   16   15   28                                                       
CONECT   17   22   24                                                       
CONECT   18   22   28                                                       
CONECT   19    1    2    9                                                  
CONECT   20    3   10   13                                                  
CONECT   21   11   12   15                                                  
CONECT   22   17   18   25                                                  
CONECT   23   14   24   26                                                  
CONECT   24   17   23   31                                                  
CONECT   25   22   26   27                                                  
CONECT   26   23   25   29                                                  
CONECT   27   25   28   30                                                  
CONECT   28   16   18   27                                                  
CONECT   29   26                                                            
CONECT   30   27                                                            
CONECT   31    4   24                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
6-(3,7-Dimethyl-2,6-octadienyl)-2,3-dihydro-7-hydroxy-5-methoxy-2-(2-phenylethyl)-1H-isoindol-1-one, 9ci	HMDB

Chemical Formula

C₂₇H₃₃NO₃

Average Mass

419.5558 Da

Monoisotopic Mass

419.24604 Da

IUPAC Name

6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-2,3-dihydro-1H-isoindol-1-one

Traditional Name

6-[(2Z)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3H-isoindol-1-one

CAS Registry Number

140381-53-9

SMILES

COC1=C(C\C=C(\C)CCC=C(C)C)C(O)=C2C(=O)N(CCC3=CC=CC=C3)CC2=C1

InChI Identifier

InChI=1S/C27H33NO3/c1-19(2)9-8-10-20(3)13-14-23-24(31-4)17-22-18-28(27(30)25(22)26(23)29)16-15-21-11-6-5-7-12-21/h5-7,9,11-13,17,29H,8,10,14-16,18H2,1-4H3/b20-13-

InChI Key

ULSKNVPXNYBAQZ-MOSHPQCFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
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 isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Aromatic monoterpenoid
Bicyclic monoterpenoid
Isoindolone
Monoterpenoid
Isoindole
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	6.3	ALOGPS
logP	6.61	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	129.34 m³·mol⁻¹	ChemAxon
Polarizability	50.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0038587

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017977

KNApSAcK ID

Not Available

Chemspider ID

30777272

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752403

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hericerin (NP0049165)

MOL for NP0049165 (Hericerin)

3D MOL for NP0049165 (Hericerin)

3D SDF for NP0049165 (Hericerin)

3D-SDF for NP0049165 (Hericerin)

PDB for NP0049165 (Hericerin)

3D PDB for NP0049165 (Hericerin)

SMILES for NP0049165 (Hericerin)

INCHI for NP0049165 (Hericerin)

Structure for NP0049165 (Hericerin)

3D Structure for NP0049165 (Hericerin)