NP-MRD: Showing NP-Card for 6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one (NP0158535)

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Record Information

Version

2.0

Created at

2022-09-02 16:08:49 UTC

Updated at

2022-09-02 16:08:49 UTC

NP-MRD ID

NP0158535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Hericerin belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one is found in Hericium erinaceus. 6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one was first documented in 2012 (PMID: 22670711). Based on a literature review a small amount of articles have been published on Hericerin (PMID: 25306354) (PMID: 33246107) (PMID: 32269298).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022218082D          

 31 33  0  0  0  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6284    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022218082D          

 31 33  0  0  0  0            999 V2000
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0158535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(=O)N(CCC3=CC=CC=C3)C2)C(O)=C1C\C=C(/C)CCC=C(C)C

> <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-DEDYPNTBSA-N

> <FORMULA>
C27H33NO3

> <MOLECULAR_WEIGHT>
419.565

> <EXACT_MASS>
419.246043927

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.93568558951331

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(2E)-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>
14.600160436910663

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804896376313884

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6425560404008497

> <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-[(2E)-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.199   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.533   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.533  -0.237   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.866  -1.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.199  -1.007   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      -1.173   2.843   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.793   0.175   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.333   0.175   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.103   1.509   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.333   2.843   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   22    5                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃NO₃

Average Mass

419.5650 Da

Monoisotopic Mass

419.24604 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(=O)N(CCC3=CC=CC=C3)C2)C(O)=C1C\C=C(/C)CCC=C(C)C

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-DEDYPNTBSA-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
Hericium erinaceus	LOTUS Database	35616633

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
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Ether
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organic oxygen 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)	-1.6	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	49.94 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434842

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102195678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li W, Zhou W, Kim EJ, Shim SH, Kang HK, Kim YH: Isolation and identification of aromatic compounds in Lion's Mane Mushroom and their anticancer activities. Food Chem. 2015 Mar 1;170:336-42. doi: 10.1016/j.foodchem.2014.08.078. Epub 2014 Aug 23. [PubMed:25306354 ]
Ryu SH, Hong SM, Khan Z, Lee SK, Vishwanath M, Turk A, Yeon SW, Jo YH, Lee DH, Lee JK, Hwang BY, Jung JK, Kim SY, Lee MK: Neurotrophic isoindolinones from the fruiting bodies of Hericium erinaceus. Bioorg Med Chem Lett. 2021 Jan 1;31:127714. doi: 10.1016/j.bmcl.2020.127714. Epub 2020 Nov 25. [PubMed:33246107 ]
Zheng Z, Chen B, Wang K, Bao L, Wang Z, Xie L, Guo C, Liu H: A concise total synthesis and PPAR activation activity of hericerin from Hericium erinaceum. J Antibiot (Tokyo). 2020 Sep;73(9):646-649. doi: 10.1038/s41429-020-0303-8. Epub 2020 Apr 8. [PubMed:32269298 ]
Kobayashi S, Inoue T, Ando A, Tamanoi H, Ryu I, Masuyama A: Total synthesis and structural revision of hericerin. J Org Chem. 2012 Jul 6;77(13):5819-22. doi: 10.1021/jo300719m. Epub 2012 Jun 14. [PubMed:22670711 ]
LOTUS database [Link]

Showing NP-Card for 6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one (NP0158535)

MOL for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

3D MOL for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

3D SDF for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

3D-SDF for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

PDB for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

3D PDB for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

SMILES for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

INCHI for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

Structure for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)

3D Structure for NP0158535 (6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-7-hydroxy-5-methoxy-2-(2-phenylethyl)-3h-isoindol-1-one)