NP-MRD: Showing NP-Card for (1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol (NP0239908)

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Record Information

Version

1.0

Created at

2022-09-06 23:35:37 UTC

Updated at

2022-09-06 23:35:37 UTC

NP-MRD ID

NP0239908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol

Description

Erinacine C belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol is found in Hericium erinaceus. It was first documented in 2015 (PMID: 28955459). Based on a literature review a significant number of articles have been published on Erinacine C (PMID: 33066380) (PMID: 31547327) (PMID: 29580208) (PMID: 27716564).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072201352D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072201352D          

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M  END
> <DATABASE_ID>
NP0239908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2[C@H]3CC=C(CO)[C@H]4O[C@@H]5[C@@H](O)[C@H](O)CO[C@H]5O[C@@H]4[C@]3(C)CC[C@@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O6/c1-13(2)15-7-8-24(3)9-10-25(4)16(18(15)24)6-5-14(11-26)20-22(25)31-23-21(30-20)19(28)17(27)12-29-23/h5,13,16-17,19-23,26-28H,6-12H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,24-,25-/m1/s1

> <INCHI_KEY>
DMPGFSQMXITJPT-ZCKYJUNOSA-N

> <FORMULA>
C25H38O6

> <MOLECULAR_WEIGHT>
434.573

> <EXACT_MASS>
434.266838944

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.990568168926615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,10R,14R,16R,17S,18R,21S)-13-(hydroxymethyl)-2,5-dimethyl-8-(propan-2-yl)-15,20,22-trioxapentacyclo[12.8.0.0^{2,10}.0^{5,9}.0^{16,21}]docosa-8,12-diene-17,18-diol

> <JCHEM_LOGP>
2.3078391346666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.265070178350502

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.826333856947972

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7616621121864258

> <JCHEM_POLAR_SURFACE_AREA>
88.38000000000001

> <JCHEM_REFRACTIVITY>
116.66879999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,10R,14R,16R,17S,18R,21S)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0^{2,10}.0^{5,9}.0^{16,21}]docosa-8,12-diene-17,18-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.588  -0.471   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.119  -0.934   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.016   0.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.214  -2.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.626  -3.052   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.027  -2.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.945  -0.876   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.096   0.147   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.614  -0.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.508   1.138   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.041   0.990   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.355  -1.465   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.882  -1.268   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.817  -2.493   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.223  -3.914   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.157  -5.138   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.685  -4.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.278  -3.520   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.805  -3.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.344  -2.296   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.937  -0.875   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.696  -4.111   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.762  -2.886   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.281  -3.309   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.464  -4.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.133  -4.842   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.731  -5.480   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.478  -4.585   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.170  -6.094   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.026  -4.918   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.807  -3.591   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20                                                            
CONECT   22   15   23                                                       
CONECT   23   22   12   24                                                  
CONECT   24   23    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    5   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30    4                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₆

Average Mass

434.5730 Da

Monoisotopic Mass

434.26684 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C1=C2[C@H]3CC=C(CO)[C@H]4O[C@@H]5[C@@H](O)[C@H](O)CO[C@H]5O[C@@H]4[C@]3(C)CC[C@@]2(C)CC1

InChI Identifier

InChI=1S/C25H38O6/c1-13(2)15-7-8-24(3)9-10-25(4)16(18(15)24)6-5-14(11-26)20-22(25)31-23-21(30-20)19(28)17(27)12-29-23/h5,13,16-17,19-23,26-28H,6-12H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,24-,25-/m1/s1

InChI Key

DMPGFSQMXITJPT-ZCKYJUNOSA-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 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
Para-dioxane
Monosaccharide
Oxane
Secondary alcohol
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Primary 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

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

8427864

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10252378

PDB ID

Not Available

ChEBI ID

187640

Good Scents ID

Not Available

References

General References

Shen T, Morlock G, Zorn H: Production of cyathane type secondary metabolites by submerged cultures of Hericium erinaceus and evaluation of their antibacterial activity by direct bioautography. Fungal Biol Biotechnol. 2015 Dec 22;2:8. doi: 10.1186/s40694-015-0018-y. eCollection 2015. [PubMed:28955459 ]
Rascher M, Wittstein K, Winter B, Rupcic Z, Wolf-Asseburg A, Stadler M, Koster RW: Erinacine C Activates Transcription from a Consensus ETS DNA Binding Site in Astrocytic Cells in Addition to NGF Induction. Biomolecules. 2020 Oct 14;10(10):1440. doi: 10.3390/biom10101440. [PubMed:33066380 ]
Wang LY, Huang CS, Chen YH, Chen CC, Chen CC, Chuang CH: Anti-Inflammatory Effect of Erinacine C on NO Production Through Down-Regulation of NF-kappaB and Activation of Nrf2-Mediated HO-1 in BV2 Microglial Cells Treated with LPS. Molecules. 2019 Sep 12;24(18):3317. doi: 10.3390/molecules24183317. [PubMed:31547327 ]
Premnath P, Reck M, Wittstein K, Stadler M, Wagner-Dobler I: Screening for inhibitors of mutacin synthesis in Streptococcus mutans using fluorescent reporter strains. BMC Microbiol. 2018 Mar 27;18(1):24. doi: 10.1186/s12866-018-1170-3. [PubMed:29580208 ]
Wolters N, Schabronath C, Schembecker G, Merz J: Efficient conversion of pretreated brewer's spent grain and wheat bran by submerged cultivation of Hericium erinaceus. Bioresour Technol. 2016 Dec;222:123-129. doi: 10.1016/j.biortech.2016.09.121. Epub 2016 Oct 1. [PubMed:27716564 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol (NP0239908)

MOL for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

3D MOL for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

3D SDF for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

3D-SDF for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

PDB for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

3D PDB for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

SMILES for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

INCHI for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

Structure for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)

3D Structure for NP0239908 ((1r,2r,5r,10r,14r,16r,17s,18r,21s)-13-(hydroxymethyl)-8-isopropyl-2,5-dimethyl-15,20,22-trioxapentacyclo[12.8.0.0²,¹⁰.0⁵,⁹.0¹⁶,²¹]docosa-8,12-diene-17,18-diol)