NP-MRD: Showing NP-Card for Erinacine R (NP0086327)

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Record Information

Version

2.0

Created at

2022-04-29 06:38:29 UTC

Updated at

2022-04-29 06:38:29 UTC

NP-MRD ID

NP0086327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erinacine R

Description

Erinacine R belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Erinacine R is found in Hericium erinaceum . Based on a literature review a small amount of articles have been published on Erinacine R.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208382D          

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 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 11 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
  6 31  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  4 34  1  0  0  0  0
 32 35  1  1  0  0  0
 32 36  1  0  0  0  0
  9 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@H](OC(C)=O)C(C=O)=C[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@]1(C)CC(=O)[C@@]1(C)CCC(C(C)C)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O9/c1-13(2)16-6-7-26(4)20(31)10-27(5)17(22(16)26)9-19(35-14(3)29)15(11-28)8-21(27)36-25-24(33)23(32)18(30)12-34-25/h8,11,13,17-19,21,23-25,30,32-33H,6-7,9-10,12H2,1-5H3/t17-,18-,19-,21+,23+,24-,25+,26-,27-/m1/s1

> <INCHI_KEY>
SRARCXKPZDYZMB-GYGNKXPFSA-N

> <FORMULA>
C27H38O9

> <MOLECULAR_WEIGHT>
506.592

> <EXACT_MASS>
506.251582804

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.59764913251914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,5aR,6S,9R,10aR)-8-formyl-3a,5a-dimethyl-4-oxo-1-(propan-2-yl)-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-9-yl acetate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.077917654666666

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.40306187946776

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.245758552830935

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265808793602282

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
129.19469999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5aR,6S,9R,10aR)-8-formyl-1-isopropyl-3a,5a-dimethyl-4-oxo-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,5H,6H,9H,10H,10aH-cyclohepta[e]inden-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.317  -7.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.399  -6.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.889  -6.889   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.992  -5.014   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.954  -3.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.491  -3.722   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       5.031  -3.747   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       4.182  -2.345   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.335  -1.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.768  -0.921   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.689  -2.027   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.056  -0.532   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.535  -0.102   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.902   1.393   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.381   1.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.492   0.757   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.971   1.187   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.125  -0.738   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.237  -1.804   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.646  -1.168   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.279  -2.664   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.877  -3.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.851  -4.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.228  -5.238   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.514  -4.391   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.632  -5.487   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.950  -6.994   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.414  -7.472   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.560  -6.443   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.732  -8.979   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.136  -5.120   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.107  -2.525   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.378  -2.933   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.449  -4.471   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.131  -1.334   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.798  -1.149   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.951   0.138   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6   32                                                  
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8   36                                                       
CONECT   10    8                                                            
CONECT   11    8   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20                                                            
CONECT   22   11   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26    6                                                       
CONECT   32    5   33   35   36                                             
CONECT   33   32   34                                                       
CONECT   34   33    4                                                       
CONECT   35   32                                                            
CONECT   36   32    9   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₉

Average Mass

506.5920 Da

Monoisotopic Mass

506.25158 Da

IUPAC Name

(3aS,5aR,6S,9R,10aR)-8-formyl-3a,5a-dimethyl-4-oxo-1-(propan-2-yl)-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]inden-9-yl acetate

Traditional Name

(3aS,5aR,6S,9R,10aR)-8-formyl-1-isopropyl-3a,5a-dimethyl-4-oxo-6-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}-2H,3H,5H,6H,9H,10H,10aH-cyclohepta[e]inden-9-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@H](OC(C)=O)C(C=O)=C[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@]1(C)CC(=O)[C@@]1(C)CCC(C(C)C)=C21

InChI Identifier

InChI=1S/C27H38O9/c1-13(2)16-6-7-26(4)20(31)10-27(5)17(22(16)26)9-19(35-14(3)29)15(11-28)8-21(27)36-25-24(33)23(32)18(30)12-34-25/h8,11,13,17-19,21,23-25,30,32-33H,6-7,9-10,12H2,1-5H3/t17-,18-,19-,21+,23+,24-,25+,26-,27-/m1/s1

InChI Key

SRARCXKPZDYZMB-GYGNKXPFSA-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, 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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hericium erinaceus	Fungi	KNApSAcK

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
Monosaccharide
Oxane
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Aldehyde
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	1.4	ALOGPS
logP	1.08	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.25	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.19 m³·mol⁻¹	ChemAxon
Polarizability	52.6 Å³	ChemAxon
Number of Rings	4	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

C00056528

Chemspider ID

78437975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102392649

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Erinacine R (NP0086327)

MOL for NP0086327 (Erinacine R)

3D MOL for NP0086327 (Erinacine R)

3D SDF for NP0086327 (Erinacine R)

3D-SDF for NP0086327 (Erinacine R)

PDB for NP0086327 (Erinacine R)

3D PDB for NP0086327 (Erinacine R)

SMILES for NP0086327 (Erinacine R)

INCHI for NP0086327 (Erinacine R)

Structure for NP0086327 (Erinacine R)

3D Structure for NP0086327 (Erinacine R)