NP-MRD: Showing NP-Card for [(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate (NP0261270)

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Record Information

Version

2.0

Created at

2022-09-08 03:40:24 UTC

Updated at

2022-09-08 03:40:24 UTC

NP-MRD ID

NP0261270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate

Description

Erinacine K belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate is found in Hericium erinaceus. Based on a literature review very few articles have been published on Erinacine K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082205402D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082205402D          

 35 38  0  0  1  0            999 V2000
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  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  6  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  2  0  0  0  0
 23 31  1  0  0  0  0
 32 31  1  1  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261270

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O8/c1-14(2)17-6-7-26(4)8-9-27(5)18(22(17)26)11-19(29)16(12-33-15(3)28)10-21(27)35-25-24(32)23(31)20(30)13-34-25/h10,14,18-21,23-25,29-32H,6-9,11-13H2,1-5H3/t18-,19?,20-,21+,23+,24-,25+,26-,27-/m1/s1

> <INCHI_KEY>
CKGZNZCRUPISHK-AMRAMDROSA-N

> <FORMULA>
C27H42O8

> <MOLECULAR_WEIGHT>
494.625

> <EXACT_MASS>
494.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.161679083899685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3aR,5aR,6S,10aR)-9-hydroxy-3a,5a-dimethyl-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-8-yl]methyl acetate

> <JCHEM_LOGP>
1.4313535126666654

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.373432169814617

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.243458573201734

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0085151967961634

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
129.4844

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.919  -4.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.830  -2.945   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.116  -2.099   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.453  -2.254   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.363  -0.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.013  -0.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.012   1.514   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.176   2.493   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.808   3.989   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.920   5.055   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.399   4.625   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.510   5.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.143   7.187   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.255   8.252   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.664   7.616   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.297   9.112   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.553   6.550   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.074   6.980   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.682   2.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.096   3.600   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.529   3.462   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.066   3.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.757   1.996   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.734   3.187   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.242   1.588   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.314   0.050   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.873  -0.493   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.465  -1.978   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.975  -2.368   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.548  -3.074   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.911   0.709   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.373   0.799   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.728  -0.599   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.232  -0.966   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.915  -2.473   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17                                                            
CONECT   19    8   20   21   32                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   23   32                                                  
CONECT   32   31   19   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33    6   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₈

Average Mass

494.6250 Da

Monoisotopic Mass

494.28797 Da

IUPAC Name

[(3aR,5aR,6S,10aR)-9-hydroxy-3a,5a-dimethyl-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-8-yl]methyl acetate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H42O8/c1-14(2)17-6-7-26(4)8-9-27(5)18(22(17)26)11-19(29)16(12-33-15(3)28)10-21(27)35-25-24(32)23(31)20(30)13-34-25/h10,14,18-21,23-25,29-32H,6-9,11-13H2,1-5H3/t18-,19?,20-,21+,23+,24-,25+,26-,27-/m1/s1

InChI Key

CKGZNZCRUPISHK-AMRAMDROSA-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
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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
logP	1.43	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.48 m³·mol⁻¹	ChemAxon
Polarizability	54.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

17243936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16085268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate (NP0261270)

MOL for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

3D MOL for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

3D SDF for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

3D-SDF for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

PDB for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

3D PDB for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

SMILES for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

INCHI for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

Structure for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)

3D Structure for NP0261270 ([(3ar,5ar,6s,10ar)-9-hydroxy-1-isopropyl-3a,5a-dimethyl-6-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-2h,3h,4h,5h,6h,9h,10h,10ah-cyclohepta[e]inden-8-yl]methyl acetate)