NP-MRD: Showing NP-Card for 1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone (NP0255541)

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Record Information

Version

2.0

Created at

2022-09-07 20:04:53 UTC

Updated at

2022-09-07 20:04:53 UTC

NP-MRD ID

NP0255541

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone

Description

Eremopetasinorol belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. Eremopetasinorol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Eremopetasinorol has been detected, but not quantified in, green vegetables. 1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone is found in Ligularia muliensis and Petasites japonicus. This could make eremopetasinorol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    4.2114   -0.2403   -1.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1950   -1.0750   -0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710   -2.2693   -0.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8795   -0.5369   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8869   -1.1765    0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2392   -0.2674    0.6280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0915    0.4315    1.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158    0.6682   -0.5360 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9005    1.8276   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3079    1.3301   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6744    0.0676    0.0757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5175    0.3636    1.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -0.8692    0.4796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4664   -2.0561   -0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4588    0.8869   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9951   -0.8586   -1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6424    0.5377   -0.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    0.3186   -1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0017   -2.2261    0.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947    0.8941    2.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1127   -0.4001    2.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9412    1.0752    2.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2646    0.1467   -1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    2.6377   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443    2.3355    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4470    1.2750   -1.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    2.1872   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3511   -0.5082   -0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    1.2065    1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660   -1.3189    1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4852   -2.4762   -0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8804   -2.8335    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937   -1.7729   -1.4276 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7623    1.5880    0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624    1.1075   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8 15  1  0
 15  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  1
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 13  1  0
  6  8  1  0
 14 31  1  0
 14 32  1  0
 14 33  1  0
 13 30  1  1
 11 28  1  6
 12 29  1  0
 10 26  1  0
 10 27  1  0
  9 24  1  0
  9 25  1  0
  8 23  1  6
 15 34  1  0
 15 35  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv0541 05061304502D          

 15 16  0  0  0  0            999 V2000
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    2.7559    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
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    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
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    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
    2.0701    1.9354    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
   -1.8659    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255541

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)CCC2CC(=CC12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-8-12(15)5-4-11-6-10(9(2)14)7-13(8,11)3/h7-8,11-12,15H,4-6H2,1-3H3

> <INCHI_KEY>
GBUDXEBRIWMUIF-UHFFFAOYSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.088205018501974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(5-hydroxy-3a,4-dimethyl-3a,4,5,6,7,7a-hexahydro-1H-inden-2-yl)ethan-1-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.903352101

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.67974999507759

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.30114088388175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.91743864916394

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
60.7851

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

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       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.036   5.144   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       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.483   4.176   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   13                                                            
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6   10   11                                                       
CONECT    7   10   13                                                       
CONECT    8    1   12   13                                                  
CONECT    9    2   10   14                                                  
CONECT   10    6    7    9                                                  
CONECT   11    4    6   13                                                  
CONECT   12    5    8   15                                                  
CONECT   13    3    7    8   11                                             
CONECT   14    9                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀O₂

Average Mass

208.2967 Da

Monoisotopic Mass

208.14633 Da

IUPAC Name

1-(5-hydroxy-3a,4-dimethyl-3a,4,5,6,7,7a-hexahydro-1H-inden-2-yl)ethan-1-one

Traditional Name

1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone

CAS Registry Number

Not Available

SMILES

CC1C(O)CCC2CC(=CC12C)C(C)=O

InChI Identifier

InChI=1S/C13H20O2/c1-8-12(15)5-4-11-6-10(9(2)14)7-13(8,11)3/h7-8,11-12,15H,4-6H2,1-3H3

InChI Key

GBUDXEBRIWMUIF-UHFFFAOYSA-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
Ligularia muliensis	LOTUS Database	35616633
Petasites japonicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.79	ALOGPS
logP	1.9	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	19.3	ChemAxon
pKa (Strongest Basic)	-0.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.79 m³·mol⁻¹	ChemAxon
Polarizability	24.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029668

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000851

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750892

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone (NP0255541)

MOL for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

3D MOL for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

3D SDF for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

3D-SDF for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

PDB for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

3D PDB for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

SMILES for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

INCHI for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

Structure for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)

3D Structure for NP0255541 (1-(5-hydroxy-3a,4-dimethyl-1,4,5,6,7,7a-hexahydroinden-2-yl)ethanone)