NP-MRD: Showing NP-Card for 1Œ≤-Hydroxyalantolactone (NP0136985)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:09 UTC

Updated at

2022-05-30 16:38:09 UTC

NP-MRD ID

NP0136985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1Œ≤-Hydroxyalantolactone

Description

1Beta-Hydroxyalantolactone, also known as ij-5 compound, belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 1Beta-Hydroxyalantolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1beta-Hydroxyalantolactone has been detected, but not quantified in, herbs and spices. 1Œ≤-Hydroxyalantolactone is found in Inula japonica. This could make 1beta-hydroxyalantolactone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    3.6294    2.1112    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1963    1.0483   -0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0376   -0.0456   -0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078   -0.0647   -0.6451 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1806   -1.0863   -1.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -0.8773   -0.3441 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7974   -1.5790   -0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4967   -0.8161   -0.6493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9566   -0.3507   -2.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3567    0.3022    0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7733    1.0407    0.4037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8355    0.6440   -0.5159 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5105    0.6242    1.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5817    2.1205    1.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8266    0.2579    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494   -1.1835    0.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4975   -1.7935   -0.0413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9909   -2.1401    1.2228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6834    2.2258    0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    2.9079    0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1921   -1.0760    0.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7594   -2.5968   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9704   -1.8115   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1966   -0.5378   -2.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629    0.7386   -2.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422   -0.9647   -2.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    1.8333    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976    0.8383   -1.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531    0.1078    2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835    2.3846    2.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    2.7014    0.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    2.5014    1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314    0.4814    1.2537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127    0.9088   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3683   -1.7407    0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5193   -1.3014   -0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -2.7039   -0.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392   -3.1088    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17  8  1  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 12  1  0
 12 11  1  0
 11 10  2  0
 10 13  1  0
 10  8  1  0
 12  6  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 13 29  1  1
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
  7 22  1  0
  7 23  1  0
  6 21  1  1
  1 19  1  0
  1 20  1  0
 12 28  1  6
 11 27  1  0
M  END


  Mrv0541 05061306162D          

 18 20  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1830    0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4130    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2380    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9280    2.3174    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
  8  4  1  0  0  0  0
  9  2  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(O)C2(C)CC3OC(=O)C(=C)C3C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h6,8,10,12-13,16H,2,4-5,7H2,1,3H3

> <INCHI_KEY>
FRNIMDDQCZHAFA-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.143458359490367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.069230584666667

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.643735131192376

> <JCHEM_PKA_STRONGEST_BASIC>
-2.954630253616455

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.7854

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-5,8a-dimethyl-3-methylidene-3aH,5H,6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.942   0.369   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.466   1.834   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.371   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.911   3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.466   4.326   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    5    8                                                       
CONECT    5    4   13                                                       
CONECT    6   10   11                                                       
CONECT    7   12   15                                                       
CONECT    8    1    4   11                                                  
CONECT    9    2   10   14                                                  
CONECT   10    6    9   12                                                  
CONECT   11    6    8   15                                                  
CONECT   12    7   10   18                                                  
CONECT   13    5   15   16                                                  
CONECT   14    9   17   18                                                  
CONECT   15    3    7   11   13                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
1b-Hydroxyalantolactone	Generator
1Β-hydroxyalantolactone	Generator
1-Hydroxy-5,11(13)-eudesmadien-12,8-olide	HMDB
[3AR-(3aalpha,5beta,8beta,8abeta,9aalpha)]-3a,5,6,7,8,8a,9,9a-octahydro-8-hydroxy-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one	HMDB
IJ-5 compound	MeSH
1-Hydroxyalantolactone	MeSH

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3175 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

8-hydroxy-5,8a-dimethyl-3-methylidene-2H,3H,3aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

8-hydroxy-5,8a-dimethyl-3-methylidene-3aH,5H,6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

CC1CCC(O)C2(C)CC3OC(=O)C(=C)C3C=C12

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-13(16)15(3)7-12-10(6-11(8)15)9(2)14(17)18-12/h6,8,10,12-13,16H,2,4-5,7H2,1,3H3

InChI Key

FRNIMDDQCZHAFA-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
Inula japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	2.29	ALOGPS
logP	2.07	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.79 m³·mol⁻¹	ChemAxon
Polarizability	27.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031970

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008662

KNApSAcK ID

C00012894

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

78117269

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1Œ≤-Hydroxyalantolactone (NP0136985)

MOL for NP0136985 (1Œ≤-Hydroxyalantolactone)

3D MOL for NP0136985 (1Œ≤-Hydroxyalantolactone)

3D SDF for NP0136985 (1Œ≤-Hydroxyalantolactone)

3D-SDF for NP0136985 (1Œ≤-Hydroxyalantolactone)

PDB for NP0136985 (1Œ≤-Hydroxyalantolactone)

3D PDB for NP0136985 (1Œ≤-Hydroxyalantolactone)

SMILES for NP0136985 (1Œ≤-Hydroxyalantolactone)

INCHI for NP0136985 (1Œ≤-Hydroxyalantolactone)

Structure for NP0136985 (1Œ≤-Hydroxyalantolactone)

3D Structure for NP0136985 (1Œ≤-Hydroxyalantolactone)