NP-MRD: Showing NP-Card for 3-(1,2-dihydroxybutyl)isochromen-1-one (NP0264358)

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Record Information

Version

2.0

Created at

2022-09-08 07:50:58 UTC

Updated at

2022-09-08 07:50:58 UTC

NP-MRD ID

NP0264358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(1,2-dihydroxybutyl)isochromen-1-one

Description

Artemidiol belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1. Artemidiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Artemidiol has been detected, but not quantified in, herbs and spices. 3-(1,2-dihydroxybutyl)isochromen-1-one is found in Artemisia dracunculus. This could make artemidiol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.6242    1.8124    0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773    0.4203    0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400   -0.6483   -0.0699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9688   -0.5149   -0.7108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695   -0.7206   -1.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9591   -1.8527   -1.8997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3105   -0.8328   -0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998    0.2820   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8005    0.2965   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5830    1.4344   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    1.4035    0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741    0.2278    0.7583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877   -0.9056    0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -0.8752    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460   -1.9619    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269   -3.0263    0.8939 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.9165   -0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6406    2.2474    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0437    2.4782    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3446    1.8586   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6600    0.2338    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4251    0.3084    1.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7715   -1.6249    0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161    0.1256   -1.4736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7525    0.1380   -1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4560   -2.6365   -1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1491    1.2376   -1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1506    2.3260   -0.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5006    2.3024    0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    0.2178    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9530   -1.8345    1.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17  7  1  0
 14  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  1
  4 24  1  0
  5 25  1  6
  6 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
M  END


  Mrv0541 05061305252D          

 17 18  0  0  0  0            999 V2000
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264358

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O4/c1-2-10(14)12(15)11-7-8-5-3-4-6-9(8)13(16)17-11/h3-7,10,12,14-15H,2H2,1H3

> <INCHI_KEY>
CRXSSRPVDGICML-UHFFFAOYSA-N

> <FORMULA>
C13H14O4

> <MOLECULAR_WEIGHT>
234.2479

> <EXACT_MASS>
234.089208936

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.09115690092898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(1,2-dihydroxybutyl)-1H-isochromen-1-one

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.5173155523333333

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.939539444942277

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.864513152186483

> <JCHEM_PKA_STRONGEST_BASIC>
-3.203817020469371

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
63.75410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(1,2-dihydroxybutyl)isochromen-1-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      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   10                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    9                                                       
CONECT    7    8   11                                                       
CONECT    8    5    7    9                                                  
CONECT    9    6    8   13                                                  
CONECT   10    2   12   14                                                  
CONECT   11    7   12   17                                                  
CONECT   12   10   11   15                                                  
CONECT   13    9   16   17                                                  
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
3-(1,2-Dihydroxybutyl)-1H-2-benzopyran-1-one	HMDB

Chemical Formula

C₁₃H₁₄O₄

Average Mass

234.2479 Da

Monoisotopic Mass

234.08921 Da

IUPAC Name

3-(1,2-dihydroxybutyl)-1H-isochromen-1-one

Traditional Name

3-(1,2-dihydroxybutyl)isochromen-1-one

CAS Registry Number

Not Available

SMILES

CCC(O)C(O)C1=CC2=CC=CC=C2C(=O)O1

InChI Identifier

InChI=1S/C13H14O4/c1-2-10(14)12(15)11-7-8-5-3-4-6-9(8)13(16)17-11/h3-7,10,12,14-15H,2H2,1H3

InChI Key

CRXSSRPVDGICML-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
Artemisia dracunculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarins and derivatives. These are polycyclic compounds containing an isochromane which bears a ketone at the carbon C1.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isocoumarins and derivatives

Sub Class

Not Available

Direct Parent

Isocoumarins and derivatives

Alternative Parents

Substituents

Isocoumarin
Benzopyran
2-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
1,2-diol
Lactone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.14	ALOGPS
logP	1.52	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.75 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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030648

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002554

KNApSAcK ID

Not Available

Chemspider ID

10352939

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23246261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(1,2-dihydroxybutyl)isochromen-1-one (NP0264358)

MOL for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

3D MOL for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

3D SDF for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

3D-SDF for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

PDB for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

3D PDB for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

SMILES for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

INCHI for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

Structure for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)

3D Structure for NP0264358 (3-(1,2-dihydroxybutyl)isochromen-1-one)