NP-MRD: Showing NP-Card for Xanthotoxol (NP0045372)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:49 UTC

Updated at

2022-03-17 19:18:49 UTC

NP-MRD ID

NP0045372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanthotoxol

Description

Xanthotoxol, also known as 8-hydroxypsoralen, belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group. It is one of the major active ingredients in Cnidium monnieri. Xanthotoxol is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthotoxol exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Xanthotoxol has been detected, but not quantified in, several different foods, such as parsley, herbs and spices, fats and oils, fruits, and green vegetables. This could make xanthotoxol a potential biomarker for the consumption of these foods. Xanthotoxol O-methyltransferase (8-hydroxyfuranocoumarin 8-O-methyltransferase) is an enzyme that uses S-adenosyl methionine and xanthotoxol to produce S-adenosylhomocysteine and O-methylxanthotoxol (xanthotoxin or methoxsalen). Xanthotoxol is a potentially toxic compound. Xanthotoxol is found in Aegle marmelos , Angelica archangelica , Angelica dahurica, Angelica furcijuga, Angelica japonica, Angelica saxatilis, Angelica taiwaniana, Archangelicia tschimganica, Archidendron chevalieri, Aspergillus flavus, Casimiroa edulis, Citrus canaliculata, Poncirus trifoliata , Clausena anisata , Clausena lansium, Cnidium monnieri , Deverra triradiata, Ferula moschata, Foeniculum vulgare, Glehnia littoralis , Hansenia weberbaueriana, Heracleum lanatum var. asiaticum , Notopterygium incisum , Pastinaka sativa, Peucedanum japonicum, Peucedanum rubricaule, Pleurospermum rivulorum, Prangos uloptera, Rhadinothamnus rudis, Seseli elatum, Skimmia laureola, Taxus chinensis and Trifolium pratense. Xanthotoxol is a furanocoumarin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

Xanthotoxol
  Mrv1572001071617272D          

 21 23  0  0  0  0            999 V2000
    6.0576    0.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105    0.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5624    1.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769   -0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480   -0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2769   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8480   -0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5624   -1.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5624    0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0576   -1.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105   -1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5391   -0.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629   -0.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3629   -0.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5624   -1.8626    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2165   -1.6762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1163   -1.8912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0506   -0.5261    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9210   -1.2133    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0055    1.3797    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 13  1  0  0  0  0
  2  8  1  0  0  0  0
  2 15  1  0  0  0  0
  3 10  1  0  0  0  0
  3 21  1  0  0  0  0
  4 15  2  0  0  0  0
  5  7  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 12  1  0  0  0  0
  7 10  1  0  0  0  0
  8 10  2  0  0  0  0
  9 16  1  0  0  0  0
 11 13  2  0  0  0  0
 11 17  1  0  0  0  0
 12 14  2  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

> <INCHI_KEY>
JWVYQQGERKEAHW-UHFFFAOYSA-N

> <FORMULA>
C11H6O4

> <MOLECULAR_WEIGHT>
202.165

> <EXACT_MASS>
202.026608673

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
19.008932072653543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.288917694333333

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.19114208397817

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9271450364723006

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
52.3706

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xanthotoxol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Xanthotoxol                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      11.308   0.257   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.806   0.611   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.516   2.098   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   0.595   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.850  -1.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.183  -1.752   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.850  -0.212   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.183  -0.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.516  -2.522   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.516   0.558   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.308  -2.221   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.806  -2.575   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.206  -0.982   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.411  -1.784   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.411  -0.180   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       8.516  -3.477   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      11.604  -3.129   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       5.817  -3.530   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      13.161  -0.982   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.586  -2.265   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       9.344   2.575   0.000  0.00  0.00           H+0
CONECT    1    7   13                                                       
CONECT    2    8   15                                                       
CONECT    3   10   21                                                       
CONECT    4   15                                                            
CONECT    5    7    9   11                                                  
CONECT    6    8    9   12                                                  
CONECT    7    1    5   10                                                  
CONECT    8    2    6   10                                                  
CONECT    9    5    6   16                                                  
CONECT   10    3    7    8                                                  
CONECT   11    5   13   17                                                  
CONECT   12    6   14   18                                                  
CONECT   13    1   11   19                                                  
CONECT   14   12   15   20                                                  
CONECT   15    2    4   14                                                  
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxyfuranocoumarin	ChEBI
8-Hydroxypsoralen	ChEBI

Chemical Formula

C₁₁H₆O₄

Average Mass

202.1650 Da

Monoisotopic Mass

202.02661 Da

IUPAC Name

9-hydroxy-7H-furo[3,2-g]chromen-7-one

Traditional Name

xanthotoxol

CAS Registry Number

2009-24-7

SMILES

[H]OC1=C2OC(=O)C([H])=C([H])C2=C([H])C2=C1OC([H])=C2[H]

InChI Identifier

InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

InChI Key

JWVYQQGERKEAHW-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, 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
Aegle marmelos	Plant	KNApSAcK
Angelica archangelica	Plant	KNApSAcK
Angelica dahurica	LOTUS Database	35616633
Angelica furcijuga	Plant	KNApSAcK
Angelica japonica	LOTUS Database	35616633
Angelica saxatilis	LOTUS Database	35616633
Angelica taiwaniana	Plant	KNApSAcK
Archangelicia tschimganica	-	KNApSAcK
Archidendron chevalieri	LOTUS Database	35616633
Aspergillus flavus	Fungi	KNApSAcK
Casimiroa edulis	LOTUS Database	35616633
Citrus canaliculata	LOTUS Database	35616633
Citrus trifoliata	Plant	KNApSAcK
Clausena anisata	Plant	KNApSAcK
Clausena lansium	LOTUS Database	35616633
Cnidium monnieri	Plant	KNApSAcK
Deverra triradiata	LOTUS Database	35616633
Ferula moschata	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Foeniculum vulgare	LOTUS Database	35616633
Glehnia littoralis	Plant	KNApSAcK
Hansenia weberbaueriana	LOTUS Database	35616633
Heracleum lanatum var. asiaticum	Plant	KNApSAcK
Notopterygium incisum	Plant	KNApSAcK
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pastinaka sativa	-	KNApSAcK
Petroselinum crispum	FooDB	KNAPSACK
Peucedanum japonicum	LOTUS Database	35616633
Peucedanum rubricaule	Plant	KNApSAcK
Pleurospermum rivulorum	Plant	KNApSAcK
Prangos uloptera	LOTUS Database	35616633
Rhadinothamnus rudis	LOTUS Database	35616633
Seseli elatum	LOTUS Database	35616633
Skimmia laureola	LOTUS Database	35616633
Taxus chinensis	Plant	KNApSAcK
Trifolium pratense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C8 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

8-hydroxypsoralens

Alternative Parents

Substituents

8-hydroxypsoralen
Benzopyran
1-benzopyran
Benzofuran
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

8-hydroxyfurocoumarin (CHEBI:15709 )
Furanocoumarins (C00841 )
an 8-hydroxyfurocoumarin (CPD-13041 )

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	1.9	ALOGPS
logP	2.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.37 m³·mol⁻¹	ChemAxon
Polarizability	19.01 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