NP-MRD: Showing NP-Card for 5-hydroxyxanthotoxin (NP0247626)

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Record Information

Version

1.0

Created at

2022-09-07 09:32:44 UTC

Updated at

2022-09-07 09:32:44 UTC

NP-MRD ID

NP0247626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxyxanthotoxin

Description

5-Hydroxyxanthotoxin belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. 5-Hydroxyxanthotoxin is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-hydroxyxanthotoxin is found in Angelica dahurica, Apis cerana and Niphogeton ternata. It was first documented in 1987 (PMID: 2886306). 5-Hydroxyxanthotoxin is a potentially toxic compound (PMID: 17703773) (PMID: 22930555) (PMID: 23234138) (PMID: 18589748).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310051709242D          

 17 19  0  0  0  0            999 V2000
   -0.0000    2.4750    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
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6985    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    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    0.8250    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
    1.4289    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
  7  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  2  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  1  1  0  0  0  0
 15 12  1  0  0  0  0
 16  5  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC(=O)C=CC2=C(O)C2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H8O5/c1-15-12-10-7(4-5-16-10)9(14)6-2-3-8(13)17-11(6)12/h2-5,14H,1H3

> <INCHI_KEY>
XPFCGZWOHNGDSP-UHFFFAOYSA-N

> <FORMULA>
C12H8O5

> <MOLECULAR_WEIGHT>
232.1889

> <EXACT_MASS>
232.037173366

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.847685182033263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.4812464286666667

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.754974605314304

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8661446855476886

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
58.83380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyxanthotoxin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.132   2.016   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    3    6                                                       
CONECT    3    2    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4   16                                                       
CONECT    6    2    9   11                                                  
CONECT    7    4    9   10                                                  
CONECT    8    3   13   17                                                  
CONECT    9    6    7   14                                                  
CONECT   10    7   12   16                                                  
CONECT   11    6   12   17                                                  
CONECT   12   10   11   15                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    1   12                                                       
CONECT   16    5   10                                                       
CONECT   17    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-9-methoxy-7H-furo[3,2-g]benzopyran-7-one	ChEBI
5-Hydroxy-8-methoxypsoralen	ChEBI

Chemical Formula

C₁₂H₈O₅

Average Mass

232.1889 Da

Monoisotopic Mass

232.03717 Da

IUPAC Name

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

Traditional Name

5-hydroxyxanthotoxin

CAS Registry Number

Not Available

SMILES

COC1=C2OC(=O)C=CC2=C(O)C2=C1OC=C2

InChI Identifier

InChI=1S/C12H8O5/c1-15-12-10-7(4-5-16-10)9(14)6-2-3-8(13)17-11(6)12/h2-5,14H,1H3

InChI Key

XPFCGZWOHNGDSP-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
Angelica dahurica	LOTUS Database	35616633
Apis cerana	LOTUS Database	35616633
Niphogeton ternata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy 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-methoxypsoralens

Alternative Parents

Substituents

5-hydroxypsoralen
8-methoxypsoralen
1-benzopyran
Benzopyran
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

psoralens (CHEBI:2082 )

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	1.83	ALOGPS
logP	1.48	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	58.83 m³·mol⁻¹	ChemAxon
Polarizability	21.85 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

HMDB0149139

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02951

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5385192

PDB ID

Not Available

ChEBI ID

2082

Good Scents ID

Not Available

References

General References

Jiang YY, Liu B, Shi RB, Tu GZ: [Isolation and structure identification of chemical constituents from Saposhnikovia divaricata (Turcz.) Schischk]. Yao Xue Xue Bao. 2007 May;42(5):505-10. [PubMed:17703773 ]
Chen Z, Wang J, Chen D, Fan G, Wu Y: Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract. Electrophoresis. 2012 Sep;33(18):2884-91. doi: 10.1002/elps.201200120. Epub 2012 Aug 28. [PubMed:22930555 ]
Zhao A, Yang X, Yang X, Liu J, Wang Q, Wang W: [A new natural product from root of Angelica dahurica cv. Qibaizhi]. Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(16):2400-7. [PubMed:23234138 ]
Ren DC, Qian SH, Yang NY, Xie N, Duan JA: [Chemical constituents of Changium smyrnioides]. Zhong Yao Cai. 2008 Jan;31(1):47-9. [PubMed:18589748 ]
Mays DC, Hecht SG, Unger SE, Pacula CM, Climie JM, Sharp DE, Gerber N: Disposition of 8-methoxypsoralen in the rat. Induction of metabolism in vivo and in vitro and identification of urinary metabolites by thermospray mass spectrometry. Drug Metab Dispos. 1987 May-Jun;15(3):318-28. [PubMed:2886306 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxyxanthotoxin (NP0247626)

MOL for NP0247626 (5-hydroxyxanthotoxin)

3D MOL for NP0247626 (5-hydroxyxanthotoxin)

3D SDF for NP0247626 (5-hydroxyxanthotoxin)

3D-SDF for NP0247626 (5-hydroxyxanthotoxin)

PDB for NP0247626 (5-hydroxyxanthotoxin)

3D PDB for NP0247626 (5-hydroxyxanthotoxin)

SMILES for NP0247626 (5-hydroxyxanthotoxin)

INCHI for NP0247626 (5-hydroxyxanthotoxin)

Structure for NP0247626 (5-hydroxyxanthotoxin)

3D Structure for NP0247626 (5-hydroxyxanthotoxin)