NP-MRD: Showing NP-Card for 9-Hydroxy-4-methoxypsoralen (NP0048554)

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Record Information

Version

1.0

Created at

2022-03-17 20:58:17 UTC

Updated at

2022-03-17 20:58:17 UTC

NP-MRD ID

NP0048554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-Hydroxy-4-methoxypsoralen

Description

9-Hydroxy-4-methoxypsoralen, also known as 5-methoxy-8-hydroxy-psoralen or 8-hydroxybergapten, belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. 9-Hydroxy-4-methoxypsoralen is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 9-Hydroxy-4-methoxypsoralen has been detected, but not quantified in, pomes and wild celeries. This could make 9-hydroxy-4-methoxypsoralen a potential biomarker for the consumption of these foods. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). 9-Hydroxy-4-methoxypsoralen is a potentially toxic compound. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. Not listed by IARC. 9-Hydroxy-4-methoxypsoralen is found in Ammi majus, Angelica dahurica, Angelica japonica, Casimiroa edulis, Citrus junos and Toddalia asiatica. Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09051417072D          

 17 19  0  0  0  0            999 V2000
    1.4289   -1.6500    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    1.2375    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
   -2.1434    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
    0.7145   -1.2375    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
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  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 10  1  0  0  0  0
 16  5  1  0  0  0  0
 16 11  1  0  0  0  0
 17  8  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=CC(=O)OC2=C(O)C2=C1C=CO2

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

> <INCHI_KEY>
MVJHUMZXIJPVHV-UHFFFAOYSA-N

> <FORMULA>
C12H8O5

> <MOLECULAR_WEIGHT>
232.1889

> <EXACT_MASS>
232.037173366

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.817753382616168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
2.1312464286666666

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.447980145376384

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8665908185646356

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
58.83380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   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   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   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   3.850   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   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   10   12                                                  
CONECT    7    4   10   11                                                  
CONECT    8    3   13   17                                                  
CONECT    9   11   12   14                                                  
CONECT   10    6    7   15                                                  
CONECT   11    7    9   16                                                  
CONECT   12    6    9   17                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    1   10                                                       
CONECT   16    5   11                                                       
CONECT   17    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
5-Methoxy-8-hydroxy-psoralen	HMDB
8-Hydroxy-5-methoxypsoralen	HMDB
8-Hydroxybergapten	HMDB
9-Hydroxy-4-methoxy-7H-furo(3,2-g)(1)benzopyran-7-one	HMDB
9-Hydroxy-4-methoxyfuro[3,2-g][1]benzopyran-7-one, 9ci	HMDB
9-Hydroxy-5-methoxypsoralen	HMDB
9-Hydroxybergapten	HMDB
Carbonyl selenide	HMDB

Chemical Formula

C₁₂H₈O₅

Average Mass

232.1889 Da

Monoisotopic Mass

232.03717 Da

IUPAC Name

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

Traditional Name

9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one

CAS Registry Number

1603-47-0

SMILES

COC1=C2C=CC(=O)OC2=C(O)C2=C1C=CO2

InChI Identifier

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

InChI Key

MVJHUMZXIJPVHV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammi majus	LOTUS Database	35616633
Angelica dahurica	LOTUS Database	35616633
Angelica japonica	LOTUS Database	35616633
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Casimiroa edulis	LOTUS Database	35616633
Citrus junos	LOTUS Database	35616633
Toddalia asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

5-methoxypsoralens

Alternative Parents

Substituents

5-methoxypsoralen
8-hydroxypsoralen
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

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	1.86	ALOGPS
logP	2.13	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	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	21.82 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

HMDB0036628

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015546

KNApSAcK ID

Not Available

Chemspider ID

2340886

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3083726

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 9-Hydroxy-4-methoxypsoralen (NP0048554)

MOL for NP0048554 (9-Hydroxy-4-methoxypsoralen)

3D MOL for NP0048554 (9-Hydroxy-4-methoxypsoralen)

3D SDF for NP0048554 (9-Hydroxy-4-methoxypsoralen)

3D-SDF for NP0048554 (9-Hydroxy-4-methoxypsoralen)

PDB for NP0048554 (9-Hydroxy-4-methoxypsoralen)

3D PDB for NP0048554 (9-Hydroxy-4-methoxypsoralen)

SMILES for NP0048554 (9-Hydroxy-4-methoxypsoralen)

INCHI for NP0048554 (9-Hydroxy-4-methoxypsoralen)

Structure for NP0048554 (9-Hydroxy-4-methoxypsoralen)

3D Structure for NP0048554 (9-Hydroxy-4-methoxypsoralen)