NP-MRD: Showing NP-Card for Psoralidin (NP0047832)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:42 UTC

Updated at

2022-03-17 20:46:42 UTC

NP-MRD ID

NP0047832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psoralidin

Description

Psoralidin belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, psoralidin is considered to be a flavonoid lipid molecule. It has the capability to inhibit protein tyrosine phosphatase 1B, a key metabolite involved in insulin signaling. To form the ring of psoralidin, an intramolecular cyclization occurs, finished off by a microwave assisted cross metathesis reaction. Structurally, psoralidin is a coumestan derivative; it has an isopentenyl group at the second carbon position of coumestrol. Psoralidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Psoralidin has been detected, but not quantified in, a few different foods, such as fruits, lima beans, and pulses. This could make psoralidin a potential biomarker for the consumption of these foods. Psoralidin is a natural phenolic compound found in the seeds of Psoralea corylifolia. Dopamine levels changed as well as a result of psoralidin consumption. Psoralidin raised 5-hydroxytryptamine and 5-hydroxyindoleacetic acid levels in the brain. Recently, it has shown activity in vitro against gastric, colon, prostate, and breast cancer lines. Psoralidin is found in Apis cerana, Psoralea corylifolia , Dolichos bifloru, Psoralea coryfolia and Dolichos biflorus . Psoralidin was first documented in 2014 (PMID: 24507928). Psoralidin production starts with a based catalyzed condensation between phenyl acetate and acid chloride (PMID: 25216634).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307322D          

 25 28  0  0  0  0            999 V2000
    6.8417    0.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6471    0.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5654    1.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418    1.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181    0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 12  1  0  0  0  0
 22 15  1  0  0  0  0
 23 20  2  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 17  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(OC(=O)C3=C2OC2=C3C=CC(O)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3

> <INCHI_KEY>
YABIJLLNNFURIJ-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.18785761290899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
4.125888321666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.109940009002456

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.919911801174257

> <JCHEM_PKA_STRONGEST_BASIC>
-4.325477635685441

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
93.86229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
psoralidin

> <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      12.771   1.537   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.541   0.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.389   2.736   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.851   2.648   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.234   1.449   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   16                                                       
CONECT    9   15   17                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    7   15                                                  
CONECT   12    5    8   21                                                  
CONECT   13    6   16   18                                                  
CONECT   14    7   17   19                                                  
CONECT   15    9   11   22                                                  
CONECT   16    8   13   24                                                  
CONECT   17    9   14   25                                                  
CONECT   18   13   19   20                                                  
CONECT   19   14   18   24                                                  
CONECT   20   18   23   25                                                  
CONECT   21   12                                                            
CONECT   22   15                                                            
CONECT   23   20                                                            
CONECT   24   16   19                                                       
CONECT   25   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
3,9-Dihydroxy-2-prenylcoumestan	ChEBI

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3380 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

5,14-dihydroxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one

Traditional Name

psoralidin

CAS Registry Number

18642-23-4

SMILES

CC(C)=CCC1=CC2=C(OC(=O)C3=C2OC2=C3C=CC(O)=C2)C=C1O

InChI Identifier

InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3

InChI Key

YABIJLLNNFURIJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Cullen corylifolium	Plant	KNApSAcK
Dolichos bifloru	Plant	KNApSAcK
Phaseolus lunatus	FooDB	KNAPSACK
Psoralea coryfolia	Plant	KNApSAcK
Vigna unguiculata ssp. cylindrica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:8616 )
delta-lactone (CHEBI:8616 )
coumestans (CHEBI:8616 )
Coumestan flavonoids (C10523 )
Coumestanes (C10523 )
Coumestan flavonoids (LMPK12090007 )

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	4.63	ALOGPS
logP	4.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	93.86 m³·mol⁻¹	ChemAxon
Polarizability	36.19 Å³	ChemAxon
Number of Rings	4	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

HMDB0034050

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Psoralidin

METLIN ID

Not Available

PubChem Compound

5281806

PDB ID

Not Available

ChEBI ID

8616

Good Scents ID

Not Available

References

General References

Liu X, Nam JW, Song YS, Viswanath AN, Pae AN, Kil YS, Kim HD, Park JH, Seo EK, Chang M: Psoralidin, a coumestan analogue, as a novel potent estrogen receptor signaling molecule isolated from Psoralea corylifolia. Bioorg Med Chem Lett. 2014 Mar 1;24(5):1403-6. doi: 10.1016/j.bmcl.2014.01.029. Epub 2014 Jan 20. [PubMed:24507928 ]
Zhang XS, Zhao ZQ, Qin ZS, Wu K, Xia TF, Pang LQ: Herb-drug interaction between irinotecan and psoralidin-containing herbs. Eur J Drug Metab Pharmacokinet. 2015 Dec;40(4):481-4. doi: 10.1007/s13318-014-0223-8. Epub 2014 Sep 13. [PubMed:25216634 ]

Showing NP-Card for Psoralidin (NP0047832)

MOL for NP0047832 (Psoralidin)

3D MOL for NP0047832 (Psoralidin)

3D SDF for NP0047832 (Psoralidin)

3D-SDF for NP0047832 (Psoralidin)

PDB for NP0047832 (Psoralidin)

3D PDB for NP0047832 (Psoralidin)

SMILES for NP0047832 (Psoralidin)

INCHI for NP0047832 (Psoralidin)

Structure for NP0047832 (Psoralidin)

3D Structure for NP0047832 (Psoralidin)