NP-MRD: Showing NP-Card for Peucedanin (NP0045602)

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Record Information

Version

2.0

Created at

2022-03-17 19:32:33 UTC

Updated at

2022-03-17 19:32:33 UTC

NP-MRD ID

NP0045602

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Peucedanin

Description

Peucedanin is found in Angelica decursiva , Lythrum salicaria, Meum athamanticum , Myrrhis odorata , Opopanax hispidus, Oppopanax chironium, Pastinaca silvestris, Peucedanum morisonii, Peucedanum officinale , Peucedanum ruthenicum, Peucedanum stenocarpum, Peucedanum tauricum and Prangos pabularia . Peucedanin was first documented in 1959 (PMID: 13841833).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221262D          

 19 21  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   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 O   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
    2.8579    0.0000    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
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6119   -2.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -2.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    2.1434   -1.2375    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC3=C(C=CC(=O)O3)C=C12)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3

> <INCHI_KEY>
YQBNJPACAUPNLV-UHFFFAOYSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.5537132756696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-2-(propan-2-yl)-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
2.8718682946666663

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2570871709816775

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
70.99820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
peucedanin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.578  -5.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   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  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.578  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.348  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.348  -0.206   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-Isopropyl-3-methoxy-7H-furo[3,2-g]chromen-7-one	ChEBI
3-Methoxy-2-(1-methylethyl)-7H-furo(3,2-g)(1)benzopyran-7-one	ChEBI
4-Methoxy-5-isopropylfuro(2,3:6,7)coumarin	ChEBI
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid delta-lactone	ChEBI
Oreoselone methyl ether	ChEBI
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylate delta-lactone	Generator
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylate δ-lactone	Generator
6-Hydroxy-2-isopropyl-3-methoxy-5-benzofuranacrylic acid δ-lactone	Generator

Chemical Formula

C₁₅H₁₄O₄

Average Mass

258.2693 Da

Monoisotopic Mass

258.08921 Da

IUPAC Name

3-methoxy-2-(propan-2-yl)-7H-furo[3,2-g]chromen-7-one

Traditional Name

peucedanin

CAS Registry Number

133-26-6

SMILES

COC1=C(OC2=CC3=C(C=CC(=O)O3)C=C12)C(C)C

InChI Identifier

InChI=1S/C15H14O4/c1-8(2)14-15(17-3)10-6-9-4-5-13(16)18-11(9)7-12(10)19-14/h4-8H,1-3H3

InChI Key

YQBNJPACAUPNLV-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
Angelica decursiva	Plant	KNApSAcK
Anthriscus cerefolium	FooDB	KNAPSACK
Daucus carota	FooDB	KNAPSACK
Daucus carota ssp. sativus	FooDB	KNAPSACK
Lythrum salicaria	LOTUS Database	35616633
Meum athamanticum	Plant	KNApSAcK
Myrrhis odorata	Plant	KNApSAcK
Opopanax hispidus	LOTUS Database	35616633
Oppopanax chironium	-	KNApSAcK
Pastinaca silvestris	Plant	KNApSAcK
Peucedanum morisonii	Plant	KNApSAcK
Peucedanum officinale	Plant	KNApSAcK
Peucedanum ruthenicum	Plant	KNApSAcK
Peucedanum stenocarpum	Plant	KNApSAcK
Peucedanum tauricum	Plant	KNApSAcK
Prangos pabularia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:8034 )
lactone (CHEBI:8034 )
furanocoumarin (CHEBI:8034 )
Furanocoumarins (C09283 )

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	3.41	ALOGPS
logP	2.87	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001509

KNApSAcK ID

C00002491

Chemspider ID

Not Available

KEGG Compound ID

C09283

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8616

PDB ID

Not Available

ChEBI ID

8034

Good Scents ID

Not Available

References

General References

Muckensturm B, Boulanger A, Ouahabi S, Reduron JP: A new irregular diterpenoid from Opopanax chironium. Fitoterapia. 2005 Dec;76(7-8):768-70. doi: 10.1016/j.fitote.2005.06.005. Epub 2005 Oct 17. [PubMed:16229971 ]
VERMEL' EM, KRUGLIAK-SYRKINA SA: [Effect of peucedanin and phosphoramides on tranplanted animal tumors]. Vopr Onkol. 1959;5(7):43-51. [PubMed:13841833 ]
Chinou I, Widelski J, Fokialakis N, Magiatis P, Glowniak K: Coumarins from Peucedanum luxurians. Fitoterapia. 2007 Sep;78(6):448-9. doi: 10.1016/j.fitote.2007.04.004. Epub 2007 May 24. [PubMed:17582700 ]
Manayi A, Saeidnia S, Ostad SN, Hadjiakhoondi A, Ardekani MR, Vazirian M, Akhtar Y, Khanavi M: Chemical constituents and cytotoxic effect of the main compounds of Lythrum salicaria L. Z Naturforsch C J Biosci. 2013 Sep-Oct;68(9-10):367-75. [PubMed:24459770 ]
Bartnik M, Arczewska M, Hoser AA, Mroczek T, Kaminski DM, Glowniak K, Gagos M, Wozniak K: Single crystal X-ray diffraction, spectroscopic and mass spectrometric studies of furanocoumarin peucedanin. Nat Prod Commun. 2014 Jan;9(1):71-4. [PubMed:24660466 ]
Ghasemi S, Habibi Z: A new dihydrofuranocoumarin from Opopanax hispidus (Friv.) Griseb. Nat Prod Res. 2014;28(21):1808-12. doi: 10.1080/14786419.2014.947487. Epub 2014 Sep 2. [PubMed:25179742 ]
Zheltakov MM, Vinokurov IN: [Treatment with peucedanin of patients with alopecia areata and alopecia totalis]. Sov Med. 1965 Aug;28(8):126-9. [PubMed:5869450 ]
Ananichev AV, Pakaln DA: [The determination of peucedanin in the roots of Peucedanum morisoni with thin-layer chromatography]. Med Prom SSSR. 1966 Nov;20(11):51-3. [PubMed:6000884 ]

Showing NP-Card for Peucedanin (NP0045602)

MOL for NP0045602 (Peucedanin)

3D MOL for NP0045602 (Peucedanin)

3D SDF for NP0045602 (Peucedanin)

3D-SDF for NP0045602 (Peucedanin)

PDB for NP0045602 (Peucedanin)

3D PDB for NP0045602 (Peucedanin)

SMILES for NP0045602 (Peucedanin)

INCHI for NP0045602 (Peucedanin)

Structure for NP0045602 (Peucedanin)

3D Structure for NP0045602 (Peucedanin)