NP-MRD: Showing NP-Card for exo-Dehydrochalepin (NP0085338)

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Record Information

Version

2.0

Created at

2022-04-29 05:53:59 UTC

Updated at

2022-04-29 05:53:59 UTC

NP-MRD ID

NP0085338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

exo-Dehydrochalepin

Description

Exo-Dehydrochalepin 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. Exo-Dehydrochalepin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, exo-Dehydrochalepin has been detected, but not quantified in, herbs and spices. exo-Dehydrochalepin is found in Ruta graveolens . This could make exo-dehydrochalepin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -5.0386    0.8739   -1.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0117   -0.1548   -0.5686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0909   -0.2670    0.5902 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6285   -1.2902    1.6043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    1.0414    1.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330   -0.6683    0.1999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781    0.1680    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3956   -0.1821    0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6235    0.6839    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8993    0.3404    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1740   -0.8412   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1187   -1.6806   -0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.3790   -0.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2009   -2.1337   -0.7596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393   -1.8496   -0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037   -2.6237   -0.7089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -0.9273   -0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0241    0.4356   -0.7694 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4407    0.5838   -0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9674    1.2432    0.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4252   -0.0714   -1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1829    1.0966    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3595    1.6919   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7241    0.9073   -2.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6985   -0.9715   -0.7455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130   -1.7660    2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1699   -2.0894    1.0523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818   -0.7761    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4126    0.9558    2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0608    1.3573    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6880    1.8750    0.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8325    1.1300    0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3995    1.6356    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059   -2.6203   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034    0.9246   -1.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0241    1.2885    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3290    1.7386    1.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9789   -0.1496   -2.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3724    0.4883   -1.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6170   -1.0917   -0.9995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0705    2.1786    0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542    0.8956    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 20  2  3
 19 18  1  0
 18 22  1  0
 22 10  1  0
 10  9  2  0
  9  8  1  0
  8 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  6  1  0
  6  7  2  0
  6  3  1  0
  3  4  1  1
  3  5  1  0
  3  2  1  0
  2  1  2  3
 13 12  1  0
 12 11  2  0
 11 17  1  0
 17 18  1  0
 11 10  1  0
  7  8  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
 20 36  1  0
 20 37  1  0
 18 35  1  6
 22 41  1  0
 22 42  1  0
  9 33  1  0
  7 32  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  5 31  1  0
  2 25  1  0
  1 23  1  0
  1 24  1  0
 12 34  1  0
M  END


  Mrv0541 05061310492D          

 22 24  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.3020    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
    2.1434   -0.4125    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
    3.6425   -0.2549    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
    4.9524    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
    2.8579    0.0000    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
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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   -0.4125    0.0000 C   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
    3.6425    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
  6  1  2  0  0  0  0
 11  2  2  0  0  0  0
 11  3  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19  4  1  0  0  0  0
 19  5  1  0  0  0  0
 19  6  1  0  0  0  0
 19 14  1  0  0  0  0
 20 18  2  0  0  0  0
 21 15  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-6-19(4,5)14-8-12-7-13-9-15(11(2)3)21-16(13)10-17(12)22-18(14)20/h6-8,10,15H,1-2,9H2,3-5H3

> <INCHI_KEY>
VSCRFQYWCSFUIR-UHFFFAOYSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.3603

> <EXACT_MASS>
296.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.59593105229962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2-methylbut-3-en-2-yl)-2-(prop-1-en-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.267721070333334

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.88823520316673

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
87.06320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-methylbut-3-en-2-yl)-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.014   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.014  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.564  -2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.104   0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.244   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.704   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    1   19                                                       
CONECT    7   12   13                                                       
CONECT    8   12   14                                                       
CONECT    9   13   15                                                       
CONECT   10   16   17                                                       
CONECT   11    2    3   15                                                  
CONECT   12    7    8   17                                                  
CONECT   13    7    9   16                                                  
CONECT   14    8   18   19                                                  
CONECT   15    9   11   21                                                  
CONECT   16   10   13   21                                                  
CONECT   17   10   12   22                                                  
CONECT   18   14   20   22                                                  
CONECT   19    4    5    6   14                                             
CONECT   20   18                                                            
CONECT   21   15   16                                                       
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3603 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

6-(2-methylbut-3-en-2-yl)-2-(prop-1-en-2-yl)-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

6-(2-methylbut-3-en-2-yl)-2-(prop-1-en-2-yl)-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC(=C)C1CC2=CC3=C(OC(=O)C(=C3)C(C)(C)C=C)C=C2O1

InChI Identifier

InChI=1S/C19H20O3/c1-6-19(4,5)14-8-12-7-13-9-15(11(2)3)21-16(13)10-17(12)22-18(14)20/h6-8,10,15H,1-2,9H2,3-5H3

InChI Key

VSCRFQYWCSFUIR-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
Ruta graveolens	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
Coumaran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	4.35	ALOGPS
logP	4.27	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	87.06 m³·mol⁻¹	ChemAxon
Polarizability	33.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039071

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018570

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14135678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for exo-Dehydrochalepin (NP0085338)

MOL for NP0085338 (exo-Dehydrochalepin)

3D MOL for NP0085338 (exo-Dehydrochalepin)

3D SDF for NP0085338 (exo-Dehydrochalepin)

3D-SDF for NP0085338 (exo-Dehydrochalepin)

PDB for NP0085338 (exo-Dehydrochalepin)

3D PDB for NP0085338 (exo-Dehydrochalepin)

SMILES for NP0085338 (exo-Dehydrochalepin)

INCHI for NP0085338 (exo-Dehydrochalepin)

Structure for NP0085338 (exo-Dehydrochalepin)

3D Structure for NP0085338 (exo-Dehydrochalepin)