NP-MRD: Showing NP-Card for Chalepensin (NP0051437)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:15 UTC

Updated at

2022-04-27 22:48:16 UTC

NP-MRD ID

NP0051437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chalepensin

Description

6-(2-Methylbut-3-en-2-yl)-7H-furo[3,2-g]chromen-7-one, also known as 3-(alpha,alpha-dimethylallyl)psoralen, 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. Chalepensin is found in Boenninghausenia albiflora, Boenninghausenia spp., Clausena lansium, Psilopeganum sinense, Ruta chalepensis , Ruta graveolens , Ruta montana and Stauranthus perforatus. 6-(2-Methylbut-3-en-2-yl)-7H-furo[3,2-g]chromen-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.5026   -0.5041   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2849   -0.9835   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5044   -0.2753    0.2840 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7530    1.2120    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9502   -0.7636    1.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637   -0.5245    0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2034    0.5234   -0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1516    0.2733   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622    1.3174   -0.2906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197    1.0457   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.8320   -0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113    0.9689   -0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1622   -0.2460   -0.3657 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8490   -0.2576   -0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9408   -1.2836   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -1.0304    0.0294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7352   -2.0228    0.2197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -1.8010    0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3932   -2.7306    0.4836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0889    0.4672   -2.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831   -1.0906   -2.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6909   -1.9490   -0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4501    1.6713   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8554    1.3678    0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742    1.7144    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3927   -1.7854    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927   -0.8788    2.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6626   -0.0627    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5049    1.5600   -0.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212    2.3331   -0.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5138    2.8970   -0.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6341    1.3155   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2720   -2.3098    0.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  1
  3  5  1  0
  3  2  1  0
  2  1  2  3
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
 18  6  1  0
 10 14  1  0
  9  8  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
  7 29  1  0
 15 33  1  0
 12 32  1  0
 11 31  1  0
  9 30  1  0
M  END


  Mrv1533004241518432D          

 19 21  0  0  0  0            999 V2000
    5.0832    3.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082    1.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1=CC2=C(OC1=O)C=C1OC=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3

> <INCHI_KEY>
FYCCCUNGXGKNJV-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.222125021375035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
3.5102490653333334

> <ALOGPS_LOGS>
-4.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8927448650056133

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
73.0166

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chalepensin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       9.489   5.717   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.029   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592   5.153   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    8                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    9   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
3-(alpha,alpha-Dimethylallyl)psoralen	Kegg
3-(a,a-Dimethylallyl)psoralen	Generator
3-(Α,α-dimethylallyl)psoralen	Generator

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

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

Traditional Name

chalepensin

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=CC2=C(OC1=O)C=C1OC=CC1=C2

InChI Identifier

InChI=1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3

InChI Key

FYCCCUNGXGKNJV-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
Boenninghausenia albiflora	LOTUS Database	35616633
Boenninghausenia spp.	Plant	KNApSAcK
Clausena lansium	LOTUS Database	35616633
Psilopeganum sinense	Plant	KNApSAcK
Ruta chalepensis	Plant	KNApSAcK
Ruta graveolens	Plant	KNApSAcK
Ruta montana	LOTUS Database	35616633
Stauranthus perforatus	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
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furanocoumarin (CHEBI:3572 )
Furanocoumarins (C09165 )

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	4.18	ALOGPS
logP	3.51	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	73.02 m³·mol⁻¹	ChemAxon
Polarizability	27.22 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002456

Chemspider ID

Not Available

KEGG Compound ID

C09165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chalepensin (NP0051437)

MOL for NP0051437 (Chalepensin)

3D MOL for NP0051437 (Chalepensin)

3D SDF for NP0051437 (Chalepensin)

3D-SDF for NP0051437 (Chalepensin)

PDB for NP0051437 (Chalepensin)

3D PDB for NP0051437 (Chalepensin)

SMILES for NP0051437 (Chalepensin)

INCHI for NP0051437 (Chalepensin)

Structure for NP0051437 (Chalepensin)

3D Structure for NP0051437 (Chalepensin)