NP-MRD: Showing NP-Card for 2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate (NP0255068)

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Record Information

Version

1.0

Created at

2022-09-07 19:25:44 UTC

Updated at

2022-09-07 19:25:44 UTC

NP-MRD ID

NP0255068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate

Description

2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. 2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate is found in Angelica archangelica and Angelica keiskei. Based on a literature review very few articles have been published on 2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221252D          

 31 33  0  0  0  0            999 V2000
   -1.4688   -0.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4431   -1.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7161   -2.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903   -2.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148   -1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7122   -2.0639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480   -2.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9765   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3664    0.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910    0.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6256   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309072221252D          

 31 33  0  0  0  0            999 V2000
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   -0.7161   -2.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0255068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OC1C(OC2=CC=C3C=CC(=O)OC3=C12)C(C)(C)OC(=O)C(\C)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O7/c1-7-13(3)22(26)30-20-18-16(11-9-15-10-12-17(25)29-19(15)18)28-21(20)24(5,6)31-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7+,14-8-

> <INCHI_KEY>
RVGGCRQPGKFZDS-GUZOQHLSSA-N

> <FORMULA>
C24H26O7

> <MOLECULAR_WEIGHT>
426.465

> <EXACT_MASS>
426.167853177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.24141424901817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
5.239271929333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901387533458658

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
115.20799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.742  -1.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.694  -3.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.337  -3.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.289  -5.475   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.028  -3.125   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.076  -1.585   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.329  -3.853   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.638  -3.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.450  -4.350   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.827  -1.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.947  -2.230   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.060  -0.694   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.556  -0.327   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.284   1.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.823   1.078   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.635  -0.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.174  -0.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.985  -1.492   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.257  -2.849   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.068  -4.158   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.718  -2.897   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.907  -1.588   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.367  -1.636   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.373  -2.812   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.740  -4.308   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.219  -4.738   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.331  -3.672   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.586  -6.233   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.474  -7.299   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.065  -6.663   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.432  -8.159   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22   13   24                                                  
CONECT   24   23   11   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₆O₇

Average Mass

426.4650 Da

Monoisotopic Mass

426.16785 Da

IUPAC Name

2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

2-(9-{[(2E)-2-methylbut-2-enoyl]oxy}-2-oxo-8H,9H-furo[2,3-h]chromen-8-yl)propan-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)OC1C(OC2=CC=C3C=CC(=O)OC3=C12)C(C)(C)OC(=O)C(\C)=C/C

InChI Identifier

InChI=1S/C24H26O7/c1-7-13(3)22(26)30-20-18-16(11-9-15-10-12-17(25)29-19(15)18)28-21(20)24(5,6)31-23(27)14(4)8-2/h7-12,20-21H,1-6H3/b13-7+,14-8-

InChI Key

RVGGCRQPGKFZDS-GUZOQHLSSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 archangelica	LOTUS Database	35616633
Angelica keiskei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Angular furanocoumarins

Alternative Parents

Substituents

Angular furanocoumarin
Benzopyran
1-benzopyran
Coumaran
Alkyl aryl ether
Fatty acid ester
Pyranone
Dicarboxylic acid or derivatives
Pyran
Fatty acyl
Benzenoid
Heteroaromatic compound
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	5.24	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.21 m³·mol⁻¹	ChemAxon
Polarizability	44.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4478008

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319786

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate (NP0255068)

MOL for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

PDB for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

Structure for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0255068 (2-(9-{[(2e)-2-methylbut-2-enoyl]oxy}-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl)propan-2-yl (2z)-2-methylbut-2-enoate)