NP-MRD: Showing NP-Card for Oxyimperatorin (NP0139479)

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Record Information

Version

2.0

Created at

2022-06-29 19:56:18 UTC

Updated at

2022-06-29 19:56:18 UTC

NP-MRD ID

NP0139479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxyimperatorin

Description

9-[(3,3-Dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one 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. 9-[(3,3-Dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxyimperatorin is found in Angelica dahurica, Angelica lucida, Halocnemum strobilaceum, Orixa japonica, Phebalium canaliculatum, Prangos bucharica, Prangos uloptera, Skimmia laureola, Thamnosma texana and Zeravschania regeliana. 9-[(3,3-Dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
    5.0782    0.9647    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8138    0.1315   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0384   -1.1860   -0.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0455   -0.0265    1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5565    0.7794    0.0753 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2491    0.3206   -0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812    0.3356    0.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0419   -0.0239    0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3817   -1.3461    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909   -2.4177    0.8504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488   -3.4670    0.9134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7319   -3.0871    0.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -1.7262    0.3365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895   -0.8196   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461    0.5097   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329    1.4102   -0.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9531    2.7233   -0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6225    3.0330   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2894    4.2349   -0.7497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7288    2.1373   -0.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363    0.8625   -0.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8889    1.9195   -0.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9587    0.4954   -0.3863 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2456    1.1740    1.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705   -1.8288   -0.0691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067   -1.0101   -1.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1353   -1.7017   -1.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484    1.8522    0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3189   -0.6306   -1.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9617    1.1037   -1.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0978   -4.4572    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199   -3.7001    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7122   -1.1618   -0.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3694    1.1370   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6937    3.4659   -1.0503 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8 21  2  0
 21 20  1  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  5  2  1  0
  9  8  1  0
 15 21  1  0
 12 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  1
  6 29  1  0
  6 30  1  0
 17 35  1  0
 16 34  1  0
 14 33  1  0
 11 31  1  0
 12 32  1  0
M  END


  Mrv1652310051709282D          

 21 24  0  0  0  0            999 V2000
    2.3846   -4.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0166   -5.2394    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    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
    3.5724   -1.2375    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18  6  1  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC1COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3

> <INCHI_KEY>
CTJZWFCPUDPLME-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.173160958900258

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.323230061666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.905332184537682

> <JCHEM_POLAR_SURFACE_AREA>
61.2

> <JCHEM_REFRACTIVITY>
74.65460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(3,3-dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       4.451  -7.737   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.631  -9.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.898  -8.264   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.438  -8.264   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3    4    9                                                       
CONECT    4    3   12                                                       
CONECT    5    6   10                                                       
CONECT    6    5   18                                                       
CONECT    7    9   10                                                       
CONECT    8   11   19                                                       
CONECT    9    3    7   14                                                  
CONECT   10    5    7   13                                                  
CONECT   11    8   16   21                                                  
CONECT   12    4   17   20                                                  
CONECT   13   10   15   18                                                  
CONECT   14    9   15   20                                                  
CONECT   15   13   14   19                                                  
CONECT   16    1    2   11   21                                             
CONECT   17   12                                                            
CONECT   18    6   13                                                       
CONECT   19    8   15                                                       
CONECT   20   12   14                                                       
CONECT   21   11   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2794 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

9-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-[(3,3-dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC1COC1=C2OC(=O)C=CC2=CC2=C1OC=C2

InChI Identifier

InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3

InChI Key

CTJZWFCPUDPLME-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, 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 dahurica	LOTUS Database	35616633
Angelica lucida	LOTUS Database	35616633
Halocnemum strobilaceum	LOTUS Database	35616633
Orixa japonica	LOTUS Database	35616633
Phebalium canaliculatum	LOTUS Database	35616633
Prangos bucharica	LOTUS Database	35616633
Prangos uloptera	LOTUS Database	35616633
Skimmia laureola	LOTUS Database	35616633
Thamnosma texana	LOTUS Database	35616633
Zeravschania regeliana	LOTUS Database	35616633

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
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.78	ALOGPS
logP	2.32	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	29.17 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

HMDB0149174

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

182251

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oxyimperatorin (NP0139479)

MOL for NP0139479 (Oxyimperatorin)

3D MOL for NP0139479 (Oxyimperatorin)

3D SDF for NP0139479 (Oxyimperatorin)

3D-SDF for NP0139479 (Oxyimperatorin)

PDB for NP0139479 (Oxyimperatorin)

3D PDB for NP0139479 (Oxyimperatorin)

SMILES for NP0139479 (Oxyimperatorin)

INCHI for NP0139479 (Oxyimperatorin)

Structure for NP0139479 (Oxyimperatorin)

3D Structure for NP0139479 (Oxyimperatorin)