NP-MRD: Showing NP-Card for 6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one (NP0236253)

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Record Information

Version

2.0

Created at

2022-09-06 19:06:13 UTC

Updated at

2022-09-06 19:06:13 UTC

NP-MRD ID

NP0236253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one

Description

50886-70-9, Also known as clausindine or rutolide, 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. 6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one is found in Ruta chalepensis, Ruta graveolens and Ruta montana. 50886-70-9 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.7464    1.1944   -1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4580   -0.0121   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6615   -0.5221    0.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -1.1633   -0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1550   -0.3486    0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8306    0.1715    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2330   -0.6214   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5576   -0.2328   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6200   -1.0178   -0.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256   -0.6162   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1768   -1.1302   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0945   -0.1844   -0.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385    0.8282    0.2906 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1482    0.6551    0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0910    1.4570    0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7873    1.0213    0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7970    1.7891    0.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4548    1.4079    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797    2.2042    1.1148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9897    2.0822   -0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6734    1.1188   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426    1.5525   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1945    0.3236    1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2541   -1.1641   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2623   -1.1505    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052   -0.9975   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9913   -2.1899   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213   -0.9476    1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0497   -1.6122   -0.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4576   -1.9955   -0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3459   -2.1026   -0.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1720   -0.2290   -0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3086    2.4317    1.0111 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  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
  5  2  1  0
 18  6  1  0
 10 14  1  0
  9  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  7 29  1  0
 15 33  1  0
 12 32  1  0
 11 31  1  0
  9 30  1  0
M  END


  Mrv1533004161507372D          

 19 22  0  0  0  0            999 V2000
   -1.6002    0.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9683   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    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
    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 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
    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 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
    4.3570   -1.4924    0.0000 O   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 O   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
    0.0000   -1.6500    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  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
 16 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>
NP0236253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC1C1=CC2=C(OC1=O)C=C1OC=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-16(2)8-12(16)11-6-10-5-9-3-4-18-13(9)7-14(10)19-15(11)17/h3-7,12H,8H2,1-2H3

> <INCHI_KEY>
IXLICOBIKMGSAV-UHFFFAOYSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.32946467788961

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.1929615803333338

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8926338750517546

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
71.11789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.987   0.527   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.540  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.807  -1.517   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   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       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    2    6                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Clausindine	MeSH
Rutolide	MeSH

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

6-(2,2-dimethylcyclopropyl)-7H-furo[3,2-g]chromen-7-one

Traditional Name

6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)CC1C1=CC2=C(OC1=O)C=C1OC=CC1=C2

InChI Identifier

InChI=1S/C16H14O3/c1-16(2)8-12(16)11-6-10-5-9-3-4-18-13(9)7-14(10)19-15(11)17/h3-7,12H,8H2,1-2H3

InChI Key

IXLICOBIKMGSAV-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
Ruta chalepensis	LOTUS Database	35616633
Ruta graveolens	LOTUS Database	35616633
Ruta montana	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
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

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	3.96	ALOGPS
logP	3.19	ChemAxon
logS	-4	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	1	ChemAxon
Refractivity	71.12 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	4	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

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

170935

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one (NP0236253)

MOL for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

3D MOL for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

3D SDF for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

3D-SDF for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

PDB for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

3D PDB for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

SMILES for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

INCHI for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

Structure for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)

3D Structure for NP0236253 (6-(2,2-dimethylcyclopropyl)furo[3,2-g]chromen-7-one)