NP-MRD: Showing NP-Card for cyclocumarol (NP0251830)

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Record Information

Version

2.0

Created at

2022-09-07 15:08:35 UTC

Updated at

2022-09-07 15:08:35 UTC

NP-MRD ID

NP0251830

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyclocumarol

Description

Pyranocoumarin, also known as cyclocoumarol or cumopyran, belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. cyclocumarol is found in Cullen corylifolium and Glycyrrhiza uralensis. Pyranocoumarin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -0.0981    4.2968   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9518    3.2827    0.2451 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331    2.0360   -0.2072 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6601    1.9705   -1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6687    1.4843    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880    0.2207   -0.4557 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3081   -0.3084   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1568   -0.8483   -1.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3939   -1.3520   -0.7996 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8603   -1.3399    0.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0614   -0.8202    1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8113   -0.3117    1.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395   -0.7105   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033   -0.2063    0.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4542   -1.0590    0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7001   -0.5352    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7375   -1.3919    0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485   -2.7555    0.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3218   -3.2488    0.4626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2408   -2.4110    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696   -2.8773   -0.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339   -2.0812   -0.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0953   -2.5808   -0.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405    1.1498    0.2522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9161    4.1436    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787    5.2201    0.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1310    4.5673   -1.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2623    2.3709   -2.1440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5736    2.5619   -2.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962    0.9277   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4614    1.1321    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054    2.1966    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0324    0.5479   -1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -0.8618   -2.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0001   -1.7600   -1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8534   -1.7489    0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4128   -0.8035    2.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772    0.1001    1.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8354    0.5463    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7082   -0.9991    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3688   -3.4297    0.9696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1365   -4.3141    0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 24  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 24  3  1  0
 20 15  1  0
 12  7  1  0
 22 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  6
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END


  Mrv1533004201504412D          

 24 27  0  0  0  0            999 V2000
    5.0092   -0.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3772   -0.5841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    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
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    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    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(C)CC(C2=CC=CC=C2)C2=C(O1)C1=CC=CC=C1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20(22-2)12-15(13-8-4-3-5-9-13)17-18(24-20)14-10-6-7-11-16(14)23-19(17)21/h3-11,15H,12H2,1-2H3

> <INCHI_KEY>
ZGFASEKBKWVCGP-UHFFFAOYSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.36

> <EXACT_MASS>
322.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.31791819479951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-2-methyl-4-phenyl-2H,3H,4H,5H-pyrano[3,2-c]chromen-5-one

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
3.2283132676666657

> <ALOGPS_LOGS>
-4.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2381656418964875

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
90.97550000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclocumarol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       9.351  -0.100   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.171  -1.090   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.184   4.771   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    7   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
Cyclocumarol, (2R-trans)-isomer	MeSH
Cyclocumarol, (trans)-(+-)-isomer	MeSH
Cyclocumarol, (2S-trans)-isomer	MeSH
Cumopyran	MeSH
Methanopyranorin	MeSH
Cumopyrin	MeSH
Cyclocoumarol	MeSH
Methopyranorin	MeSH
3,4-Dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano-(3,2-c)(1)-benzopyran-5-one	MeSH
Cyclocumarol, (2S-cis)-isomer	MeSH
Cyclocumarol	MeSH

Chemical Formula

C₂₀H₁₈O₄

Average Mass

322.3600 Da

Monoisotopic Mass

322.12051 Da

IUPAC Name

2-methoxy-2-methyl-4-phenyl-2H,3H,4H,5H-pyrano[3,2-c]chromen-5-one

Traditional Name

cyclocumarol

CAS Registry Number

Not Available

SMILES

COC1(C)CC(C2=CC=CC=C2)C2=C(O1)C1=CC=CC=C1OC2=O

InChI Identifier

InChI=1S/C20H18O4/c1-20(22-2)12-15(13-8-4-3-5-9-13)17-18(24-20)14-10-6-7-11-16(14)23-19(17)21/h3-11,15H,12H2,1-2H3

InChI Key

ZGFASEKBKWVCGP-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
Cullen corylifolium	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Benzopyran
1-benzopyran
Ketal
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous ester
Lactone
Oxacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
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	3.98	ALOGPS
logP	3.23	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	90.98 m³·mol⁻¹	ChemAxon
Polarizability	34.32 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

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

10606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for cyclocumarol (NP0251830)

MOL for NP0251830 (cyclocumarol)

3D MOL for NP0251830 (cyclocumarol)

3D SDF for NP0251830 (cyclocumarol)

3D-SDF for NP0251830 (cyclocumarol)

PDB for NP0251830 (cyclocumarol)

3D PDB for NP0251830 (cyclocumarol)

SMILES for NP0251830 (cyclocumarol)

INCHI for NP0251830 (cyclocumarol)

Structure for NP0251830 (cyclocumarol)

3D Structure for NP0251830 (cyclocumarol)