NP-MRD: Showing NP-Card for 6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one (NP0305452)

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Record Information

Version

2.0

Created at

2022-09-10 21:18:21 UTC

Updated at

2022-09-10 21:18:22 UTC

NP-MRD ID

NP0305452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one

Description

6-[(2R)-2,3-dihydroxy-3-methylbutoxy]-5-methoxy-2H-furo[2,3-h]chromen-2-one 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. 6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one is found in Heracleum grandiflorum and Heracleum leskovii. Based on a literature review very few articles have been published on 6-[(2R)-2,3-dihydroxy-3-methylbutoxy]-5-methoxy-2H-furo[2,3-h]chromen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.4834   -2.4151   -1.9178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.0032   -1.8283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7045   -0.3015   -0.6971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8770   -0.0724    0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4088   -0.5540    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    0.1222   -0.1463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7254   -0.7789    0.0213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8954   -1.0735    1.3755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9995   -0.1467   -0.4623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3349    1.0629    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1118   -1.1613   -0.2118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9606    0.1962   -1.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3408    0.6345    1.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.0043    2.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6520    1.6796    3.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8448    1.7811    2.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6564    1.1238    1.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    0.8776    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7109    1.3575    0.4454 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5128    1.1505   -0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844    1.6165   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1486    0.4572   -1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727   -0.0400   -1.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    0.1768   -0.6998 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4002   -2.6862   -2.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4472   -2.6808   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -2.9572   -1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776    1.1131    0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690    0.2949   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5484   -1.6823   -0.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728   -0.4207    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478    0.9179    1.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    1.9752   -0.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4238    1.1391    0.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0120   -0.9563   -0.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6640   -2.1622   -0.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2965   -1.1315    0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -0.5627   -2.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    2.0896    4.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393    2.2697    3.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8782    0.3338   -2.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5483   -0.5877   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 24  2  0
 24 23  1  0
 23 22  2  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  4  3  1  0
 18 24  1  0
 13 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 23 42  1  0
 22 41  1  0
 16 40  1  0
 15 39  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  6
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
M  END


  Mrv1652309102223182D          

 24 26  0  0  1  0            999 V2000
    0.3691    2.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8429    2.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4529    3.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    3.9187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7121    3.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4975    4.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    5.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    4.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2245    5.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  4 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
  3 24  2  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=CC(=O)OC2=C2C=COC2=C1OC[C@@H](O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O7/c1-17(2,20)11(18)8-23-16-14(21-3)9-4-5-12(19)24-13(9)10-6-7-22-15(10)16/h4-7,11,18,20H,8H2,1-3H3/t11-/m1/s1

> <INCHI_KEY>
SYCQEMIWUFVJHN-LLVKDONJSA-N

> <FORMULA>
C17H18O7

> <MOLECULAR_WEIGHT>
334.324

> <EXACT_MASS>
334.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.53057924287254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(2R)-2,3-dihydroxy-3-methylbutoxy]-5-methoxy-2H-furo[2,3-h]chromen-2-one

> <JCHEM_LOGP>
1.0038552236666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.118688153539214

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.196270912286924

> <JCHEM_PKA_STRONGEST_BASIC>
-2.86285841986135

> <JCHEM_POLAR_SURFACE_AREA>
98.36000000000001

> <JCHEM_REFRACTIVITY>
84.62789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(2R)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.689   4.793   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.307   4.649   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.579   6.006   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.390   7.315   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.929   7.267   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.662   8.672   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.934  10.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.305   7.944   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.019   9.400   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    4   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   18                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₇

Average Mass

334.3240 Da

Monoisotopic Mass

334.10525 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C2C=CC(=O)OC2=C2C=COC2=C1OC[C@@H](O)C(C)(C)O

InChI Identifier

InChI=1S/C17H18O7/c1-17(2,20)11(18)8-23-16-14(21-3)9-4-5-12(19)24-13(9)10-6-7-22-15(10)16/h4-7,11,18,20H,8H2,1-3H3/t11-/m1/s1

InChI Key

SYCQEMIWUFVJHN-LLVKDONJSA-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
Heracleum grandiflorum	LOTUS Database	35616633
Heracleum leskovii	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
Benzofuran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Tertiary alcohol
Furan
Heteroaromatic compound
Secondary alcohol
Lactone
1,2-diol
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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

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

67032848

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15596587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one (NP0305452)

MOL for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

3D MOL for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

3D SDF for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

3D-SDF for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

PDB for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

3D PDB for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

SMILES for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

INCHI for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

Structure for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)

3D Structure for NP0305452 (6-[(2r)-2,3-dihydroxy-3-methylbutoxy]-5-methoxyfuro[2,3-h]chromen-2-one)