NP-MRD: Showing NP-Card for 2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate (NP0143228)

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Record Information

Version

2.0

Created at

2022-09-01 21:55:49 UTC

Updated at

2022-09-01 21:55:49 UTC

NP-MRD ID

NP0143228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate

Description

2-{9-Hydroxy-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate 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-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate is found in Tordylium apulum. 2-{9-Hydroxy-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -4.0374    2.1843   -1.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7554    0.9727   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7394    0.4398   -0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5158    0.4145   -0.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2307   -0.7265    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.9509   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5796   -0.5046    1.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7584   -0.9924    0.1870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2236   -1.2177   -1.0731 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -0.9219   -1.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2371   -1.2738   -1.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -0.8245   -1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7234    0.0184   -0.4392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9640    0.5055   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0735    1.3394    0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394    1.6536    1.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    2.4275    2.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    1.1905    1.3810 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476    0.3905    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -0.0806    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0523    0.1679    0.7142 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1506    0.0582    2.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7688    2.7950   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437    2.8234   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5165    1.9366   -2.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5629   -2.4185    0.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6419   -1.7727   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2374   -2.7362   -0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9241   -1.1019    2.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6284   -0.7308    1.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763    0.5616    1.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -1.8873    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742   -1.9293   -2.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3737   -1.1039   -2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7993    0.2133   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0492    1.7367    1.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3644    1.1487    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5835   -0.8048    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 13  2  0
 13 12  1  0
 12 11  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 21  8  1  0
 18 19  1  0
 11 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  1
 21 37  1  1
 22 38  1  0
 12 34  1  0
 11 33  1  0
 14 35  1  0
 15 36  1  0
M  END


  Mrv1652308211909092D          

 22 24  0  0  0  0            999 V2000
    6.4908   -0.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7959    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -1.0931    0.0000 C   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
    0.3245    1.1395    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
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7896   -0.4364    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
    2.7983    1.0622    0.0000 C   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
    2.3637    0.3610    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
    1.5391    0.3867    0.0000 C   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
    4.3613   -0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8153    0.3882    0.0000 O   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
    2.6996   -1.0703    0.0000 O   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
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0626   -0.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  2  0  0  0  0
 18 11  2  0  0  0  0
 19 13  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)C1OC2=C(C1O)C1=C(C=C2)C=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-8(17)22-16(2,3)15-13(19)12-10(20-15)6-4-9-5-7-11(18)21-14(9)12/h4-7,13,15,19H,1-3H3

> <INCHI_KEY>
GZMKMMSCOHLOLH-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.518352748619748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{9-hydroxy-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.2545228703333333

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.829383905942965

> <JCHEM_PKA_STRONGEST_BASIC>
-3.748227479540547

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
76.6999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{9-hydroxy-2-oxo-8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      12.116  -1.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.952   0.578   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.330  -2.040   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.807  -0.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.141  -0.731   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.855   0.725   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.039  -1.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.450  -1.543   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8    1   17   22                                                  
CONECT    9    4    5   14                                                  
CONECT   10    6   12   20                                                  
CONECT   11    7   18   21                                                  
CONECT   12   10   13   14                                                  
CONECT   13   12   15   19                                                  
CONECT   14    9   12   21                                                  
CONECT   15   13   16   20                                                  
CONECT   16    2    3   15   22                                             
CONECT   17    8                                                            
CONECT   18   11                                                            
CONECT   19   13                                                            
CONECT   20   10   15                                                       
CONECT   21   11   14                                                       
CONECT   22    8   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2-{9-hydroxy-2-oxo-2H,8H,9H-furo[2,3-H]chromen-8-yl}propan-2-yl acetic acid	Generator

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

2-{9-hydroxy-2-oxo-2H,8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate

Traditional Name

2-{9-hydroxy-2-oxo-8H,9H-furo[2,3-h]chromen-8-yl}propan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C)(C)C1OC2=C(C1O)C1=C(C=C2)C=CC(=O)O1

InChI Identifier

InChI=1S/C16H16O6/c1-8(17)22-16(2,3)15-13(19)12-10(20-15)6-4-9-5-7-11(18)21-14(9)12/h4-7,13,15,19H,1-3H3

InChI Key

GZMKMMSCOHLOLH-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
Tordylium apulum	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
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
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
logP	2.21	ALOGPS
logP	1.25	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	30.52 Å³	ChemAxon
Number of Rings	3	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

HMDB0129092

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087943

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

131835378

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-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate (NP0143228)

MOL for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

3D MOL for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

3D SDF for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

3D-SDF for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

PDB for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

3D PDB for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

SMILES for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

INCHI for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

Structure for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)

3D Structure for NP0143228 (2-{9-hydroxy-2-oxo-8h,9h-furo[2,3-h]chromen-8-yl}propan-2-yl acetate)