NP-MRD: Showing NP-Card for 2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate (NP0238278)

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Record Information

Version

2.0

Created at

2022-09-06 21:38:49 UTC

Updated at

2022-09-06 21:38:49 UTC

NP-MRD ID

NP0238278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate

Description

AC1NRVEO 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. 2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate is found in Dorstenia contrajerva and Dorstenia excentrica. AC1NRVEO 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
    5.9121    1.2770    2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5197    0.7073    2.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444   -0.4691    2.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4352    1.4206    1.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    1.0439    1.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751   -0.0428    0.6769 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2906    0.5157   -0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5837   -1.1743    1.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904   -0.3546    0.7027 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0055   -1.3835   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3623   -0.9189   -0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894   -1.5171   -1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5699   -0.8465   -1.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5992   -1.4376   -2.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7458   -0.6925   -2.6087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8858    0.5866   -2.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9455    1.2724   -2.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8804    1.1115   -1.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636    0.4394   -1.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7432    1.0303   -0.5595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    0.3693   -0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3878    0.7537    0.3747 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6141    0.6174    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3083    1.4394    3.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8366    2.2563    1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4467    1.8992    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    0.6731    2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698    0.9823   -1.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7534   -0.3335   -1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0964    1.2795   -0.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -1.8621    0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615   -0.7675    1.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -1.4339   -1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302   -2.3900    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2763   -2.5294   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   -2.4576   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5791   -1.1161   -3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765    2.0520   -0.1963 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
  6  7  1  0
  6  8  1  1
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 19  2  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22  9  1  0
 21 11  1  0
 14 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 12 35  1  0
 15 37  1  0
 14 36  1  0
 20 38  1  0
M  END


  Mrv1533004191514032D          

 22 24  0  0  0  0            999 V2000
   -1.9317   -0.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192   -1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9317   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6942   -1.2210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433   -1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-9(17)20-8-16(2,19)14-6-11-5-10-3-4-15(18)22-12(10)7-13(11)21-14/h3-5,7,14,19H,6,8H2,1-2H3

> <INCHI_KEY>
MZOKXKVSVDATRK-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.08928233543398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propyl acetate

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.1266090506666664

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.242652282525167

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5674638916234924

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
77.0361

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-{7-oxo-2H,3H-furo[3,2-g]chromen-2-yl}propyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -3.606  -0.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.836  -2.279   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.606  -3.613   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.296  -2.279   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.526  -3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.014  -3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.014  -5.153   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.014  -2.073   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.925  -5.153   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   11   22                                                  
CONECT   22   21    9                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

2-hydroxy-2-{7-oxo-2H,3H,7H-furo[3,2-g]chromen-2-yl}propyl acetate

Traditional Name

2-hydroxy-2-{7-oxo-2H,3H-furo[3,2-g]chromen-2-yl}propyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC(C)(O)C1CC2=CC3=C(OC(=O)C=C3)C=C2O1

InChI Identifier

InChI=1S/C16H16O6/c1-9(17)20-8-16(2,19)14-6-11-5-10-3-4-15(18)22-12(10)7-13(11)21-14/h3-5,7,14,19H,6,8H2,1-2H3

InChI Key

MZOKXKVSVDATRK-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
Dorstenia contrajerva	LOTUS Database	35616633
Dorstenia excentrica	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
Coumaran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
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	1.73	ALOGPS
logP	1.13	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-3.6	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	4	ChemAxon
Refractivity	77.04 m³·mol⁻¹	ChemAxon
Polarizability	31.09 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

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

5248682

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate (NP0238278)

MOL for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

3D MOL for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

3D SDF for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

3D-SDF for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

PDB for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

3D PDB for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

SMILES for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

INCHI for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

Structure for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)

3D Structure for NP0238278 (2-hydroxy-2-{7-oxo-2h,3h-furo[3,2-g]chromen-2-yl}propyl acetate)