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Showing NP-Card for (2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate (NP0226479)

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Record Information
Version2.0
Created at2022-09-06 05:31:48 UTC
Updated at2022-09-06 05:31:48 UTC
NP-MRD IDNP0226479
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate
Description(2S)-3-(acetyloxy)-1-{4-methoxy-7-oxo-7H-furo[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. (2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate is found in Dorstenia foetida. Based on a literature review very few articles have been published on (2S)-3-(acetyloxy)-1-{4-methoxy-7-oxo-7H-furo[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)


  Mrv1652309062207312D          

 29 31  0  0  1  0            999 V2000
   -0.2211    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356    1.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030    2.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0164    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    2.4750    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 14 28  2  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 10 29  2  0  0  0  0
M  END
Download

3D MOL for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)

Download
3D SDF for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)

  Mrv1652309062207312D          

 29 31  0  0  1  0            999 V2000
   -0.2211    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356    1.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5893    1.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5030    2.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0164    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    2.4750    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 14 28  2  0  0  0  0
 28 29  1  0  0  0  0
  3 29  1  0  0  0  0
 10 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=COC2=CC2=C1C=C(C[C@H](OC(C)=O)C(C)(C)OC(C)=O)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C21H22O8/c1-11(22)27-18(21(3,4)29-12(2)23)9-13-8-15-17(28-20(13)24)10-16-14(6-7-26-16)19(15)25-5/h6-8,10,18H,9H2,1-5H3/t18-/m0/s1

> <INCHI_KEY>
WCGGDCPOSLLLNB-SFHVURJKSA-N

> <FORMULA>
C21H22O8

> <MOLECULAR_WEIGHT>
402.399

> <EXACT_MASS>
402.131467668

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.08292537383255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-3-(acetyloxy)-1-{4-methoxy-7-oxo-7H-furo[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate

> <JCHEM_LOGP>
2.137319859666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8307747243419015

> <JCHEM_POLAR_SURFACE_AREA>
101.27000000000001

> <JCHEM_REFRACTIVITY>
101.06220000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)
Download
PDB for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.413   1.953   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.953   1.953   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.723   3.286   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.263   3.286   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.293   2.142   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.700   2.768   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.539   4.300   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.033   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.263   5.954   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.723   5.954   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.953   7.287   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.413   7.287   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.357   8.621   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.357   5.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.897   5.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.897   3.286   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   1.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.897   0.619   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.207   1.953   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.207   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.747   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.517   3.286   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.057   3.286   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.747   1.953   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.413   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.953   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   14   29                                                       
CONECT   29   28    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

Download
3D PDB for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)
Download
SMILES for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)
COC1=C2C=COC2=CC2=C1C=C(C[C@H](OC(C)=O)C(C)(C)OC(C)=O)C(=O)O2
Download
INCHI for NP0226479 ((2s)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate)
InChI=1S/C21H22O8/c1-11(22)27-18(21(3,4)29-12(2)23)9-13-8-15-17(28-20(13)24)10-16-14(6-7-26-16)19(15)25-5/h6-8,10,18H,9H2,1-5H3/t18-/m0/s1
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View in JSmol
Synonyms
ValueSource
(2S)-3-(Acetyloxy)-1-{4-methoxy-7-oxo-7H-furo[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetic acidGenerator
Chemical FormulaC21H22O8
Average Mass402.3990 Da
Monoisotopic Mass402.13147 Da
IUPAC Name(2S)-3-(acetyloxy)-1-{4-methoxy-7-oxo-7H-furo[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate
Traditional Name(2S)-3-(acetyloxy)-1-{4-methoxy-7-oxofuro[3,2-g]chromen-6-yl}-3-methylbutan-2-yl acetate
CAS Registry NumberNot Available
SMILES
COC1=C2C=COC2=CC2=C1C=C(C[C@H](OC(C)=O)C(C)(C)OC(C)=O)C(=O)O2
InChI Identifier
InChI=1S/C21H22O8/c1-11(22)27-18(21(3,4)29-12(2)23)9-13-8-15-17(28-20(13)24)10-16-14(6-7-26-16)19(15)25-5/h6-8,10,18H,9H2,1-5H3/t18-/m0/s1
InChI KeyWCGGDCPOSLLLNB-SFHVURJKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dorstenia foetidaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassFuranocoumarins  
Direct Parent5-methoxypsoralens  
Alternative Parents
Substituents
  • 5-methoxypsoralen
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzofuran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Heteroaromatic compound
    • 

  • Furan
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Carboxylic acid derivative
    • 

  • Ether
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.14ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area101.27 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.06 m³·mol⁻¹ChemAxon
Polarizability40.08 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162869601  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]