NP-MRD: Showing NP-Card for (1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate (NP0284772)

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Record Information

Version

2.0

Created at

2022-09-09 12:38:37 UTC

Updated at

2022-09-09 12:38:37 UTC

NP-MRD ID

NP0284772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate

Description

(1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-4-yl]propyl 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. Based on a literature review very few articles have been published on (1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-4-yl]propyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092214382D          

 32 34  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8090    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6340    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    0.1576    0.0000 O   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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
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  8 32  1  0  0  0  0
M  END

     RDKit          3D

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    5.1707    1.0976    0.3134 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1081   -1.0020   -0.8279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0414    0.3425   -0.4691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782    1.0216   -0.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7019   -1.7056   -0.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
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 31 62  1  0
M  END


  Mrv1652309092214382D          

 32 34  0  0  1  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0284772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)C1=C2O[C@@H](CC2=C2OC(=O)C=C([C@H](CC)OC(C)=O)C2=C1O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-7-11(3)20(27)19-21(28)18-13(15(8-2)30-12(4)25)10-17(26)32-22(18)14-9-16(24(5,6)29)31-23(14)19/h10-11,15-16,28-29H,7-9H2,1-6H3/t11-,15-,16-/m0/s1

> <INCHI_KEY>
VBJCSMQHVABALD-UVBJJODRSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
47.66284994435307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-4-yl]propyl acetate

> <JCHEM_LOGP>
3.7234128726666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.29646620635619

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.4375369460896

> <JCHEM_PKA_STRONGEST_BASIC>
-3.106456827940497

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
116.67800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-8H,9H-furo[2,3-h]chromen-4-yl]propyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.798   2.786   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.703   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.243   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.783   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.243  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.243   3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.798   0.294   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   10   24                                                  
CONECT   24   23    7   25                                                  
CONECT   25   24                                                            
CONECT   26    9   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   27    8                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1S)-1-[(8S)-5-Hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-2H,8H,9H-furo[2,3-H]chromen-4-yl]propyl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4960 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

(1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-2H,8H,9H-furo[2,3-h]chromen-4-yl]propyl acetate

Traditional Name

(1S)-1-[(8S)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2S)-2-methylbutanoyl]-2-oxo-8H,9H-furo[2,3-h]chromen-4-yl]propyl acetate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)C1=C2O[C@@H](CC2=C2OC(=O)C=C([C@H](CC)OC(C)=O)C2=C1O)C(C)(C)O

InChI Identifier

InChI=1S/C24H30O8/c1-7-11(3)20(27)19-21(28)18-13(15(8-2)30-12(4)25)10-17(26)32-22(18)14-9-16(24(5,6)29)31-23(14)19/h10-11,15-16,28-29H,7-9H2,1-6H3/t11-,15-,16-/m0/s1

InChI Key

VBJCSMQHVABALD-UVBJJODRSA-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

Not Available

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
Butyrophenone
Benzopyran
1-benzopyran
Coumaran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	3.72	ChemAxon
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.68 m³·mol⁻¹	ChemAxon
Polarizability	47.66 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	Yes	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

162885733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate (NP0284772)

MOL for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

3D MOL for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

3D SDF for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

3D-SDF for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

PDB for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

3D PDB for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

SMILES for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

INCHI for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

Structure for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)

3D Structure for NP0284772 ((1s)-1-[(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2s)-2-methylbutanoyl]-2-oxo-8h,9h-furo[2,3-h]chromen-4-yl]propyl acetate)