NP-MRD: Showing NP-Card for 3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0287716)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 17:02:44 UTC

Updated at

2022-09-09 17:02:44 UTC

NP-MRD ID

NP0287716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

Description

3-Hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)-2,3-dihydrofuran-2-one belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one is found in Cydonia oblonga. Based on a literature review very few articles have been published on 3-hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)-2,3-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.8954    2.2340    0.7678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2696    0.9975    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6427   -0.1408    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4804   -0.1935    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174   -1.2757    0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166   -2.5690    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6617   -0.9040   -0.7912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7707   -1.5979   -1.9877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7626   -1.0397   -0.2190 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8930   -2.5303    0.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926   -0.6775   -1.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6661    0.1878   -1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5163    0.4579   -2.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273    1.4155   -2.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3507    1.9326   -2.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1815    1.8073   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062    2.7744    0.0283 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417    1.0772   -0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094    1.2075    1.1327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9165    0.5484   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2662    1.2958   -1.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0100    0.8826   -0.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5678    3.0437    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    2.1434   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8606    2.5769    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1326    1.0202    2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492   -1.0236    1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596   -2.5803    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1499   -2.6864    0.8118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -3.4352    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6299   -2.1115   -2.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7559   -0.4487    0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4615   -2.7832    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4898   -3.1586   -0.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0080   -2.7077    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5237   -1.2460   -2.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3692    3.6028    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    0.2833    1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2608    1.9434    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6104    1.6776    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
  7 20  1  0
 20 21  2  0
 20 22  1  0
 22  4  1  0
 18 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
M  END


  Mrv1652309092219012D          

 22 23  0  0  0  0            999 V2000
    1.6624   -5.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -4.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118   -3.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967   -2.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418   -2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572   -1.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7092   -1.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572   -1.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -1.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0682   -1.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0063   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5584    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3868    1.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013    1.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875    2.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7144    1.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214    1.2050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3788    0.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913   -0.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3767   -2.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1613   -1.8748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -2.9144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  4  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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=CC1=C(C)C(O)(C(C)C=C2OC(=O)C(O)=C2C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O6/c1-5-6-11-10(4)16(20,15(19)22-11)8(2)7-12-9(3)13(17)14(18)21-12/h5-8,17,20H,1-4H3

> <INCHI_KEY>
JEAPGXVBGVXTDF-UHFFFAOYSA-N

> <FORMULA>
C16H18O6

> <MOLECULAR_WEIGHT>
306.314

> <EXACT_MASS>
306.1103383

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.51702750482587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)-2,3-dihydrofuran-2-one

> <JCHEM_LOGP>
1.358707272

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.519552158680684

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.38912834834687

> <JCHEM_PKA_STRONGEST_BASIC>
-3.439834482244102

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
82.5658

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₆

Average Mass

306.3140 Da

Monoisotopic Mass

306.11034 Da

IUPAC Name

3-hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)-2,3-dihydrofuran-2-one

Traditional Name

3-hydroxy-3-[1-(4-hydroxy-3-methyl-5-oxofuran-2-ylidene)propan-2-yl]-4-methyl-5-(prop-1-en-1-yl)furan-2-one

CAS Registry Number

Not Available

SMILES

CC=CC1=C(C)C(O)(C(C)C=C2OC(=O)C(O)=C2C)C(=O)O1

InChI Identifier

InChI=1S/C16H18O6/c1-5-6-11-10(4)16(20,15(19)22-11)8(2)7-12-9(3)13(17)14(18)21-12/h5-8,17,20H,1-4H3

InChI Key

JEAPGXVBGVXTDF-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
Cydonia oblonga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Enol ester
Lactone
Carboxylic acid ester
Oxacycle
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.36	ChemAxon
pKa (Strongest Acidic)	8.39	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.57 m³·mol⁻¹	ChemAxon
Polarizability	31.52 Å³	ChemAxon
Number of Rings	2	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

163081598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one (NP0287716)

MOL for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D MOL for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D SDF for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D-SDF for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

PDB for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D PDB for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

SMILES for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

INCHI for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

Structure for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)

3D Structure for NP0287716 (3-hydroxy-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one)