NP-MRD: Showing NP-Card for 3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one (NP0231128)

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Record Information

Version

2.0

Created at

2022-09-06 11:50:26 UTC

Updated at

2022-09-06 11:50:26 UTC

NP-MRD ID

NP0231128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one

Description

3-Hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring. 3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one is found in Pestalotiopsis virgatula. Based on a literature review very few articles have been published on 3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    3.5976    0.7826   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4476   -0.6903    0.2453 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3922   -1.4041   -0.4756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0834   -1.1812   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9318   -2.0999   -0.8319 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -0.6055    0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -1.2908    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4639   -1.1291   -1.2619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960    0.1761   -1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571    0.3975   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865    1.3070   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403    2.1944   -1.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6154    1.2783    0.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097    0.3679    1.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -0.5363    1.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5316   -0.5191    0.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.0601   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6680    1.0383    0.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0391    1.3509    0.7346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6051   -0.7959    1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691   -2.0343   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7969    0.4684    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -0.7773    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202   -2.3597    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175    0.1580   -2.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0979    0.9123   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9177    2.8490   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4181    1.9896    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8930    0.3481    2.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0248   -1.2549    2.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  7  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  6 22  1  0
  6 23  1  0
  7 24  1  6
  9 25  1  0
  9 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv1652309062213502D          

 16 17  0  0  0  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  7 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(=O)CC1OCC2=C(O)C=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-7(13)11(15)5-12-8-3-2-4-10(14)9(8)6-16-12/h2-4,7,12-14H,5-6H2,1H3

> <INCHI_KEY>
BBGDMJGYFNHPDK-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.24

> <EXACT_MASS>
222.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.71450433016551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one

> <JCHEM_LOGP>
1.1525893656666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.70765949544322

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.943913194439014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.362787992273619

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
58.362000000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10    7                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2400 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one

Traditional Name

3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one

CAS Registry Number

Not Available

SMILES

CC(O)C(=O)CC1OCC2=C(O)C=CC=C12

InChI Identifier

InChI=1S/C12H14O4/c1-7(13)11(15)5-12-8-3-2-4-10(14)9(8)6-16-12/h2-4,7,12-14H,5-6H2,1H3

InChI Key

BBGDMJGYFNHPDK-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
Pestalotiopsis virgatula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Acyloin
Benzenoid
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Dialkyl ether
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
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	1.15	ChemAxon
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.36 m³·mol⁻¹	ChemAxon
Polarizability	22.71 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

22369769

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44715271

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-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one (NP0231128)

MOL for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

3D MOL for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

3D SDF for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

3D-SDF for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

PDB for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

3D PDB for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

SMILES for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

INCHI for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

Structure for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)

3D Structure for NP0231128 (3-hydroxy-1-(4-hydroxy-1,3-dihydro-2-benzofuran-1-yl)butan-2-one)