NP-MRD: Showing NP-Card for (-)-Xylogranatin K (NP0082128)

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Record Information

Version

2.0

Created at

2022-04-29 03:11:07 UTC

Updated at

2022-04-29 03:11:07 UTC

NP-MRD ID

NP0082128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Xylogranatin K

Description

Xylogranatin K belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (-)-Xylogranatin K is found in Xylocarpus granatum . Based on a literature review very few articles have been published on Xylogranatin K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205112D          

 37 40  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  1  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    0.6979    0.0000 C   0  0  2  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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 33 34  1  0  0  0  0
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 36 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292205112D          

 37 40  0  0  1  0            999 V2000
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 24 28  1  0  0  0  0
  3 29  1  1  0  0  0
 29 30  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  1 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0082128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C2=C(OC(=C2)C2=CC(=O)O[C@@H](C3=COC=C3)[C@]2(C)CCC(O)=O)[C@H](C)[C@@H](CC(=O)OC)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O9/c1-15-18(12-22(31)33-5)27(2,3)26(34-6)17-11-20(36-24(15)17)19-13-23(32)37-25(16-8-10-35-14-16)28(19,4)9-7-21(29)30/h8,10-11,13-15,18,25-26H,7,9,12H2,1-6H3,(H,29,30)/t15-,18-,25+,26+,28-/m1/s1

> <INCHI_KEY>
YBVQEMYZAAIYCJ-NXZFLPEMSA-N

> <FORMULA>
C28H34O9

> <MOLECULAR_WEIGHT>
514.571

> <EXACT_MASS>
514.220282675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
54.66649364572004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2R,3R)-2-(furan-3-yl)-4-[(4R,6R,7R)-4-methoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid

> <ALOGPS_LOGP>
4.22

> <JCHEM_LOGP>
3.9316268256666658

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.952415880148754

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5996758086012917

> <JCHEM_POLAR_SURFACE_AREA>
125.41000000000001

> <JCHEM_REFRACTIVITY>
132.0094

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R,3R)-2-(furan-3-yl)-4-[(4R,6R,7R)-4-methoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4H-1-benzofuran-2-yl]-3-methyl-6-oxo-2H-pyran-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.400   0.175   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -3.400   2.843   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.036   5.716   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.324   6.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.378   7.978   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.737   8.701   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.928   8.794   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.216   4.993   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.773   6.917   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -3.918   7.948   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.251   7.178   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.931   5.671   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.797   2.019   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.074   0.767   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.258   6.693   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3   31   32                                             
CONECT    3    2    4   29                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   11   18   23                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17                                                            
CONECT   24   16   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29    3   30                                                       
CONECT   30   29                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    1   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₉

Average Mass

514.5710 Da

Monoisotopic Mass

514.22028 Da

IUPAC Name

3-[(2R,3R)-2-(furan-3-yl)-4-[(4R,6R,7R)-4-methoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-4,5,6,7-tetrahydro-1-benzofuran-2-yl]-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid

Traditional Name

3-[(2R,3R)-2-(furan-3-yl)-4-[(4R,6R,7R)-4-methoxy-6-(2-methoxy-2-oxoethyl)-5,5,7-trimethyl-6,7-dihydro-4H-1-benzofuran-2-yl]-3-methyl-6-oxo-2H-pyran-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CO[C@H]1C2=C(OC(=C2)C2=CC(=O)O[C@@H](C3=COC=C3)[C@]2(C)CCC(O)=O)[C@H](C)[C@@H](CC(=O)OC)C1(C)C

InChI Identifier

InChI=1S/C28H34O9/c1-15-18(12-22(31)33-5)27(2,3)26(34-6)17-11-20(36-24(15)17)19-13-23(32)37-25(16-8-10-35-14-16)28(19,4)9-7-21(29)30/h8,10-11,13-15,18,25-26H,7,9,12H2,1-6H3,(H,29,30)/t15-,18-,25+,26+,28-/m1/s1

InChI Key

YBVQEMYZAAIYCJ-NXZFLPEMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Xylocarpus granatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Tricarboxylic acid or derivatives
Dihydropyranone
Pyran
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	4.22	ALOGPS
logP	3.93	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.41 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.01 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00048917

Chemspider ID

27023687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24786828

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Xylogranatin K (NP0082128)

MOL for NP0082128 ((-)-Xylogranatin K)

3D MOL for NP0082128 ((-)-Xylogranatin K)

3D SDF for NP0082128 ((-)-Xylogranatin K)

3D-SDF for NP0082128 ((-)-Xylogranatin K)

PDB for NP0082128 ((-)-Xylogranatin K)

3D PDB for NP0082128 ((-)-Xylogranatin K)

SMILES for NP0082128 ((-)-Xylogranatin K)

INCHI for NP0082128 ((-)-Xylogranatin K)

Structure for NP0082128 ((-)-Xylogranatin K)

3D Structure for NP0082128 ((-)-Xylogranatin K)