NP-MRD: Showing NP-Card for {6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0194229)

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Record Information

Version

2.0

Created at

2022-09-04 11:51:29 UTC

Updated at

2022-09-04 11:51:29 UTC

NP-MRD ID

NP0194229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Description

{6-[Cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. {6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate is found in Phyllagathis rotundifolia. {6-[Cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241508502D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241508502D          

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   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  3  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 35 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(C#N)C2=CC=CC=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H25NO14/c29-10-19(12-4-2-1-3-5-12)41-28-24(37)25(43-27(39)14-8-17(32)22(35)18(33)9-14)23(36)20(42-28)11-40-26(38)13-6-15(30)21(34)16(31)7-13/h1-9,19-20,23-25,28,30-37H,11H2

> <INCHI_KEY>
YBXFOTINCCIAPR-UHFFFAOYSA-N

> <FORMULA>
C28H25NO14

> <MOLECULAR_WEIGHT>
599.501

> <EXACT_MASS>
599.127504489

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.59030837697666

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.352156633

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.405929170226894

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.804459361417338

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6641634241222407

> <JCHEM_POLAR_SURFACE_AREA>
256.69

> <JCHEM_REFRACTIVITY>
141.62580000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -1.334  -8.470   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17    3   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   18   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    2   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   35                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Value	Source
{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₈H₂₅NO₁₄

Average Mass

599.5010 Da

Monoisotopic Mass

599.12750 Da

IUPAC Name

{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

Traditional Name

{6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(C#N)C2=CC=CC=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C28H25NO14/c29-10-19(12-4-2-1-3-5-12)41-28-24(37)25(43-27(39)14-8-17(32)22(35)18(33)9-14)23(36)20(42-28)11-40-26(38)13-6-15(30)21(34)16(31)7-13/h1-9,19-20,23-25,28,30-37H,11H2

InChI Key

YBXFOTINCCIAPR-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
Phyllagathis rotundifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aralkylamine
Piperidine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic oxygen 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	2.53	ALOGPS
logP	2.35	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	256.69 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.63 m³·mol⁻¹	ChemAxon
Polarizability	56.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate (NP0194229)

MOL for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

PDB for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

Structure for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0194229 ({6-[cyano(phenyl)methoxy]-3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)oxan-2-yl}methyl 3,4,5-trihydroxybenzoate)