NP-MRD: Showing NP-Card for 2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0195333)

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Record Information

Version

2.0

Created at

2022-09-04 13:10:19 UTC

Updated at

2022-09-04 13:10:20 UTC

NP-MRD ID

NP0195333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-(4-{[3,4-Dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups. 2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Saussurea costus. 2-(4-{[3,4-Dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500262D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241500262D          

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    0.8995   -5.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7245   -4.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419   -3.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369   -2.8135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469   -2.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2719   -2.8049    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 16 35  1  0  0  0  0
 13 36  1  0  0  0  0
 10 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1OCC(O)(CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(OC)=C2)C1(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O13/c1-35-17-8-14(4-5-15(17)29)23-26(34,11-28)25(33,12-37-23)9-13-3-6-16(18(7-13)36-2)38-24-22(32)21(31)20(30)19(10-27)39-24/h3-8,19-24,27-34H,9-12H2,1-2H3

> <INCHI_KEY>
LTWSTSXCASUIMQ-UHFFFAOYSA-N

> <FORMULA>
C26H34O13

> <MOLECULAR_WEIGHT>
554.545

> <EXACT_MASS>
554.199941155

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.98407741391533

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-1.5433767353333327

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.681805823181541

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.900654512995956

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
207.98999999999998

> <JCHEM_REFRACTIVITY>
131.72300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <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  C   UNK     0      15.474  -8.132   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.009  -8.608   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.865  -7.577   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.400  -8.053   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.255  -7.023   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.576  -5.516   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.040  -5.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.185  -6.071   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.649  -5.595   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.791  -7.499   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.315  -8.963   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.775  -8.963   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.299  -7.499   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.892  -8.125   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.529  -6.165   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.989  -6.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.219  -4.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.679  -4.831   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.909  -6.165   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.631  -6.165   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.401  -4.831   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.941  -4.831   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.711  -3.498   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.251  -3.498   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.021  -4.831   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.941  -2.164   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.711  -0.830   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.401  -2.164   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.631  -0.830   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.631  -3.498   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.909  -3.498   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.679  -7.499   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.909  -8.832   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.679 -10.166   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.219  -7.499   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.545  -6.594   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.789  -5.252   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.301  -5.252   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.841  -5.236   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   36                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   36                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   19   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   16                                                       
CONECT   36   13   10   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₃

Average Mass

554.5450 Da

Monoisotopic Mass

554.19994 Da

IUPAC Name

2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1OCC(O)(CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(OC)=C2)C1(O)CO

InChI Identifier

InChI=1S/C26H34O13/c1-35-17-8-14(4-5-15(17)29)23-26(34,11-28)25(33,12-37-23)9-13-3-6-16(18(7-13)36-2)38-24-22(32)21(31)20(30)19(10-27)39-24/h3-8,19-24,27-34H,9-12H2,1-2H3

InChI Key

LTWSTSXCASUIMQ-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
Saussurea costus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexacarboxylic acids and derivatives. These are carboxylic acids containing exactly six carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Hexacarboxylic acids and derivatives

Direct Parent

Hexacarboxylic acids and derivatives

Alternative Parents

Substituents

Hexacarboxylic acid or derivatives
Agarofuran
Sesquiterpenoid
Benzoate ester
Furoic acid ester
Benzoic acid or derivatives
Furoic acid or derivatives
Benzoyl
Oxepane
Fatty acid ester
Benzenoid
Fatty acyl
Cyclitol or derivatives
Monocyclic benzene moiety
Tetrahydrofuran
Tertiary alcohol
Heteroaromatic compound
Furan
Cyclic alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	-0.29	ALOGPS
logP	-1.5	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.72 m³·mol⁻¹	ChemAxon
Polarizability	53.98 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

73087830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0195333)

MOL for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0195333 (2-(4-{[3,4-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)