NP-MRD: Showing NP-Card for 2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0228640)

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Record Information

Version

2.0

Created at

2022-09-06 08:22:24 UTC

Updated at

2022-09-06 08:22:24 UTC

NP-MRD ID

NP0228640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{4-[3A,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as imidazodiazepines. These are organic compounds containing an imidazole ring fused to a diazepine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms. 2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Valeriana prionophylla. 2-{4-[3A,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-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


  Mrv1533004201502582D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201502582D          

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    4.3684    5.1202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1556    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9626    2.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007    1.3686    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  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  1  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 20 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1OCC2(O)C(OCC12O)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O13/c1-34-16-7-12(3-5-14(16)28)22-25(32)10-37-23(26(25,33)11-36-22)13-4-6-15(17(8-13)35-2)38-24-21(31)20(30)19(29)18(9-27)39-24/h3-8,18-24,27-33H,9-11H2,1-2H3

> <INCHI_KEY>
IBQVOWQTGYYRJP-UHFFFAOYSA-N

> <FORMULA>
C26H32O13

> <MOLECULAR_WEIGHT>
552.529

> <EXACT_MASS>
552.18429109

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.903091477385075

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.10

> <JCHEM_LOGP>
-1.3006693100000002

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.427359355042862

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.894660475425948

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
196.98999999999998

> <JCHEM_REFRACTIVITY>
129.4204

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -2.071  -6.756   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.595  -5.291   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.088  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.924  -4.331   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.449  -5.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.942  -6.116   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.466  -7.580   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.834   1.834   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.204  -0.476   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.834  -2.786   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.775   2.235   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.744   3.379   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.220   4.844   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.727   5.164   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.203   6.629   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.709   6.949   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.739   5.804   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.246   6.124   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.276   4.980   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.800   3.515   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.722   7.589   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.228   7.909   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.691   8.734   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.167  10.198   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.185   8.413   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.154   9.558   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.757   4.019   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.264   4.340   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.294   3.195   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.281   2.555   0.000  0.00  0.00           C+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   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   10   13   19                                             
CONECT   19   18                                                            
CONECT   20   15   21   39                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34                                                            
CONECT   36   23   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   20                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₃

Average Mass

552.5290 Da

Monoisotopic Mass

552.18429 Da

IUPAC Name

2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1OCC2(O)C(OCC12O)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(OC)=C1

InChI Identifier

InChI=1S/C26H32O13/c1-34-16-7-12(3-5-14(16)28)22-25(32)10-37-23(26(25,33)11-36-22)13-4-6-15(17(8-13)35-2)38-24-21(31)20(30)19(29)18(9-27)39-24/h3-8,18-24,27-33H,9-11H2,1-2H3

InChI Key

IBQVOWQTGYYRJP-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
Valeriana prionophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazodiazepines. These are organic compounds containing an imidazole ring fused to a diazepine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazodiazepines

Sub Class

Not Available

Direct Parent

Imidazodiazepines

Alternative Parents

Substituents

Imidazo-meta-diazepine
Imidazodiazepine
Meta-diazepine
N-substituted imidazole
Azole
Heteroaromatic compound
Imidazole
Oxolane
Chlorohydrin
Halohydrin
Secondary alcohol
Amidine
Formamidine
Carboxylic acid amidine
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Alkyl halide
Hydrocarbon derivative
Organic oxygen compound
Alkyl chloride
Alcohol
Amine
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Primary 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	0.1	ALOGPS
logP	-1.3	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.42 m³·mol⁻¹	ChemAxon
Polarizability	52.9 Å³	ChemAxon
Number of Rings	5	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

72822690

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-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0228640)

MOL for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0228640 (2-{4-[3a,6a-dihydroxy-4-(4-hydroxy-3-methoxyphenyl)-tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol)