NP-MRD: Showing NP-Card for 2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol (NP0294391)

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Record Information

Version

2.0

Created at

2022-09-10 02:54:47 UTC

Updated at

2022-09-10 02:54:47 UTC

NP-MRD ID

NP0294391

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol

Description

2,3-Bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol is found in Astronium urundeuva. 2,3-Bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161515272D          

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M  END

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  Mrv1533004161515272D          

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  2 20  1  0  0  0  0
 13 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 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
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(C(C(C2=CC=C(O)C=C2)C2=CC(O)=C(O)C=C12)C(=O)C1=CC=C(O)C=C1O)C(=O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O10/c31-14-3-1-13(2-4-14)25-19-11-23(36)24(37)12-20(19)30(40)27(29(39)18-8-6-16(33)10-22(18)35)26(25)28(38)17-7-5-15(32)9-21(17)34/h1-12,25-27,30-37,40H

> <INCHI_KEY>
AULXDIRHWKUVNR-UHFFFAOYSA-N

> <FORMULA>
C30H24O10

> <MOLECULAR_WEIGHT>
544.512

> <EXACT_MASS>
544.136946973

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
54.22657433151287

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
4.900429357

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.095607294689037

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.529930874469089

> <JCHEM_PKA_STRONGEST_BASIC>
-4.910866357168776

> <JCHEM_POLAR_SURFACE_AREA>
195.98

> <JCHEM_REFRACTIVITY>
143.5256

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.532  -3.241   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    5   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    2   13                                                  
CONECT   21    4   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29                                                            
CONECT   31    3   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₀

Average Mass

544.5120 Da

Monoisotopic Mass

544.13695 Da

IUPAC Name

2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol

Traditional Name

2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol

CAS Registry Number

Not Available

SMILES

OC1C(C(C(C2=CC=C(O)C=C2)C2=CC(O)=C(O)C=C12)C(=O)C1=CC=C(O)C=C1O)C(=O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C30H24O10/c31-14-3-1-13(2-4-14)25-19-11-23(36)24(37)12-20(19)30(40)27(29(39)18-8-6-16(33)10-22(18)35)26(25)28(38)17-7-5-15(32)9-21(17)34/h1-12,25-27,30-37,40H

InChI Key

AULXDIRHWKUVNR-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
Astronium urundeuva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
1-aryltetralin lignan
2-naphthalenecarboxylic acid or derivatives
Alkyl-phenylketone
Tetralin
Phenylketone
Benzoyl
Resorcinol
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.69	ALOGPS
logP	4.9	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	195.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	143.53 m³·mol⁻¹	ChemAxon
Polarizability	54.23 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	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

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 2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol (NP0294391)

MOL for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

3D MOL for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

3D SDF for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

3D-SDF for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

PDB for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

3D PDB for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

SMILES for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

INCHI for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

Structure for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)

3D Structure for NP0294391 (2,3-bis(2,4-dihydroxybenzoyl)-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphthalene-1,6,7-triol)