NP-MRD: Showing NP-Card for nortangeretin (NP0257040)

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Record Information

Version

2.0

Created at

2022-09-07 22:03:07 UTC

Updated at

2022-09-07 22:03:07 UTC

NP-MRD ID

NP0257040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nortangeretin

Description

5,6,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, also known as nortangeretin or 5,6,7,8,4'-pentahydroxyflavone, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). 5,6,7,8-Tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). nortangeretin is found in Rhizophagus intraradices and Marrubium cylleneum. A pentahydroxyflavone that is flavone substituted by hydroxy groups at positions 5, 6, 7, 8, and 4' respectively.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    1.6524   -3.1679   -0.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -2.0075   -0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227   -1.8410   -0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7283   -0.5716   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -0.3130   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955    1.0000   -0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9395    1.2884   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668    0.2679   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2270    0.5403   -0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4716   -1.0508   -0.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010   -1.3181   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1130    0.4544    0.0117 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128    0.3208    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995    1.4431    0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6309    2.7082    0.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5696    1.3117    0.1293 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499    2.4762    0.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2018    0.0896    0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5817   -0.0219    0.1640 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3878   -1.0534    0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -2.2408    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0259   -0.9361    0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -2.7286   -0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9022    1.8378   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2805    2.3322   -0.0829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5406    1.5055   -0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921   -1.8647   -0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7972   -2.3598   -0.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6385    2.8646    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9390    3.3901    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1433    0.8165    0.1960 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -3.1719    0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 11  1  0
 11 10  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 22  1  0
 22 20  2  0
 20 21  1  0
 20 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 14  1  0
 14 15  1  0
 14 13  2  0
 13 12  1  0
 10  8  1  0
 12  4  1  0
 13 22  1  0
  9 26  1  0
  7 25  1  0
  6 24  1  0
 11 28  1  0
 10 27  1  0
  3 23  1  0
 21 32  1  0
 19 31  1  0
 17 30  1  0
 15 29  1  0
M  END


  Mrv1652308211920252D          

 22 24  0  0  0  0            999 V2000
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   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
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16  7  1  0  0  0  0
 17  8  2  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  9  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(O)=C(O)C(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)9-5-8(17)10-11(18)12(19)13(20)14(21)15(10)22-9/h1-5,16,18-21H

> <INCHI_KEY>
SPZXXUUDYMHBSG-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.238

> <EXACT_MASS>
302.042652662

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.563762542311494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.099558490333333

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.48694658682337

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.334106635223918

> <JCHEM_PKA_STRONGEST_BASIC>
-5.118329918789597

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
76.87570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nortangeretin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   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      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    3    6                                                       
CONECT    2    4    6                                                       
CONECT    3    1    7                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    1    2    9                                                  
CONECT    7    3    4   16                                                  
CONECT    8    5   10   17                                                  
CONECT    9    5    6   22                                                  
CONECT   10    8   11   15                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   21                                                  
CONECT   15   10   14   22                                                  
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Nortangeretin	ChEBI
5,6,7,8,4'-Pentahydroxyflavone	Kegg

Chemical Formula

C₁₅H₁₀O₇

Average Mass

302.2380 Da

Monoisotopic Mass

302.04265 Da

IUPAC Name

5,6,7,8-tetrahydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

nortangeretin

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(O)=C(O)C(O)=C2O1

InChI Identifier

InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)9-5-8(17)10-11(18)12(19)13(20)14(21)15(10)22-9/h1-5,16,18-21H

InChI Key

SPZXXUUDYMHBSG-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
Glomus intraradices	LOTUS Database	35616633
Marrubium cylleneum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
6-hydroxyflavonoid
7-hydroxyflavonoid
8-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pentahydroxyflavone (CHEBI:79553 )

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	2.43	ALOGPS
logP	2.1	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.33	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0130175

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB088993

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15031

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

96506

PDB ID

Not Available

ChEBI ID

79553

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for nortangeretin (NP0257040)

MOL for NP0257040 (nortangeretin)

3D MOL for NP0257040 (nortangeretin)

3D SDF for NP0257040 (nortangeretin)

3D-SDF for NP0257040 (nortangeretin)

PDB for NP0257040 (nortangeretin)

3D PDB for NP0257040 (nortangeretin)

SMILES for NP0257040 (nortangeretin)

INCHI for NP0257040 (nortangeretin)

Structure for NP0257040 (nortangeretin)

3D Structure for NP0257040 (nortangeretin)