NP-MRD: Showing NP-Card for Nevadensin (NP0046030)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:47:15 UTC

Updated at

2022-03-17 19:47:15 UTC

NP-MRD ID

NP0046030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nevadensin

Description

Nevadensin is found in Achillea ligustica, Aconitum sachalinense, Ambrosia trifida, Artemisia rupestris, Baccharis grisebachii, Baccharis salicifolia, Biebersteinia orphanidis, Calanticaria bicolor, Cheilanthes argentea, Condea albida, Acanthopanax trifoliatus , Gardenia lucida, Gardenia resinifera, Helianthus annuus, Helianthus argophyllus, Helianthus longifolius, Helianthus microcephalus, Helianthus spp., Hyptis albida, Iva nevadensis, Lysionotus denticulosus, Lysionotus pauciflora, Madia capitata, Madia sativa, Mentha piperita, Ocimum canum , Ocimum americanum L.var.pilosum (Willd.) Paton , Ocimum gratissimum, Ocimum minimum L. , Ocimum x citriodorum Vis., Ononis natrix , Rosa centifolia , Simsia cronquistii, Tamarix dioica , Tithonia calva, Tithonia longiradiata, Tithonia pedunculata and Viguiera rosei. Nevadensin was first documented in 2011 (PMID: 21775221).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215572D          

 25 27  0  0  0  0            999 V2000
    1.0718   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7869   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3568   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9291    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9291   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 24  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  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
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3

> <INCHI_KEY>
KRFBMPVGAYGGJE-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.725886669036726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.94

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.364155850586517

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.629087342656156

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2404856001107385

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nevadensin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.001  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.001  -2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.336  -3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.668  -2.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.668  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.336  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.666   3.465   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.666   1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.666   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.666  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.666  -1.155   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.333   3.465   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.333   1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.001   1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.333  -1.155   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.333  -2.695   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.668  -3.465   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.002  -1.155   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.668  -0.385   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.668   1.155   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.002   1.925   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -7.334   1.155   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.002  -3.465   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.334  -2.695   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8                                                            
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   15                                                       
CONECT   12   13                                                            
CONECT   13   12   14   21                                                  
CONECT   14    8   13   15                                                  
CONECT   15   11   14   16                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   16   19   21                                                  
CONECT   21   13   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    4   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
5,7-Hydroxy-4',6,8-trimethoxyflavone	ChEBI
Pedunculin	ChEBI

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3154 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

5,7-dihydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

nevadensin

CAS Registry Number

10176-66-6

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(O)C(OC)=C2O

InChI Identifier

InChI=1S/C18H16O7/c1-22-10-6-4-9(5-7-10)12-8-11(19)13-14(20)17(23-2)15(21)18(24-3)16(13)25-12/h4-8,20-21H,1-3H3

InChI Key

KRFBMPVGAYGGJE-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Achillea ligustica	LOTUS Database	35616633
Aconitum sachalinense	LOTUS Database	35616633
Ambrosia trifida	Plant	KNApSAcK
Artemisia rupestris	LOTUS Database	35616633
Baccharis grisebachii	Plant	KNApSAcK
Baccharis salicifolia	LOTUS Database	35616633
Biebersteinia orphanidis	Plant	KNApSAcK
Calanticaria bicolor	LOTUS Database	35616633
Cheilanthes argentea	Plant	KNApSAcK
Condea albida	LOTUS Database	35616633
Eleutherococcus trifoliatus	Plant	KNApSAcK
Gardenia lucida	Plant	KNApSAcK
Gardenia resinifera	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Helianthus argophyllus	LOTUS Database	35616633
Helianthus longifolius	LOTUS Database	35616633
Helianthus microcephalus	LOTUS Database	35616633
Helianthus spp.	Plant	KNApSAcK
Hyptis albida	Plant	KNApSAcK
Iva nevadensis	Plant	KNApSAcK
Lysionotus denticulosus	LOTUS Database	35616633
Lysionotus pauciflorus	Plant	KNApSAcK
Madia capitata	Plant	KNApSAcK
Madia sativa	LOTUS Database	35616633
Mentha piperita	LOTUS Database	35616633
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocimum americanum	Plant	KNApSAcK
Ocimum americanum L.var.pilosum (Willd.) Paton	Plant	KNApSAcK
Ocimum basilicum	FooDB	KNAPSACK
Ocimum gratissimum	LOTUS Database	35616633
Ocimum minimum L.	Plant	KNApSAcK
Ocimum x citriodorum Vis.	Plant	KNApSAcK
Ononis natrix	Plant	KNApSAcK
Rosa centifolia	Plant	KNApSAcK
Simsia cronquistii	Plant	KNApSAcK
Tamarix dioica	Plant	KNApSAcK
Tithonia calva	Plant	KNApSAcK
Tithonia longiradiata	LOTUS Database	35616633
Tithonia pedunculata	LOTUS Database	35616633
Viguiera rosei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
7-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Phenol ether
Anisole
Methoxybenzene
Phenoxy compound
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:7545 )
trimethoxyflavone (CHEBI:7545 )
flavones (C10111 )
Flavones and Flavonols (C10111 )
Flavones and Flavonols (LMPK12111442 )

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	2.94	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	34.73 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002751

KNApSAcK ID

C00001075

Chemspider ID

Not Available

KEGG Compound ID

C10111

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160921

PDB ID

Not Available

ChEBI ID

7545

Good Scents ID

Not Available

References

General References

Tong X, Xiao X, Li G: On-line coupling of dynamic microwave-assisted extraction with high-speed counter-current chromatography for continuous isolation of nevadensin from Lyeicnotus pauciflorus Maxim. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Aug 15;879(24):2397-402. doi: 10.1016/j.jchromb.2011.06.035. Epub 2011 Jul 2. [PubMed:21775221 ]
Berim A, Gang DR: Characterization of two candidate flavone 8-O-methyltransferases suggests the existence of two potential routes to nevadensin in sweet basil. Phytochemistry. 2013 Aug;92:33-41. doi: 10.1016/j.phytochem.2013.05.001. Epub 2013 Jun 6. [PubMed:23747095 ]
Alhusainy W, Paini A, van den Berg JH, Punt A, Scholz G, Schilter B, van Bladeren PJ, Taylor S, Adams TB, Rietjens IM: In vivo validation and physiologically based biokinetic modeling of the inhibition of SULT-mediated estragole DNA adduct formation in the liver of male Sprague-Dawley rats by the basil flavonoid nevadensin. Mol Nutr Food Res. 2013 Nov;57(11):1969-78. doi: 10.1002/mnfr.201300144. Epub 2013 Jul 26. [PubMed:23894034 ]
Alhusainy W, Williams GM, Jeffrey AM, Iatropoulos MJ, Taylor S, Adams TB, Rietjens IM: The natural basil flavonoid nevadensin protects against a methyleugenol-induced marker of hepatocarcinogenicity in male F344 rat. Food Chem Toxicol. 2014 Dec;74:28-34. doi: 10.1016/j.fct.2014.08.016. Epub 2014 Sep 10. [PubMed:25218219 ]

Showing NP-Card for Nevadensin (NP0046030)

MOL for NP0046030 (Nevadensin)

3D MOL for NP0046030 (Nevadensin)

3D SDF for NP0046030 (Nevadensin)

3D-SDF for NP0046030 (Nevadensin)

PDB for NP0046030 (Nevadensin)

3D PDB for NP0046030 (Nevadensin)

SMILES for NP0046030 (Nevadensin)

INCHI for NP0046030 (Nevadensin)

Structure for NP0046030 (Nevadensin)

3D Structure for NP0046030 (Nevadensin)