NP-MRD: Showing NP-Card for Santin (NP0050628)

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Record Information

Version

2.0

Created at

2022-04-27 21:59:34 UTC

Updated at

2022-04-27 21:59:34 UTC

NP-MRD ID

NP0050628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Santin

Description

Santin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, santin is considered to be a flavonoid lipid molecule. Santin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Santin is found in Achillea atrata, Achillea collina, Achillea latiloba, Achillea ligustica, Achillea multifida, Aeonium spp., Ageratina espinosara, Agnorhiza bolanderi, Ajania fruticulosa , Alluaudia sp., Alnus glutinosa , Alnus japonica , Anthemis tinctoria , Artemisia alba, Artemisia barrelieri, Balsamorhiza careyana, Betula ermanii, Brickellia eupatorioides, Brickellia scoparia, Cistus albanicus, Digitalis orientalis, Dodonaea viscosa, Drummondita hassellii, Eupatorium cannabinum , Galeana pratensis, Grindelia glutinosa, Grindelia squarrosa, Grindelia tarapacana, Juglans cinerea , Micromelum hirsutum, Pericome caudata, Perityle lemmonii, Perityle vaseyi, Picradeniopsis xylopoda, Psilostrophe cooperi, Salvia pedicellata, Stevia berlandieri, Stevia origanoides, Tanacetum densum, Tanacetum microphyllum, Tanacetum parthenium , Tanacetum vulgare and Valeriana laxiflora. A trimethoxyflavone that is flavone substituted by methoxy groups at positions 3, 6 and 4' and hydroxy groups at positions 5 and 7 respectively.

Structure

MOL SDF PDB SMILES InChI

  Mrv1533004161515552D          

 25 27  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -2.1434    1.2375    0.0000 O   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
   -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
  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(O)C=C2O1

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

> <INCHI_KEY>
DWZAJFZEYZIHPO-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.319

> <EXACT_MASS>
344.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.80829735715207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.5609149653333327

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.48440633551664

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.911619355187063

> <JCHEM_PKA_STRONGEST_BASIC>
-4.406427160642112

> <JCHEM_POLAR_SURFACE_AREA>
94.45

> <JCHEM_REFRACTIVITY>
90.57800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
santin

> <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  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.335   1.540   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       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18    4   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-3,6,4'-trimethoxy flavone	ChEBI
5,7-Dihydroxy-3,6,4'-trimethoxyflavone	MeSH

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3190 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

5,7-dihydroxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

santin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(O)C=C2O1

InChI Identifier

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

InChI Key

DWZAJFZEYZIHPO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea atrata	Plant	KNApSAcK
Achillea collina	LOTUS Database	35616633
Achillea latiloba	Plant	KNApSAcK
Achillea ligustica	LOTUS Database	35616633
Achillea multifida	Plant	KNApSAcK
Aeonium spp.	Plant	KNApSAcK
Ageratina espinosara	Plant	KNApSAcK
Agnorhiza bolanderi	LOTUS Database	35616633
Ajania fruticulosa	Plant	KNApSAcK
Alluaudia sp.	Plant	KNApSAcK
Alnus glutinosa	Plant	KNApSAcK
Alnus japonica	Plant	KNApSAcK
Anthemis tinctoria	Plant	KNApSAcK
Artemisia alba	LOTUS Database	35616633
Artemisia barrelieri	Plant	KNApSAcK
Balsamorhiza careyana	LOTUS Database	35616633
Betula ermanii	Plant	KNApSAcK
Brickellia eupatorioides	Plant	KNApSAcK
Brickellia scoparia	LOTUS Database	35616633
Cistus albanicus	Plant	KNApSAcK
Digitalis orientalis	Plant	KNApSAcK
Dodonaea viscosa	LOTUS Database	35616633
Drummondita hassellii	Plant	KNApSAcK
Eupatorium cannabinum	Plant	KNApSAcK
Galeana pratensis	LOTUS Database	35616633
Grindelia glutinosa	Plant	KNApSAcK
Grindelia squarrosa	Plant	KNApSAcK
Grindelia tarapacana	Plant	KNApSAcK
Juglans cinerea	Plant	KNApSAcK
Micromelum hirsutum	LOTUS Database	35616633
Pericome caudata	LOTUS Database	35616633
Perityle lemmonii	Plant	KNApSAcK
Perityle vaseyi	LOTUS Database	35616633
Picradeniopsis xylopoda	LOTUS Database	35616633
Psilostrophe cooperi	LOTUS Database	35616633
Salvia pedicellata	Plant	KNApSAcK
Stevia berlandieri	Plant	KNApSAcK
Stevia origanoides	LOTUS Database	35616633
Tanacetum densum	LOTUS Database	35616633
Tanacetum microphyllum	Plant	KNApSAcK
Tanacetum parthenium	Plant	KNApSAcK
Tanacetum vulgare	Plant	KNApSAcK
Valeriana laxiflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Pyranone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:9024 )
trimethoxyflavone (CHEBI:9024 )
flavonols (C10180 )
Flavones and Flavonols (C10180 )
Flavones and Flavonols (LMPK12112861 )

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	2.98	ALOGPS
logP	2.56	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.91	ChemAxon
pKa (Strongest Basic)	-4.4	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	90.58 m³·mol⁻¹	ChemAxon
Polarizability	34.81 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

Not Available

KNApSAcK ID

C00001096

Chemspider ID

Not Available

KEGG Compound ID

C10180

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Santin_(flavonol)

METLIN ID

Not Available

PubChem Compound

5281695

PDB ID

Not Available

ChEBI ID

9024

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Santin (NP0050628)

MOL for NP0050628 (Santin)

3D MOL for NP0050628 (Santin)

3D SDF for NP0050628 (Santin)

3D-SDF for NP0050628 (Santin)

PDB for NP0050628 (Santin)

3D PDB for NP0050628 (Santin)

SMILES for NP0050628 (Santin)

INCHI for NP0050628 (Santin)

Structure for NP0050628 (Santin)

3D Structure for NP0050628 (Santin)