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Showing NP-Card for Cirsilineol (NP0048851)

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Record Information
Version2.0
Created at2022-03-17 21:03:11 UTC
Updated at2022-03-17 21:03:11 UTC
NP-MRD IDNP0048851
Secondary Accession NumbersNone
Natural Product Identification
Common NameCirsilineol
Description Cirsilineol is found in Achillea millefolium, Ajania fastigiata, Aloysia citrodora, Anisomeles indica, Arnica longifolia, Artemisia annua, Artemisia argyi, Artemisia assoana, Artemisia capillaris, Artemisia carvifolia, Artemisia halodendron, Artemisia herba-alba , Artemisia monosperma, Artemisia oliveriana, Artemisia rubripes, Artemisia rutifolia, Artemisia vestita , Artemisia xanthochroa, Baccharis sagittalis, Blumea lacera , Centaurea brugueriana, Centaurea diffusa, Centaurea macrocephala, Centaurea napifolia, Centaurea pullata, Centaurea sulphurea, Cirsium lineare, Citrus reticulata, Eupatorium lindleyanum, Heterotheca grandiflora, Lantana montevidensis, Lippia citriodora , Lycopus europaeus , Mentha spicata, Ocimum basilicum, Ocimum kilimandscharicum, Ocimum kilimandscharicum L. , Ocimum spp., Ocimum tenuiflorum, Ocimum tenuiflorum L. , Ocimum x citriodorum Vis., Oncosiphon grandiflorum, Origanum calcaratum, Origanum dictamnus , Origanum floribundum, Origanum majorana , Origanum microphyllum, Origanum onites , Origanum syriacum , Origanum vulgare subsp. Glandulosum , Origanum vulgare subsp. Hirtum , Palafoxia sphacelata, Pentzia calva, Salvia lavandulaefolia, Salvia tomentosa, Sideritis leucantha, Sideritis mugronensis, Sideritis spp., Tecomella undulata , Teucrium alyssifolium, Teucrium fruticans, Teucrium marum , Teucrium orientale, Thymus herba-barona , Thymus saturejoides, Tillandsia utriculata and Ziziphora hispanica . Cirsilineol was first documented in 2014 (PMID: 24689280).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048851 (Cirsilineol)


  Mrv0541 02241219012D          

 25 27  0  0  0  0            999 V2000
   -1.4280    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -2.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708    1.2370    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
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 20  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  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
 23 24  1  0  0  0  0
M  END
Download

3D MOL for NP0048851 (Cirsilineol)

Download
3D SDF for NP0048851 (Cirsilineol)

  Mrv0541 02241219012D          

 25 27  0  0  0  0            999 V2000
   -1.4280    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5708   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -2.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5708    1.2370    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
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8 25  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 20  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  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
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC

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

> <INCHI_KEY>
VKOSQMWSWLZQPA-UHFFFAOYSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.93525892149046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.471368644422

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.866247934618931

> <JCHEM_PKA_STRONGEST_BASIC>
-4.368720010472823

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cirsilineol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048851 (Cirsilineol)
Download
PDB for NP0048851 (Cirsilineol)
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  O   UNK     0      -2.666   4.618   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.666   3.079   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.332   2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.332   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.666   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.000   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.000   2.309   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.331   3.079   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   4.618   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   3.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.331   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.331  -1.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.666  -2.309   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.334  -1.539   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.334   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.000   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.666   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.666  -1.539   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.000  -2.309   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.000  -3.848   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.334  -4.618   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.666   2.309   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7   25                                                       
CONECT    9   10                                                            
CONECT   10    3    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13    4   12                                                       
CONECT   14    6   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   12   19   21                                                  
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Download
3D PDB for NP0048851 (Cirsilineol)
Download
SMILES for NP0048851 (Cirsilineol)
COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC
Download
INCHI for NP0048851 (Cirsilineol)
InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
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View in JSmol
Synonyms
ValueSource
AnisomelinMetaCyc
5,4'-Dihydroxy-6,7,3'-trimethoxyflavoneMetaCyc
EupatrinMetaCyc
FastigeninMetaCyc
5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-oneMetaCyc
4',5-Dihydroxy-3',6,7-trimethoxyflavoneMeSH
4',5-Dihydroxy-3',6,7-trimethoxy-flavoneMeSH
Chemical FormulaC18H16O7
Average Mass344.3154 Da
Monoisotopic Mass344.08960 Da
IUPAC Name5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one
Traditional Namecirsilineol
CAS Registry Number41365-32-6
SMILES
COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC
InChI Identifier
InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
InChI KeyVKOSQMWSWLZQPA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Ajania fastigiataLOTUS Database
Aloysia citrodoraLOTUS Database
Aloysia triphyllaFooDB
Anisomeles Anisomeles indicaLOTUS Database
Arnica longifoliaLOTUS Database
Artemisia annuaLOTUS Database
Artemisia argyiLOTUS Database
Artemisia assoanaLOTUS Database
Artemisia capillarisLOTUS Database
Artemisia carvifoliaLOTUS Database
Artemisia dracunculusFooDB
Artemisia halodendronLOTUS Database
Artemisia herba-albaPlant
Artemisia monospermaLOTUS Database
Artemisia oliverianaPlant
Artemisia rubripesLOTUS Database
Artemisia rutifoliaLOTUS Database
Artemisia vestitaPlant
Artemisia xanthochroaLOTUS Database
Baccharis sagittalisLOTUS Database
Blumea laceraPlant
Centaurea bruguerianaLOTUS Database
Centaurea diffusaLOTUS Database
Centaurea macrocephalaPlant
Centaurea napifoliaLOTUS Database
Centaurea pullataLOTUS Database
Centaurea sulphureaLOTUS Database
Cirsium linearePlant
Citrus reticulataLOTUS Database
Eupatorium lindleyanumLOTUS Database
Heterotheca grandifloraPlant
Hyssopus officinalis L.FooDB
Lantana montevidensisLOTUS Database
Lippia citriodoraPlant
Lycopus europaeusPlant
Mentha spicataLOTUS Database
Ocimum basilicumLOTUS Database
Ocimum kilimandscharicumLOTUS Database
Ocimum kilimandscharicum L.Plant
Ocimum spp.Plant
Ocimum tenuiflorumLOTUS Database
Ocimum tenuiflorum L.Plant
Ocimum x citriodorum Vis.Plant
Oncosiphon grandiflorumPlant
Origanum calcaratumPlant
Origanum dictamnusPlant
Origanum floribundumPlant
Origanum majoranaPlant
Origanum microphyllumPlant
Origanum onitesPlant
Origanum syriacumPlant
Origanum vulgare subsp. GlandulosumPlant
Origanum vulgare subsp. HirtumPlant
Palafoxia sphacelataPlant
Pentzia calvaLOTUS Database
Salvia lavandulaefoliaPlant
Salvia officinalisFooDB
Salvia tomentosaPlant
Sideritis leucanthaLOTUS Database
Sideritis mugronensisPlant
Sideritis spp.Plant
Tecomella undulataPlant
Teucrium alyssifoliumPlant
Teucrium fruticansLOTUS Database
Teucrium marumPlant
Teucrium orientaleLOTUS Database
Thymus herba-baronaPlant
Thymus satureioidesLOTUS Database
Thymus vulgarisFooDB
Tillandsia utriculataPlant
Ziziphora hispanicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassO-methylated flavonoids  
Direct Parent7-O-methylated flavonoids  
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
    • 

  • 6-methoxyflavonoid-skeleton
    • 

  • 7-methoxyflavonoid-skeleton
    • 

  • 4'-hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • Flavone
    • 

  • Hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • Methoxyphenol
    • 

  • 1-benzopyran
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Pyran
    • 

  • Monocyclic benzene moiety
    • 

  • Vinylogous acid
    • 

  • Heteroaromatic compound
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.93ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability34.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016702  
KNApSAcK IDC00013595  
Chemspider IDNot Available
KEGG Compound IDC10032  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCirsilineol  
METLIN IDNot Available
PubChem Compound162464  
PDB IDNot Available
ChEBI ID3718  
Good Scents IDNot Available
References
General References
  1. Uehara A, Kitajima J, Kokubugata G, Iwashina T: Further characterization of foliar flavonoids in Crossostephium chinense and their geographic variation. Nat Prod Commun. 2014 Feb;9(2):163-4. [PubMed:24689280  ] 
  2. Hajdu Z, Hohmann J, Forgo P, Mathe I, Molnar J, Zupko I: Antiproliferative activity of Artemisia asiatica extract and its constituents on human tumor cell lines. Planta Med. 2014 Dec;80(18):1692-7. doi: 10.1055/s-0034-1383146. Epub 2014 Oct 8. [PubMed:25295671  ]