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Showing NP-Card for Suberosin (NP0046580)

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Record Information
Version2.0
Created at2022-03-17 20:08:14 UTC
Updated at2022-03-17 20:08:14 UTC
NP-MRD IDNP0046580
Secondary Accession NumbersNone
Natural Product Identification
Common NameSuberosin
Description Suberosin is found in Angelica dahurica, Citropsis articulata, Citrus depressa, Citrus japonica, Citrus maxima, Citrus paradisi, Citrus sinensis, Hesperethusa crenulata, Luvunga sarmentosa (Bl.) Kurz., Plantitenia absinthifolia, Platytaenia dasycarpa, Plumbago zeylanica , Prangos bucharica, Prangos lipskyi, Prangos lophoptera, Prangos pabularia Lindl. , Semenovia dasycarpa, Toddalia asiatica and Zanthoxylum ovalifolium. Suberosin was first documented in 2007 (PMID: 17179947).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046580 (Suberosin)


  Mrv0541 02241221492D          

 18 19  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   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
    5.0013   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    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
    4.2868   -1.6500    0.0000 C   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
    3.5724   -2.8875    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
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3D MOL for NP0046580 (Suberosin)

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3D SDF for NP0046580 (Suberosin)

  Mrv0541 02241221492D          

 18 19  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 O   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
    5.0013   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    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
    4.2868   -1.6500    0.0000 C   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
    3.5724   -2.8875    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   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC=C(C)C)C=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4,6-9H,5H2,1-3H3

> <INCHI_KEY>
RSZDAYHEZSRVHS-UHFFFAOYSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.505267433752287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.3542553490000007

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.840926847825866

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
72.25460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
suberosin

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046580 (Suberosin)
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PDB for NP0046580 (Suberosin)
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       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    2                                                       
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

Download
3D PDB for NP0046580 (Suberosin)
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SMILES for NP0046580 (Suberosin)
COC1=C(CC=C(C)C)C=C2C=CC(=O)OC2=C1
Download
INCHI for NP0046580 (Suberosin)
InChI=1S/C15H16O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4,6-9H,5H2,1-3H3
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View in JSmol
Synonyms
ValueSource
7-Methoxy-6-(3-methyl-2-buten-1-yl)-2H-chromen-2-oneChEBI
7-Methoxy-6-prenylcoumarinChEBI
Chemical FormulaC15H16O3
Average Mass244.2857 Da
Monoisotopic Mass244.10994 Da
IUPAC Name7-methoxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
Traditional Namesuberosin
CAS Registry Number581-31-7
SMILES
COC1=C(CC=C(C)C)C=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C15H16O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4,6-9H,5H2,1-3H3
InChI KeyRSZDAYHEZSRVHS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica dahuricaLOTUS Database
Citropsis articulataLOTUS Database
Citrus depressaLOTUS Database
Citrus japonicaLOTUS Database
Citrus limonFooDB
Citrus maximaLOTUS Database
Citrus paradisiLOTUS Database
Citrus reticulataFooDB
Citrus sinensisLOTUS Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Hesperethusa crenulataPlant
Luvunga sarmentosa (Bl.) Kurz.Plant
Plantitenia absinthifolia-
Platytaenia dasycarpa-
Plumbago zeylanicaPlant
Prangos bucharicaPlant
Prangos lipskyiLOTUS Database
Prangos lophopteraLOTUS Database
Prangos pabulariaPlant
Semenovia dasycarpaLOTUS Database
Toddalia asiaticaLOTUS Database
Zanthoxylum ovalifoliumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCoumarins and derivatives  
Sub ClassNot Available
Direct ParentCoumarins and derivatives  
Alternative Parents
Substituents
  • Coumarin
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Alkyl aryl ether
    • 

  • Pyranone
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP3.5ALOGPS
logP3.35ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.25 m³·mol⁻¹ChemAxon
Polarizability26.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005065  
KNApSAcK IDC00037864  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68486  
PDB IDNot Available
ChEBI ID69041  
Good Scents IDNot Available
References
General References
  1. Lacroix D, Prado S, Kamoga D, Kasenene J, Bodo B: Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark. J Nat Prod. 2011 Oct 28;74(10):2286-9. doi: 10.1021/np2004825. Epub 2011 Oct 10. [PubMed:21985060  ] 
  2. Chen YC, Tsai WJ, Wu MH, Lin LC, Kuo YC: Suberosin inhibits proliferation of human peripheral blood mononuclear cells through the modulation of the transcription factors NF-AT and NF-kappaB. Br J Pharmacol. 2007 Feb;150(3):298-312. doi: 10.1038/sj.bjp.0706987. Epub 2006 Dec 18. [PubMed:17179947  ] 
  3. Golfakhrabadi F, Abdollahi M, Ardakani MR, Saeidnia S, Akbarzadeh T, Ahmadabadi AN, Ebrahimi A, Yousefbeyk F, Hassanzadeh A, Khanavi M: Anticoagulant activity of isolated coumarins (suberosin and suberenol) and toxicity evaluation of Ferulago carduchorum in rats. Pharm Biol. 2014 Oct;52(10):1335-40. doi: 10.3109/13880209.2014.892140. Epub 2014 Jul 14. [PubMed:25017518  ]