NP-MRD: Showing NP-Card for Demethylsuberosin (NP0137388)

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Record Information

Version

2.0

Created at

2022-05-30 16:51:02 UTC

Updated at

2022-05-30 16:51:02 UTC

NP-MRD ID

NP0137388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylsuberosin

Description

Demethylsuberosin is found in Aegle marmelos, Angelica genuflexa, Angelica gigas, Angelica keiskei, Boronia algida, Boronia lanceolata, Brosimum rubescens, Citropsis articulata, Citrus aurantium, Citrus limonia, Citrus medica, Citrus sinensis, Citrus sulcata, Feroniella lucida, Glehnia littoralis, Limonia acidissima and Prangos uloptera. Demethylsuberosin was first documented in 2008 (PMID: 17997069).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    3.8173    0.5455   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2010    0.3056    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0599   -0.2696    1.3918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9413    0.5768    0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9562    1.1360   -0.4161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3092    0.3608   -0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3848    0.8864    0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5880    0.2249    0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784    0.7284    0.9313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8417    0.0046    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9289   -1.1816    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0249   -1.8503    0.1810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8691   -1.6148   -0.4268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125   -0.9672   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6345   -1.4838   -1.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4191   -0.8151   -1.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6598   -1.3688   -1.8580 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8419   -0.3889   -1.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633    1.4050   -1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8986    0.8192   -0.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -1.3308    1.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9882    0.3003    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -0.3031    2.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875    0.3599    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3715    1.1401   -1.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    2.1823   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160    1.8274    0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599    1.6647    1.4597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7155    0.3664    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7338   -2.4099   -1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138   -0.8503   -1.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8 14  2  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16  6  1  0
  9  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  7 27  1  0
 10 29  1  0
  9 28  1  0
 15 30  1  0
 17 31  1  0
M  END


  Mrv1533004251511352D          

 17 18  0  0  0  0            999 V2000
   -2.1434   -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
   -0.7145   -0.4125    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
    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
    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
    2.8579   -1.6500    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
    0.7145   -1.2375    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
   -1.4289    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  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(OC(=O)C=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-9(2)3-4-10-7-11-5-6-14(16)17-13(11)8-12(10)15/h3,5-8,15H,4H2,1-2H3

> <INCHI_KEY>
FIDUIAPDSKSUGO-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.263

> <EXACT_MASS>
230.094294311

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.973473506972404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.2083612930000003

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.639983967730846

> <JCHEM_PKA_STRONGEST_BASIC>
-6.940648093896989

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.77230000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethylsuberosin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+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  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    5   16                                                  
CONECT   16   15                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-6-prenylcoumarin	ChEBI
7-Demethylsuberosin	Kegg

Chemical Formula

C₁₄H₁₄O₃

Average Mass

230.2630 Da

Monoisotopic Mass

230.09429 Da

IUPAC Name

7-hydroxy-6-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

demethylsuberosin

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC2=C(OC(=O)C=C2)C=C1O

InChI Identifier

InChI=1S/C14H14O3/c1-9(2)3-4-10-7-11-5-6-14(16)17-13(11)8-12(10)15/h3,5-8,15H,4H2,1-2H3

InChI Key

FIDUIAPDSKSUGO-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
Aegle marmelos	LOTUS Database	35616633
Angelica genuflexa	LOTUS Database	35616633
Angelica gigas	LOTUS Database	35616633
Angelica keiskei	LOTUS Database	35616633
Boronia algida	LOTUS Database	35616633
Boronia lanceolata	LOTUS Database	35616633
Brosimum rubescens	LOTUS Database	35616633
Citropsis articulata	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus limonia	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Citrus sinensis	LOTUS Database	35616633
Citrus sulcata	LOTUS Database	35616633
Feroniella lucida	LOTUS Database	35616633
Glehnia littoralis	LOTUS Database	35616633
Limonia acidissima	LOTUS Database	35616633
Prangos uloptera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:69042 )
a coumarin (CPD-8192 )

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	3.36	ALOGPS
logP	3.21	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.77 m³·mol⁻¹	ChemAxon
Polarizability	24.97 Å³	ChemAxon
Number of Rings	2	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

FDB030814

KNApSAcK ID

C00030108

Chemspider ID

Not Available

KEGG Compound ID

C18083

BioCyc ID

CPD-8192

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316525

PDB ID

Not Available

ChEBI ID

69042

Good Scents ID

Not Available

References

General References

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 ]
Ahn MJ, Lee MK, Kim YC, Sung SH: The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography-diode array detector coupled with electrospray ionization/mass spectrometry. J Pharm Biomed Anal. 2008 Jan 22;46(2):258-66. doi: 10.1016/j.jpba.2007.09.020. Epub 2007 Sep 26. [PubMed:17997069 ]
Karamat F, Olry A, Munakata R, Koeduka T, Sugiyama A, Paris C, Hehn A, Bourgaud F, Yazaki K: A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley. Plant J. 2014 Feb;77(4):627-38. doi: 10.1111/tpj.12409. Epub 2014 Jan 24. [PubMed:24354545 ]
Kang GJ, Yang SJ, Zhou HY, Yang ZM, Chen LY: [Chemical constituents of pattra medicine Euodia lepta]. Zhong Yao Cai. 2014 Jan;37(1):74-6. [PubMed:25090710 ]
Kim HJ, Kim HM, Ryu B, Lee WS, Shin JS, Lee KT, Jang DS: Constituents of PG201 (Layla((R))), a multi-component phytopharmaceutical, with inhibitory activity on LPS-induced nitric oxide and prostaglandin E2 productions in macrophages. Arch Pharm Res. 2016 Feb;39(2):231-239. doi: 10.1007/s12272-015-0654-z. Epub 2015 Aug 26. [PubMed:26306655 ]

Showing NP-Card for Demethylsuberosin (NP0137388)

MOL for NP0137388 (Demethylsuberosin)

3D MOL for NP0137388 (Demethylsuberosin)

3D SDF for NP0137388 (Demethylsuberosin)

3D-SDF for NP0137388 (Demethylsuberosin)

PDB for NP0137388 (Demethylsuberosin)

3D PDB for NP0137388 (Demethylsuberosin)

SMILES for NP0137388 (Demethylsuberosin)

INCHI for NP0137388 (Demethylsuberosin)

Structure for NP0137388 (Demethylsuberosin)

3D Structure for NP0137388 (Demethylsuberosin)