NP-MRD: Showing NP-Card for 5-De-O-methyltoddanol (NP0085434)

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Record Information

Version

2.0

Created at

2022-04-29 05:57:48 UTC

Updated at

2022-04-29 05:57:49 UTC

NP-MRD ID

NP0085434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-De-O-methyltoddanol

Description

5-De-O-methyltoddanol belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. 5-De-O-methyltoddanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-De-O-methyltoddanol has been detected, but not quantified in, citrus. 5-De-O-methyltoddanol is found in Citrus grandis . This could make 5-de-O-methyltoddanol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.0230    0.7018   -0.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358   -0.3995   -0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4329   -1.4033   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0732   -0.6661   -0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9214   -1.8914    0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    0.4358    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339    0.3234    0.1272 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8268    1.2891    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1187    2.3367    1.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7379    3.3487    2.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799    1.2851    0.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226    0.2815    0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2343    0.2684    0.5335 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0075   -0.6347    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2490   -0.5509    0.2140 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4430   -1.6538   -0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0743   -1.6775   -0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719   -0.7057   -0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870   -0.6859   -0.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2916   -1.6901   -1.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4113    1.4859    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0945    0.8699   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0563   -1.7505   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4575   -0.9670   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5082   -2.3301   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691   -0.7410   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3898   -2.5591   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5400    1.4396   -0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7174    0.5307    1.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572    3.8835    2.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2262    4.1237    1.5462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5091    3.0036    2.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146    2.0488    1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0260   -2.4259   -1.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -2.4906   -1.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7700   -2.4331   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 18  2  0
 18 17  1  0
 17 16  2  0
 16 14  1  0
 14 15  2  0
 14 13  1  0
 18 19  1  0
 19 20  1  0
 19  7  2  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  7  8  1  0
 13 12  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 17 35  1  0
 16 34  1  0
 20 36  1  0
  6 28  1  0
  6 29  1  0
  4 26  1  6
  5 27  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv0541 05061312432D          

 20 21  0  0  0  0            999 V2000
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    1.4289    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    0.7145    1.2375    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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19  3  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=CC(=O)O2)C(O)=C1CC(O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-8(2)11(16)6-10-12(19-3)7-13-9(15(10)18)4-5-14(17)20-13/h4-5,7,11,16,18H,1,6H2,2-3H3

> <INCHI_KEY>
LMUSYGSJXWROBU-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.2845

> <EXACT_MASS>
276.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.324719624972452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.877812630666666

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.507596143641361

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.749290609169849

> <JCHEM_PKA_STRONGEST_BASIC>
-3.050945791623864

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
74.6785

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3   19                                                            
CONECT    4    5    9                                                       
CONECT    5    4   14                                                       
CONECT    6   10   11                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   11                                                  
CONECT    9    4   13   15                                                  
CONECT   10    6   12   15                                                  
CONECT   11    6    8   16                                                  
CONECT   12    7   10   19                                                  
CONECT   13    7    9   20                                                  
CONECT   14    5   17   20                                                  
CONECT   15    9   10   18                                                  
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    3   12                                                       
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-6-(2-hydroxy-3-methyl-3-butenyl)-7-methoxy-2H-1-benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2845 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

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

Traditional Name

5-hydroxy-6-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxychromen-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=CC(=O)O2)C(O)=C1CC(O)C(C)=C

InChI Identifier

InChI=1S/C15H16O5/c1-8(2)11(16)6-10-12(19-3)7-13-9(15(10)18)4-5-14(17)20-13/h4-5,7,11,16,18H,1,6H2,2-3H3

InChI Key

LMUSYGSJXWROBU-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
Citrus maxima	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

Hydroxycoumarins

Alternative Parents

Substituents

Hydroxycoumarin
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.9	ALOGPS
logP	1.88	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.68 m³·mol⁻¹	ChemAxon
Polarizability	28.32 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

HMDB0041520

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021496

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753155

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-De-O-methyltoddanol (NP0085434)

MOL for NP0085434 (5-De-O-methyltoddanol)

3D MOL for NP0085434 (5-De-O-methyltoddanol)

3D SDF for NP0085434 (5-De-O-methyltoddanol)

3D-SDF for NP0085434 (5-De-O-methyltoddanol)

PDB for NP0085434 (5-De-O-methyltoddanol)

3D PDB for NP0085434 (5-De-O-methyltoddanol)

SMILES for NP0085434 (5-De-O-methyltoddanol)

INCHI for NP0085434 (5-De-O-methyltoddanol)

Structure for NP0085434 (5-De-O-methyltoddanol)

3D Structure for NP0085434 (5-De-O-methyltoddanol)