NP-MRD: Showing NP-Card for 6Œ±-Hydroxymedicarpin (NP0137012)

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Record Information

Version

2.0

Created at

2022-05-30 16:38:58 UTC

Updated at

2022-05-30 16:38:58 UTC

NP-MRD ID

NP0137012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6Œ±-Hydroxymedicarpin

Description

(E)-4'-Methylresveratrol 3-glucoside belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton (E)-4'-Methylresveratrol 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (E)-4'-Methylresveratrol 3-glucoside has been detected, but not quantified in, green vegetables. 6Œ±-Hydroxymedicarpin is found in Melilotus messanensis. This could make (e)-4'-methylresveratrol 3-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
    5.5241    1.3209   -0.9627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1802    0.1321   -0.2941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8382   -0.2009   -0.1507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -1.3610    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430   -1.7185    0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1484   -0.8937    0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775    0.2762   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257    0.5934   -0.6412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2830    0.9159   -0.9148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    0.5335    0.0728 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0469    0.6331   -0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6239    1.4502   -1.1838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934    1.4330   -1.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8404    0.6149   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2177    0.6151   -0.8835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2654   -0.2203    0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -0.2006    0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3235   -1.0268    1.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9818   -1.4907    1.3486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3126   -0.9692    0.1348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6977   -1.6014   -1.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0522    1.3967   -1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163    1.4041   -1.0382 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156    2.1888   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2393   -1.9894    0.8877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8211   -2.6137    1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1278    1.4975   -1.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3221    0.9650    1.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9586    2.1006   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4325    2.0938   -2.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8390    1.2230   -0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9367   -0.8588    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4066   -1.2852    2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561   -2.6070    1.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -2.3504   -1.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  6 20  1  0
 20 21  1  6
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 11 10  1  0
 10  9  1  0
  4  3  1  0
 10 20  1  0
  9  7  1  0
 16 17  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  8 27  1  0
  5 26  1  0
  4 25  1  0
 21 35  1  0
 19 33  1  0
 19 34  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 10 28  1  1
M  END

  Mrv0541 05061307352D          

 21 24  0  0  0  0            999 V2000
   -0.9390   -2.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2284   -0.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-19-10-3-5-12-14(7-10)21-15-11-4-2-9(17)6-13(11)20-8-16(12,15)18/h2-7,15,17-18H,8H2,1H3

> <INCHI_KEY>
SXKBOSYKWYQHMV-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.068586789054443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.8540430143333333

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.070665661490725

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413465455675777

> <JCHEM_PKA_STRONGEST_BASIC>
-4.094446231951658

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
74.14900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol

> <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      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.160  -1.380   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   11                                                       
CONECT    5    3   12                                                       
CONECT    6    9   13                                                       
CONECT    7   10   14                                                       
CONECT    8   16   20                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   19                                                  
CONECT   11    4   13   15                                                  
CONECT   12    5   14   16                                                  
CONECT   13    6   11   20                                                  
CONECT   14    7   12   21                                                  
CONECT   15   11   16   21                                                  
CONECT   16    8   12   15   18                                             
CONECT   17    9                                                            
CONECT   18   16                                                            
CONECT   19    1   10                                                       
CONECT   20    8   13                                                       
CONECT   21   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,6a-Dihydroxy-9-methoxypterocarpan	HMDB
6a-Hydroxymedicarpin	HMDB, Generator
6Α-hydroxymedicarpin	Generator

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2794 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol

Traditional Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

InChI=1S/C16H14O5/c1-19-10-3-5-12-14(7-10)21-15-11-4-2-9(17)6-13(11)20-8-16(12,15)18/h2-7,15,17-18H,8H2,1H3

InChI Key

SXKBOSYKWYQHMV-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
Melilotus messanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Secondary alcohol
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.05	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.15 m³·mol⁻¹	ChemAxon
Polarizability	29.07 Å³	ChemAxon
Number of Rings	4	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

HMDB0034117

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012385

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

131751528

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6Œ±-Hydroxymedicarpin (NP0137012)

MOL for NP0137012 (6Œ±-Hydroxymedicarpin)

3D MOL for NP0137012 (6Œ±-Hydroxymedicarpin)

3D SDF for NP0137012 (6Œ±-Hydroxymedicarpin)

3D-SDF for NP0137012 (6Œ±-Hydroxymedicarpin)

PDB for NP0137012 (6Œ±-Hydroxymedicarpin)

3D PDB for NP0137012 (6Œ±-Hydroxymedicarpin)

SMILES for NP0137012 (6Œ±-Hydroxymedicarpin)

INCHI for NP0137012 (6Œ±-Hydroxymedicarpin)

Structure for NP0137012 (6Œ±-Hydroxymedicarpin)

3D Structure for NP0137012 (6Œ±-Hydroxymedicarpin)