NP-MRD: Showing NP-Card for Coriandrone D (NP0045496)

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Record Information

Version

2.0

Created at

2022-03-17 19:20:57 UTC

Updated at

2022-03-17 19:20:57 UTC

NP-MRD ID

NP0045496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Coriandrone D

Description

Coriandrone D belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. Coriandrone D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Coriandrone D has been detected, but not quantified in, corianders and herbs and spices. Coriandrone D is found in Coriandrum sativum. This could make coriandrone D a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219462D          

 25 26  0  0  0  0            999 V2000
   -0.3533    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4984    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3602   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2134    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 25  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(CC(OC(C)=O)C(C)(C)O)C(O)=C2C(=O)OC(C)CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O7/c1-9-6-11-7-13(23-5)12(16(20)15(11)17(21)24-9)8-14(18(3,4)22)25-10(2)19/h7,9,14,20,22H,6,8H2,1-5H3

> <INCHI_KEY>
ZSKZYWHCOISHNI-UHFFFAOYSA-N

> <FORMULA>
C18H24O7

> <MOLECULAR_WEIGHT>
352.379

> <EXACT_MASS>
352.152203122

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.28501501388334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-1-(8-hydroxy-6-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)-3-methylbutan-2-yl acetate

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.451203322666666

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.29137676305994

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.384807052709423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.10883567523487

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
89.99770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-1-(8-hydroxy-6-methoxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)-3-methylbutan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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  C   UNK     0      -0.659   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.659  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.672  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.002  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.002   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.672   1.537   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.664  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.664   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334   1.537   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.334  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.672  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.994   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.994   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.994  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.329  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.329   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.664   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.664   3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.998   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.664  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.664  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.998  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.998  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.998   1.540   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    5    9                                                       
CONECT   11    7                                                            
CONECT   12    3                                                            
CONECT   13    1   14                                                       
CONECT   14   13                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    9                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-1-(8-hydroxy-6-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)-3-methylbutan-2-yl acetic acid	Generator

Chemical Formula

C₁₈H₂₄O₇

Average Mass

352.3790 Da

Monoisotopic Mass

352.15220 Da

IUPAC Name

3-hydroxy-1-(8-hydroxy-6-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-yl)-3-methylbutan-2-yl acetate

Traditional Name

3-hydroxy-1-(8-hydroxy-6-methoxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-7-yl)-3-methylbutan-2-yl acetate

CAS Registry Number

177795-33-4

SMILES

COC1=C(CC(OC(C)=O)C(C)(C)O)C(O)=C2C(=O)OC(C)CC2=C1

InChI Identifier

InChI=1S/C18H24O7/c1-9-6-11-7-13(23-5)12(16(20)15(11)17(21)24-9)8-14(18(3,4)22)25-10(2)19/h7,9,14,20,22H,6,8H2,1-5H3

InChI Key

ZSKZYWHCOISHNI-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
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Carbonyl group
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	2.02	ALOGPS
logP	2.45	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	90 m³·mol⁻¹	ChemAxon
Polarizability	36.29 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

HMDB0029972

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001259

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

131750936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Coriandrone D (NP0045496)

MOL for NP0045496 (Coriandrone D)

3D MOL for NP0045496 (Coriandrone D)

3D SDF for NP0045496 (Coriandrone D)

3D-SDF for NP0045496 (Coriandrone D)

PDB for NP0045496 (Coriandrone D)

3D PDB for NP0045496 (Coriandrone D)

SMILES for NP0045496 (Coriandrone D)

INCHI for NP0045496 (Coriandrone D)

Structure for NP0045496 (Coriandrone D)

3D Structure for NP0045496 (Coriandrone D)