NP-MRD: Showing NP-Card for Isoarnottinin (NP0063166)

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Record Information

Version

2.0

Created at

2022-04-28 07:38:10 UTC

Updated at

2022-04-28 07:38:10 UTC

NP-MRD ID

NP0063166

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoarnottinin

Description

AKOS022663070 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. Isoarnottinin is found in Ammi majus . AKOS022663070 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.2119   -0.8800   -1.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8418    0.0801   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6314    0.5778   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5815    0.2018   -1.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6357   -0.3610   -0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7359   -1.6338    0.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453   -2.4719    0.0627 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9020   -2.1171    0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106   -1.3058    0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9333   -0.0349    0.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.7817    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346    2.0512   -0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7477    2.4569   -0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7024    3.6482   -1.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086    1.6654   -0.7579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802    0.4333   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208    0.4659    0.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4572    1.3569    1.7711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7121   -1.8372   -1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9320   -0.4014   -2.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3242   -1.0288   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4517    1.2843    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    1.0955   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9786   -0.5798   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3263   -3.4102    0.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9534   -3.1252    1.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -1.6214    1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9701    0.4113    0.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7646    2.7446   -0.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083   -0.4381    1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7635    0.9568    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7216    1.0348    2.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 16  2  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  2  0
  3  2  2  0
  2  1  1  0
  2 17  1  0
 17 18  1  0
 16  5  1  0
 11 10  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 12 29  1  0
 11 28  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv1652310051708312D          

 19 20  0  0  0  0            999 V2000
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.0000    3.3000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    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    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
    2.1434    2.0625    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    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  2  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063166

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC1=C(O)C=CC2=C1OC(=O)C=C2)=C(\C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-9(8-15)2-5-11-12(16)6-3-10-4-7-13(17)18-14(10)11/h2-4,6-7,15-16H,5,8H2,1H3/b9-2+

> <INCHI_KEY>
TXAQUMCUNALGRP-XNWCZRBMSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.262

> <EXACT_MASS>
246.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.524409547122453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]-2H-chromen-2-one

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
1.927590136333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.166907179129094

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.64238619608476

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7258165657079365

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.54700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -2.667   6.160   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2    5    9   19                                                  
CONECT    3    6   10                                                       
CONECT    4    7   10                                                       
CONECT    5    2   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   13                                                       
CONECT    8    9   15                                                       
CONECT    9    1    2    8                                                  
CONECT   10    3    4   14                                                  
CONECT   11    5   12   14                                                  
CONECT   12    6   11   16                                                  
CONECT   13    7   17   18                                                  
CONECT   14   10   11   18                                                  
CONECT   15    8                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   13   14                                                       
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄O₄

Average Mass

246.2620 Da

Monoisotopic Mass

246.08921 Da

IUPAC Name

7-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]-2H-chromen-2-one

Traditional Name

7-hydroxy-8-[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]chromen-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(CC1=C(O)C=CC2=C1OC(=O)C=C2)=C(\C)CO

InChI Identifier

InChI=1S/C14H14O4/c1-9(8-15)2-5-11-12(16)6-3-10-4-7-13(17)18-14(10)11/h2-4,6-7,15-16H,5,8H2,1H3/b9-2+

InChI Key

TXAQUMCUNALGRP-XNWCZRBMSA-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
Ammi majus	Plant	KNApSAcK

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
Phenol
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
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	2.19	ALOGPS
logP	1.93	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.55 m³·mol⁻¹	ChemAxon
Polarizability	25.52 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

HMDB0148697

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

14102503

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isoarnottinin (NP0063166)

MOL for NP0063166 (Isoarnottinin)

3D MOL for NP0063166 (Isoarnottinin)

3D SDF for NP0063166 (Isoarnottinin)

3D-SDF for NP0063166 (Isoarnottinin)

PDB for NP0063166 (Isoarnottinin)

3D PDB for NP0063166 (Isoarnottinin)

SMILES for NP0063166 (Isoarnottinin)

INCHI for NP0063166 (Isoarnottinin)

Structure for NP0063166 (Isoarnottinin)

3D Structure for NP0063166 (Isoarnottinin)