NP-MRD: Showing NP-Card for Acutilobin (NP0085123)

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Record Information

Version

2.0

Created at

2022-04-29 05:43:49 UTC

Updated at

2022-04-29 05:43:49 UTC

NP-MRD ID

NP0085123

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acutilobin

Description

(3S)-2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Acutilobin is found in Angelica acutiloba . Based on a literature review very few articles have been published on (3S)-2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    5.4213    0.7919    2.0348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6724    0.2516    0.8805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3771    0.3840    0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6288    1.0919    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475   -0.1483   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2468   -0.7691   -1.3034 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -0.0327   -0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969   -0.5722   -1.6490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2820   -1.6838   -1.0926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5084   -1.1466   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9752   -1.6649    0.7492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1203   -1.1094    1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -1.6380    2.4875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7331   -1.0702    3.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180   -0.0445    2.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3714    0.4983    2.7432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8472    0.4233    1.1661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715   -0.0763    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2847    0.4234   -0.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470   -0.1023   -1.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5774    0.3169   -2.2878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    0.4481   -2.4101 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1764    1.8665   -1.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2029    0.4162   -3.8932 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106    0.6532    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    1.8972    2.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1271    0.2952    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2154   -0.2639    0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975    1.6537    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2510    1.7718    2.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1103    0.3345    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -1.0683   -2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684   -2.2783   -0.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -2.3586   -1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390   -2.4772    1.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0659   -2.4441    2.9704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1582   -1.4329    3.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7765    1.2355   -1.0792 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1309    1.9116   -0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    2.2096   -2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429    2.5255   -2.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6259   -0.6055   -4.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0300    1.1307   -4.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6679    0.6081   -4.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 18  2  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
 15 14  1  0
 14 13  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 22  8  1  0
 20 10  1  0
 13 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  8 32  1  6
  9 33  1  0
  9 34  1  0
 11 35  1  0
 14 37  1  0
 13 36  1  0
 19 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 24 42  1  0
 24 43  1  0
 24 44  1  0
M  END


  Mrv1652304292207432D          

 24 26  0  0  1  0            999 V2000
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    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  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
   -2.1434   -1.2375    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
   -1.4289    0.8250    0.0000 O   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
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  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  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  4  0  0  0
 13 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
  9 23  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  6 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085123

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)O[C@H]1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1

> <INCHI_KEY>
AGABNGOXUSXQDD-INIZCTEOSA-N

> <FORMULA>
C19H20O5

> <MOLECULAR_WEIGHT>
328.364

> <EXACT_MASS>
328.131073744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.19785517880633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.85

> <JCHEM_LOGP>
3.9453308416666673

> <ALOGPS_LOGS>
-4.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8919257245617835

> <JCHEM_POLAR_SURFACE_AREA>
61.83

> <JCHEM_REFRACTIVITY>
90.1707

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-2,2-dimethyl-8-oxo-3H,4H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    4    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   13                                                            
CONECT   19   11   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23                                                       
CONECT   23    9   22   24                                                  
CONECT   24   23    6                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(3S)-2,2-Dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₉H₂₀O₅

Average Mass

328.3640 Da

Monoisotopic Mass

328.13107 Da

IUPAC Name

(3S)-2,2-dimethyl-8-oxo-2H,3H,4H,8H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate

Traditional Name

(3S)-2,2-dimethyl-8-oxo-3H,4H-pyrano[3,2-g]chromen-3-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)O[C@H]1CC2=CC3=C(OC(=O)C=C3)C=C2OC1(C)C

InChI Identifier

InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/t16-/m0/s1

InChI Key

AGABNGOXUSXQDD-INIZCTEOSA-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
Angelica acutiloba	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
1-benzopyran
Benzopyran
Chromane
Pyranone
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Pyran
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.85	ALOGPS
logP	3.95	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.17 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	3	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

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

162986926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Acutilobin (NP0085123)

MOL for NP0085123 (Acutilobin)

3D MOL for NP0085123 (Acutilobin)

3D SDF for NP0085123 (Acutilobin)

3D-SDF for NP0085123 (Acutilobin)

PDB for NP0085123 (Acutilobin)

3D PDB for NP0085123 (Acutilobin)

SMILES for NP0085123 (Acutilobin)

INCHI for NP0085123 (Acutilobin)

Structure for NP0085123 (Acutilobin)

3D Structure for NP0085123 (Acutilobin)