NP-MRD: Showing NP-Card for Divaricatol (NP0072856)

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Record Information

Version

2.0

Created at

2022-04-28 18:08:02 UTC

Updated at

2022-04-28 18:08:02 UTC

NP-MRD ID

NP0072856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Divaricatol

Description

Divaricatol belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. Divaricatol is found in Saposhnikovia divaricata and Saposhnikovia divaricata Schischkin. Based on a literature review very few articles have been published on Divaricatol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    5.6990    1.3532    1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2649    0.9951    1.4079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6023    1.1755    2.4404 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    0.4257    0.3495 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013    0.0129    0.2656 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4587    0.8687   -0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614    0.3859   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2475   -0.8268    0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5672   -1.2070    0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5908   -0.3798   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8410   -0.7454   -0.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7793    0.0268   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1914   -0.4624   -0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1021    0.4629   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5857    1.2427   -1.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2845    1.6783   -1.3759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0180    2.7869   -1.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2966    0.8356   -0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9601    1.1887   -0.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044    2.4257   -1.5778 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -1.6952    0.5517 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -1.4439    0.0559 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0601   -1.9040   -1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918   -2.2458    0.9046 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3462    0.4638    1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9944    2.0345    2.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831    1.9391    0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8835    0.2555    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5668    1.9228   -0.2871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    0.8704   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8263   -2.1541    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -0.7303    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2933   -1.3912   -1.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4399    0.9853   -0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4300    1.8205   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2622    2.7039   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -2.3537   -1.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8114   -1.1297   -2.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3521   -2.7439   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5380   -3.1968    1.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801   -1.6707    1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9090   -2.5797    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8 21  1  0
 21 22  1  0
 22 23  1  6
 22 24  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 22  5  1  0
 18 10  1  0
 19  7  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  1
  6 29  1  0
  6 30  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
  9 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 20 36  1  0
M  END


  Mrv1652304282220082D          

 24 26  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   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
    2.1434    1.2375    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
    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   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
    4.2868    0.8250    0.0000 C   0  0  1  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1113   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC2=C(OC1(C)C)C=C1OC(CO)=CC(=O)C1=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O7/c1-8(19)22-14-5-10-12(24-17(14,2)3)6-13-15(16(10)21)11(20)4-9(7-18)23-13/h4,6,14,18,21H,5,7H2,1-3H3/t14-/m0/s1

> <INCHI_KEY>
DJEFKGJBMQEDCR-AWEZNQCLSA-N

> <FORMULA>
C17H18O7

> <MOLECULAR_WEIGHT>
334.324

> <EXACT_MASS>
334.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.08008456591246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-9-hydroxy-13-(hydroxymethyl)-5,5-dimethyl-11-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,12-tetraen-6-yl acetate

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.5612373830000004

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.089907716459098

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.182492786160175

> <JCHEM_PKA_STRONGEST_BASIC>
-3.083479075539981

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
84.5756

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-9-hydroxy-13-(hydroxymethyl)-5,5-dimethyl-11-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,12-tetraen-6-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   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  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.541  -0.054   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.818  -1.306   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12                                                            
CONECT   14    3                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17    1                                                       
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₇

Average Mass

334.3240 Da

Monoisotopic Mass

334.10525 Da

IUPAC Name

(6S)-9-hydroxy-13-(hydroxymethyl)-5,5-dimethyl-11-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,12-tetraen-6-yl acetate

Traditional Name

(6S)-9-hydroxy-13-(hydroxymethyl)-5,5-dimethyl-11-oxo-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1,3(8),9,12-tetraen-6-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC2=C(OC1(C)C)C=C1OC(CO)=CC(=O)C1=C2O

InChI Identifier

InChI=1S/C17H18O7/c1-8(19)22-14-5-10-12(24-17(14,2)3)6-13-15(16(10)21)11(20)4-9(7-18)23-13/h4,6,14,18,21H,5,7H2,1-3H3/t14-/m0/s1

InChI Key

DJEFKGJBMQEDCR-AWEZNQCLSA-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
Saposhnikovia divaricata	LOTUS Database	35616633
Saposhnikovia divaricata Schischkin	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Aromatic alcohol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen 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	1.56	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.58 m³·mol⁻¹	ChemAxon
Polarizability	34.08 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

C00032913

Chemspider ID

8149703

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9974111

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Divaricatol (NP0072856)

MOL for NP0072856 (Divaricatol)

3D MOL for NP0072856 (Divaricatol)

3D SDF for NP0072856 (Divaricatol)

3D-SDF for NP0072856 (Divaricatol)

PDB for NP0072856 (Divaricatol)

3D PDB for NP0072856 (Divaricatol)

SMILES for NP0072856 (Divaricatol)

INCHI for NP0072856 (Divaricatol)

Structure for NP0072856 (Divaricatol)

3D Structure for NP0072856 (Divaricatol)