NP-MRD: Showing NP-Card for {6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0199966)

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Record Information

Version

1.0

Created at

2022-09-04 18:42:29 UTC

Updated at

2022-09-04 18:42:29 UTC

NP-MRD ID

NP0199966

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Description

{6-[(2,5-Dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). {6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate is found in Eucalyptus cypellocarpa. {6-[(2,5-Dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191514102D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191514102D          

 38 41  0  0  0  0            999 V2000
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    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  2  0  0  0  0
 19 32  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 15 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199966

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CCC(=CC1)C(=O)OCC1OC(OC2=CC(O)=C3C(=O)CC(C)(O)OC3=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O12/c1-25(2,33)13-6-4-12(5-7-13)23(32)35-11-18-20(29)21(30)22(31)24(37-18)36-14-8-15(27)19-16(28)10-26(3,34)38-17(19)9-14/h4,8-9,13,18,20-22,24,27,29-31,33-34H,5-7,10-11H2,1-3H3

> <INCHI_KEY>
BNOXWGIIFHBMQJ-UHFFFAOYSA-N

> <FORMULA>
C26H34O12

> <MOLECULAR_WEIGHT>
538.546

> <EXACT_MASS>
538.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.92868374613486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[(2,5-dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.233998439999998

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.714588718865349

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.596626875731653

> <JCHEM_PKA_STRONGEST_BASIC>
-0.873124645754053

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
129.90910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[(2,5-dihydroxy-2-methyl-4-oxo-3H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001 -17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.461 -16.170   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.541 -16.170   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.195  -3.757   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   23   32                                                  
CONECT   32   31   19                                                       
CONECT   33   17   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   15   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
{6-[(2,5-dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₂

Average Mass

538.5460 Da

Monoisotopic Mass

538.20503 Da

IUPAC Name

{6-[(2,5-dihydroxy-2-methyl-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

Traditional Name

{6-[(2,5-dihydroxy-2-methyl-4-oxo-3H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CCC(=CC1)C(=O)OCC1OC(OC2=CC(O)=C3C(=O)CC(C)(O)OC3=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H34O12/c1-25(2,33)13-6-4-12(5-7-13)23(32)35-11-18-20(29)21(30)22(31)24(37-18)36-14-8-15(27)19-16(28)10-26(3,34)38-17(19)9-14/h4,8-9,13,18,20-22,24,27,29-31,33-34H,5-7,10-11H2,1-3H3

InChI Key

BNOXWGIIFHBMQJ-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
Eucalyptus cypellocarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiosulfinic acid esters

Sub Class

Not Available

Direct Parent

Thiosulfinic acid esters

Alternative Parents

Substituents

Thiosulfinic acid ester
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	1.01	ALOGPS
logP	1.23	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-0.87	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.91 m³·mol⁻¹	ChemAxon
Polarizability	53.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate (NP0199966)

MOL for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D MOL for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D SDF for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D-SDF for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

PDB for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D PDB for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

SMILES for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

INCHI for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

Structure for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)

3D Structure for NP0199966 ({6-[(2,5-dihydroxy-2-methyl-4-oxo-3h-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methyl 4-(2-hydroxypropan-2-yl)cyclohex-1-ene-1-carboxylate)