NP-MRD: Showing NP-Card for 9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one (NP0309939)

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Record Information

Version

2.0

Created at

2022-09-11 04:52:00 UTC

Updated at

2022-09-11 04:52:00 UTC

NP-MRD ID

NP0309939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one

Description

9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one is found in Xanthium pungens.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.8460   -2.2052    1.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281   -1.3679    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8501   -0.2858    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7015    0.3173   -0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5325   -0.2184    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430   -1.5202    1.0230 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620    0.4456   -0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    1.5271   -1.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1594    2.3835   -1.8488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6454    3.4027   -2.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680    2.2396   -1.6744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    3.0086   -2.2190 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7571    1.2142   -0.8750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098    0.2676   -0.1929 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3597    0.3385    1.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5604    0.0019    1.6377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5398   -0.4449    0.6726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7715   -0.8021    0.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473   -1.2555   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710   -0.3741   -0.0709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8106   -0.8974   -1.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4085    1.3811   -1.1921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5074   -2.5899    2.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0945   -3.0280    0.7226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6868   -1.4866    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8869    0.0264   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314    4.0970   -2.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -0.7397   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3658    0.6699    1.9549 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8393    0.0505    2.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2665   -0.4944   -0.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0627   -0.7601    2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0818   -2.2813    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995   -1.3190   -1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4804   -0.3245    0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6616    0.6527   -0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3395   -1.6719   -0.7118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615    2.0428   -1.7233 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
  4 22  2  0
 22  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14  7  1  0
  7  5  2  0
  5  6  1  0
  6  2  1  0
  5  4  1  0
  7  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
 22 38  1  0
 10 27  1  0
 14 28  1  6
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 19 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1652309112206522D          

 22 24  0  0  0  0            999 V2000
    4.4568    0.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.1142    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2356   -1.1665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8924    0.0377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    1.0146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933    1.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293    2.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    2.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416    2.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1056    3.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9090    3.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554   -0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  2  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
  9 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
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 22  1  0  0  0  0
  4 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC2=CC3=C(O)C(=O)OC(\C=C/C=C/CCO)C3=C2S1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4S/c1-10-8-11-9-12-14(16(11)22-10)13(21-17(20)15(12)19)6-4-2-3-5-7-18/h2-4,6,8-9,13,18-19H,5,7H2,1H3/b3-2+,6-4-

> <INCHI_KEY>
RYITUELVDVMRLK-ZPYFUIHZSA-N

> <FORMULA>
C17H16O4S

> <MOLECULAR_WEIGHT>
316.37

> <EXACT_MASS>
316.076930169

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.57383833745405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-12-[(1Z,3E)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0^{2,6}]dodeca-1,4,6,8-tetraen-10-one

> <JCHEM_LOGP>
1.235162422333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.90384186203418

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.344695685034461

> <JCHEM_PKA_STRONGEST_BASIC>
-1.981241352249275

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
94.047

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-12-[(1Z,3E)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0^{2,6}]dodeca-1,4,6,8-tetraen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       8.319   1.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.864   1.199   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.417  -0.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.878  -0.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.373   1.150   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       5.601   2.080   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       2.833   1.120   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.387  -0.354   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.887  -0.704   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.440  -2.177   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.166   0.420   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.666   0.070   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.281   1.894   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.781   2.244   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.228   3.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.175   4.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.325   4.492   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.378   5.615   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.878   5.266   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.930   6.390   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.430   6.040   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.650  -1.234   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    8    4                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₄S

Average Mass

316.3700 Da

Monoisotopic Mass

316.07693 Da

IUPAC Name

9-hydroxy-12-[(1Z,3E)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0^{2,6}]dodeca-1,4,6,8-tetraen-10-one

Traditional Name

9-hydroxy-12-[(1Z,3E)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0^{2,6}]dodeca-1,4,6,8-tetraen-10-one

CAS Registry Number

Not Available

SMILES

CC1=CC2=CC3=C(O)C(=O)OC(\C=C/C=C/CCO)C3=C2S1

InChI Identifier

InChI=1S/C17H16O4S/c1-10-8-11-9-12-14(16(11)22-10)13(21-17(20)15(12)19)6-4-2-3-5-7-18/h2-4,6,8-9,13,18-19H,5,7H2,1H3/b3-2+,6-4-

InChI Key

RYITUELVDVMRLK-ZPYFUIHZSA-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
Xanthium pungens	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.24	ChemAxon
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-2	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	4	ChemAxon
Refractivity	94.05 m³·mol⁻¹	ChemAxon
Polarizability	32.57 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one (NP0309939)

MOL for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

3D MOL for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

3D SDF for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

3D-SDF for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

PDB for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

3D PDB for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

SMILES for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

INCHI for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

Structure for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)

3D Structure for NP0309939 (9-hydroxy-12-[(1z,3e)-6-hydroxyhexa-1,3-dien-1-yl]-4-methyl-11-oxa-3-thiatricyclo[6.4.0.0²,⁶]dodeca-1,4,6,8-tetraen-10-one)