NP-MRD: Showing NP-Card for Schisanlactone C (NP0139178)

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Record Information

Version

1.0

Created at

2022-06-29 19:42:43 UTC

Updated at

2022-06-29 19:42:43 UTC

NP-MRD ID

NP0139178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Schisanlactone C

Description

16-[1-Hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]Nonadeca-1(12),2,4-trien-6-one belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. 16-[1-Hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]Nonadeca-1(12),2,4-trien-6-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241513242D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241513242D          

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 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
 12 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139178

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC(OC1=O)C(C)(O)C1CCC2(C)C3=C(CCC12C)C=C1C=CC(=O)OC(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O5/c1-18-7-11-24(34-26(18)32)30(6,33)23-14-16-28(4)22-10-9-21-19(8-12-25(31)35-27(21,2)3)17-20(22)13-15-29(23,28)5/h7-8,12,17,21,23-24,33H,9-11,13-16H2,1-6H3

> <INCHI_KEY>
QZQNSZDOEZMGEJ-UHFFFAOYSA-N

> <FORMULA>
C30H40O5

> <MOLECULAR_WEIGHT>
480.645

> <EXACT_MASS>
480.287574388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.6418964685479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-[1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4-trien-6-one

> <ALOGPS_LOGP>
6.35

> <JCHEM_LOGP>
5.166284552000002

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.781696524845579

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3316859400325427

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
138.2274

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-[1-hydroxy-1-(5-methyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4-trien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      16.491  -4.811   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.282  -3.857   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.851  -4.427   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.642  -3.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.863  -1.949   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.294  -1.379   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      15.503  -2.333   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.934  -1.763   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.654  -0.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.608   0.214   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.701  -2.204   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.445  -0.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.506   1.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.062   2.031   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.108   0.822   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.391   2.185   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.571   0.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.890  -0.659   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.745  -1.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.281  -1.840   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.963  -0.459   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.947  -1.643   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.385  -0.987   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.190  -0.015   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.977  -0.964   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.479  -0.607   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.176   0.787   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.716   0.802   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.506   2.168   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.011   2.496   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.356   3.890   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.224   3.445   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.205   1.524   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.419   2.473   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.917   2.116   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   35                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   15   22                                             
CONECT   22   21                                                            
CONECT   23   18   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   24   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   17                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₅

Average Mass

480.6450 Da

Monoisotopic Mass

480.28757 Da

IUPAC Name

16-[1-hydroxy-1-(5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4-trien-6-one

Traditional Name

16-[1-hydroxy-1-(5-methyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-8,8,13,17-tetramethyl-7-oxatetracyclo[10.7.0.0³,⁹.0¹³,¹⁷]nonadeca-1(12),2,4-trien-6-one

CAS Registry Number

Not Available

SMILES

CC1=CCC(OC1=O)C(C)(O)C1CCC2(C)C3=C(CCC12C)C=C1C=CC(=O)OC(C)(C)C1CC3

InChI Identifier

InChI=1S/C30H40O5/c1-18-7-11-24(34-26(18)32)30(6,33)23-14-16-28(4)22-10-9-21-19(8-12-25(31)35-27(21,2)3)17-20(22)13-15-29(23,28)5/h7-8,12,17,21,23-24,33H,9-11,13-16H2,1-6H3

InChI Key

QZQNSZDOEZMGEJ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	6.35	ALOGPS
logP	5.17	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.23 m³·mol⁻¹	ChemAxon
Polarizability	54.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

435760

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Schisanlactone C (NP0139178)

MOL for NP0139178 (Schisanlactone C)

3D MOL for NP0139178 (Schisanlactone C)

3D SDF for NP0139178 (Schisanlactone C)

3D-SDF for NP0139178 (Schisanlactone C)

PDB for NP0139178 (Schisanlactone C)

3D PDB for NP0139178 (Schisanlactone C)

SMILES for NP0139178 (Schisanlactone C)

INCHI for NP0139178 (Schisanlactone C)

Structure for NP0139178 (Schisanlactone C)

3D Structure for NP0139178 (Schisanlactone C)