NP-MRD: Showing NP-Card for 5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate (NP0223766)

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Record Information

Version

2.0

Created at

2022-09-06 01:57:15 UTC

Updated at

2022-09-06 01:57:15 UTC

NP-MRD ID

NP0223766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

Description

5-Hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadecan-14-yl 1-methyl butanedioate belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate is found in Bufo gargarizans. 5-Hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadecan-14-yl 1-methyl butanedioate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512392D          

 37 42  0  0  0  0            999 V2000
    9.1116    3.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2994    3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5828    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251512392D          

 37 42  0  0  0  0            999 V2000
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   -1.3820   -2.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -2.7469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6929   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 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
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
 22 29  1  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 30 36  1  0  0  0  0
 15 37  1  0  0  0  0
 10 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCC(=O)OC1CCC2(C)C(CCC3C2CCC2(C)C(C(O)C4OC324)C2=COC(=O)C=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O8/c1-27-12-10-18(36-23(32)9-8-21(30)34-3)14-17(27)5-6-20-19(27)11-13-28(2)24(16-4-7-22(31)35-15-16)25(33)26-29(20,28)37-26/h4,7,15,17-20,24-26,33H,5-6,8-14H2,1-3H3

> <INCHI_KEY>
ONGYSNZKOXRFQH-UHFFFAOYSA-N

> <FORMULA>
C29H38O8

> <MOLECULAR_WEIGHT>
514.615

> <EXACT_MASS>
514.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.75984370139773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.7784938053333326

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.755583150652406

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3431079299046385

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000003

> <JCHEM_REFRACTIVITY>
132.4385

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      17.008   6.471   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.492   6.199   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      14.969   4.751   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      15.962   3.574   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      13.453   4.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.930   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.414   2.761   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.421   3.938   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.891   1.312   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.375   1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.852  -0.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.336  -0.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.343   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.820  -0.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.866   1.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.357   2.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.834   1.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.827   0.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.304  -1.221   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.788  -1.492   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.795  -0.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.123  -1.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.256  -0.264   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.172   1.215   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.621   1.738   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.102   2.079   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.529   2.660   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.318   1.134   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.689  -1.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.109  -2.907   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.054  -4.122   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.580  -3.912   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.525  -5.127   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.160  -2.485   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.215  -1.269   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.382   2.218   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16   37                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   18   22   27                                             
CONECT   30   24   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   30                                                       
CONECT   37   15   10                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0,.0,.0,]octadecan-14-yl 1-methyl butanedioic acid	Generator
5-Hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioic acid	Generator

Chemical Formula

C₂₉H₃₈O₈

Average Mass

514.6150 Da

Monoisotopic Mass

514.25667 Da

IUPAC Name

5-hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-5-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

Traditional Name

5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)CCC(=O)OC1CCC2(C)C(CCC3C2CCC2(C)C(C(O)C4OC324)C2=COC(=O)C=C2)C1

InChI Identifier

InChI=1S/C29H38O8/c1-27-12-10-18(36-23(32)9-8-21(30)34-3)14-17(27)5-6-20-19(27)11-13-28(2)24(16-4-7-22(31)35-15-16)25(33)26-29(20,28)37-26/h4,7,15,17-20,24-26,33H,5-6,8-14H2,1-3H3

InChI Key

ONGYSNZKOXRFQH-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
Bufo gargarizans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Steroid ester
Naphthopyran
Naphthalene
Pyranone
Fatty acid methyl ester
Fatty acid ester
Oxane
Pyran
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Heteroaromatic compound
Methyl ester
Secondary alcohol
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen 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	3.1	ALOGPS
logP	2.78	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.76	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.44 m³·mol⁻¹	ChemAxon
Polarizability	55.76 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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 5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate (NP0223766)

MOL for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

3D MOL for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

3D SDF for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

3D-SDF for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

PDB for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

3D PDB for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

SMILES for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

INCHI for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

Structure for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)

3D Structure for NP0223766 (5-hydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-14-yl 1-methyl butanedioate)