NP-MRD: Showing NP-Card for 7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione (NP0292677)

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Record Information

Version

2.0

Created at

2022-09-10 00:19:08 UTC

Updated at

2022-09-10 00:19:08 UTC

NP-MRD ID

NP0292677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione

Description

467-53-8 Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione is found in Digitalis purpurea. 467-53-8 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519332D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004151519332D          

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  9 10  1  0  0  0  0
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 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 27 28  2  0  0  0  0
 26 29  1  0  0  0  0
 18 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(C)C4C(CC=C3C2)C2C(=O)CC3C(C)OC(C4=O)C23C)OC(C)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O7/c1-13-18-11-19(29)22-17-7-6-15-10-16(35-21-12-20(32-5)24(30)14(2)33-21)8-9-27(15,3)23(17)25(31)26(34-13)28(18,22)4/h6,13-14,16-18,20-24,26,30H,7-12H2,1-5H3

> <INCHI_KEY>
WOLJVUSLKTUJMB-UHFFFAOYSA-N

> <FORMULA>
C28H40O7

> <MOLECULAR_WEIGHT>
488.621

> <EXACT_MASS>
488.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.64978775779538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.7937405636666663

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.17601219496874

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.215140228437445

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5794955853507338

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
128.05760000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      12.882  -7.426   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.275  -6.011   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.198  -4.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.592  -3.362   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.514  -2.129   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.908  -0.714   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.379  -0.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.772   0.884   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.243   1.067   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.320  -0.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.714   1.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.791   0.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.869  -1.216   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.475  -2.632   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.004  -2.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.927  -1.582   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.456  -1.764   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.339  -1.034   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.240  -1.613   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.721  -3.063   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.353  -0.355   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.275   0.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.297   2.418   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.064   3.341   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.768   2.873   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.656   1.615   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.185   1.432   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.107   2.665   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.733   0.382   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.686  -0.748   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.043  -2.312   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      15.650  -3.727   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.179  -3.910   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.727  -4.960   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.334  -6.376   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13   27                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16    7                                                       
CONECT   18   13   19   29                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29   26   18   22   30                                             
CONECT   30   29                                                            
CONECT   31    5   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₇

Average Mass

488.6210 Da

Monoisotopic Mass

488.27740 Da

IUPAC Name

7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione

Traditional Name

7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(C)C4C(CC=C3C2)C2C(=O)CC3C(C)OC(C4=O)C23C)OC(C)C1O

InChI Identifier

InChI=1S/C28H40O7/c1-13-18-11-19(29)22-17-7-6-15-10-16(35-21-12-20(32-5)24(30)14(2)33-21)8-9-27(15,3)23(17)25(31)26(34-13)28(18,22)4/h6,13-14,16-18,20-24,26,30H,7-12H2,1-5H3

InChI Key

WOLJVUSLKTUJMB-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
Digitalis purpurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
11-oxosteroid
15-oxosteroid
Oxosteroid
Naphthofuran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Ether
Acetal
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
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	3.43	ALOGPS
logP	2.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	128.06 m³·mol⁻¹	ChemAxon
Polarizability	54.65 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

164605

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione (NP0292677)

MOL for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

3D MOL for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

3D SDF for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

3D-SDF for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

PDB for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

3D PDB for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

SMILES for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

INCHI for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

Structure for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)

3D Structure for NP0292677 (7-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-10,15,19-trimethyl-14-oxapentacyclo[11.5.1.0²,¹¹.0⁵,¹⁰.0¹⁶,¹⁹]nonadec-4-ene-12,18-dione)