NP-MRD: Showing NP-Card for ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate (NP0299965)

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Record Information

Version

2.0

Created at

2022-09-10 12:06:23 UTC

Updated at

2022-09-10 12:06:23 UTC

NP-MRD ID

NP0299965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate

Description

Ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-3-hydroxybutanoate belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate is found in Digitalis purpurea. Based on a literature review very few articles have been published on ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-3-hydroxybutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214062D          

 32 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102214062D          

 32 35  0  0  1  0            999 V2000
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 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 13 31  1  0  0  0  0
 10 31  1  0  0  0  0
 31 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0299965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O5/c1-6-31-24(29)16-27(5,30)23-10-9-21-20-8-7-18-15-19(32-17(2)28)11-13-25(18,3)22(20)12-14-26(21,23)4/h18-23,30H,6-16H2,1-5H3/t18-,19+,20+,21+,22+,23+,25+,26+,27+/m1/s1

> <INCHI_KEY>
UHFCYOHOYMULGY-DVOQQEMGSA-N

> <FORMULA>
C27H44O5

> <MOLECULAR_WEIGHT>
448.644

> <EXACT_MASS>
448.318874517

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.59755640413525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-hydroxybutanoate

> <JCHEM_LOGP>
4.362029311666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.500253444937066

> <JCHEM_PKA_STRONGEST_BASIC>
-3.017389143184528

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
123.27759999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.104  -9.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.366  -8.084   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.731  -5.442   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.871  -3.977   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.832  -5.696   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   31                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   14   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   13   10   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
Ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]-3-hydroxybutanoic acid	Generator

Chemical Formula

C₂₇H₄₄O₅

Average Mass

448.6440 Da

Monoisotopic Mass

448.31887 Da

IUPAC Name

ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-hydroxybutanoate

Traditional Name

ethyl (3S)-3-[(1S,2S,5S,7R,10R,11S,14S,15S)-5-(acetyloxy)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(C)=O

InChI Identifier

InChI=1S/C27H44O5/c1-6-31-24(29)16-27(5,30)23-10-9-21-20-8-7-18-15-19(32-17(2)28)11-13-25(18,3)22(20)12-14-26(21,23)4/h18-23,30H,6-16H2,1-5H3/t18-,19+,20+,21+,22+,23+,25+,26+,27+/m1/s1

InChI Key

UHFCYOHOYMULGY-DVOQQEMGSA-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 monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
Steroid ester
20-hydroxysteroid
Hydroxysteroid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.36	ChemAxon
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	123.28 m³·mol⁻¹	ChemAxon
Polarizability	52.6 Å³	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

162877383

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate (NP0299965)

MOL for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

3D MOL for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

3D SDF for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

3D-SDF for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

PDB for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

3D PDB for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

SMILES for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

INCHI for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

Structure for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)

3D Structure for NP0299965 (ethyl (3s)-3-[(1s,3as,3br,5ar,7s,9as,9bs,11as)-7-(acetyloxy)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-hydroxybutanoate)