NP-MRD: Showing NP-Card for (1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate (NP0327968)

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Record Information

Version

2.0

Created at

2022-09-12 11:01:02 UTC

Updated at

2022-09-12 11:01:02 UTC

NP-MRD ID

NP0327968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate

Description

WQFOPIVURAPREB-ZCOBHXJYSA- belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. (1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate is found in Anodendron affine. Based on a literature review very few articles have been published on WQFOPIVURAPREB-ZCOBHXJYSA-.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213012D          

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M  END

     RDKit          3D

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  Mrv1652309122213012D          

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 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  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  1  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](OC(C)=O)[C@@H](O)C[C@]4(C)[C@H]3C(=O)C[C@]2(C)[C@H]1C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O9/c1-13(28)35-20-8-16-5-6-17-24(25(16,3)9-18(20)30)19(31)10-26(4)23(15-7-22(32)34-12-15)21(36-14(2)29)11-27(17,26)33/h7,16-18,20-21,23-24,30,33H,5-6,8-12H2,1-4H3/t16-,17-,18+,20-,21+,23+,24-,25+,26-,27+/m1/s1

> <INCHI_KEY>
WQFOPIVURAPREB-ZCOBHXJYSA-N

> <FORMULA>
C27H36O9

> <MOLECULAR_WEIGHT>
504.576

> <EXACT_MASS>
504.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.45658142632517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,7R,10R,11S,13S,14R,15R)-5-(acetyloxy)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_LOGP>
0.5698924543333321

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.796578857073683

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.814117995381067

> <JCHEM_PKA_STRONGEST_BASIC>
-3.167435928626535

> <JCHEM_POLAR_SURFACE_AREA>
136.43

> <JCHEM_REFRACTIVITY>
125.5213

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,7R,10R,11S,13S,14R,15R)-5-(acetyloxy)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.757  -0.136   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.580  -1.129   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.132  -0.605   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.832  -5.696   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      18.871  -3.977   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   28                                             
CONECT    8    7                                                            
CONECT    9    7   10   24                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   12   23   24                                             
CONECT   23   22                                                            
CONECT   24   22    9   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    7   29   30                                             
CONECT   29   28                                                            
CONECT   30   28    5   31                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₉

Average Mass

504.5760 Da

Monoisotopic Mass

504.23593 Da

IUPAC Name

(1S,2S,4S,5R,7R,10R,11S,13S,14R,15R)-5-(acetyloxy)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

Traditional Name

(1S,2S,4S,5R,7R,10R,11S,13S,14R,15R)-5-(acetyloxy)-4,11-dihydroxy-2,15-dimethyl-17-oxo-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](OC(C)=O)[C@@H](O)C[C@]4(C)[C@H]3C(=O)C[C@]2(C)[C@H]1C1=CC(=O)OC1

InChI Identifier

InChI=1S/C27H36O9/c1-13(28)35-20-8-16-5-6-17-24(25(16,3)9-18(20)30)19(31)10-26(4)23(15-7-22(32)34-12-15)21(36-14(2)29)11-27(17,26)33/h7,16-18,20-21,23-24,30,33H,5-6,8-12H2,1-4H3/t16-,17-,18+,20-,21+,23+,24-,25+,26-,27+/m1/s1

InChI Key

WQFOPIVURAPREB-ZCOBHXJYSA-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
Anodendron affine	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-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

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
Steroid ester
2-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
Tricarboxylic acid or derivatives
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	0.57	ChemAxon
pKa (Strongest Acidic)	6.81	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	136.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.52 m³·mol⁻¹	ChemAxon
Polarizability	52.46 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

10270271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate (NP0327968)

MOL for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

3D MOL for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

3D SDF for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

3D-SDF for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

PDB for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

3D PDB for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

SMILES for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

INCHI for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

Structure for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)

3D Structure for NP0327968 ((1r,2s,3as,3br,5ar,7r,8s,9as,9bs,11ar)-7-(acetyloxy)-3a,8-dihydroxy-9a,11a-dimethyl-10-oxo-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-2-yl acetate)