NP-MRD: Showing NP-Card for 9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate (NP0314312)

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Record Information

Version

2.0

Created at

2022-09-11 12:20:54 UTC

Updated at

2022-09-11 12:20:54 UTC

NP-MRD ID

NP0314312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate

Description

2-Formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-3-yl acetate 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. 2-Formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181502432D          

 34 38  0  0  0  0            999 V2000
   -1.1199    2.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4002    1.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8683    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5 32  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004181502432D          

 34 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0314312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(O)CC2(O)CCC3C(CCC4(C)C(CCC34O)C3=COC(=O)C=C3)C12C=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-15(28)34-21-11-17(29)12-24(31)9-6-20-19(25(21,24)14-27)5-8-23(2)18(7-10-26(20,23)32)16-3-4-22(30)33-13-16/h3-4,13-14,17-21,29,31-32H,5-12H2,1-2H3

> <INCHI_KEY>
RKMAEUSVJAICNS-UHFFFAOYSA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.71797405476398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-3-yl acetate

> <ALOGPS_LOGP>
1.30

> <JCHEM_LOGP>
0.21526441666666615

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.217145838081581

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.98348005872312

> <JCHEM_PKA_STRONGEST_BASIC>
0.2958399979706273

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
121.38839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-formyl-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -2.090   3.982   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.614   2.534   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.130   2.263   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.621   1.357   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.198  -4.166   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.246   3.352   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.771   3.142   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.716   4.357   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.352   1.715   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.739   1.715   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   32                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   14   18   24                                             
CONECT   24   23                                                            
CONECT   25   20   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
CONECT   32   15    5   10   33                                             
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
2-Formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0,.0,]heptadecan-3-yl acetic acid	Generator
2-Formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5500 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

2-formyl-5,7,11-trihydroxy-15-methyl-14-(2-oxo-2H-pyran-5-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-3-yl acetate

Traditional Name

2-formyl-5,7,11-trihydroxy-15-methyl-14-(6-oxopyran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(O)CC2(O)CCC3C(CCC4(C)C(CCC34O)C3=COC(=O)C=C3)C12C=O

InChI Identifier

InChI=1S/C26H34O8/c1-15(28)34-21-11-17(29)12-24(31)9-6-20-19(25(21,24)14-27)5-8-23(2)18(7-10-26(20,23)32)16-3-4-22(30)33-13-16/h3-4,13-14,17-21,29,31-32H,5-12H2,1-2H3

InChI Key

RKMAEUSVJAICNS-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 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
19-oxosteroid
3-hydroxysteroid
14-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
Pyranone
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Aldehyde
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	1.3	ALOGPS
logP	0.22	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.39 m³·mol⁻¹	ChemAxon
Polarizability	49.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

73833576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate (NP0314312)

MOL for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

3D MOL for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

3D SDF for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

3D-SDF for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

PDB for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

3D PDB for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

SMILES for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

INCHI for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

Structure for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)

3D Structure for NP0314312 (9a-formyl-3a,5a,7-trihydroxy-11a-methyl-1-(6-oxopyran-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-9-yl acetate)