NP-MRD: Showing NP-Card for 5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one (NP0253699)

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Record Information

Version

2.0

Created at

2022-09-07 17:38:49 UTC

Updated at

2022-09-07 17:38:49 UTC

NP-MRD ID

NP0253699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one

Description

3Beta-Methoxy-12beta,14-dihydroxybufa-4,20,22-trienolide 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-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one is found in Drimia maritima. Based on a literature review a small amount of articles have been published on 3beta-Methoxy-12beta,14-dihydroxybufa-4,20,22-trienolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219382D          

 30 34  0  0  1  0            999 V2000
   -3.5850   -0.4847    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
   -2.2411   -0.9702    0.0000 C   0  0  2  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
   -0.3653   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1953   -0.5346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4756    0.2414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.3866    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5680    1.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195   -0.2441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1794    0.4982    0.0000 C   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


  Mrv1652309072219382D          

 30 34  0  0  1  0            999 V2000
   -3.5850   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0253699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@H](CC[C@]4(O)[C@@H]3CCC2=C1)C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O5/c1-23-10-8-17(29-3)12-16(23)5-6-19-20(23)13-21(26)24(2)18(9-11-25(19,24)28)15-4-7-22(27)30-14-15/h4,7,12,14,17-21,26,28H,5-6,8-11,13H2,1-3H3/t17-,18+,19+,20-,21+,23-,24-,25-/m0/s1

> <INCHI_KEY>
LJZHYURIHAAOET-ZPTBPFKNSA-N

> <FORMULA>
C25H34O5

> <MOLECULAR_WEIGHT>
414.542

> <EXACT_MASS>
414.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.92936911192491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,2R,5S,10R,11S,14S,15S,16R)-11,16-dihydroxy-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2H-pyran-2-one

> <JCHEM_LOGP>
2.439404919

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.805017390260392

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.966691950116427

> <JCHEM_PKA_STRONGEST_BASIC>
-2.976552048503253

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
115.45139999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,2R,5S,10R,11S,14S,15S,16R)-11,16-dihydroxy-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.692  -0.905   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.699  -2.082   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.183  -1.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.191  -2.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.675  -2.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.682  -3.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.834  -3.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.357  -2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.365  -0.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.888   0.451   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.404   0.722   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.927   2.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.396  -0.456   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.068   0.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.936  -0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.881   0.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.301   2.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.246   3.352   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.771   3.142   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.716   4.357   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.352   1.715   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.406   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.364  -1.985   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.089  -2.849   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.873  -1.904   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.504  -3.399   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.151  -1.269   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.628   0.179   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.144  -0.092   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.660  -0.363   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   16                                                       
CONECT   23   15   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   13   26                                             
CONECT   26   25                                                            
CONECT   27    9    5   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    3                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
3b-Methoxy-12b,14-dihydroxybufa-4,20,22-trienolide	Generator
3Β-methoxy-12β,14-dihydroxybufa-4,20,22-trienolide	Generator

Chemical Formula

C₂₅H₃₄O₅

Average Mass

414.5420 Da

Monoisotopic Mass

414.24062 Da

IUPAC Name

5-[(1S,2R,5S,10R,11S,14S,15S,16R)-11,16-dihydroxy-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2H-pyran-2-one

Traditional Name

5-[(1S,2R,5S,10R,11S,14S,15S,16R)-11,16-dihydroxy-5-methoxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@]4(C)[C@H](CC[C@]4(O)[C@@H]3CCC2=C1)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C25H34O5/c1-23-10-8-17(29-3)12-16(23)5-6-19-20(23)13-21(26)24(2)18(9-11-25(19,24)28)15-4-7-22(27)30-14-15/h4,7,12,14,17-21,26,28H,5-6,8-11,13H2,1-3H3/t17-,18+,19+,20-,21+,23-,24-,25-/m0/s1

InChI Key

LJZHYURIHAAOET-ZPTBPFKNSA-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
Drimia maritima	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
12-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Pyranone
Pyran
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Secondary alcohol
Lactone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	2.44	ChemAxon
pKa (Strongest Acidic)	13.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	115.45 m³·mol⁻¹	ChemAxon
Polarizability	45.93 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

101101717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one (NP0253699)

MOL for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

3D MOL for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

3D SDF for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

3D-SDF for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

PDB for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

3D PDB for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

SMILES for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

INCHI for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

Structure for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)

3D Structure for NP0253699 (5-[(1r,3as,3br,7s,9ar,9bs,11r,11as)-3a,11-dihydroxy-7-methoxy-9a,11a-dimethyl-1h,2h,3h,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]pyran-2-one)