NP-MRD: Showing NP-Card for 1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione (NP0209311)

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Record Information

Version

2.0

Created at

2022-09-05 06:40:11 UTC

Updated at

2022-09-05 06:40:11 UTC

NP-MRD ID

NP0209311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione

Description

14-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-3,6-dione belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. 1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione is found in Physalis viscosa. 14-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-3,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201506242D          

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M  END

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  Mrv1533004201506242D          

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  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209311

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC=C4C(=O)CCC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O7/c1-15-14-22(35-23(31)16(15)2)26(5,32)28(34)13-12-27(33)18-6-7-19-20(29)8-9-21(30)25(19,4)17(18)10-11-24(27,28)3/h7,17-18,22,32-34H,6,8-14H2,1-5H3

> <INCHI_KEY>
XIQHFYLSBZLWQD-UHFFFAOYSA-N

> <FORMULA>
C28H38O7

> <MOLECULAR_WEIGHT>
486.605

> <EXACT_MASS>
486.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.60856184107621

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-3,6-dione

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.6954242403333337

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.83569252335666

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.71706099468333

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2035513858775975

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
129.48219999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       0.133  -8.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.656  -6.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.336  -5.731   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.852  -6.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.187  -4.283   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.806  -3.106   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.703  -4.012   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.696  -5.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.172  -6.638   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.211  -4.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.483  -6.434   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.940  -3.402   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.839  -6.183   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    2                                                       
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   34                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   34                                             
CONECT   18   17                                                            
CONECT   19   17   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   22   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   19   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   13   17   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₇

Average Mass

486.6050 Da

Monoisotopic Mass

486.26175 Da

IUPAC Name

14-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-3,6-dione

Traditional Name

14-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-11,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC=C4C(=O)CCC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H38O7/c1-15-14-22(35-23(31)16(15)2)26(5,32)28(34)13-12-27(33)18-6-7-19-20(29)8-9-21(30)25(19,4)17(18)10-11-24(27,28)3/h7,17-18,22,32-34H,6,8-14H2,1-5H3

InChI Key

XIQHFYLSBZLWQD-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
Physalis viscosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
20-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
4-oxosteroid
17-hydroxysteroid
Delta-5-steroid
Dihydropyranone
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Lactone
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
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	2.43	ALOGPS
logP	2.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.48 m³·mol⁻¹	ChemAxon
Polarizability	52.61 Å³	ChemAxon
Number of Rings	5	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

73800703

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione (NP0209311)

MOL for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

3D MOL for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

3D SDF for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

3D-SDF for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

PDB for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

3D PDB for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

SMILES for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

INCHI for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

Structure for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)

3D Structure for NP0209311 (1-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-1,3a-dihydroxy-9a,11a-dimethyl-2h,3h,3bh,4h,7h,8h,9bh,10h,11h-cyclopenta[a]phenanthrene-6,9-dione)