NP-MRD: Showing NP-Card for 6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0215457)

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Record Information

Version

2.0

Created at

2022-09-05 15:05:23 UTC

Updated at

2022-09-05 15:05:23 UTC

NP-MRD ID

NP0215457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

Description

4-Deoxyphysalolactone 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. 4-Deoxyphysalolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-deoxyphysalolactone has been detected, but not quantified in, fruits. 6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one is found in Physalis peruviana and Withania somnifera. This could make 4-deoxyphysalolactone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212002D          

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M  END

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M  END


  Mrv0541 02241212002D          

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    3.6066    0.9510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052    2.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1755    3.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 21  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 22  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 24  1  0  0  0  0
 17 33  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 32  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 34  2  0  0  0  0
 30 31  2  0  0  0  0
 30 35  1  0  0  0  0
 31 32  1  0  0  0  0
 31 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)CC=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H39ClO7/c1-15-13-21(36-22(31)16(15)2)25(5,32)28(35)12-11-26(33)18-14-19(29)27(34)9-6-7-20(30)24(27,4)17(18)8-10-23(26,28)3/h6-7,17-19,21,32-35H,8-14H2,1-5H3

> <INCHI_KEY>
DSFWZSDSZFDOMA-UHFFFAOYSA-N

> <FORMULA>
C28H39ClO7

> <MOLECULAR_WEIGHT>
523.058

> <EXACT_MASS>
522.238431309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
55.23850702339567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.8864990566666657

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.252930699270312

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.601932994422036

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2001338502441907

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
134.97289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.732  -2.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.732  -4.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.398  -4.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.066  -4.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.066  -2.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.398  -1.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.732  -4.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.400  -4.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.400  -2.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.732  -1.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071  -1.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.071  -0.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.400   0.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.732  -0.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.387  -2.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.284  -1.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.387   0.233   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.398  -0.230   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.066  -5.627   0.000  0.00  0.00           O+0
HETATM   20 Cl   UNK     0      -2.732  -6.398   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0      -4.066  -0.999   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.071  -3.315   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.071   1.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.387   1.775   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.050   2.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.724   2.547   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.387   3.318   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.061   1.775   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.395   2.547   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.395   4.087   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.061   4.855   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.724   4.087   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.878   0.631   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.732   1.775   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.730   4.858   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.061   6.398   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10   21                                             
CONECT    6    1    5   18                                                  
CONECT    7    4    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   22                                             
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   24   33                                             
CONECT   18    6                                                            
CONECT   19    4                                                            
CONECT   20    7                                                            
CONECT   21    5                                                            
CONECT   22   11                                                            
CONECT   23   12                                                            
CONECT   24   17   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24   28   32                                                  
CONECT   27   24                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   36                                                  
CONECT   32   26   31                                                       
CONECT   33   17                                                            
CONECT   34   29                                                            
CONECT   35   30                                                            
CONECT   36   31                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
6-Chloro-5,14,17,20-tetrahydroxy-1-oxowitha-2,24-dienolide	HMDB

Chemical Formula

C₂₈H₃₉ClO₇

Average Mass

523.0580 Da

Monoisotopic Mass

522.23843 Da

IUPAC Name

6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-(1-{8-chloro-7,11,14-trihydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(Cl)C4(O)CC=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H39ClO7/c1-15-13-21(36-22(31)16(15)2)25(5,32)28(35)12-11-26(33)18-14-19(29)27(34)9-6-7-20(30)24(27,4)17(18)8-10-23(26,28)3/h6-7,17-19,21,32-35H,8-14H2,1-5H3

InChI Key

DSFWZSDSZFDOMA-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 peruviana	LOTUS Database	35616633
Withania somnifera	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

Not Available

Substituents

Not Available

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	2.28	ALOGPS
logP	2.89	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.6	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	134.97 m³·mol⁻¹	ChemAxon
Polarizability	55.24 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

HMDB0034346

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012707

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

13743195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one (NP0215457)

MOL for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D MOL for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D SDF for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D-SDF for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

PDB for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D PDB for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

SMILES for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

INCHI for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

Structure for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)

3D Structure for NP0215457 (6-(1-{5-chloro-1,3a,5a-trihydroxy-9a,11a-dimethyl-9-oxo-2h,3h,3bh,4h,5h,6h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-1-hydroxyethyl)-3,4-dimethyl-5,6-dihydropyran-2-one)