NP-MRD: Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one (NP0243335)

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Record Information

Version

2.0

Created at

2022-09-07 03:51:50 UTC

Updated at

2022-09-07 03:51:51 UTC

NP-MRD ID

NP0243335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

Description

4Beta-Hydroxywithanolide E 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. Thus, 4beta-hydroxywithanolide e is considered to be a sterol lipid molecule. 4Beta-Hydroxywithanolide E is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4beta-hydroxywithanolide e has been detected, but not quantified in, fruits. 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one is found in Physalis cinerascens, Physalis peruviana and Physalis viscosa. This could make 4beta-hydroxywithanolide e a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307322D          

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M  END

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M  END


  Mrv0541 05061307322D          

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 11 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14 12  1  0  0  0  0
 15  2  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 15  1  0  0  0  0
 23  3  1  0  0  0  0
 23  9  1  0  0  0  0
 24  4  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
 25  5  1  0  0  0  0
 25 20  1  0  0  0  0
 26 10  1  0  0  0  0
 26 17  1  0  0  0  0
 26 23  1  0  0  0  0
 27 11  1  0  0  0  0
 27 23  1  0  0  0  0
 27 25  1  0  0  0  0
 28 19  1  0  0  0  0
 28 21  1  0  0  0  0
 28 24  1  0  0  0  0
 29 18  2  0  0  0  0
 30 19  1  0  0  0  0
 31 22  2  0  0  0  0
 32 25  1  0  0  0  0
 33 26  1  0  0  0  0
 34 27  1  0  0  0  0
 35 20  1  0  0  0  0
 35 22  1  0  0  0  0
 36 21  1  0  0  0  0
 36 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,8-13H2,1-5H3

> <INCHI_KEY>
UPBUGICUKQIKTJ-UHFFFAOYSA-N

> <FORMULA>
C28H38O8

> <MOLECULAR_WEIGHT>
502.5965

> <EXACT_MASS>
502.256668192

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
53.557253918182916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.7746146259999995

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.371491467248873

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.642618878036064

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2010147477534394

> <JCHEM_POLAR_SURFACE_AREA>
136.82

> <JCHEM_REFRACTIVITY>
129.61929999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      16.469   6.914   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.773   9.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.450   5.758   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.692   3.368   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.324   4.584   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.037   1.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.049   0.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.019   4.148   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.346   4.929   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.167   2.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.062   3.419   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.871   6.312   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.384   0.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.996   7.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.648   8.863   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.031   2.608   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.371   1.849   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.364   2.587   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.389  -0.493   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.397   6.760   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.056  -0.471   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.175   9.312   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.686   4.170   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.704   1.828   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.272   5.709   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.699   2.630   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.147   4.658   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.716   0.288   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.352   4.127   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.401  -2.033   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      12.827  10.812   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      10.221   6.834   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.872   1.100   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       9.556   6.110   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.050   8.260   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       4.729  -1.252   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   15                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   25                                                            
CONECT    6    7   18                                                       
CONECT    7    6   19                                                       
CONECT    8    9   16                                                       
CONECT    9    8   23                                                       
CONECT   10   11   26                                                       
CONECT   11   10   27                                                       
CONECT   12   14   20                                                       
CONECT   13   17   21                                                       
CONECT   14    1   12   15                                                  
CONECT   15    2   14   22                                                  
CONECT   16    8   17   24                                                  
CONECT   17   13   16   26                                                  
CONECT   18    6   24   29                                                  
CONECT   19    7   28   30                                                  
CONECT   20   12   25   35                                                  
CONECT   21   13   28   36                                                  
CONECT   22   15   31   35                                                  
CONECT   23    3    9   26   27                                             
CONECT   24    4   16   18   28                                             
CONECT   25    5   20   27   32                                             
CONECT   26   10   17   23   33                                             
CONECT   27   11   23   25   34                                             
CONECT   28   19   21   24   36                                             
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   22                                                            
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   20   22                                                       
CONECT   36   21   28                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
4b-Hydroxywithanolide e	Generator
4Β-hydroxywithanolide e	Generator
4-b-HYDROXY-withanolide e	HMDB
4-beta-Hydroxy-withanolide e	HMDB
4-beta-Hydroxywithanolide e	HMDB
5,6b-Epoxy-4b,14a,17b,20S-tetrahydroxy-1-oxo-5b,22R-witha-2,24-dienolide	HMDB

Chemical Formula

C₂₈H₃₈O₈

Average Mass

502.5965 Da

Monoisotopic Mass

502.25667 Da

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C28H38O8/c1-14-12-20(35-22(31)15(14)2)25(5,32)27(34)11-10-26(33)17-13-21-28(36-21)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30,32-34H,8-13H2,1-5H3

InChI Key

UPBUGICUKQIKTJ-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 cinerascens	LOTUS Database	35616633
Physalis peruviana	LOTUS Database	35616633
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
5,6-epoxysteroid
Dihydropyranone
Oxepane
Cyclohexenone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Polyol
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	0.95	ALOGPS
logP	1.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.64	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.62 m³·mol⁻¹	ChemAxon
Polarizability	53.56 Å³	ChemAxon
Number of Rings	6	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

HMDB0034059

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012308

KNApSAcK ID

Not Available

Chemspider ID

3061871

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3836120

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one (NP0243335)

MOL for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D MOL for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D SDF for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D-SDF for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

PDB for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D PDB for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

SMILES for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

INCHI for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

Structure for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)

3D Structure for NP0243335 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one)