NP-MRD: Showing NP-Card for (+)-Withanolide A (NP0072567)

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Record Information

Version

2.0

Created at

2022-04-28 17:54:09 UTC

Updated at

2022-04-28 17:54:10 UTC

NP-MRD ID

NP0072567

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Withanolide A

Description

Withanolide a 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, withanolide a is considered to be a sterol. (+)-Withanolide A is found in Discopodium penninervium, Exodeconus maritimus, Lycium chinense , Withania coagulans , Withania somnifera and Withania somnifera DUNAL . Based on a literature review very few articles have been published on Withanolide a.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219542D          

 34 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282219542D          

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M  END
> <DATABASE_ID>
NP0072567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@@H]4[C@@]4(O)CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1

> <INCHI_KEY>
DXWHOKCXBGLTMQ-SFQAJKIESA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
51.68305320824545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
3.7034455059999978

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.85865391456004

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.016008923436715

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3314307765309374

> <JCHEM_POLAR_SURFACE_AREA>
96.36000000000001

> <JCHEM_REFRACTIVITY>
126.9481

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.889   5.740   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.958  -0.689   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.396   6.038   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.828   4.148   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.028   7.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.448   8.740   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.922   8.951   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.342  10.377   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.393   9.956   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.466   0.217   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11   34                                             
CONECT    5    4    6    8   33                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4   12                                                  
CONECT   12   11   10                                                       
CONECT   13    9   14   19                                                  
CONECT   14   13   15   17   32                                             
CONECT   15   14   16                                                       
CONECT   16   15    8                                                       
CONECT   17   14   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20   17   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23                                                       
CONECT   30   26                                                            
CONECT   31   25                                                            
CONECT   32   14                                                            
CONECT   33    5                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
(20R,22R)-O-(3)-alpha-L-Rhamnopyranosyl(1-4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide	MeSH
3-Rhamnopyranosyl(1-4)-glucopyranosyl-12-diacetoxy-20-hydroxywitha-5,24-dienolide	MeSH
Withanolide 1	MeSH

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one

Traditional Name

(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0^{2,4}.0^{5,10}.0^{14,18}]octadec-7-en-9-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3[C@@H]4O[C@@H]4[C@@]4(O)CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C28H38O6/c1-14-13-20(33-24(30)15(14)2)27(5,31)18-9-8-16-21-17(10-12-25(16,18)3)26(4)19(29)7-6-11-28(26,32)23-22(21)34-23/h6-7,16-18,20-23,31-32H,8-13H2,1-5H3/t16-,17-,18-,20+,21-,22-,23-,25-,26-,27+,28-/m0/s1

InChI Key

DXWHOKCXBGLTMQ-SFQAJKIESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Discopodium penninervium	LOTUS Database	35616633
Exodeconus maritimus	-	KNApSAcK
Lycium chinense	Plant	KNApSAcK
Withania coagulans	Plant	KNApSAcK
Withania somnifera	LOTUS Database	35616633
Withania somnifera DUNAL	Plant	KNApSAcK

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
Cyclohexenone
Dihydropyranone
Oxepane
Pyran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
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	2.62	ALOGPS
logP	3.7	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	13.02	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	51.68 Å³	ChemAxon
Number of Rings	6	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

C00032513

Chemspider ID

9469353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11294368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Withanolide A (NP0072567)

MOL for NP0072567 ((+)-Withanolide A)

3D MOL for NP0072567 ((+)-Withanolide A)

3D SDF for NP0072567 ((+)-Withanolide A)

3D-SDF for NP0072567 ((+)-Withanolide A)

PDB for NP0072567 ((+)-Withanolide A)

3D PDB for NP0072567 ((+)-Withanolide A)

SMILES for NP0072567 ((+)-Withanolide A)

INCHI for NP0072567 ((+)-Withanolide A)

Structure for NP0072567 ((+)-Withanolide A)

3D Structure for NP0072567 ((+)-Withanolide A)