NP-MRD: Showing NP-Card for 16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one (NP0327655)

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Record Information

Version

2.0

Created at

2022-09-12 10:26:22 UTC

Updated at

2022-09-12 10:26:23 UTC

NP-MRD ID

NP0327655

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

Description

(14Alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 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 (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (14alpha,17beta,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide has been detected, but not quantified in, fruits. 16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one is found in Withania coagulans. This could make (14alpha,17beta,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209132D          

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  Mrv0541 02241209132D          

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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 32  2  0  0  0  0
 27 28  2  0  0  0  0
 27 31  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327655

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3

> <INCHI_KEY>
KOYNICXFSFFIPU-UHFFFAOYSA-N

> <FORMULA>
C28H36O5

> <MOLECULAR_WEIGHT>
452.5824

> <EXACT_MASS>
452.256274262

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.59744940399742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.1624895173333325

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.354132419117398

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.192701016871212

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5879889332831096

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
126.39549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-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      -7.314  -2.744   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.314  -4.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.980  -5.058   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.648  -4.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.648  -2.744   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.980  -1.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.314  -5.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.982  -4.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.982  -2.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.314  -1.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.653  -1.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.653  -0.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.982   0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.314  -0.441   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.805  -2.449   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.702  -1.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.805   0.029   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.980  -0.433   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.648  -1.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.052   1.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.283   1.495   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.033   1.366   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.252   2.642   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.792   1.814   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.820   0.667   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.327   0.983   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.805   2.446   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.777   3.593   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.267   3.274   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.255   5.058   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.314   2.765   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.358  -0.166   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.373   0.405   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    1    5   18                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   33                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   21   22                                             
CONECT   18    6                                                            
CONECT   19    5                                                            
CONECT   20   12                                                            
CONECT   21   17   23   24   33                                             
CONECT   22   17                                                            
CONECT   23   21                                                            
CONECT   24   21   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   24   28                                                       
CONECT   30   28                                                            
CONECT   31   27                                                            
CONECT   32   26                                                            
CONECT   33   11   21                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
(14a,17b,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	Generator
(14Α,17β,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	Generator

Chemical Formula

C₂₈H₃₆O₅

Average Mass

452.5824 Da

Monoisotopic Mass

452.25627 Da

IUPAC Name

16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

Traditional Name

16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C

InChI Identifier

InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3

InChI Key

KOYNICXFSFFIPU-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
Withania coagulans	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	4.32	ALOGPS
logP	4.16	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.4 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	6	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

HMDB0032685

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010642

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

73699089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one (NP0327655)

MOL for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D MOL for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D SDF for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D-SDF for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

PDB for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D PDB for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

SMILES for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

INCHI for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

Structure for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)

3D Structure for NP0327655 (16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one)