NP-MRD: Showing NP-Card for 2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol (NP0267548)

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Record Information

Version

2.0

Created at

2022-09-08 12:21:47 UTC

Updated at

2022-09-08 12:21:47 UTC

NP-MRD ID

NP0267548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

Description

Piericidin C belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on Piericidin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214212D          

 33 34  0  0  0  0            999 V2000
    4.8347   10.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6100   10.0290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7532    9.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5285    8.9343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6717    8.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4470    7.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5902    7.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3655    6.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9975    7.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5088    5.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8768    5.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1015    5.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4695    5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6128    4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943    5.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0623    4.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2056    4.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871    5.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    6.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551    4.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0231    5.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676    3.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2426    3.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    3.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8136    3.9434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0398    7.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1830    6.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2645    7.8737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6325    7.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1212    8.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3460    8.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027    9.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
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 18 19  1  0  0  0  0
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 20 21  1  0  0  0  0
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 22 23  1  0  0  0  0
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 23 24  1  0  0  0  0
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  5 27  2  0  0  0  0
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 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

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    8.2715    0.7073    1.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5298   -0.1502    2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4261    0.2512    0.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3392   -0.4089   -2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082214212D          

 33 34  0  0  0  0            999 V2000
    4.8347   10.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=NC(C\C=C(/C)C\C=C\C(\C)=C\C(C)C(O)C2(C)OC2C(C)C)=C(C)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO5/c1-16(2)25-27(7,33-25)24(30)19(5)15-18(4)12-10-11-17(3)13-14-21-20(6)22(29)23(31-8)26(28-21)32-9/h10,12-13,15-16,19,24-25,30H,11,14H2,1-9H3,(H,28,29)/b12-10+,17-13+,18-15+

> <INCHI_KEY>
UAGQCXVZFVQITG-VVNSMQMESA-N

> <FORMULA>
C27H41NO5

> <MOLECULAR_WEIGHT>
459.627

> <EXACT_MASS>
459.298473424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.34002678311859

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E,5E,7E)-10-hydroxy-3,7,9-trimethyl-10-[2-methyl-3-(propan-2-yl)oxiran-2-yl]deca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

> <JCHEM_LOGP>
5.447932176999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.661302228395904

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.905232087189333

> <JCHEM_PKA_STRONGEST_BASIC>
1.9352439702042679

> <JCHEM_POLAR_SURFACE_AREA>
84.34

> <JCHEM_REFRACTIVITY>
134.97109999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E,5E,7E)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.025  19.247   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.472  18.721   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.739  17.204   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      12.186  16.677   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      12.454  15.161   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.901  14.634   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.168  13.117   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.616  12.591   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.795  13.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.883  11.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.703  10.084   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.256  10.611   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.076   9.621   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.344   8.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.629  10.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.450   9.158   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.717   7.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   9.685   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.735  11.201   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.823   8.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.643   9.685   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.593   7.361   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.053   7.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.719   6.591   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.719   5.051   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.385   7.361   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.274  14.171   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.542  12.654   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.827  14.698   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.647  13.708   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.560  16.214   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.113  16.741   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.845  18.258   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   20   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    5   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₅

Average Mass

459.6270 Da

Monoisotopic Mass

459.29847 Da

IUPAC Name

2-[(2E,5E,7E)-10-hydroxy-3,7,9-trimethyl-10-[2-methyl-3-(propan-2-yl)oxiran-2-yl]deca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

Traditional Name

2-[(2E,5E,7E)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol

CAS Registry Number

Not Available

SMILES

COC1=NC(C\C=C(/C)C\C=C\C(\C)=C\C(C)C(O)C2(C)OC2C(C)C)=C(C)C(O)=C1OC

InChI Identifier

InChI=1S/C27H41NO5/c1-16(2)25-27(7,33-25)24(30)19(5)15-18(4)12-10-11-17(3)13-14-21-20(6)22(29)23(31-8)26(28-21)32-9/h10,12-13,15-16,19,24-25,30H,11,14H2,1-9H3,(H,28,29)/b12-10+,17-13+,18-15+

InChI Key

UAGQCXVZFVQITG-VVNSMQMESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alkyl aryl ether
Dihydropyridine
Methylpyridine
Hydropyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous ester
Secondary alcohol
Cyclic ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.45	ChemAxon
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	1.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.34 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.97 m³·mol⁻¹	ChemAxon
Polarizability	52.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

4947082

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol (NP0267548)

MOL for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

3D MOL for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

3D SDF for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

3D-SDF for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

PDB for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

3D PDB for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

SMILES for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

INCHI for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

Structure for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)

3D Structure for NP0267548 (2-[(2e,5e,7e)-10-hydroxy-10-(3-isopropyl-2-methyloxiran-2-yl)-3,7,9-trimethyldeca-2,5,7-trien-1-yl]-5,6-dimethoxy-3-methylpyridin-4-ol)