NP-MRD: Showing NP-Card for methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate (NP0309744)

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Record Information

Version

2.0

Created at

2022-09-11 04:33:19 UTC

Updated at

2022-09-11 04:33:19 UTC

NP-MRD ID

NP0309744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate

Description

Methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-3,6-dihydro-2H-pyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate is found in Talaromyces wortmannii. Based on a literature review very few articles have been published on methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-3,6-dihydro-2H-pyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112206332D          

 33 34  0  0  1  0            999 V2000
    1.6640   -7.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509   -6.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0947   -7.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3468   -6.3271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1753   -5.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -6.5820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  7 13  1  0  0  0  0
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 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309112206332D          

 33 34  0  0  1  0            999 V2000
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 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 24 22  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0309744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](C)[C@@H]1OC(=O)[C@H](C)[C@@]1(C)\C=C\C=C\C=C\C=C(/C)[C@@H]1O[C@@H](C)C(C)=C[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O6/c1-17(22-27(7,30)16-18(2)21(5)32-22)14-12-10-9-11-13-15-26(6)20(4)25(29)33-23(26)19(3)24(28)31-8/h9-16,19-23,30H,1-8H3/b11-9+,12-10+,15-13+,17-14+/t19-,20+,21+,22+,23+,26-,27-/m1/s1

> <INCHI_KEY>
IQUZSSIAEVCETL-FKIVWCGPSA-N

> <FORMULA>
C27H38O6

> <MOLECULAR_WEIGHT>
458.595

> <EXACT_MASS>
458.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.484309726006565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-3,6-dihydro-2H-pyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate

> <JCHEM_LOGP>
4.339369843999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.58482658494529

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4177968517449298

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
132.9537

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.106 -13.396   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.962 -12.365   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.497 -12.841   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.177 -14.347   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.647 -11.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.327 -10.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.112 -12.286   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.588 -13.751   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.128 -13.751   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.033 -14.997   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.604 -12.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.068 -11.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.358 -11.381   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.114 -10.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.602 -10.040   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.062 -10.023   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.306  -8.682   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.234  -8.666   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.990  -7.324   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.530  -7.308   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.286  -5.966   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.826  -5.950   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.610  -7.276   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.582  -4.608   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.798  -3.283   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.554  -1.941   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.770  -0.616   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.094  -1.925   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.850  -0.583   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.878  -3.251   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.122  -4.592   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.436  -5.395   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.191  -6.131   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   24   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-3,6-dihydro-2H-pyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoic acid	Generator

Chemical Formula

C₂₇H₃₈O₆

Average Mass

458.5950 Da

Monoisotopic Mass

458.26684 Da

IUPAC Name

methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-3,6-dihydro-2H-pyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate

Traditional Name

methyl (2R)-2-[(2S,3R,4R)-3-[(1E,3E,5E,7E)-8-[(2S,3R,6S)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](C)[C@@H]1OC(=O)[C@H](C)[C@@]1(C)\C=C\C=C\C=C\C=C(/C)[C@@H]1O[C@@H](C)C(C)=C[C@@]1(C)O

InChI Identifier

InChI=1S/C27H38O6/c1-17(22-27(7,30)16-18(2)21(5)32-22)14-12-10-9-11-13-15-26(6)20(4)25(29)33-23(26)19(3)24(28)31-8/h9-16,19-23,30H,1-8H3/b11-9+,12-10+,15-13+,17-14+/t19-,20+,21+,22+,23+,26-,27-/m1/s1

InChI Key

IQUZSSIAEVCETL-FKIVWCGPSA-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
Talaromyces wortmannii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Tertiary alcohol
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	4.34	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.95 m³·mol⁻¹	ChemAxon
Polarizability	52.48 Å³	ChemAxon
Number of Rings	2	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

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

162923970

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate (NP0309744)

MOL for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

3D MOL for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

3D SDF for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

3D-SDF for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

PDB for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

3D PDB for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

SMILES for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

INCHI for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

Structure for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)

3D Structure for NP0309744 (methyl (2r)-2-[(2s,3r,4r)-3-[(1e,3e,5e,7e)-8-[(2s,3r,6s)-3-hydroxy-3,5,6-trimethyl-2,6-dihydropyran-2-yl]nona-1,3,5,7-tetraen-1-yl]-3,4-dimethyl-5-oxooxolan-2-yl]propanoate)