NP-MRD: Showing NP-Card for 5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid (NP0255928)

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Record Information

Version

2.0

Created at

2022-09-07 20:35:46 UTC

Updated at

2022-09-07 20:35:46 UTC

NP-MRD ID

NP0255928

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid

Description

5-(Hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid 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. Based on a literature review very few articles have been published on 5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]Trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222352D          

 35 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652309072222352D          

 35 38  0  0  0  0            999 V2000
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0255928

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC=CC=CC1(C)OC(C2C(C)OC3=CC(=O)C(C)(O)C4=C3C2OC(C)C4C)=C(C(O)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-7-8-9-10-11-26(5)24(29)20(25(30)31)23(35-26)18-15(4)33-16-12-17(28)27(6,32)21-13(2)14(3)34-22(18)19(16)21/h8-15,18,22,32H,7H2,1-6H3,(H,30,31)

> <INCHI_KEY>
UGTPPMCFRXTUNF-UHFFFAOYSA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.41827192485755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid

> <JCHEM_LOGP>
2.751337521

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.267876876388989

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.338398924390629

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8399812877343384

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
132.4809

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0     -12.940   5.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.433   5.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.957   3.789   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.451   3.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.975   2.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.469   1.684   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.438   2.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.684   3.733   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -5.408   1.684   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.184   1.273   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.194   2.987   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.162   3.842   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.018   4.872   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.338   6.378   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.553   4.396   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.668   4.162   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.295   5.569   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   34                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   28                                                  
CONECT   23   22   15   24                                                  
CONECT   24   23   11   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29                                                  
CONECT   29   28                                                            
CONECT   30   10   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   30    7   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
5-(Hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0,]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylate	Generator

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxo-4,5-dihydrofuran-3-carboxylic acid

Traditional Name

5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0^{5,13}]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC=CC=CC1(C)OC(C2C(C)OC3=CC(=O)C(C)(O)C4=C3C2OC(C)C4C)=C(C(O)=O)C1=O

InChI Identifier

InChI=1S/C27H32O8/c1-7-8-9-10-11-26(5)24(29)20(25(30)31)23(35-26)18-15(4)33-16-12-17(28)27(6,32)21-13(2)14(3)34-22(18)19(16)21/h8-15,18,22,32H,7H2,1-6H3,(H,30,31)

InChI Key

UGTPPMCFRXTUNF-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

Not Available

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

Pyran
Oxane
3-furanone
Acyloin
Vinylogous ester
Tertiary alcohol
Dihydrofuran
Cyclic ketone
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.75	ChemAxon
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.48 m³·mol⁻¹	ChemAxon
Polarizability	51.42 Å³	ChemAxon
Number of Rings	4	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

163059117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid (NP0255928)

MOL for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

3D MOL for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

3D SDF for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

3D-SDF for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

PDB for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

3D PDB for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

SMILES for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

INCHI for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

Structure for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)

3D Structure for NP0255928 (5-(hexa-1,3-dien-1-yl)-2-{10-hydroxy-3,7,8,10-tetramethyl-11-oxo-2,6-dioxatricyclo[7.3.1.0⁵,¹³]trideca-1(12),9(13)-dien-4-yl}-5-methyl-4-oxofuran-3-carboxylic acid)