NP-MRD: Showing NP-Card for [7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid (NP0289383)

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Record Information

Version

2.0

Created at

2022-09-09 19:32:50 UTC

Updated at

2022-09-09 19:32:50 UTC

NP-MRD ID

NP0289383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid

Description

2-[7-(Furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]Octadecan-13-yl]acetic acid belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. [7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid is found in Citrus sudachi. 2-[7-(Furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]Octadecan-13-yl]acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251503462D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251503462D          

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M  END
> <DATABASE_ID>
NP0289383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC(CC(O)=O)C2(C)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O8/c1-22(2)15-10-16(27)25(5)14(24(15,4)17(33-22)11-18(28)29)6-8-23(3)19(13-7-9-31-12-13)32-21(30)20-26(23,25)34-20/h7,9,12,14-15,17,19-20H,6,8,10-11H2,1-5H3,(H,28,29)

> <INCHI_KEY>
HEKGWBIGPAUHQK-UHFFFAOYSA-N

> <FORMULA>
C26H32O8

> <MOLECULAR_WEIGHT>
472.534

> <EXACT_MASS>
472.20971799

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.5429847025913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.073491172999998

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.9812022024484

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.132013608001409

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8525521489537415

> <JCHEM_POLAR_SURFACE_AREA>
115.57000000000001

> <JCHEM_REFRACTIVITY>
116.4367

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.453   2.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.826   3.340   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.365   0.325   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.040  -2.078   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.348  -2.891   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.298  -4.431   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.706  -2.165   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.505  -1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.896   3.938   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.254   2.848   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.803  -1.856   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.182   0.499   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.652   3.125   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.373   2.489   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.287  -2.127   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.151  -3.401   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.206  -4.617   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.242  -4.094   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.192  -2.555   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   12                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   16   21   27                                             
CONECT   30   23   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
2-[7-(Furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0,.0,.0,]octadecan-13-yl]acetate	Generator
2-[7-(Furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetate	Generator

Chemical Formula

C₂₆H₃₂O₈

Average Mass

472.5340 Da

Monoisotopic Mass

472.20972 Da

IUPAC Name

2-[7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid

Traditional Name

[7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC1(C)OC(CC(O)=O)C2(C)C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1

InChI Identifier

InChI=1S/C26H32O8/c1-22(2)15-10-16(27)25(5)14(24(15,4)17(33-22)11-18(28)29)6-8-23(3)19(13-7-9-31-12-13)32-21(30)20-26(23,25)34-20/h7,9,12,14-15,17,19-20H,6,8,10-11H2,1-5H3,(H,28,29)

InChI Key

HEKGWBIGPAUHQK-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
Citrus sudachi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
11-oxosteroid
Oxosteroid
2-oxosteroid
Naphthopyran
Naphthalene
Delta valerolactone
Dioxepane
Delta_valerolactone
1,4-dioxepane
Dicarboxylic acid or derivatives
Pyran
Oxane
Tetrahydrofuran
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Lactone
Ether
Oxirane
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.69	ALOGPS
logP	3.07	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.44 m³·mol⁻¹	ChemAxon
Polarizability	48.54 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

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

12309587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid (NP0289383)

MOL for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

3D MOL for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

3D SDF for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

3D-SDF for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

PDB for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

3D PDB for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

SMILES for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

INCHI for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

Structure for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)

3D Structure for NP0289383 ([7-(furan-3-yl)-1,8,12,15,15-pentamethyl-5,18-dioxo-3,6,14-trioxapentacyclo[9.7.0.0²,⁴.0²,⁸.0¹²,¹⁶]octadecan-13-yl]acetic acid)