NP-MRD: Showing NP-Card for (1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione (NP0216950)

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Record Information

Version

2.0

Created at

2022-09-05 17:07:08 UTC

Updated at

2022-09-05 17:07:08 UTC

NP-MRD ID

NP0216950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione

Description

CHEMBL403494 belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione is found in Ekebergia capensis. Based on a literature review very few articles have been published on CHEMBL403494.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219072D          

 32 37  0  0  1  0            999 V2000
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    3.6850    0.2566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052219072D          

 32 37  0  0  1  0            999 V2000
    5.4731    1.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0216950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=CC=CO3)[C@@]2(C)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O6/c1-22(2)16-13-18(28)25(5)15(23(16,3)10-9-17(22)27)8-11-24(4)19(14-7-6-12-30-14)31-21(29)20-26(24,25)32-20/h6-7,9-10,12,15-16,19-20H,8,11,13H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1

> <INCHI_KEY>
IOKOUNZOTKHZGX-OASIGRBWSA-N

> <FORMULA>
C26H30O6

> <MOLECULAR_WEIGHT>
438.52

> <EXACT_MASS>
438.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.304967740851836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,7R,8S,11R,12S,17R)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15,19-trione

> <JCHEM_LOGP>
4.342387731999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.723586662702477

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9106436300661236

> <JCHEM_POLAR_SURFACE_AREA>
86.11000000000001

> <JCHEM_REFRACTIVITY>
114.89670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,7R,8S,11R,12S,17R)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15,19-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      10.216   3.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.227   2.886   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.206  -3.403   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.277  -4.632   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.178  -4.128   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.148  -2.588   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.350   2.516   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   32                                             
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   21   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30   32                                                       
CONECT   32   31   30   19   14                                             
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₆

Average Mass

438.5200 Da

Monoisotopic Mass

438.20424 Da

IUPAC Name

(1R,2R,4S,7R,8S,11R,12S,17R)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15,19-trione

Traditional Name

(1R,2R,4S,7R,8S,11R,12S,17R)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-ene-5,15,19-trione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2CC(=O)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=CC=CO3)[C@@]2(C)C=CC1=O

InChI Identifier

InChI=1S/C26H30O6/c1-22(2)16-13-18(28)25(5)15(23(16,3)10-9-17(22)27)8-11-24(4)19(14-7-6-12-30-14)31-21(29)20-26(24,25)32-20/h6-7,9-10,12,15-16,19-20H,8,11,13H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1

InChI Key

IOKOUNZOTKHZGX-OASIGRBWSA-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
Ekebergia capensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
1,4-dioxepane
Delta valerolactone
Cyclohexenone
Dioxepane
Delta_valerolactone
Pyran
Oxane
Heteroaromatic compound
Furan
Carboxylic acid ester
Ketone
Cyclic ketone
Lactone
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	4.34	ChemAxon
pKa (Strongest Acidic)	18.72	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.11 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.9 m³·mol⁻¹	ChemAxon
Polarizability	46.3 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

23314718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44448283

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione (NP0216950)

MOL for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

3D MOL for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

3D SDF for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

3D-SDF for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

PDB for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

3D PDB for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

SMILES for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

INCHI for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

Structure for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)

3D Structure for NP0216950 ((1r,2r,4s,7r,8s,11r,12s,17r)-7-(furan-2-yl)-1,8,12,16,16-pentamethyl-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-ene-5,15,19-trione)