NP-MRD: Showing NP-Card for 18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate (NP0188828)

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Record Information

Version

2.0

Created at

2022-09-04 05:13:08 UTC

Updated at

2022-09-04 05:13:08 UTC

NP-MRD ID

NP0188828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate

Description

18-(Furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]Henicosa-1(21),4-dien-11-yl acetate 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. 18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate is found in Citrus aurantium. 18-(Furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]Henicosa-1(21),4-dien-11-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523212D          

 36 41  0  0  0  0            999 V2000
    3.0839    3.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2776    2.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234    3.5545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0253    2.1578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795    1.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3858    1.7209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400    1.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6877    0.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648   -0.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503   -0.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191523212D          

 36 41  0  0  0  0            999 V2000
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 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C(CC=CC(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O8/c1-15(29)33-20-13-19-17(7-6-8-21(30)35-25(19,2)3)18-9-11-26(4)22(16-10-12-32-14-16)34-24(31)23-28(26,36-23)27(18,20)5/h6,8-10,12,14,17,19-20,22-23H,7,11,13H2,1-5H3

> <INCHI_KEY>
VIZDPIMTQWFZEF-UHFFFAOYSA-N

> <FORMULA>
C28H32O8

> <MOLECULAR_WEIGHT>
496.556

> <EXACT_MASS>
496.20971799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
51.44646560653652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
3.498858923666665

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.08768238504236

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8727242151495993

> <JCHEM_POLAR_SURFACE_AREA>
104.57000000000001

> <JCHEM_REFRACTIVITY>
127.13609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.757   5.820   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.251   5.494   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.217   6.635   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.781   4.028   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.815   2.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.320   3.212   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.355   2.071   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.884   0.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.588  -0.765   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.054  -1.235   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.424  -0.531   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.894   0.935   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.429   1.061   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.191   2.305   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.724   2.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.290   4.208   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.932   4.096   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.379   0.280   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.908  -1.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.402  -1.512   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.368  -0.371   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.897  -1.837   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.863  -0.696   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.172   0.445   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.299   1.911   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.735   3.052   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.805   2.236   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.310   2.562   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.839   1.095   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.344   1.421   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.178   2.952   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.392  -2.163   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.301  -3.405   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.401  -4.654   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.066  -4.183   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.071  -2.643   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   21   27   30                                             
CONECT   30   29    5   18   31                                             
CONECT   31   30                                                            
CONECT   32   23   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
18-(Furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0,.0,.0,]henicosa-1(21),4-dien-11-yl acetic acid	Generator
18-(Furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₂O₈

Average Mass

496.5560 Da

Monoisotopic Mass

496.20972 Da

IUPAC Name

18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate

Traditional Name

18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C(CC=CC(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1

InChI Identifier

InChI=1S/C28H32O8/c1-15(29)33-20-13-19-17(7-6-8-21(30)35-25(19,2)3)18-9-11-26(4)22(16-10-12-32-14-16)34-24(31)23-28(26,36-23)27(18,20)5/h6,8-10,12,14,17,19-20,22-23H,7,11,13H2,1-5H3

InChI Key

VIZDPIMTQWFZEF-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 aurantium	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
Tricarboxylic acid or derivatives
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
Oxane
Pyran
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	4.16	ALOGPS
logP	3.5	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.57 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.14 m³·mol⁻¹	ChemAxon
Polarizability	51.45 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate (NP0188828)

MOL for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

3D MOL for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

3D SDF for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

3D-SDF for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

PDB for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

3D PDB for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

SMILES for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

INCHI for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

Structure for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)

3D Structure for NP0188828 (18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate)