NP-MRD: Showing NP-Card for 8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0147430)

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Record Information

Version

2.0

Created at

2022-09-02 03:01:54 UTC

Updated at

2022-09-02 03:01:54 UTC

NP-MRD ID

NP0147430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

Description

Diosbulbin I 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. 8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate is found in Dioscorea bulbifera. Diosbulbin I is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201504532D          

 37 42  0  0  0  0            999 V2000
    3.7039    5.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413    5.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1916    3.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9800    2.9048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    2.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8187    0.7192    0.0000 O   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


  Mrv1533004201504532D          

 37 42  0  0  0  0            999 V2000
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 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 24 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 31 35  1  0  0  0  0
  6 36  1  0  0  0  0
 36 37  2  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)OC2CC3C(=O)OC(CC3(C)C3CC4CC(C23)C(=O)O4)C2=COC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O8/c1-29-14-24(17-9-10-34-15-17)37-28(32)22(29)13-23(26-20-11-19(12-21(26)29)35-27(20)31)36-25(30)8-5-16-3-6-18(33-2)7-4-16/h3-10,15,19-24,26H,11-14H2,1-2H3

> <INCHI_KEY>
NFXKFVAWBBOWIJ-UHFFFAOYSA-N

> <FORMULA>
C29H30O8

> <MOLECULAR_WEIGHT>
506.551

> <EXACT_MASS>
506.194067926

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71988209730157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
4.141470986666667

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883518972190603

> <JCHEM_POLAR_SURFACE_AREA>
101.27000000000001

> <JCHEM_REFRACTIVITY>
131.2409

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       6.914  10.808   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.730   9.502   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.008   8.142   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.824   6.836   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.102   5.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.563   5.422   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.840   4.062   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.301   4.008   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.579   2.648   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.395   1.342   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.039   2.594   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.317   1.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.222   1.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.945  -0.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.484  -0.234   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.300   1.072   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.206  -1.594   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.390  -2.900   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.851  -2.846   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.128  -1.486   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.312  -2.792   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.411  -1.432   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.023  -2.844   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.510  -3.246   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.011  -1.535   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.647   0.211   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.133  -0.072   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.812  -0.796   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.225  -0.183   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       3.751  -2.335   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.113  -4.260   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.437  -5.644   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.545  -6.714   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -5.904  -5.991   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.637  -4.475   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.746   6.728   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.469   8.088   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   12   22                                                  
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   24                                                       
CONECT   31   18   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
CONECT   36    6   37                                                       
CONECT   37   36    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
8-(Furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₉H₃₀O₈

Average Mass

506.5510 Da

Monoisotopic Mass

506.19407 Da

IUPAC Name

8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

Traditional Name

8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)OC2CC3C(=O)OC(CC3(C)C3CC4CC(C23)C(=O)O4)C2=COC=C2)C=C1

InChI Identifier

InChI=1S/C29H30O8/c1-29-14-24(17-9-10-34-15-17)37-28(32)22(29)13-23(26-20-11-19(12-21(26)29)35-27(20)31)36-25(30)8-5-16-3-6-18(33-2)7-4-16/h3-10,15,19-24,26H,11-14H2,1-2H3

InChI Key

NFXKFVAWBBOWIJ-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
Dioscorea bulbifera	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
Cinnamic acid or derivatives
Cinnamic acid ester
Naphthalene
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Caprolactone
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Monocyclic benzene moiety
Fatty acyl
Gamma butyrolactone
Benzenoid
Oxane
Pyran
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Ether
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	3.53	ALOGPS
logP	4.14	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	101.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.24 m³·mol⁻¹	ChemAxon
Polarizability	53.72 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

74929149

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate (NP0147430)

MOL for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D MOL for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D SDF for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

PDB for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D PDB for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

SMILES for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

INCHI for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

Structure for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)

3D Structure for NP0147430 (8-(furan-3-yl)-10-methyl-6,15-dioxo-7,14-dioxatetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecan-3-yl 3-(4-methoxyphenyl)prop-2-enoate)