NP-MRD: Showing NP-Card for 14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate (NP0252334)

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Record Information

Version

2.0

Created at

2022-09-07 15:48:30 UTC

Updated at

2022-09-07 15:48:30 UTC

NP-MRD ID

NP0252334

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate

Description

14-Oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). 14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate is found in Anthriscus sylvestris. 14-Oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500122D          

 36 40  0  0  0  0            999 V2000
    1.9233   -6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -5.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0668    0.1271    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


  Mrv1533004181500122D          

 36 40  0  0  0  0            999 V2000
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 13 36  1  0  0  0  0
 28 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252334

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(OC(=O)C(C)=CC)C2=CC3=C(OCO3)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O9/c1-6-13(2)26(28)36-24-16-10-19-18(34-12-35-19)9-15(16)22(23-17(24)11-33-27(23)29)14-7-20(30-3)25(32-5)21(8-14)31-4/h6-10,17,22-24H,11-12H2,1-5H3

> <INCHI_KEY>
HNLUKMPUUDEEQB-UHFFFAOYSA-N

> <FORMULA>
C27H28O9

> <MOLECULAR_WEIGHT>
496.512

> <EXACT_MASS>
496.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.133900750500814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.835735504

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.26709537166706

> <JCHEM_POLAR_SURFACE_AREA>
98.75

> <JCHEM_REFRACTIVITY>
127.73479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       3.590 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   36                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   15   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24                                                            
CONECT   28   20   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   13   28                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
14-oxo-16-(3,4,5-Trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0,.0,]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoic acid	Generator
14-oxo-16-(3,4,5-Trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₇H₂₈O₉

Average Mass

496.5120 Da

Monoisotopic Mass

496.17333 Da

IUPAC Name

14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate

Traditional Name

14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C1C2C(COC2=O)C(OC(=O)C(C)=CC)C2=CC3=C(OCO3)C=C12

InChI Identifier

InChI=1S/C27H28O9/c1-6-13(2)26(28)36-24-16-10-19-18(34-12-35-19)9-15(16)22(23-17(24)11-33-27(23)29)14-7-20(30-3)25(32-5)21(8-14)31-4/h6-10,17,22-24H,11-12H2,1-5H3

InChI Key

HNLUKMPUUDEEQB-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
Anthriscus sylvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Tetralin
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Fatty acid ester
Gamma butyrolactone
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Ether
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	3.74	ALOGPS
logP	3.84	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	98.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.73 m³·mol⁻¹	ChemAxon
Polarizability	50.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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 14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate (NP0252334)

MOL for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

3D MOL for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

3D SDF for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

3D-SDF for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

PDB for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

3D PDB for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

SMILES for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

INCHI for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

Structure for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)

3D Structure for NP0252334 (14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-10-yl 2-methylbut-2-enoate)