NP-MRD: Showing NP-Card for (10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate (NP0228788)

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Record Information

Version

2.0

Created at

2022-09-06 08:34:42 UTC

Updated at

2022-09-06 08:34:43 UTC

NP-MRD ID

NP0228788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate

Description

SCHEMBL16540904 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). (10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate is found in Anthriscus sylvestris. Based on a literature review very few articles have been published on SCHEMBL16540904.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210342D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309062210342D          

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M  END
> <DATABASE_ID>
NP0228788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)[C@H]1[C@@H]2[C@H](COC2=O)[C@@H](OC(=O)C(\C)=C/C)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/b13-6-/t17-,22+,23-,24-/m0/s1

> <INCHI_KEY>
HNLUKMPUUDEEQB-KOOYKLTJSA-N

> <FORMULA>
C27H28O9

> <MOLECULAR_WEIGHT>
496.512

> <EXACT_MASS>
496.173332482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
51.24857631575384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R,15R,16R)-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.835735504

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.26709537166706

> <JCHEM_POLAR_SURFACE_AREA>
98.75000000000001

> <JCHEM_REFRACTIVITY>
127.73479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R,16R)-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.547   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.590  -0.533   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.925  -9.773   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.925 -11.313   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258  -9.773   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.258 -11.313   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.591 -12.083   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924  -9.003   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.590  -9.773   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.257  -9.003   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924  -7.463   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13   34                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   16                                                       
CONECT   28   15   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    8   28                                                  
CONECT   34   12   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   11                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₉

Average Mass

496.5120 Da

Monoisotopic Mass

496.17333 Da

IUPAC Name

(10R,11R,15R,16R)-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(10R,11R,15R,16R)-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-10-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1[C@@H]2[C@H](COC2=O)[C@@H](OC(=O)C(\C)=C/C)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/b13-6-/t17-,22+,23-,24-/m0/s1

InChI Key

HNLUKMPUUDEEQB-KOOYKLTJSA-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
Oxolane
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	3.84	ChemAxon
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	51.25 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

102088115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate (NP0228788)

MOL for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

3D MOL for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

3D SDF for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

3D-SDF for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

PDB for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

3D PDB for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

SMILES for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

INCHI for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

Structure for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)

3D Structure for NP0228788 ((10r,11r,15r,16r)-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 (2z)-2-methylbut-2-enoate)