NP-MRD: Showing NP-Card for (10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate (NP0304795)

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Record Information

Version

2.0

Created at

2022-09-10 20:08:29 UTC

Updated at

2022-09-10 20:08:30 UTC

NP-MRD ID

NP0304795

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate

Description

CHEMBL453819 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,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate is found in Hernandia ovigera. Based on a literature review very few articles have been published on CHEMBL453819.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222082D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102222082D          

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M  END
> <DATABASE_ID>
NP0304795

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2[C@H](COC2=O)[C@@H](OC(C)=O)C2=C1C(OC)=C1OCOC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C25H26O10/c1-11(26)35-21-13-8-17-23(34-10-33-17)24(31-5)19(13)18(20-14(21)9-32-25(20)27)12-6-15(28-2)22(30-4)16(7-12)29-3/h6-8,14,18,20-21H,9-10H2,1-5H3/t14-,18+,20+,21-/m0/s1

> <INCHI_KEY>
YYMZKKXIDKRNCK-XVPDYNCKSA-N

> <FORMULA>
C25H26O10

> <MOLECULAR_WEIGHT>
486.473

> <EXACT_MASS>
486.152597037

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.37510142890611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(10R,11R,15S,16R)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-10-yl acetate

> <JCHEM_LOGP>
1.906252414

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.190904124321803

> <JCHEM_POLAR_SURFACE_AREA>
107.98000000000002

> <JCHEM_REFRACTIVITY>
119.5197

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15S,16R)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.471 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.471  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.137  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.137  -7.463   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -5.153   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.864  -6.693   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.198  -7.463   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.662  -4.859   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.568  -3.613   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.662  -2.367   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.197  -0.533   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.137   0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.137   1.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.471  -0.533   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.137  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.602  -2.367   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.507  -3.613   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.602  -4.859   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.077  -6.323   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.137  -4.383   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.530  -7.463   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.530  -9.003   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.864  -9.773   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.864 -11.313   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.197  -9.773   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.197 -11.313   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.530 -12.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10                                                       
CONECT   18    8   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   23                                                  
CONECT   29    5   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₆O₁₀

Average Mass

486.4730 Da

Monoisotopic Mass

486.15260 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2[C@H](COC2=O)[C@@H](OC(C)=O)C2=C1C(OC)=C1OCOC1=C2

InChI Identifier

InChI=1S/C25H26O10/c1-11(26)35-21-13-8-17-23(34-10-33-17)24(31-5)19(13)18(20-14(21)9-32-25(20)27)12-6-15(28-2)22(30-4)16(7-12)29-3/h6-8,14,18,20-21H,9-10H2,1-5H3/t14-,18+,20+,21-/m0/s1

InChI Key

YYMZKKXIDKRNCK-XVPDYNCKSA-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
Hernandia ovigera	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
Gamma butyrolactone
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Lactone
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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

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

552412

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636677

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,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate (NP0304795)

MOL for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

3D MOL for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

3D SDF for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

3D-SDF for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

PDB for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

3D PDB for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

SMILES for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

INCHI for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

Structure for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)

3D Structure for NP0304795 ((10r,11r,15s,16r)-2-methoxy-14-oxo-16-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1(9),2,7-trien-10-yl acetate)