NP-MRD: Showing NP-Card for 18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate (NP0318555)

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Record Information

Version

2.0

Created at

2022-09-11 19:07:21 UTC

Updated at

2022-09-11 19:07:21 UTC

NP-MRD ID

NP0318555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate

Description

18,19-Dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]Henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate is found in Kadsura coccinea. 18,19-Dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]Henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151516412D          

 33 37  0  0  0  0            999 V2000
    6.6123   -0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8298   -0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121   -0.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4296   -0.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -0.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203   -1.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2904   -0.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435   -0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291    0.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981    1.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    1.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268    2.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5348    2.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4712    3.5479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3984    1.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004151516412D          

 33 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0318555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1C(C)C(C)CC2=CC(OC)=C(OC)C(=O)C22COC3=C4OCOC4=CC1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-6-18(26)33-20-13(3)12(2)7-14-8-16(28-4)22(29-5)24(27)25(14)10-30-23-19(25)15(20)9-17-21(23)32-11-31-17/h8-9,12-13,20H,6-7,10-11H2,1-5H3

> <INCHI_KEY>
KHQMXOUCRGMHIQ-UHFFFAOYSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.491

> <EXACT_MASS>
456.178417862

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.2120742941224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4,9,11(21),16,18-pentaen-12-yl propanoate

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.8414551643333334

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.292138790254414

> <JCHEM_POLAR_SURFACE_AREA>
89.52000000000001

> <JCHEM_REFRACTIVITY>
119.7705

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4,9,11(21),16,18-pentaen-12-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      12.343  -1.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.882  -1.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.729  -0.729   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.037   0.780   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.269  -1.217   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.116  -0.196   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.731  -0.870   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.825  -2.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.275  -0.368   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.254  -1.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.601   1.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.103   2.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.509   2.636   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.730   3.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.865   5.087   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.746   6.623   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.017   7.493   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.161   4.174   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.076   5.413   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.488   3.147   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.515   4.686   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.988   5.136   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.805   3.921   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.341   3.813   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.450   4.882   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.809   4.158   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.541   2.642   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.016   2.428   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.154   1.152   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.618   1.260   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.943   2.645   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.205   4.206   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.744   2.993   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   12   21   31                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29    6   31                                                  
CONECT   31   30   20   23                                                  
CONECT   32   14   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
18,19-Dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0,.0,.0,]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoic acid	Generator
18,19-Dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoic acid	Generator

Chemical Formula

C₂₅H₂₈O₈

Average Mass

456.4910 Da

Monoisotopic Mass

456.17842 Da

IUPAC Name

18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4,9,11(21),16,18-pentaen-12-yl propanoate

Traditional Name

18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4,9,11(21),16,18-pentaen-12-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1C(C)C(C)CC2=CC(OC)=C(OC)C(=O)C22COC3=C4OCOC4=CC1=C23

InChI Identifier

InChI=1S/C25H28O8/c1-6-18(26)33-20-13(3)12(2)7-14-8-16(28-4)22(29-5)24(27)25(14)10-30-23-19(25)15(20)9-17-21(23)32-11-31-17/h8-9,12-13,20H,6-7,10-11H2,1-5H3

InChI Key

KHQMXOUCRGMHIQ-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
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Benzodioxole
Coumaran
Alkyl aryl ether
Benzenoid
Vinylogous ester
Carboxylic acid ester
Ketone
Acetal
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	2.82	ALOGPS
logP	2.84	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	89.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	119.77 m³·mol⁻¹	ChemAxon
Polarizability	48.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14729089

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate (NP0318555)

MOL for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

3D MOL for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

3D SDF for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

3D-SDF for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

PDB for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

3D PDB for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

SMILES for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

INCHI for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

Structure for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)

3D Structure for NP0318555 (18,19-dimethoxy-13,14-dimethyl-20-oxo-3,6,8-trioxapentacyclo[9.9.1.0¹,¹⁶.0⁴,²¹.0⁵,⁹]henicosa-4(21),5(9),10,16,18-pentaen-12-yl propanoate)