NP-MRD: Showing NP-Card for (2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one (NP0260368)

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Record Information

Version

2.0

Created at

2022-09-08 02:31:05 UTC

Updated at

2022-09-08 02:31:05 UTC

NP-MRD ID

NP0260368

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one

Description

CHEMBL1081696 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. (2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one is found in Schisandra arisanensis. Based on a literature review very few articles have been published on CHEMBL1081696.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204312D          

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 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 10 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1OC)C1=C(OC)C3=C(OCO3)C=C1[C@H](C(=O)C(\C)=C/C)[C@@](C)(O)[C@@H](C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-8-13(2)22(28)21-16-11-18-25(35-12-34-18)26(33-7)20(16)19-15(9-14(3)27(21,4)30)10-17(31-5)24(32-6)23(19)29/h8,10-11,14,21,29-30H,9,12H2,1-7H3/b13-8-/t14-,21+,27-/m0/s1

> <INCHI_KEY>
KBYDHOPBQPIANF-OQJDONTRSA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.75940617428157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-1-[(9S,10S,11S)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one

> <JCHEM_LOGP>
4.424966687666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.599948302962293

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.565502924964726

> <JCHEM_PKA_STRONGEST_BASIC>
-3.132533894440072

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
130.9084

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-1-[(9S,10S,11S)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.687  10.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895   9.269   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.677   8.326   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.885   6.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.252   8.909   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.044  10.435   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.034   7.966   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.439   6.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.979   6.487   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.755   5.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.991   3.820   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.451   3.813   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.687   2.476   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.463   1.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.675   5.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.189   4.738   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.852   5.503   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.522   4.727   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.529   3.187   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.802   2.411   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.139   3.175   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.866   2.423   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.872   0.883   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.542   0.107   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.196   3.198   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.231   2.059   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.447   6.988   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.211   8.325   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.268   9.543   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.697   8.731   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.196  10.187   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.547  10.015   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.026   2.680   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.430   3.313   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.263   4.843   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   30                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12   33                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    8   16                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   16   26                                                  
CONECT   26   25                                                            
CONECT   27   17   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    7   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   11   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   10                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

(2Z)-1-[(9S,10S,11S)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one

Traditional Name

(2Z)-1-[(9S,10S,11S)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0^{2,7}.0^{14,18}]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1OC)C1=C(OC)C3=C(OCO3)C=C1[C@H](C(=O)C(\C)=C/C)[C@@](C)(O)[C@@H](C)C2

InChI Identifier

InChI=1S/C27H32O8/c1-8-13(2)22(28)21-16-11-18-25(35-12-34-18)26(33-7)20(16)19-15(9-14(3)27(21,4)30)10-17(31-5)24(32-6)23(19)29/h8,10-11,14,21,29-30H,9,12H2,1-7H3/b13-8-/t14-,21+,27-/m0/s1

InChI Key

KBYDHOPBQPIANF-OQJDONTRSA-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
Schisandra arisanensis	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
Dibenzocyclooctane lignan
Benzodioxole
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
B'-hydroxy-alpha,beta-unsaturated-ketone
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Alcohol
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	4.42	ChemAxon
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	130.91 m³·mol⁻¹	ChemAxon
Polarizability	50.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

24661108

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46883431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one (NP0260368)

MOL for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

3D MOL for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

3D SDF for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

3D-SDF for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

PDB for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

3D PDB for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

SMILES for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

INCHI for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

Structure for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)

3D Structure for NP0260368 ((2z)-1-[(9s,10s,11s)-3,10-dihydroxy-4,5,19-trimethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.0²,⁷.0¹⁴,¹⁸]nonadeca-1(19),2(7),3,5,12,14(18)-hexaen-11-yl]-2-methylbut-2-en-1-one)