NP-MRD: Showing NP-Card for 12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one (NP0161929)

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Record Information

Version

2.0

Created at

2022-09-02 20:14:25 UTC

Updated at

2022-09-02 20:14:25 UTC

NP-MRD ID

NP0161929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one

Description

12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on 12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]Octadeca-1(10),2(7),3,5,11,13,15,17-octaen-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022222142D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022222142D          

 35 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0161929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(OC(=O)C3=CC(C)=CC(OC)=C23)C2=C(C=CC(O)=C12)[C@H]1O[C@@H]([C@H](C)O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H26O9/c1-10-7-14-18(16(8-10)32-3)13-9-17(33-4)20-15(28)6-5-12(19(20)24(13)35-26(14)31)25-22(30)21(29)23(34-25)11(2)27/h5-9,11,21-23,25,27-30H,1-4H3/t11-,21-,22+,23-,25+/m0/s1

> <INCHI_KEY>
BYFOTBZTKXSZHH-IVGBOYDBSA-N

> <FORMULA>
C26H26O9

> <MOLECULAR_WEIGHT>
482.485

> <EXACT_MASS>
482.157682417

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.844145533375666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.098906796

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73721767419216

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.522826963564917

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0537466829921094

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
124.91239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.846   4.553   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.350   3.098   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.366   1.352   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.358   0.188   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.862  -1.267   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.375  -1.558   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.879  -3.013   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.383  -0.394   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.895  -0.685   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.903   0.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.415   0.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.399   1.934   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.887   2.225   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.383   3.680   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.870   3.971   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.879   1.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.846   0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.342  -2.140   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.815  -2.588   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.845  -4.128   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.108  -5.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.503  -4.355   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.977  -6.543   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.390  -4.632   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.942  -6.105   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.461  -3.403   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.079  -3.433   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.179   1.061   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.830   2.225   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.326   3.680   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.342   1.934   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   10    5                                                  
CONECT   19    6   20   35                                                  
CONECT   20   19   21   31                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21   30                                                  
CONECT   30   29                                                            
CONECT   31   20   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3   19                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₆O₉

Average Mass

482.4850 Da

Monoisotopic Mass

482.15768 Da

IUPAC Name

12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one

Traditional Name

12-[(2R,3R,4S,5S)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0^{2,7}.0^{11,16}]octadeca-1(10),2,4,6,11,13,15,17-octaen-8-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(OC(=O)C3=CC(C)=CC(OC)=C23)C2=C(C=CC(O)=C12)[C@H]1O[C@@H]([C@H](C)O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H26O9/c1-10-7-14-18(16(8-10)32-3)13-9-17(33-4)20-15(28)6-5-12(19(20)24(13)35-26(14)31)25-22(30)21(29)23(34-25)11(2)27/h5-9,11,21-23,25,27-30H,1-4H3/t11-,21-,22+,23-,25+/m0/s1

InChI Key

BYFOTBZTKXSZHH-IVGBOYDBSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Naphthopyran
1-naphthol
Isocoumarin
Coumarin
C-glycosyl compound
2-benzopyran
1-benzopyran
Naphthalene
Benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Lactone
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
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	2.25	ALOGPS
logP	2.1	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	124.91 m³·mol⁻¹	ChemAxon
Polarizability	49.84 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	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

162882547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one (NP0161929)

MOL for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

3D MOL for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

3D SDF for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

3D-SDF for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

PDB for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

3D PDB for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

SMILES for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

INCHI for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

Structure for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)

3D Structure for NP0161929 (12-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[(1s)-1-hydroxyethyl]oxolan-2-yl]-15-hydroxy-3,17-dimethoxy-5-methyl-9-oxatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1(10),2(7),3,5,11(16),12,14,17-octaen-8-one)