NP-MRD: Showing NP-Card for (1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate (NP0236247)

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Record Information

Version

2.0

Created at

2022-09-06 19:05:46 UTC

Updated at

2022-09-06 19:05:46 UTC

NP-MRD ID

NP0236247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate

Description

(1S,2S,6S,7S,9S,11S,13R,14S,15R,16S,17R)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-16-yl acetate belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate is found in Picrasma quassioides. Based on a literature review very few articles have been published on (1S,2S,6S,7S,9S,11S,13R,14S,15R,16S,17R)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadec-4-en-16-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062221052D          

 32 35  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1468    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    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


  Mrv1652309062221052D          

 32 35  0  0  1  0            999 V2000
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0236247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](OC(C)=O)[C@H]2[C@@]3(C)[C@H](C[C@H]4[C@H](C)C=C(OC)C(=O)[C@]24C)O[C@H](O)C[C@H]3[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O8/c1-11-8-14(29-6)20(27)22(3)13(11)9-16-23(4)15(10-17(26)32-16)24(5,28)21(30-7)18(19(22)23)31-12(2)25/h8,11,13,15-19,21,26,28H,9-10H2,1-7H3/t11-,13+,15-,16+,17+,18+,19-,21-,22+,23-,24+/m1/s1

> <INCHI_KEY>
CZEONSLVJRHIIJ-PYWLYBNASA-N

> <FORMULA>
C24H36O8

> <MOLECULAR_WEIGHT>
452.544

> <EXACT_MASS>
452.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.91702017083404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6S,7S,9S,11S,13R,14S,15R,16S,17R)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

> <JCHEM_LOGP>
1.0952209463333313

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.748937875098836

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.429969772256445

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3588535682631395

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
115.6073

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,7S,9S,11S,13R,14S,15R,16S,17R)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-16-yl acetate

> <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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.141   2.987   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.151   1.273   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   31                                                  
CONECT   27   26    7   28   29                                             
CONECT   28   27                                                            
CONECT   29   27    3   30                                                  
CONECT   30   29                                                            
CONECT   31   26    9   14   32                                             
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,6S,7S,9S,11S,13R,14S,15R,16S,17R)-11,14-Dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0,.0,]heptadec-4-en-16-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₆O₈

Average Mass

452.5440 Da

Monoisotopic Mass

452.24102 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](OC(C)=O)[C@H]2[C@@]3(C)[C@H](C[C@H]4[C@H](C)C=C(OC)C(=O)[C@]24C)O[C@H](O)C[C@H]3[C@]1(C)O

InChI Identifier

InChI=1S/C24H36O8/c1-11-8-14(29-6)20(27)22(3)13(11)9-16-23(4)15(10-17(26)32-16)24(5,28)21(30-7)18(19(22)23)31-12(2)25/h8,11,13,15-19,21,26,28H,9-10H2,1-7H3/t11-,13+,15-,16+,17+,18+,19-,21-,22+,23-,24+/m1/s1

InChI Key

CZEONSLVJRHIIJ-PYWLYBNASA-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
Picrasma quassioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Quassinoid
Naphthopyran
Naphthalene
Cyclohexenone
Pyran
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Hemiacetal
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

162871873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate (NP0236247)

MOL for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D MOL for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D SDF for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D-SDF for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

PDB for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D PDB for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

SMILES for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

INCHI for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

Structure for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)

3D Structure for NP0236247 ((1s,2s,6s,7s,9s,11s,13r,14s,15r,16s,17r)-11,14-dihydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-3-oxo-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadec-4-en-16-yl acetate)