NP-MRD: Showing NP-Card for l-olivosyl-oleandolide (NP0288286)

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Record Information

Version

2.0

Created at

2022-09-09 17:55:38 UTC

Updated at

2022-09-09 17:55:38 UTC

NP-MRD ID

NP0288286

Secondary Accession Numbers

None

Natural Product Identification

Common Name

l-olivosyl-oleandolide

Description

3-O-(alpha-L-olivosyl)oleandolide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Thus, 3-O-(alpha-L-olivosyl)oleandolide is considered to be a macrolide. 3-O-(alpha-L-olivosyl)oleandolide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. l-olivosyl-oleandolide is found in Apis cerana. Based on a literature review very few articles have been published on 3-O-(alpha-L-olivosyl)oleandolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309092219552D          

 36 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END

  Mrv1652309092219552D          

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  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 22 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0288286

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@H](C[C@H](O)[C@H]1O)O[C@H]1[C@H](C)[C@@H](O)[C@@H](C)C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O10/c1-11-9-26(10-33-26)24(31)14(4)21(29)12(2)16(6)35-25(32)15(5)23(13(3)20(11)28)36-19-8-18(27)22(30)17(7)34-19/h11-23,27-30H,8-10H2,1-7H3/t11-,12-,13+,14+,15+,16+,17-,18-,19-,20-,21-,22-,23-,26+/m0/s1

> <INCHI_KEY>
SBBLTTCUMKGRJI-GYHYDPCPSA-N

> <FORMULA>
C26H44O10

> <MOLECULAR_WEIGHT>
516.628

> <EXACT_MASS>
516.293447617

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.878772519420416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-12-{[(2R,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6,14-dihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

> <JCHEM_LOGP>
1.6568963736666662

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.14065198144522

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.113457490324258

> <JCHEM_PKA_STRONGEST_BASIC>
-2.963138631391656

> <JCHEM_POLAR_SURFACE_AREA>
155.28

> <JCHEM_REFRACTIVITY>
127.442

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
L-olivosyl-oleandolide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.644   4.771   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.264   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.574   0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.671  -1.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.344  -3.231   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.114  -4.565   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.114  -1.897   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.654  -1.897   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.804  -0.564   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.644  -3.231   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4    6                                                       
CONECT    6    5    4                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24                                                       
CONECT   33   22   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
L-Olivosyl-oleandolide	ChEBI
3-O-(a-L-Olivosyl)oleandolide	Generator
3-O-(Α-L-olivosyl)oleandolide	Generator

Chemical Formula

C₂₆H₄₄O₁₀

Average Mass

516.6280 Da

Monoisotopic Mass

516.29345 Da

IUPAC Name

(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-12-{[(2R,4S,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-6,14-dihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

Traditional Name

L-olivosyl-oleandolide

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@H](C[C@H](O)[C@H]1O)O[C@H]1[C@H](C)[C@@H](O)[C@@H](C)C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@@H]1C

InChI Identifier

InChI=1S/C26H44O10/c1-11-9-26(10-33-26)24(31)14(4)21(29)12(2)16(6)35-25(32)15(5)23(13(3)20(11)28)36-19-8-18(27)22(30)17(7)34-19/h11-23,27-30H,8-10H2,1-7H3/t11-,12-,13+,14+,15+,16+,17-,18-,19-,20-,21-,22-,23-,26+/m0/s1

InChI Key

SBBLTTCUMKGRJI-GYHYDPCPSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:29614 )
glycoside (CHEBI:29614 )
macrolide (CHEBI:29614 )
Macrolides and lactone polyketides (C11991 )
Macrolides and lactone polyketides (LMPK04000032 )

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	1.66	ChemAxon
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	155.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.44 m³·mol⁻¹	ChemAxon
Polarizability	53.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

391741

KEGG Compound ID

C11991

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443565

PDB ID

Not Available

ChEBI ID

29614

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for l-olivosyl-oleandolide (NP0288286)

MOL for NP0288286 (l-olivosyl-oleandolide)

3D MOL for NP0288286 (l-olivosyl-oleandolide)

3D SDF for NP0288286 (l-olivosyl-oleandolide)

3D-SDF for NP0288286 (l-olivosyl-oleandolide)

PDB for NP0288286 (l-olivosyl-oleandolide)

3D PDB for NP0288286 (l-olivosyl-oleandolide)

SMILES for NP0288286 (l-olivosyl-oleandolide)

INCHI for NP0288286 (l-olivosyl-oleandolide)

Structure for NP0288286 (l-olivosyl-oleandolide)

3D Structure for NP0288286 (l-olivosyl-oleandolide)