NP-MRD: Showing NP-Card for Oleaside A (NP0139109)

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Record Information

Version

1.0

Created at

2022-06-29 19:39:44 UTC

Updated at

2022-06-29 19:39:44 UTC

NP-MRD ID

NP0139109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oleaside A

Description

OLEASIDE A belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Oleaside A is found in Daphnis nerii and Nerium oleander. OLEASIDE A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508032D          

 37 42  0  0  0  0            999 V2000
    9.1385    2.7782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9335    1.9791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9340    0.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1395    0.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9346   -0.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1400   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9351   -1.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1405   -1.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3469   -1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004251508032D          

 37 42  0  0  0  0            999 V2000
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    6.5499    1.3128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7548    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1652    2.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5494    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7543    3.1332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 10 29  1  0  0  0  0
 15 29  1  0  0  0  0
 25 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  2  0  0  0  0
 12 32  1  0  0  0  0
  7 32  1  0  0  0  0
  5 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(OC2CCC3(C)C(CCC45CCC(C6=CC(=O)OC6)C(C)(CCC34)C5=O)C2)OC(C)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-17-26(32)22(34-4)15-25(36-17)37-20-6-9-28(2)19(14-20)5-11-30-12-7-21(18-13-24(31)35-16-18)29(3,27(30)33)10-8-23(28)30/h13,17,19-23,25-26,32H,5-12,14-16H2,1-4H3

> <INCHI_KEY>
DFDVWAJDFYYBAC-UHFFFAOYSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.675

> <EXACT_MASS>
516.308703757

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.38841452461503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{6-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9,13-dimethyl-17-oxotetracyclo[11.3.1.0¹,¹⁰.0⁴,⁹]heptadecan-14-yl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
4.826218536

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.215145339613493

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.128181345576155

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5794955830234993

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
136.97109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{6-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9,13-dimethyl-17-oxotetracyclo[11.3.1.0¹,¹⁰.0⁴,⁹]heptadecan-14-yl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      17.058   5.186   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      16.676   3.694   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.193   3.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.810   1.788   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.327   1.373   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.945  -0.118   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.461  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.079  -2.025   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.596  -2.439   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.495  -1.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.114  -2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.878   0.130   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.818   1.275   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.323   0.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.816  -0.594   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.502   0.458   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.951   0.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.716  -1.481   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.263  -1.989   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.820  -3.464   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.720  -3.499   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.597  -4.765   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.228  -2.045   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.003  -1.112   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.904  -2.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.824  -3.682   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.023  -3.752   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.583  -3.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.980  -1.789   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.890  -1.564   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.001  -2.631   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.361   0.544   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.226   2.451   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.609   3.942   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.508   5.020   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.092   4.357   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.475   5.849   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   29                                             
CONECT   11   10                                                            
CONECT   12   10   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   29   30                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   19                                                       
CONECT   25   18   26   27   30                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   10   15                                                  
CONECT   30   25   15   31                                                  
CONECT   31   30                                                            
CONECT   32   12    7                                                       
CONECT   33    5   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6750 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

4-{6-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9,13-dimethyl-17-oxotetracyclo[11.3.1.0¹,¹⁰.0⁴,⁹]heptadecan-14-yl}-2,5-dihydrofuran-2-one

Traditional Name

4-{6-[(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-9,13-dimethyl-17-oxotetracyclo[11.3.1.0¹,¹⁰.0⁴,⁹]heptadecan-14-yl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

COC1CC(OC2CCC3(C)C(CCC45CCC(C6=CC(=O)OC6)C(C)(CCC34)C5=O)C2)OC(C)C1O

InChI Identifier

InChI=1S/C30H44O7/c1-17-26(32)22(34-4)15-25(36-17)37-20-6-9-28(2)19(14-20)5-11-30-12-7-21(18-13-24(31)35-16-18)29(3,27(30)33)10-8-23(28)30/h13,17,19-23,25-26,32H,5-12,14-16H2,1-4H3

InChI Key

DFDVWAJDFYYBAC-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
Daphnis nerii	LOTUS Database	35616633
Nerium oleander	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
2-furanone
Monosaccharide
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
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
logP	2.84	ALOGPS
logP	4.83	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	7.13	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	136.97 m³·mol⁻¹	ChemAxon
Polarizability	58.39 Å³	ChemAxon
Number of Rings	6	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

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

434211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oleaside A (NP0139109)

MOL for NP0139109 (Oleaside A)

3D MOL for NP0139109 (Oleaside A)

3D SDF for NP0139109 (Oleaside A)

3D-SDF for NP0139109 (Oleaside A)

PDB for NP0139109 (Oleaside A)

3D PDB for NP0139109 (Oleaside A)

SMILES for NP0139109 (Oleaside A)

INCHI for NP0139109 (Oleaside A)

Structure for NP0139109 (Oleaside A)

3D Structure for NP0139109 (Oleaside A)