NP-MRD: Showing NP-Card for (-)-Alangionoside O (NP0075079)

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Record Information

Version

2.0

Created at

2022-04-28 20:23:42 UTC

Updated at

2022-04-28 20:23:42 UTC

NP-MRD ID

NP0075079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Alangionoside O

Description

(2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (-)-Alangionoside O is found in Alangium premnifolium. Based on a literature review very few articles have been published on (2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222232D          

 37 39  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222232D          

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   -2.5234   -6.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -4.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -6.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  1  0  0  0
 11 16  1  1  0  0  0
 10 17  1  1  0  0  0
  4 18  1  1  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 23 26  1  6  0  0  0
 22 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  1  0  0  0
 22 32  1  1  0  0  0
 21 33  1  0  0  0  0
 21 34  1  0  0  0  0
  3 35  1  1  0  0  0
  2 36  1  6  0  0  0
  1 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075079

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H42O13/c1-11(25)5-6-24(33)22(2,3)7-12(8-23(24,4)32)36-21-19(31)17(29)16(28)14(37-21)10-35-20-18(30)15(27)13(26)9-34-20/h5-6,11-21,25-33H,7-10H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,17+,18+,19-,20-,21+,23-,24-/m1/s1

> <INCHI_KEY>
RIHVUVZNBNYDHR-RRVXYRROSA-N

> <FORMULA>
C24H42O13

> <MOLECULAR_WEIGHT>
538.587

> <EXACT_MASS>
538.262541412

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.408452546338424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.99

> <JCHEM_LOGP>
-2.9640512820000002

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.372960873409784

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.885356538370253

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3592743775272407

> <JCHEM_POLAR_SURFACE_AREA>
218.98999999999998

> <JCHEM_REFRACTIVITY>
125.5542

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.539  -7.646   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.816  -6.394   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.816 -10.546   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.355 -10.492   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.171 -11.798   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.448 -13.158   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.710 -11.744   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.539  -9.294   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.057 -11.370   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.611 -11.370   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10                                                            
CONECT   18    4   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   33   34                                             
CONECT   22   21   23   27   32                                             
CONECT   23   22   24   25   26                                             
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22                                                            
CONECT   33   21                                                            
CONECT   34   21                                                            
CONECT   35    3                                                            
CONECT   36    2                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₄₂O₁₃

Average Mass

538.5870 Da

Monoisotopic Mass

538.26254 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5R,6R)-2-{[(1S,3R,4R)-3,4-dihydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohexyl]oxy}-6-({[(2R,3S,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H42O13/c1-11(25)5-6-24(33)22(2,3)7-12(8-23(24,4)32)36-21-19(31)17(29)16(28)14(37-21)10-35-20-18(30)15(27)13(26)9-34-20/h5-6,11-21,25-33H,7-10H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,17+,18+,19-,20-,21+,23-,24-/m1/s1

InChI Key

RIHVUVZNBNYDHR-RRVXYRROSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Alangium premnifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
O-glycosyl compound
Glycosyl compound
Disaccharide
Cyclohexanol
Oxane
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	ALOGPS
logP	-3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	11.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	218.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	125.55 m³·mol⁻¹	ChemAxon
Polarizability	54.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162857244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Alangionoside O (NP0075079)

MOL for NP0075079 ((-)-Alangionoside O)

3D MOL for NP0075079 ((-)-Alangionoside O)

3D SDF for NP0075079 ((-)-Alangionoside O)

3D-SDF for NP0075079 ((-)-Alangionoside O)

PDB for NP0075079 ((-)-Alangionoside O)

3D PDB for NP0075079 ((-)-Alangionoside O)

SMILES for NP0075079 ((-)-Alangionoside O)

INCHI for NP0075079 ((-)-Alangionoside O)

Structure for NP0075079 ((-)-Alangionoside O)

3D Structure for NP0075079 ((-)-Alangionoside O)