NP-MRD: Showing NP-Card for (-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside (NP0080153)

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Record Information

Version

2.0

Created at

2022-04-29 01:12:32 UTC

Updated at

2022-04-29 01:12:32 UTC

NP-MRD ID

NP0080153

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside

Description

(1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside is found in Eupatorium glutinosum. Based on a literature review very few articles have been published on (1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203122D          

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M  END

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M  END


  Mrv1652304292203122D          

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    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  6  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
  8 11  1  6  0  0  0
 12 11  1  6  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
 12 17  1  0  0  0  0
 17 18  1  1  0  0  0
 16 19  1  6  0  0  0
 15 20  1  1  0  0  0
 14 21  1  6  0  0  0
 21 22  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  4 25  1  1  0  0  0
  3 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080153

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCO)CC[C@@H]1C(=CC[C@@H]2C(C)(C)[C@@H](CC[C@]12C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O9/c1-14(10-12-27)5-7-16-15(23(32)33)6-8-18-25(2,3)19(9-11-26(16,18)4)35-24-22(31)21(30)20(29)17(13-28)34-24/h6,14,16-22,24,27-31H,5,7-13H2,1-4H3,(H,32,33)/t14-,16+,17+,18+,19+,20+,21-,22+,24-,26+/m0/s1

> <INCHI_KEY>
LTEZVUVZFATCKC-NTFYDHSXSA-N

> <FORMULA>
C26H44O9

> <MOLECULAR_WEIGHT>
500.629

> <EXACT_MASS>
500.298532997

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.14390582992337

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.5410946836666657

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210548856658031

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.70317280496038

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8732430057145524

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
128.07629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   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  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.816   2.846   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   10   25                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   23   24                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
CONECT   23    7                                                            
CONECT   24    7                                                            
CONECT   25    4                                                            
CONECT   26    3   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33    2   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
(1S,4AS,6R,8as)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylate	Generator

Chemical Formula

C₂₆H₄₄O₉

Average Mass

500.6290 Da

Monoisotopic Mass

500.29853 Da

IUPAC Name

(1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxylic acid

Traditional Name

(1S,4aS,6R,8aS)-1-[(3S)-5-hydroxy-3-methylpentyl]-5,5,8a-trimethyl-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1,4,4a,6,7,8-hexahydronaphthalene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCO)CC[C@@H]1C(=CC[C@@H]2C(C)(C)[C@@H](CC[C@]12C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C26H44O9/c1-14(10-12-27)5-7-16-15(23(32)33)6-8-18-25(2,3)19(9-11-26(16,18)4)35-24-22(31)21(30)20(29)17(13-28)34-24/h6,14,16-22,24,27-31H,5,7-13H2,1-4H3,(H,32,33)/t14-,16+,17+,18+,19+,20+,21-,22+,24-,26+/m0/s1

InChI Key

LTEZVUVZFATCKC-NTFYDHSXSA-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
Eupatorium glutinosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Labdane diterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Fatty alcohol
Fatty acyl
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	1.74	ALOGPS
logP	1.54	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.7	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.08 m³·mol⁻¹	ChemAxon
Polarizability	55.14 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

163041562

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside (NP0080153)

MOL for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

3D MOL for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

3D SDF for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

3D-SDF for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

PDB for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

3D PDB for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

SMILES for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

INCHI for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

Structure for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)

3D Structure for NP0080153 ((-)-3,15-Dihydroxy-ent-labd-7-en-oic acid 3-O-beta-D-glucoside)