NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate (NP0163485)

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Record Information

Version

2.0

Created at

2022-09-02 22:08:25 UTC

Updated at

2022-09-02 22:08:25 UTC

NP-MRD ID

NP0163485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate

Description

CHEMBL517303 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. (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate is found in Calendula arvensis. Based on a literature review very few articles have been published on CHEMBL517303.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200082D          

 31 34  0  0  1  0            999 V2000
    1.4074    5.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065    4.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467    4.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2653    4.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251    5.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    3.6860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    3.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2224    2.5433    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5627    2.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6618    1.2289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.4382    1.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1404    1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395    0.2556    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  8 25  1  0  0  0  0
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  7 30  1  0  0  0  0
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M  END

     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
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   -4.2833    2.2203   -0.4881 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032200082D          

 31 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0163485

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1[C@H](O[C@]2(C)CC[C@@H]3[C@H]([C@@H]4[C@H](C)CC[C@H]24)C3(C)C)O[C@H](C)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O6/c1-12(2)22(28)30-21-20(27)19(26)14(4)29-23(21)31-25(7)11-10-16-18(24(16,5)6)17-13(3)8-9-15(17)25/h12-21,23,26-27H,8-11H2,1-7H3/t13-,14-,15+,16-,17-,18-,19+,20+,21-,23+,25-/m1/s1

> <INCHI_KEY>
KYBCKZPKDGOQLN-PHSVILLSSA-N

> <FORMULA>
C25H42O6

> <MOLECULAR_WEIGHT>
438.605

> <EXACT_MASS>
438.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.356045342249956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
4.139224275666667

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.18213403938552

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.738855551600068

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6129051235141514

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
115.8225

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.627  10.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.812   9.014   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.581   8.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.229   8.409   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.460   9.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.414   6.880   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.830   6.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.015   4.747   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.784   3.823   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.969   2.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437   2.454   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.418   2.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.729   2.006   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.914   0.477   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.834  -0.621   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.302  -0.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.472   0.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.982   0.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.891  -1.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.325  -1.651   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.713  -3.141   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.325  -1.007   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.604  -2.521   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.843  -1.262   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.432   4.143   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.663   5.068   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.080   4.464   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.478   6.597   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.710   7.521   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.062   7.201   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.877   8.730   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   30                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20                                                            
CONECT   22   15   14   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    8   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    7   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₂O₆

Average Mass

438.6050 Da

Monoisotopic Mass

438.29814 Da

IUPAC Name

(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-decahydro-1H-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate

Traditional Name

(2S,3R,4S,5R,6R)-2-{[(1aR,4R,4aS,7R,7aS,7bS)-1,1,4,7-tetramethyl-octahydro-1aH-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1[C@H](O[C@]2(C)CC[C@@H]3[C@H]([C@@H]4[C@H](C)CC[C@H]24)C3(C)C)O[C@H](C)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H42O6/c1-12(2)22(28)30-21-20(27)19(26)14(4)29-23(21)31-25(7)11-10-16-18(24(16,5)6)17-13(3)8-9-15(17)25/h12-21,23,26-27H,8-11H2,1-7H3/t13-,14-,15+,16-,17-,18-,19+,20+,21-,23+,25-/m1/s1

InChI Key

KYBCKZPKDGOQLN-PHSVILLSSA-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
Calendula arvensis	LOTUS Database	35616633

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
Aromadendrane sesquiterpenoid
Guaiane sesquiterpenoid
5,10-cycloaromadendrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
1,2-diol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	3.01	ALOGPS
logP	4.14	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.82 m³·mol⁻¹	ChemAxon
Polarizability	50.36 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

23339937

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44567062

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate (NP0163485)

MOL for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

3D MOL for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

3D SDF for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

3D-SDF for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

PDB for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

3D PDB for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

SMILES for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

INCHI for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

Structure for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)

3D Structure for NP0163485 ((2s,3r,4s,5r,6r)-2-{[(1ar,4r,4as,7r,7as,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methylpropanoate)