NP-MRD: Showing NP-Card for (2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0180293)

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Record Information

Version

2.0

Created at

2022-09-03 18:38:14 UTC

Updated at

2022-09-03 18:38:14 UTC

NP-MRD ID

NP0180293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-1,2,3,4,5,7,8,9,10,10a-decahydro-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol 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. (2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Cotula coronopifolia. Based on a literature review very few articles have been published on (2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-1,2,3,4,5,7,8,9,10,10a-decahydro-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032220382D          

 30 32  0  0  1  0            999 V2000
   -0.4331   -2.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814   -1.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.4331   -0.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475   -0.8853    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1475   -1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8620   -2.1228    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8620   -2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -3.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -1.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2910   -2.1228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -0.8853    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2910   -0.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8620    0.3522    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


  Mrv1652309032220382D          

 30 32  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0180293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@@](C)(O)[C@@H]2CCN(C)CCC=C2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H39NO7/c1-12-19(30-20-18(27)17(26)16(25)15(11-24)29-20)22(4,28)14-8-10-23(5)9-6-7-13(14)21(12,2)3/h7,12,14-20,24-28H,6,8-11H2,1-5H3/t12-,14-,15+,16+,17-,18+,19+,20-,22+/m1/s1

> <INCHI_KEY>
GAUWTQHFJRGQDO-ZQNHEOFASA-N

> <FORMULA>
C22H39NO7

> <MOLECULAR_WEIGHT>
429.554

> <EXACT_MASS>
429.2726526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
46.85648967957617

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-1,2,3,4,5,7,8,9,10,10a-decahydro-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.39834527266666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.103290005506778

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.198179370788312

> <JCHEM_PKA_STRONGEST_BASIC>
9.118757938707988

> <JCHEM_POLAR_SURFACE_AREA>
122.85000000000001

> <JCHEM_REFRACTIVITY>
112.17989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1H-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <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      -0.808  -3.963   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.525  -3.193   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.525  -1.653   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.808  -0.883   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.142  -1.653   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.142  -3.193   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.476  -3.963   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.476  -5.503   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.809  -6.273   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.809  -3.193   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.143  -3.963   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.809  -1.653   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.143  -0.883   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.476  -0.883   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.476   0.657   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.859  -0.883   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.869   0.297   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.849   0.297   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.193  -1.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.282  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.822  -0.564   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.911  -1.653   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.333  -1.063   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.911  -3.193   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.822  -4.282   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.282  -4.282   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.193  -3.193   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.859  -3.963   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.582  -5.322   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.136  -5.322   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15                                                  
CONECT   15   14                                                            
CONECT   16    3   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27    2   29   30                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₉NO₇

Average Mass

429.5540 Da

Monoisotopic Mass

429.27265 Da

IUPAC Name

(2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-1,2,3,4,5,7,8,9,10,10a-decahydro-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3S,4R,5R,6S)-2-{[(8S,9S,10S,10aR)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1H-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)[C@@](C)(O)[C@@H]2CCN(C)CCC=C2C1(C)C

InChI Identifier

InChI=1S/C22H39NO7/c1-12-19(30-20-18(27)17(26)16(25)15(11-24)29-20)22(4,28)14-8-10-23(5)9-6-7-13(14)21(12,2)3/h7,12,14-20,24-28H,6,8-11H2,1-5H3/t12-,14-,15+,16+,17-,18+,19+,20-,22+/m1/s1

InChI Key

GAUWTQHFJRGQDO-ZQNHEOFASA-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
Cotula coronopifolia	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

Benzazocine
Hexose monosaccharide
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Acetal
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary alcohol
Organonitrogen compound
Amine
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	-0.4	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	122.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	112.18 m³·mol⁻¹	ChemAxon
Polarizability	46.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162879686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0180293)

MOL for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0180293 ((2r,3s,4r,5r,6s)-2-{[(8s,9s,10s,10ar)-10-hydroxy-3,7,7,8,10-pentamethyl-2,4,5,8,9,10a-hexahydro-1h-3-benzazocin-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)