NP-MRD: Showing NP-Card for 4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one (NP0217930)

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Record Information

Version

2.0

Created at

2022-09-05 18:25:41 UTC

Updated at

2022-09-05 18:25:42 UTC

NP-MRD ID

NP0217930

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one

Description

4-Hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-decahydroazulen-2-one 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. 4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one is found in Atractylodes japonica. 4-Hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-decahydroazulen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161509122D          

 30 32  0  0  0  0            999 V2000
    0.7017    0.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -2.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642   -3.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -0.9761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -0.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193    1.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351    0.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5495    1.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3653    1.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797    2.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5783    2.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    0.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4825    0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523    0.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4537   -0.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365    0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222   -0.4787    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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  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
 22 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
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv1533004161509122D          

 30 32  0  0  0  0            999 V2000
    0.7017    0.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.6463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -2.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8642   -3.2332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -0.9761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500   -0.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193    1.0572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351    0.9342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5495    1.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3653    1.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8797    2.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5783    2.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    0.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4825    0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1523    0.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4537   -0.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3365    0.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222   -0.4787    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
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  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
 22 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
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CC(CCC(O)(CO)C2CC1=O)C(C)(C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H36O9/c1-10-12-6-11(4-5-21(28,9-23)13(12)7-14(10)24)20(2,3)30-19-18(27)17(26)16(25)15(8-22)29-19/h10-13,15-19,22-23,25-28H,4-9H2,1-3H3

> <INCHI_KEY>
KWDNQVRRYNIDTM-UHFFFAOYSA-N

> <FORMULA>
C21H36O9

> <MOLECULAR_WEIGHT>
432.51

> <EXACT_MASS>
432.235932739

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.21182103084813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-decahydroazulen-2-one

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-1.189857675333335

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.08996662663435

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195675163443845

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836721787295

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
104.96390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.310   0.888   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.454  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.123  -4.940   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.250  -4.512   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.480  -6.035   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.659  -1.822   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.916   0.769   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.120  -0.191   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.712   1.730   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.876   1.973   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.399   1.744   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.359   2.948   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.882   2.718   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.842   3.922   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.279   5.356   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.445   1.285   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.967   1.055   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.484   0.081   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.047  -1.353   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.962   0.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.001  -0.894   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    8    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    2   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₆O₉

Average Mass

432.5100 Da

Monoisotopic Mass

432.23593 Da

IUPAC Name

4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-decahydroazulen-2-one

Traditional Name

4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one

CAS Registry Number

Not Available

SMILES

CC1C2CC(CCC(O)(CO)C2CC1=O)C(C)(C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H36O9/c1-10-12-6-11(4-5-21(28,9-23)13(12)7-14(10)24)20(2,3)30-19-18(27)17(26)16(25)15(8-22)29-19/h10-13,15-19,22-23,25-28H,4-9H2,1-3H3

InChI Key

KWDNQVRRYNIDTM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Atractylodes japonica	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
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Primary 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	-0.5	ALOGPS
logP	-1.2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.96 m³·mol⁻¹	ChemAxon
Polarizability	45.21 Å³	ChemAxon
Number of Rings	3	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

73118933

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one (NP0217930)

MOL for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

3D MOL for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

3D SDF for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

3D-SDF for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

PDB for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

3D PDB for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

SMILES for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

INCHI for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

Structure for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)

3D Structure for NP0217930 (4-hydroxy-4-(hydroxymethyl)-1-methyl-7-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-octahydroazulen-2-one)