NP-MRD: Showing NP-Card for Dstramonin A (NP0331649)

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Record Information

Version

2.0

Created at

2023-05-26 16:00:49 UTC

Updated at

2025-02-11 15:47:08 UTC

NP-MRD ID

NP0331649

Natural Product DOI

https://doi.org/10.57994/0638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dstramonin A

Description

Dstramonin A 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. Dstramonin A was first documented in 2024 (PMID: 37198914). Based on a literature review very few articles have been published on Dstramonin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305262318002D          

 29 31  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6668    0.9292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1040    1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9285    1.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3656    2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    3.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3158    0.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    0.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8786    0.1720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2659   -0.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6169   -0.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  2  0  0  0  0
M  END


  Mrv1652305262318002D          

 29 31  0  0  1  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9679   -0.3837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806    0.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8423    0.9580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6668    0.9292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1040    1.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9285    1.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3656    2.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    3.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3158    0.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1403    0.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8786    0.1720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2659   -0.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    0.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6169   -0.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 15 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@H](O)C2=CC[C@@](O)(C[C@]12C)C(=C)CO[C@H]1O[C@@H](CO)C(O)[C@@H](O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O8/c1-11-4-5-14(23)13-6-7-21(27,10-20(11,13)3)12(2)9-28-19-18(26)17(25)16(24)15(8-22)29-19/h6,11,14-19,22-27H,2,4-5,7-10H2,1,3H3/t11-,14-,15-,16?,17+,18?,19-,20+,21+/m0/s1

> <INCHI_KEY>
FSCAQHLKBOUXIQ-FUHSODRDSA-N

> <FORMULA>
C21H34O8

> <MOLECULAR_WEIGHT>
414.495

> <EXACT_MASS>
414.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
43.3832246363195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R,6S)-2-({2-[(2R,5S,8S,8aR)-2,5-dihydroxy-8,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.9224082426666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.150463068944177

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204469969792648

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1877971565802405

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
104.68400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R,6S)-2-({2-[(2R,5S,8S,8aR)-2,5-dihydroxy-8,8a-dimethyl-1,3,5,6,7,8-hexahydronaphthalen-2-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+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       0.000   1.540   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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.540  -0.716   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.817   0.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.356   0.482   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.172   1.788   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.711   1.734   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.527   3.040   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.066   2.987   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.883   4.293   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.160   5.652   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.789   1.627   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.328   1.573   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.973   0.321   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.696  -1.039   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.434   0.375   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.618  -0.931   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.094   1.896   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5                                                            
CONECT    7    2    8   11                                                  
CONECT    8    7    5    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   13                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   10   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   18   28                                                  
CONECT   28   27                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₈

Average Mass

414.4950 Da

Monoisotopic Mass

414.22537 Da

IUPAC Name

(2S,4R,6S)-2-({2-[(2R,5S,8S,8aR)-2,5-dihydroxy-8,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-2-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,4R,6S)-2-({2-[(2R,5S,8S,8aR)-2,5-dihydroxy-8,8a-dimethyl-1,3,5,6,7,8-hexahydronaphthalen-2-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H](O)C2=CC[C@@](O)(C[C@]12C)C(=C)CO[C@H]1O[C@@H](CO)C(O)[C@@H](O)C1O

InChI Identifier

InChI=1S/C21H34O8/c1-11-4-5-14(23)13-6-7-21(27,10-20(11,13)3)12(2)9-28-19-18(26)17(25)16(24)15(8-22)29-19/h6,11,14-19,22-27H,2,4-5,7-10H2,1,3H3/t11-,14-,15-,16?,17+,18?,19-,20+,21+/m0/s1

InChI Key

FSCAQHLKBOUXIQ-FUHSODRDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	570075670@qq.com	黑龙江中医药大学	Pan juan	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Datura stramonium		Not Available

Chemical Taxonomy

Description

This compound 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
Eremophilane sesquiterpenoid
Sesquiterpenoid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Fatty alcohol
Fatty acyl
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	-0.92	ChemAxon
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.68 m³·mol⁻¹	ChemAxon
Polarizability	43.38 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1080/14786419.2023.2214292

Showing NP-Card for Dstramonin A (NP0331649)

MOL for NP0331649 (Dstramonin A)

3D MOL for NP0331649 (Dstramonin A)

3D SDF for NP0331649 (Dstramonin A)

3D-SDF for NP0331649 (Dstramonin A)

PDB for NP0331649 (Dstramonin A)

3D PDB for NP0331649 (Dstramonin A)

SMILES for NP0331649 (Dstramonin A)

INCHI for NP0331649 (Dstramonin A)

Structure for NP0331649 (Dstramonin A)

3D Structure for NP0331649 (Dstramonin A)