NP-MRD: Showing NP-Card for (+)-Marsin (NP0074727)

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Record Information

Version

2.0

Created at

2022-04-28 20:02:55 UTC

Updated at

2022-04-28 20:02:55 UTC

NP-MRD ID

NP0074727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Marsin

Description

1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl]ethan-1-one belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. (+)-Marsin is found in Marsdenia roylei . Based on a literature review very few articles have been published on 1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-14-yl]ethan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222022D          

 34 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282222022D          

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  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
  2 24  1  1  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 29 32  1  1  0  0  0
 28 33  1  1  0  0  0
 27 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074727

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)[C@@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O7/c1-14(28)18-9-12-27(32)20-6-5-16-13-17(34-24-23(31)22(30)21(29)15(2)33-24)7-10-25(16,3)19(20)8-11-26(18,27)4/h5,15,17-24,29-32H,6-13H2,1-4H3/t15-,17-,18+,19-,20+,21+,22+,23-,24-,25-,26+,27-/m0/s1

> <INCHI_KEY>
FQXKZRWLIJVZPF-YTRYOHOFSA-N

> <FORMULA>
C27H42O7

> <MOLECULAR_WEIGHT>
478.626

> <EXACT_MASS>
478.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.15706134368438

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.7760867386666659

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.223343150665492

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.219213398103836

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1715961056956408

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
126.07739999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.452  -1.269   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.575  -0.500   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18   23                                             
CONECT   15   14    7   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24    2   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   28                                                            
CONECT   34   27                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₇

Average Mass

478.6260 Da

Monoisotopic Mass

478.29305 Da

IUPAC Name

1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one

Traditional Name

1-[(1S,2R,5S,10R,11S,14S,15R)-11-hydroxy-2,15-dimethyl-5-{[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@H]2CC[C@]3(C)[C@H]4CC[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC=C3C2)C(C)=O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H42O7/c1-14(28)18-9-12-27(32)20-6-5-16-13-17(34-24-23(31)22(30)21(29)15(2)33-24)7-10-25(16,3)19(20)8-11-26(18,27)4/h5,15,17-24,29-32H,6-13H2,1-4H3/t15-,17-,18+,19-,20+,21+,22+,23-,24-,25-,26+,27-/m0/s1

InChI Key

FQXKZRWLIJVZPF-YTRYOHOFSA-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
Marsdenia roylei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
20-oxosteroid
Pregnane-skeleton
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-5-steroid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.78	ALOGPS
logP	1.78	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.08 m³·mol⁻¹	ChemAxon
Polarizability	53.16 Å³	ChemAxon
Number of Rings	5	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

9457991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11282994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Marsin (NP0074727)

MOL for NP0074727 ((+)-Marsin)

3D MOL for NP0074727 ((+)-Marsin)

3D SDF for NP0074727 ((+)-Marsin)

3D-SDF for NP0074727 ((+)-Marsin)

PDB for NP0074727 ((+)-Marsin)

3D PDB for NP0074727 ((+)-Marsin)

SMILES for NP0074727 ((+)-Marsin)

INCHI for NP0074727 ((+)-Marsin)

Structure for NP0074727 ((+)-Marsin)

3D Structure for NP0074727 ((+)-Marsin)