NP-MRD: Showing NP-Card for Ruscogenin (NP0052120)

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Record Information

Version

2.0

Created at

2022-04-27 23:17:24 UTC

Updated at

2022-04-27 23:17:24 UTC

NP-MRD ID

NP0052120

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ruscogenin

Description

Ruscogenin, also known as ruscorectal, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, ruscogenin is considered to be a sterol lipid molecule. Ruscogenin is found in Cordyline stricta, Liriope platyphylla , Liriope spicata, Ophiopogon japonicus , Ophiopogon planiscapus, Ruscus aculeatus , Ruscus hyrcanus, Sansevieria ehrenbergii, Tribulus aculeatus and Tribulus terrestris. Ruscogenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652306031608562D          

 40 45  0  0  1  0            999 V2000
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 40  1  6  0  0  0
M  END

     RDKit          3D

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M  END

  Mrv1652306031608562D          

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    8.4366   -2.6066    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7973   -1.4576    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1748   -3.0183    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3276   -2.7154    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 15  1  1  1  0  0  0
 15  7  1  0  0  0  0
 15 14  1  0  0  0  0
 16  2  1  6  0  0  0
 17  5  2  0  0  0  0
 17 11  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19  6  1  0  0  0  0
 20  8  1  0  0  0  0
 20 19  1  0  0  0  0
 21 13  1  0  0  0  0
 21 19  1  0  0  0  0
 22 13  1  0  0  0  0
 23 12  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25  3  1  1  0  0  0
 25  9  1  0  0  0  0
 25 21  1  0  0  0  0
 25 24  1  0  0  0  0
 26  4  1  1  0  0  0
 26 17  1  0  0  0  0
 26 20  1  0  0  0  0
 26 23  1  0  0  0  0
 27 10  1  0  0  0  0
 27 16  1  0  0  0  0
 18 28  1  1  0  0  0
 23 29  1  6  0  0  0
 30 14  1  0  0  0  0
 30 27  1  0  0  0  0
 31 22  1  0  0  0  0
 27 31  1  1  0  0  0
 15 32  1  6  0  0  0
 16 33  1  1  0  0  0
 18 34  1  6  0  0  0
 19 35  1  1  0  0  0
 20 36  1  6  0  0  0
 21 37  1  6  0  0  0
 22 38  1  6  0  0  0
 23 39  1  6  0  0  0
 24 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052120

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@]([H])(O)C[C@@]([H])(O)[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@]([H])(C)[C@@]1(CC[C@@]([H])(C)CO1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
QMQIQBOGXYYATH-IDABPMKMSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.08069619205672

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-14',16'-diol

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
3.623700380999998

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.318872264595267

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.449436263710375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7501835276837

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
121.7378

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-14',16'-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.454  -7.989   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.048  -6.825   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      21.344  -8.386   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      11.615  -4.193   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       8.576  -4.693   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      14.937  -7.365   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      25.110  -6.831   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      17.959  -3.240   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      18.114  -5.903   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      15.748  -4.866   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      14.555  -2.721   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      22.726  -5.634   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      13.678  -5.069   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    6   17                                                       
CONECT    6    5   19                                                       
CONECT    7   10   15                                                       
CONECT    8    9   20                                                       
CONECT    9    8   25                                                       
CONECT   10    7   27                                                       
CONECT   11   17   18                                                       
CONECT   12   18   23                                                       
CONECT   13   21   22                                                       
CONECT   14   15   30                                                       
CONECT   15    1    7   14   32                                             
CONECT   16    2   24   27   33                                             
CONECT   17    5   11   26                                                  
CONECT   18   11   12   28   34                                             
CONECT   19    6   20   21   35                                             
CONECT   20    8   19   26   36                                             
CONECT   21   13   19   25   37                                             
CONECT   22   13   24   31   38                                             
CONECT   23   12   26   29   39                                             
CONECT   24   16   22   25   40                                             
CONECT   25    3    9   21   24                                             
CONECT   26    4   17   20   23                                             
CONECT   27   10   16   30   31                                             
CONECT   28   18                                                            
CONECT   29   23                                                            
CONECT   30   14   27                                                       
CONECT   31   22   27                                                       
CONECT   32   15                                                            
CONECT   33   16                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   21                                                            
CONECT   38   22                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Ruscorectal	Kegg
Ruscogenin, (1beta,3alpha,25S)-isomer	MeSH
Ruscogenin, (1beta,3alpha,25R)-isomer	MeSH

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-14',16'-diol

Traditional Name

(1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,14'R,16'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-ene-14',16'-diol

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@]([H])(O)C[C@@]([H])(O)[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@]([H])(C)[C@@]1(CC[C@@]([H])(C)CO1)O2

InChI Identifier

InChI=1S/C27H42O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)13-21-19-6-5-17-11-18(28)12-23(29)26(17,4)20(19)8-9-25(21,24)3/h5,15-16,18-24,28-29H,6-14H2,1-4H3/t15-,16+,18-,19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI Key

QMQIQBOGXYYATH-IDABPMKMSA-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
Cordyline stricta	LOTUS Database	35616633
Liriope muscari	Plant	KNApSAcK
Liriope spicata	Plant	KNApSAcK
Ophiopogon japonicus	Plant	KNApSAcK
Ophiopogon planiscapus	Plant	KNApSAcK
Ruscus aculeatus	Plant	KNApSAcK
Ruscus hyrcanus	Plant	KNApSAcK
Sansevieria ehrenbergii	LOTUS Database	35616633
Tribulus aculeatus	Plant	KNApSAcK
Tribulus terrestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Spirostane skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
1-hydroxysteroid
Steroid
Delta-5-steroid
Ketal
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:8913 )
spirostan (C08909 )
Spirostanols and derivatives (LMST01080038 )

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	3.08	ALOGPS
logP	3.62	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.74 m³·mol⁻¹	ChemAxon
Polarizability	51.08 Å³	ChemAxon
Number of Rings	6	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

C00003587

Chemspider ID

Not Available

KEGG Compound ID

C08909

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441893

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ruscogenin (NP0052120)

MOL for NP0052120 (Ruscogenin)

3D MOL for NP0052120 (Ruscogenin)

3D SDF for NP0052120 (Ruscogenin)

3D-SDF for NP0052120 (Ruscogenin)

PDB for NP0052120 (Ruscogenin)

3D PDB for NP0052120 (Ruscogenin)

SMILES for NP0052120 (Ruscogenin)

INCHI for NP0052120 (Ruscogenin)

Structure for NP0052120 (Ruscogenin)

3D Structure for NP0052120 (Ruscogenin)