NP-MRD: Showing NP-Card for Australigenin (NP0085510)

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Record Information

Version

2.0

Created at

2022-04-29 06:00:43 UTC

Updated at

2022-04-29 06:00:43 UTC

NP-MRD ID

NP0085510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Australigenin

Description

Convallamarogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, convallamarogenin is considered to be a sterol. Australigenin is found in Cordyline australis. Based on a literature review very few articles have been published on Convallamarogenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208002D          

 37 42  0  0  1  0            999 V2000
   -3.0762   -0.9209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.8729    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5223   -2.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3013   -2.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6716   -1.4184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2183   -0.7291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.5886    0.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292208002D          

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 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  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
 24 29  1  0  0  0  0
 27 30  2  0  0  0  0
 24 31  1  6  0  0  0
 18 31  1  0  0  0  0
  4 32  1  6  0  0  0
  4 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
  2 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[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(CCC(=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/h16-24,28-29H,1,5-14H2,2-4H3/t16-,17-,18+,19+,20-,21-,22-,23+,24-,25-,26-,27+/m0/s1

> <INCHI_KEY>
XLHFBXMTUNORSV-XLVIIDFLSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.1785481149857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
3.7595877813333334

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.374421973880075

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.504215441737195

> <JCHEM_PKA_STRONGEST_BASIC>
-2.725746678503633

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
120.58829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.03e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -5.742  -1.719   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.205  -1.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.359  -2.916   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.821  -2.827   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.975  -4.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.562  -4.024   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.254  -2.648   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0       1.945  -1.272   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0       0.407  -1.361   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       0.318   0.176   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       1.099   0.015   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.636   0.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.482  -1.182   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.313   0.114   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.791  -2.558   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.247  -3.999   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       3.886  -3.641   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.254  -2.934   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.504  -4.453   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       5.005  -1.414   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       6.381  -2.105   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       6.373  -0.707   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.605   0.815   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.468  -1.790   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.012  -0.349   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.531  -0.099   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.507  -1.290   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.964  -2.731   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.444  -2.981   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.027  -1.041   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.777  -3.166   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      -0.284  -2.737   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      -1.130  -1.451   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.439  -0.074   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.976  -0.164   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.285   1.212   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.514  -0.253   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32   33                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   33                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29   31                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31   24   18                                                       
CONECT   32    4                                                            
CONECT   33    4    9   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[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(CCC(=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/h16-24,28-29H,1,5-14H2,2-4H3/t16-,17-,18+,19+,20-,21-,22-,23+,24-,25-,26-,27+/m0/s1

InChI Key

XLHFBXMTUNORSV-XLVIIDFLSA-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 australis	Plant	KNApSAcK

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-hydroxysteroid
Hydroxysteroid
1-hydroxysteroid
3-beta-hydroxysteroid
Steroid
Ketal
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Spirostanols and derivatives (LMST01080049 )

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	2.63	ALOGPS
logP	3.76	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	-2.7	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	120.59 m³·mol⁻¹	ChemAxon
Polarizability	51.18 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

C00055393

Chemspider ID

153748

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Australigenin (NP0085510)

MOL for NP0085510 (Australigenin)

3D MOL for NP0085510 (Australigenin)

3D SDF for NP0085510 (Australigenin)

3D-SDF for NP0085510 (Australigenin)

PDB for NP0085510 (Australigenin)

3D PDB for NP0085510 (Australigenin)

SMILES for NP0085510 (Australigenin)

INCHI for NP0085510 (Australigenin)

Structure for NP0085510 (Australigenin)

3D Structure for NP0085510 (Australigenin)