NP-MRD: Showing NP-Card for Barogenin (NP0085173)

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Record Information

Version

2.0

Created at

2022-04-29 05:46:17 UTC

Updated at

2022-04-29 05:46:17 UTC

NP-MRD ID

NP0085173

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Barogenin

Description

64161-55-3 Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. Barogenin is found in Solanum tuberosum . Based on a literature review very few articles have been published on 64161-55-3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207462D          

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M  END

     RDKit          3D

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M  END


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M  END
> <DATABASE_ID>
NP0085173

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC(=O)[C@]([H])([C@H](C)C(=O)CC[C@H](C)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-22,25,28-29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,25-,26-,27-/m0/s1

> <INCHI_KEY>
GDKGOXUWEBGZBY-CEEFRGMYSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.55218689168627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,14R,15S)-5-hydroxy-14-[(2S,6S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

> <ALOGPS_LOGP>
4.42

> <JCHEM_LOGP>
3.9076630573333326

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.20428950550309

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.49078674737361

> <JCHEM_PKA_STRONGEST_BASIC>
-1.224806155067014

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
123.80279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,14R,15S)-5-hydroxy-14-[(2S,6S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

> <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      -6.998   6.348   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.492   6.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.016   4.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.510   4.243   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.479   5.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.955   6.852   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.461   7.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.449   6.532   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.034   2.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.527   2.458   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.497   3.603   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -0.021   2.138   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -0.973   5.067   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.534   4.747   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       0.058   6.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.564   5.892   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.040   4.427   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.010   3.283   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       2.541   3.122   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       1.780   1.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.286   2.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.781   4.571   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.781   6.111   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.114   3.801   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.448   4.571   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.782   3.801   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.115   4.571   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.115   6.111   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.449   3.801   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.783   4.571   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.114   2.261   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.738   2.962   0.000  0.00  0.00           H+0
HETATM   34  O   UNK     0       4.430   1.239   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.184   5.458   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8   13                                             
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22   35                                             
CONECT   18   17   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   34                                                  
CONECT   22   21   17   23   33                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   25                                                            
CONECT   33   22                                                            
CONECT   34   21                                                            
CONECT   35   17                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

(1S,2R,5S,10S,11S,14R,15S)-5-hydroxy-14-[(2S,6S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

Traditional Name

(1S,2R,5S,10S,11S,14R,15S)-5-hydroxy-14-[(2S,6S)-7-hydroxy-6-methyl-3-oxoheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-13-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC(=O)[C@]([H])([C@H](C)C(=O)CC[C@H](C)CO)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C27H42O4/c1-16(15-28)5-8-23(30)17(2)25-24(31)14-22-20-7-6-18-13-19(29)9-11-26(18,3)21(20)10-12-27(22,25)4/h6,16-17,19-22,25,28-29H,5,7-15H2,1-4H3/t16-,17+,19-,20+,21-,22-,25-,26-,27-/m0/s1

InChI Key

GDKGOXUWEBGZBY-CEEFRGMYSA-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
Solanum tuberosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

26-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
22-oxosteroid
21-oxosteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
16-oxosteroid
Oxosteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.42	ALOGPS
logP	3.91	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.49	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	123.8 m³·mol⁻¹	ChemAxon
Polarizability	51.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054923

Chemspider ID

103884665

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101316886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Barogenin (NP0085173)

MOL for NP0085173 (Barogenin)

3D MOL for NP0085173 (Barogenin)

3D SDF for NP0085173 (Barogenin)

3D-SDF for NP0085173 (Barogenin)

PDB for NP0085173 (Barogenin)

3D PDB for NP0085173 (Barogenin)

SMILES for NP0085173 (Barogenin)

INCHI for NP0085173 (Barogenin)

Structure for NP0085173 (Barogenin)

3D Structure for NP0085173 (Barogenin)