NP-MRD: Showing NP-Card for (-)-Kuguacin S (NP0081852)

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Record Information

Version

2.0

Created at

2022-04-29 02:55:18 UTC

Updated at

2022-04-29 02:55:19 UTC

NP-MRD ID

NP0081852

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Kuguacin S

Description

Kugacin S belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (-)-Kuguacin S is found in Momordica charantia . Based on a literature review very few articles have been published on Kugacin S.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204552D          

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M  END

     RDKit          3D

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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 24 32  1  6  0  0  0
  7 33  1  1  0  0  0
  6 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C\C=C\C(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3C(=O)C=C4[C@@H](CCC(=O)C4(C)C)[C@@]3(CC[C@]12C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-19(9-8-13-26(2,3)34)20-12-14-29(7)25-23(32)17-22-21(10-11-24(33)27(22,4)5)30(25,18-31)16-15-28(20,29)6/h8,13,17-21,25,34H,9-12,14-16H2,1-7H3/b13-8+/t19-,20-,21-,25+,28-,29+,30-/m1/s1

> <INCHI_KEY>
HDXSEJMHFIDKAU-AHQZNLJJSA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.7520603150235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,10S,11S,14R,15R)-14-[(2R,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-1-carbaldehyde

> <ALOGPS_LOGP>
5.25

> <JCHEM_LOGP>
5.511879600666667

> <ALOGPS_LOGS>
-5.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.781315978829436

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.311166321343105

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5822073153256326

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
137.3735

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10S,11S,14R,15R)-14-[(2R,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-1-carbaldehyde

> <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  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.332   3.252   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.028   3.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.247  -4.122   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.666  -5.549   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.612  -6.765   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.557  -7.980   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.396  -7.710   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.827  -5.819   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1                                                            
CONECT    3    1    4    8   13                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23   34                                             
CONECT    7    6    8   21   33                                             
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    7   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    6   24                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   24                                                            
CONECT   33    7                                                            
CONECT   34    6                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

(1R,2R,10S,11S,14R,15R)-14-[(2R,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-1-carbaldehyde

Traditional Name

(1R,2R,10S,11S,14R,15R)-14-[(2R,4E)-6-hydroxy-6-methylhept-4-en-2-yl]-6,6,11,15-tetramethyl-5,9-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-1-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@H](C\C=C\C(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3C(=O)C=C4[C@@H](CCC(=O)C4(C)C)[C@@]3(CC[C@]12C)C=O

InChI Identifier

InChI=1S/C30H44O4/c1-19(9-8-13-26(2,3)34)20-12-14-29(7)25-23(32)17-22-21(10-11-24(33)27(22,4)5)30(25,18-31)16-15-28(20,29)6/h8,13,17-21,25,34H,9-12,14-16H2,1-7H3/b13-8+/t19-,20-,21-,25+,28-,29+,30-/m1/s1

InChI Key

HDXSEJMHFIDKAU-AHQZNLJJSA-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
Momordica charantia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Triterpenoid
Cucurbitacin skeleton
25-hydroxysteroid
14-alpha-methylsteroid
7-oxosteroid
Oxosteroid
3-oxosteroid
3-oxo-delta-5-steroid
Delta-5-steroid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	5.25	ALOGPS
logP	5.51	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	15.31	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.37 m³·mol⁻¹	ChemAxon
Polarizability	54.75 Å³	ChemAxon
Number of Rings	4	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

25243426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Kuguacin S (NP0081852)

MOL for NP0081852 ((-)-Kuguacin S)

3D MOL for NP0081852 ((-)-Kuguacin S)

3D SDF for NP0081852 ((-)-Kuguacin S)

3D-SDF for NP0081852 ((-)-Kuguacin S)

PDB for NP0081852 ((-)-Kuguacin S)

3D PDB for NP0081852 ((-)-Kuguacin S)

SMILES for NP0081852 ((-)-Kuguacin S)

INCHI for NP0081852 ((-)-Kuguacin S)

Structure for NP0081852 ((-)-Kuguacin S)

3D Structure for NP0081852 ((-)-Kuguacin S)