NP-MRD: Showing NP-Card for Balsaminagenin B (NP0083898)

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Record Information

Version

1.0

Created at

2022-04-29 04:47:55 UTC

Updated at

2022-04-29 04:47:56 UTC

NP-MRD ID

NP0083898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Balsaminagenin B

Description

BALSAMINAGENIN B 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. Balsaminagenin B is found in Momordica balsamina . It was first documented in 2009 (PMID: 19733087). Based on a literature review very few articles have been published on BALSAMINAGENIN B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206472D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206472D          

 38 41  0  0  1  0            999 V2000
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    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7557    0.0139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3705   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2424   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -1.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363   -2.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -2.5212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7830   -3.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 34 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(C)[C@]3([H])[C@@H](O)C=C4[C@@]([H])(CC[C@H](O)[C@]4(C)CO)[C@]3(C)CC[C@]12C)[C@H](C)C\C=C\C(C)(C)OC

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O4/c1-20(10-9-14-27(2,3)35-8)21-13-15-31(7)26-24(33)18-23-22(11-12-25(34)29(23,5)19-32)28(26,4)16-17-30(21,31)6/h9,14,18,20-22,24-26,32-34H,10-13,15-17,19H2,1-8H3/b14-9+/t20-,21-,22-,24+,25+,26-,28+,29-,30-,31+/m1/s1

> <INCHI_KEY>
ZACSSZNPODCJNA-NOXBPOAZSA-N

> <FORMULA>
C31H52O4

> <MOLECULAR_WEIGHT>
488.753

> <EXACT_MASS>
488.386560154

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
59.014565224807214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
4.688278955333333

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.226832607642525

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.435981008557999

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6145258373131751

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
144.7244

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6S,9S,10R,11S,14R,15R)-6-(hydroxymethyl)-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-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  H   UNK     0       5.978  -0.043   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.032   4.031   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.519   3.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.381   2.992   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.377   4.532   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       8.017   1.676   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       1.411   0.026   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.179  -2.545   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.748  -4.436   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.909  -4.706   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.328  -6.133   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17   23                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9   11                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21    2   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₂O₄

Average Mass

488.7530 Da

Monoisotopic Mass

488.38656 Da

IUPAC Name

(1S,2S,5S,6S,9S,10R,11S,14R,15R)-6-(hydroxymethyl)-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

Traditional Name

(1S,2S,5S,6S,9S,10R,11S,14R,15R)-6-(hydroxymethyl)-14-[(2R,4E)-6-methoxy-6-methylhept-4-en-2-yl]-1,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(C)[C@]3([H])[C@@H](O)C=C4[C@@]([H])(CC[C@H](O)[C@]4(C)CO)[C@]3(C)CC[C@]12C)[C@H](C)C\C=C\C(C)(C)OC

InChI Identifier

InChI=1S/C31H52O4/c1-20(10-9-14-27(2,3)35-8)21-13-15-31(7)26-24(33)18-23-22(11-12-25(34)29(23,5)19-32)28(26,4)16-17-30(21,31)6/h9,14,18,20-22,24-26,32-34H,10-13,15-17,19H2,1-8H3/b14-9+/t20-,21-,22-,24+,25+,26-,28+,29-,30-,31+/m1/s1

InChI Key

ZACSSZNPODCJNA-NOXBPOAZSA-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 balsamina	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
3-hydroxy-delta-5-steroid
14-alpha-methylsteroid
3-hydroxysteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
6-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ether
Dialkyl ether
Primary alcohol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
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	5.7	ALOGPS
logP	4.69	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.72 m³·mol⁻¹	ChemAxon
Polarizability	59.01 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

C00052857

Chemspider ID

24645308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44555453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ramalhete C, Molnar J, Mulhovo S, Rosario VE, Ferreira MJ: New potent P-glycoprotein modulators with the cucurbitane scaffold and their synergistic interaction with doxorubicin on resistant cancer cells. Bioorg Med Chem. 2009 Oct 1;17(19):6942-51. doi: 10.1016/j.bmc.2009.08.020. Epub 2009 Aug 15. [PubMed:19733087 ]

Showing NP-Card for Balsaminagenin B (NP0083898)

MOL for NP0083898 (Balsaminagenin B)

3D MOL for NP0083898 (Balsaminagenin B)

3D SDF for NP0083898 (Balsaminagenin B)

3D-SDF for NP0083898 (Balsaminagenin B)

PDB for NP0083898 (Balsaminagenin B)

3D PDB for NP0083898 (Balsaminagenin B)

SMILES for NP0083898 (Balsaminagenin B)

INCHI for NP0083898 (Balsaminagenin B)

Structure for NP0083898 (Balsaminagenin B)

3D Structure for NP0083898 (Balsaminagenin B)