NP-MRD: Showing NP-Card for balsaminapentaol (NP0242661)

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Record Information

Version

2.0

Created at

2022-09-07 03:01:51 UTC

Updated at

2022-09-07 03:01:51 UTC

NP-MRD ID

NP0242661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

balsaminapentaol

Description

14-(4,5-Dihydroxy-6-methylhept-6-en-2-yl)-6-(hydroxymethyl)-1,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,9-diol 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. balsaminapentaol is found in Momordica balsamina. 14-(4,5-Dihydroxy-6-methylhept-6-en-2-yl)-6-(hydroxymethyl)-1,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,9-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261517232D          

 35 38  0  0  0  0            999 V2000
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   -1.4201   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7056   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004261517232D          

 35 38  0  0  0  0            999 V2000
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   -8.8115   -1.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5868   -1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0111   -0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4177   -0.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6456   -1.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9005   -2.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0935   -2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2866   -2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4185   -2.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 30  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 11 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(O)C(O)C(C)=C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)CO)C3(C)CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-17(2)25(35)22(32)14-18(3)19-10-11-30(7)26-23(33)15-21-20(8-9-24(34)28(21,5)16-31)27(26,4)12-13-29(19,30)6/h15,18-20,22-26,31-35H,1,8-14,16H2,2-7H3

> <INCHI_KEY>
LJWAEAIXBCCHLR-UHFFFAOYSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.45008382926234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(4,5-dihydroxy-6-methylhept-6-en-2-yl)-6-(hydroxymethyl)-1,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.068920848333332

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.393403200824071

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.475817162925175

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6146472926754941

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
139.82899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
balsaminapentaol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      -6.652  -4.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.652  -3.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.318  -2.250   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.984  -3.020   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.984  -4.560   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.651  -2.250   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.651  -0.710   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.317  -3.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.017  -2.250   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.317  -4.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.986  -2.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.146  -0.719   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.653  -0.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.423  -1.732   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.328  -0.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -11.929  -2.052   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.960  -0.908   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0     -12.484   0.557   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -14.466  -1.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.942  -2.693   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.911  -3.837   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -14.387  -5.302   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.894  -5.622   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -16.924  -4.478   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -18.430  -4.798   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -16.448  -3.013   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -17.895  -2.486   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -16.821  -1.519   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -15.713  -0.449   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -12.405  -3.517   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.881  -4.982   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.375  -4.661   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.868  -4.341   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.392  -2.877   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.248  -3.907   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   34                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   34                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   21   16   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   11   14   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

14-(4,5-dihydroxy-6-methylhept-6-en-2-yl)-6-(hydroxymethyl)-1,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,9-diol

Traditional Name

balsaminapentaol

CAS Registry Number

Not Available

SMILES

CC(CC(O)C(O)C(C)=C)C1CCC2(C)C3C(O)C=C4C(CCC(O)C4(C)CO)C3(C)CCC12C

InChI Identifier

InChI=1S/C30H50O5/c1-17(2)25(35)22(32)14-18(3)19-10-11-30(7)26-23(33)15-21-20(8-9-24(34)28(21,5)16-31)27(26,4)12-13-29(19,30)6/h15,18-20,22-26,31-35H,1,8-14,16H2,2-7H3

InChI Key

LJWAEAIXBCCHLR-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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	LOTUS Database	35616633

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

Cucurbitacin skeleton
Triterpenoid
24-hydroxysteroid
23-hydroxysteroid
Hydroxysteroid
3-hydroxy-delta-5-steroid
6-hydroxysteroid
3-hydroxysteroid
7-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
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	3.28	ALOGPS
logP	3.07	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-0.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.83 m³·mol⁻¹	ChemAxon
Polarizability	57.45 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

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

75080821

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for balsaminapentaol (NP0242661)

MOL for NP0242661 (balsaminapentaol)

3D MOL for NP0242661 (balsaminapentaol)

3D SDF for NP0242661 (balsaminapentaol)

3D-SDF for NP0242661 (balsaminapentaol)

PDB for NP0242661 (balsaminapentaol)

3D PDB for NP0242661 (balsaminapentaol)

SMILES for NP0242661 (balsaminapentaol)

INCHI for NP0242661 (balsaminapentaol)

Structure for NP0242661 (balsaminapentaol)

3D Structure for NP0242661 (balsaminapentaol)