NP-MRD: Showing NP-Card for [(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate (NP0265978)

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Record Information

Version

1.0

Created at

2022-09-08 10:09:48 UTC

Updated at

2022-09-08 10:09:48 UTC

NP-MRD ID

NP0265978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate

Description

Lup-20(29)-ene-2alpha,3beta,28-triol 3,28-dipalmitate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. [(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate is found in Rheum rhabarbarum. Based on a literature review very few articles have been published on Lup-20(29)-ene-2alpha,3beta,28-triol 3,28-dipalmitate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082212092D          

 67 71  0  0  1  0            999 V2000
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M  END


  Mrv1652309082212092D          

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 29 65  1  0  0  0  0
 65 66  1  6  0  0  0
 31 67  1  0  0  0  0
 67  4  1  6  0  0  0
  7 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0265978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC[C@]12CC[C@H]([C@@H]1[C@H]1CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](OC(=O)CCCCCCCCCCCCCCC)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C62H110O5/c1-10-12-14-16-18-20-22-24-26-28-30-32-34-36-54(64)66-47-62-43-40-49(48(3)4)56(62)50-38-39-53-59(7)46-51(63)57(58(5,6)52(59)41-42-61(53,9)60(50,8)44-45-62)67-55(65)37-35-33-31-29-27-25-23-21-19-17-15-13-11-2/h49-53,56-57,63H,3,10-47H2,1-2,4-9H3/t49-,50+,51+,52-,53+,56+,57-,59-,60+,61+,62+/m0/s1

> <INCHI_KEY>
RHHIAWXSQKGCMB-NGVVZOSZSA-N

> <FORMULA>
C62H110O5

> <MOLECULAR_WEIGHT>
935.557

> <EXACT_MASS>
934.835326642

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
177

> <JCHEM_AVERAGE_POLARIZABILITY>
123.59327563951388

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,5S,8R,9R,10R,13R,14R,16R,17R,19R)-17-(hexadecanoyloxy)-16-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-5-yl]methyl hexadecanoate

> <JCHEM_LOGP>
18.934479522

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.140943569297377

> <JCHEM_PKA_STRONGEST_BASIC>
-3.174551282789327

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
281.2273

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,5S,8R,9R,10R,13R,14R,16R,17R,19R)-17-(hexadecanoyloxy)-16-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-5-yl]methyl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.016  -6.785   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.389  -8.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.295  -9.438   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.142  -8.353   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.912  -9.687   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.419  -9.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.580  -7.835   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.913  -8.605   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.247  -7.835   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.581  -8.605   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.581 -10.145   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.914  -7.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.248  -8.605   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.582  -7.835   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.915  -8.605   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.249  -7.835   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.583  -8.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.916  -7.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.250  -8.605   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.584  -7.835   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.917  -8.605   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.251  -7.835   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.585  -8.605   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.918  -7.835   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      25.252  -8.605   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      26.586  -7.835   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.825  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.664  -5.398   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.258  -4.772   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.504  -3.867   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.012  -5.677   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.395  -5.051   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.556  -3.519   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.690  -2.614   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.529  -1.083   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.717  -1.988   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.878  -0.456   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.039   1.075   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.446   1.702   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.207   1.981   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.046   3.512   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.292   4.417   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.699   3.791   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.131   5.949   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.377   6.854   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.216   8.386   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       3.462   9.291   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.301  10.822   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.547  11.728   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.386  13.259   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       5.631  14.164   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.470  15.696   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       6.716  16.601   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.555  18.133   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.801  19.038   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       7.640  20.569   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.886  21.475   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.725  23.006   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       1.614   1.354   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       1.986   2.848   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       3.150   1.247   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       1.775  -0.177   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       3.182  -0.804   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       3.343  -2.335   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       2.097  -3.240   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       3.603  -2.920   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       1.173  -7.209   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   67                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   27   67                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27    7   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   65                                             
CONECT   30   29                                                            
CONECT   31   29   32   67                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   65                                                  
CONECT   35   34   36   37   62                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   59                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57                                                            
CONECT   59   40   60   61   62                                             
CONECT   60   59                                                            
CONECT   61   59                                                            
CONECT   62   59   35   63                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   34   29   66                                             
CONECT   66   65                                                            
CONECT   67   31    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   67    0  142    0
END

View in JSmol

Synonyms

Value	Source
Lup-20(29)-ene-2a,3b,28-triol 3,28-dipalmitate	Generator
Lup-20(29)-ene-2a,3b,28-triol 3,28-dipalmitic acid	Generator
Lup-20(29)-ene-2alpha,3beta,28-triol 3,28-dipalmitic acid	Generator
Lup-20(29)-ene-2α,3β,28-triol 3,28-dipalmitate	Generator
Lup-20(29)-ene-2α,3β,28-triol 3,28-dipalmitic acid	Generator

Chemical Formula

C₆₂H₁₁₀O₅

Average Mass

935.5570 Da

Monoisotopic Mass

934.83533 Da

IUPAC Name

[(1R,2R,5S,8R,9R,10R,13R,14R,16R,17R,19R)-17-(hexadecanoyloxy)-16-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-5-yl]methyl hexadecanoate

Traditional Name

[(1R,2R,5S,8R,9R,10R,13R,14R,16R,17R,19R)-17-(hexadecanoyloxy)-16-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-5-yl]methyl hexadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@]12CC[C@H]([C@@H]1[C@H]1CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](OC(=O)CCCCCCCCCCCCCCC)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)CC2)C(C)=C

InChI Identifier

InChI=1S/C62H110O5/c1-10-12-14-16-18-20-22-24-26-28-30-32-34-36-54(64)66-47-62-43-40-49(48(3)4)56(62)50-38-39-53-59(7)46-51(63)57(58(5,6)52(59)41-42-61(53,9)60(50,8)44-45-62)67-55(65)37-35-33-31-29-27-25-23-21-19-17-15-13-11-2/h49-53,56-57,63H,3,10-47H2,1-2,4-9H3/t49-,50+,51+,52-,53+,56+,57-,59-,60+,61+,62+/m0/s1

InChI Key

RHHIAWXSQKGCMB-NGVVZOSZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rheum rhabarbarum	LOTUS Database	35616633

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
Steroid ester
Steroid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	18.93	ChemAxon
pKa (Strongest Acidic)	14.14	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	281.23 m³·mol⁻¹	ChemAxon
Polarizability	123.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

103884177

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15226244

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate (NP0265978)

MOL for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D MOL for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D SDF for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D-SDF for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

PDB for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D PDB for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

SMILES for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

INCHI for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

Structure for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)

3D Structure for NP0265978 ([(1r,3as,5ar,5br,7ar,9r,10r,11ar,11br,13ar,13br)-9-(hexadecanoyloxy)-10-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl hexadecanoate)