NP-MRD: Showing NP-Card for (2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid (NP0270066)

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Record Information

Version

2.0

Created at

2022-09-08 15:45:08 UTC

Updated at

2022-09-08 15:45:08 UTC

NP-MRD ID

NP0270066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid

Description

[(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy][(2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy]phosphinic acid belongs to the class of organic compounds known as semilysobisphosphatidic acids. These are bisphosphatidic acid analogues with three moles of fatty acid per mole of lipid. (2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid is found in Alicyclobacillus acidoterrestris. Based on a literature review very few articles have been published on [(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy][(2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy]phosphinic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082217452D          

 73 75  0  0  1  0            999 V2000
   17.0408  -39.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6945  -39.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   18.5662  -40.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3289  -40.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4378  -41.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2005  -41.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 68 73  1  0  0  0  0
M  END


  Mrv1652309082217452D          

 73 75  0  0  1  0            999 V2000
   17.0408  -39.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6945  -39.1935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0270066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCCCCCCC1CCCCCC1)CCC(=O)OC[C@H](O)COP(O)(=O)OC[C@H](COC(=O)CCCCCCCCCCCCC1CCCCC1)OC(=O)CCCCCCCCCCC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C61H113O11P/c1-53(35-23-13-12-16-26-38-54-39-27-19-20-28-40-54)47-48-60(64)68-49-57(62)50-70-73(66,67)71-52-58(72-61(65)46-34-18-11-7-6-9-15-25-37-56-43-31-22-32-44-56)51-69-59(63)45-33-17-10-5-3-2-4-8-14-24-36-55-41-29-21-30-42-55/h53-58,62H,2-52H2,1H3,(H,66,67)/t53-,57-,58-/m0/s1

> <INCHI_KEY>
HDDQHIGFLIJCEC-JMZWQWJHSA-N

> <FORMULA>
C61H113O11P

> <MOLECULAR_WEIGHT>
1053.538

> <EXACT_MASS>
1052.802051457

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
186

> <JCHEM_AVERAGE_POLARIZABILITY>
131.17246252708924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy][(2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy]phosphinic acid

> <JCHEM_LOGP>
18.948710094000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.655609256264167

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907692430707543

> <JCHEM_PKA_STRONGEST_BASIC>
-3.404003361661159

> <JCHEM_POLAR_SURFACE_AREA>
154.89000000000001

> <JCHEM_REFRACTIVITY>
295.4911

> <JCHEM_ROTATABLE_BOND_COUNT>
49

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid

> <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                                  
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HETATM    8  C   UNK     0      37.911 -79.502   0.000  0.00  0.00           C+0
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HETATM   11  C   UNK     0      41.002 -82.095   0.000  0.00  0.00           C+0
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HETATM   43  C   UNK     0      16.352 -48.972   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      14.929 -48.385   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      14.725 -46.858   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      13.302 -46.271   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.098 -44.745   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.674 -44.158   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.471 -42.631   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.047 -42.044   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       9.844 -40.517   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      11.064 -39.578   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.488 -40.165   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      12.691 -41.692   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      25.708 -58.601   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      25.505 -57.074   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      24.081 -56.487   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      26.725 -56.135   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.521 -54.608   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      27.742 -53.669   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      27.538 -52.142   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      28.759 -51.203   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      28.555 -49.676   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      29.776 -48.737   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      29.572 -47.211   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      30.793 -46.271   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      30.589 -44.745   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      31.809 -43.805   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      31.606 -42.279   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      32.826 -41.339   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      34.250 -41.926   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      34.453 -43.453   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      33.233 -44.392   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10                                                       
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   55                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   54                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   49                                                       
CONECT   55   32   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69   73                                                  
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   68                                                       
MASTER        0    0    0    0    0    0    0    0   73    0  150    0
END

View in JSmol

Synonyms

Value	Source
[(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy][(2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy]phosphinate	Generator

Chemical Formula

C₆₁H₁₁₃O₁₁P

Average Mass

1053.5380 Da

Monoisotopic Mass

1052.80205 Da

IUPAC Name

[(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy][(2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy]phosphinic acid

Traditional Name

(2S)-3-{[(4S)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2S)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCCCCCCC1CCCCCC1)CCC(=O)OC[C@H](O)COP(O)(=O)OC[C@H](COC(=O)CCCCCCCCCCCCC1CCCCC1)OC(=O)CCCCCCCCCCC1CCCCC1

InChI Identifier

InChI=1S/C61H113O11P/c1-53(35-23-13-12-16-26-38-54-39-27-19-20-28-40-54)47-48-60(64)68-49-57(62)50-70-73(66,67)71-52-58(72-61(65)46-34-18-11-7-6-9-15-25-37-56-43-31-22-32-44-56)51-69-59(63)45-33-17-10-5-3-2-4-8-14-24-36-55-41-29-21-30-42-55/h53-58,62H,2-52H2,1H3,(H,66,67)/t53-,57-,58-/m0/s1

InChI Key

HDDQHIGFLIJCEC-JMZWQWJHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alicyclobacillus acidoterrestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as semilysobisphosphatidic acids. These are bisphosphatidic acid analogues with three moles of fatty acid per mole of lipid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Semilysobisphosphatidic acids

Direct Parent

Semilysobisphosphatidic acids

Alternative Parents

Substituents

Semilysobisphosphatidic acid
Tricarboxylic acid or derivatives
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acyl
Alkyl phosphate
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	18.95	ChemAxon
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	49	ChemAxon
Refractivity	295.49 m³·mol⁻¹	ChemAxon
Polarizability	131.17 Å³	ChemAxon
Number of Rings	3	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

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

163014726

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid (NP0270066)

MOL for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

3D MOL for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

3D SDF for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

3D-SDF for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

PDB for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

3D PDB for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

SMILES for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

INCHI for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

Structure for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)

3D Structure for NP0270066 ((2s)-3-{[(4s)-11-cycloheptyl-4-methylundecanoyl]oxy}-2-hydroxypropoxy((2s)-3-[(13-cyclohexyltridecanoyl)oxy]-2-[(11-cyclohexylundecanoyl)oxy]propoxy)phosphinic acid)