NP-MRD: Showing NP-Card for 2-trans,-6-trans-farnesyl monophosphate (NP0334312)

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Record Information

Version

2.0

Created at

2024-09-09 23:06:56 UTC

Updated at

2024-09-09 23:06:56 UTC

NP-MRD ID

NP0334312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-trans,-6-trans-farnesyl monophosphate

Description

2-Trans,-6-trans-farnesyl monophosphate, also known as (2e,6e)-farnesyl phosphate or (2e,6e)-farnesol monophosphoric acid(2-), is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 2-Trans,-6-trans-farnesyl monophosphate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 2-Trans,-6-trans-farnesyl monophosphate can be found in a number of food items such as opium poppy, papaya, pepper (c. Frutescens), and corn, which makes 2-trans,-6-trans-farnesyl monophosphate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252301392D          

 22 21  0  0  0  0            999 V2000
   -5.3625   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.1434    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 13  1  0  0  0  0
  3 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 21  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  1  0  0  0  0
 11 22  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 20  1  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  CHG  2  16  -1  17  -1
M  END
> <DATABASE_ID>
NP0334312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(CC\C(C)=C(/[H])COP([O-])([O-])=O)=C(/C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H27O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H2,16,17,18)/p-2/b14-9-,15-11+

> <INCHI_KEY>
ALEWCKXBHSDCCT-GNESMGCMSA-L

> <FORMULA>
C15H25O4P

> <MOLECULAR_WEIGHT>
300.336

> <EXACT_MASS>
300.150143443

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.367910647855055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl phosphate

> <JCHEM_LOGP>
4.038531539666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.811862989729707

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.785397553289238

> <JCHEM_POLAR_SURFACE_AREA>
72.42

> <JCHEM_REFRACTIVITY>
83.61419999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0     -10.010  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.010  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.700  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.240  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.620   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.390   4.001   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       5.954   1.897   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       4.620   2.667   0.000  0.00  0.00           P+0
HETATM   21  H   UNK     0      -2.310   1.334   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7    8                                                       
CONECT    6    9   10                                                       
CONECT    7    5   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   21   14                                                  
CONECT   10    6   15                                                       
CONECT   11   22   12   15                                                  
CONECT   12   11   19                                                       
CONECT   13    1    2    7                                                  
CONECT   14    3    8    9                                                  
CONECT   15    4   10   11                                                  
CONECT   16   20                                                            
CONECT   17   20                                                            
CONECT   18   20                                                            
CONECT   19   12   20                                                       
CONECT   20   16   17   18   19                                             
CONECT   21    9                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

View in JSmol

Synonyms

Value	Source
(2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-yl phosphoric acid	Generator

Chemical Formula

C₁₅H₂₅O₄P

Average Mass

300.3360 Da

Monoisotopic Mass

300.15014 Da

IUPAC Name

(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl phosphate

Traditional Name

(2E,6Z)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl phosphate

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])COP([O-])([O-])=O)=C(/C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H27O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H2,16,17,18)/p-2/b14-9-,15-11+

InChI Key

ALEWCKXBHSDCCT-GNESMGCMSA-L

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Isoprenoid phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.04	ChemAxon
pKa (Strongest Acidic)	1.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.42 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	32.37 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

21672870

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-trans,-6-trans-farnesyl monophosphate (NP0334312)

MOL for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

3D MOL for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

3D SDF for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

3D-SDF for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

PDB for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

3D PDB for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

SMILES for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

INCHI for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

Structure for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)

3D Structure for NP0334312 (2-trans,-6-trans-farnesyl monophosphate)