NP-MRD: Showing NP-Card for [(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid (NP0204886)

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Record Information

Version

2.0

Created at

2022-09-05 00:40:36 UTC

Updated at

2022-09-05 00:40:36 UTC

NP-MRD ID

NP0204886

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid

Description

Phoslactomycin B belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. [(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid is found in Streptomyces nigrescens. [(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid was first documented in 2006 (PMID: 16619316). Based on a literature review a small amount of articles have been published on Phoslactomycin B (PMID: 19787137) (PMID: 19364501) (PMID: 19170620) (PMID: 18461955).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052202402D          

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  Mrv1652309052202402D          

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  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204886

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1C=CC(=O)OC1\C=C\C(O)(CCN)C(CC(O)\C=C\C=C\C1CCCCC1)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40NO8P/c1-2-20-12-13-24(28)33-22(20)14-15-25(29,16-17-26)23(34-35(30,31)32)18-21(27)11-7-6-10-19-8-4-3-5-9-19/h6-7,10-15,19-23,27,29H,2-5,8-9,16-18,26H2,1H3,(H2,30,31,32)/b10-6+,11-7+,15-14+

> <INCHI_KEY>
GAIPQMSJLNWRGC-VYTJGNNZSA-N

> <FORMULA>
C25H40NO8P

> <MOLECULAR_WEIGHT>
513.568

> <EXACT_MASS>
513.24915425

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.711937709918836

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1E,7E,9E)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxy}phosphonic acid

> <JCHEM_LOGP>
1.688448253151083

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.551991520935807

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5227702782235322

> <JCHEM_PKA_STRONGEST_BASIC>
9.807781676244543

> <JCHEM_POLAR_SURFACE_AREA>
159.54

> <JCHEM_REFRACTIVITY>
137.6996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1E,7E,9E)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.565  -6.366   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.105  -9.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335 -10.367   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -6.105 -11.701   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.337 -13.860   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   32  P   UNK     0      -8.002  -4.620   0.000  0.00  0.00           P+0
HETATM   33  O   UNK     0      -8.772  -5.954   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -7.232  -3.286   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   17   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀NO₈P

Average Mass

513.5680 Da

Monoisotopic Mass

513.24915 Da

IUPAC Name

{[(1E,7E,9E)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxy}phosphonic acid

Traditional Name

[(1E,7E,9E)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CCC1C=CC(=O)OC1\C=C\C(O)(CCN)C(CC(O)\C=C\C=C\C1CCCCC1)OP(O)(O)=O

InChI Identifier

InChI=1S/C25H40NO8P/c1-2-20-12-13-24(28)33-22(20)14-15-25(29,16-17-26)23(34-35(30,31)32)18-21(27)11-7-6-10-19-8-4-3-5-9-19/h6-7,10-15,19-23,27,29H,2-5,8-9,16-18,26H2,1H3,(H2,30,31,32)/b10-6+,11-7+,15-14+

InChI Key

GAIPQMSJLNWRGC-VYTJGNNZSA-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
Streptomyces nigrescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
1,3-aminoalcohol
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organic oxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Amine
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	1.69	ChemAxon
pKa (Strongest Acidic)	1.52	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	159.54 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	137.7 m³·mol⁻¹	ChemAxon
Polarizability	54.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00017683

Chemspider ID

4943562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phoslactomycin B

METLIN ID

Not Available

PubChem Compound

6439129

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sarkar SM, Wanzala EN, Shibahara S, Takahashi K, Ishihara J, Hatakeyama S: Enantio- and stereoselective route to the phoslactomycin family of antibiotics: formal synthesis of (+)-fostriecin and (+)-phoslactomycin B. Chem Commun (Camb). 2009 Oct 21;(39):5907-9. doi: 10.1039/b912267b. Epub 2009 Aug 10. [PubMed:19787137 ]
Simizu S, Teruya T, Nogawa T, Aono H, Ueki M, Uramoto M, Kobayashi Y, Osada H: Deamino-hydroxy-phoslactomycin B, a biosynthetic precursor of phoslactomycin, induces myeloid differentiation in HL-60 cells. Biochem Biophys Res Commun. 2009 Jun 12;383(4):406-10. doi: 10.1016/j.bbrc.2009.04.014. Epub 2009 Apr 11. [PubMed:19364501 ]
Druais V, Hall MJ, Corsi C, Wendeborn SV, Meyer C, Cossy J: A convergent approach toward the C1-C11 subunit of phoslactomycins and formal synthesis of phoslactomycin B. Org Lett. 2009 Feb 19;11(4):935-8. doi: 10.1021/ol8029142. [PubMed:19170620 ]
Shibahara S, Fujino M, Tashiro Y, Takahashi K, Ishihara J, Hatakeyama S: Asymmetric total synthesis of (+)-phoslactomycin B. Org Lett. 2008 Jun 5;10(11):2139-42. doi: 10.1021/ol8004672. Epub 2008 May 8. [PubMed:18461955 ]
Wang YG, Takeyama R, Kobayashi Y: Total synthesis of phoslactomycin B and its biosynthetic deamino precursor. Angew Chem Int Ed Engl. 2006 May 12;45(20):3320-3. doi: 10.1002/anie.200600458. [PubMed:16619316 ]
LOTUS database [Link]

Showing NP-Card for [(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid (NP0204886)

MOL for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

3D MOL for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

3D SDF for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

3D-SDF for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

PDB for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

3D PDB for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

SMILES for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

INCHI for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

Structure for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)

3D Structure for NP0204886 ([(1e,7e,9e)-3-(2-aminoethyl)-10-cyclohexyl-1-(3-ethyl-6-oxo-2,3-dihydropyran-2-yl)-3,6-dihydroxydeca-1,7,9-trien-4-yl]oxyphosphonic acid)