Bacteriochlorophyll A

Identification

Name
Bacteriochlorophyll A
Accession Number
DB01853  (EXPT00640)
Type
Small Molecule
Groups
Experimental
Description

A specific bacteriochlorophyll that is similar in structure to CHLOROPHYLL A.

Structure
Thumb
Synonyms
  • Bacterio-chlorophyll A
Categories
UNII
Not Available
CAS number
17499-98-8
Weight
Average: 911.524
Monoisotopic: 910.54587782
Chemical Formula
C55H74MgN4O6
InChI Key
DSJXIQQMORJERS-AGGZHOMASA-M
InChI
InChI=1S/C55H75N4O6.Mg/c1-13-39-34(7)41-29-46-48(38(11)60)36(9)43(57-46)27-42-35(8)40(52(58-42)50-51(55(63)64-12)54(62)49-37(10)44(59-53(49)50)28-45(39)56-41)23-24-47(61)65-26-25-33(6)22-16-21-32(5)20-15-19-31(4)18-14-17-30(2)3;/h25,27-32,34-35,39-40,51H,13-24,26H2,1-12H3,(H-,56,57,58,59,60,62);/q-1;+2/p-1/b33-25+;/t31-,32-,34-,35+,39-,40+,51-;/m1./s1
IUPAC Name
methyl (5R,8S,9S,16Z,18R,19R)-14-acetyl-19-ethyl-9,13,18,25-tetramethyl-4-oxo-8-(3-oxo-3-{[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy}propyl)-1,24,26,27-tetraaza-23-magnesaheptacyclo[10.10.2.1³,²².1⁷,¹⁰.1¹⁷,²⁰.0²,⁶.0¹⁵,²⁴]heptacosa-2(6),3(25),7(27),10,12,14,16,20(26),21-nonaene-5-carboxylate
SMILES
[H][C@]1(CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)\C2=C\C3=C(C)C(C(C)=O)=C4\C=C5/N=C(/C=C6\N([Mg]N34)C3=C([C@@H](C(=O)OC)C(=O)C3=C6C)C1=N2)[C@H](CC)[C@H]5C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBacteriochlorophyll a proteinNot AvailableProsthecochloris aestuarii
UBacteriochlorophyll a proteinNot AvailableChlorobium tepidum (strain ATCC 49652 / DSM 12025 / TLS)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C11242
PubChem Compound
11953947
PubChem Substance
46508595
ChemSpider
10128246
ChEBI
30033
HET
BCL

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000187 mg/mLALOGPS
logP8.16ALOGPS
logP9.34ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area122.38 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity261.63 m3·mol-1ChemAxon
Polarizability109.93 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9029
Blood Brain Barrier+0.5937
Caco-2 permeable-0.5585
P-glycoprotein substrateSubstrate0.6933
P-glycoprotein inhibitor IInhibitor0.7817
P-glycoprotein inhibitor IIInhibitor0.7799
Renal organic cation transporterNon-inhibitor0.6273
CYP450 2C9 substrateNon-substrate0.7586
CYP450 2D6 substrateNon-substrate0.8275
CYP450 3A4 substrateSubstrate0.7047
CYP450 1A2 substrateNon-inhibitor0.6568
CYP450 2C9 inhibitorNon-inhibitor0.6431
CYP450 2D6 inhibitorNon-inhibitor0.8406
CYP450 2C19 inhibitorNon-inhibitor0.6007
CYP450 3A4 inhibitorNon-inhibitor0.6364
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6481
Ames testNon AMES toxic0.5686
CarcinogenicityNon-carcinogens0.8826
BiodegradationNot ready biodegradable0.9869
Rat acute toxicity2.7482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7732
hERG inhibition (predictor II)Non-inhibitor0.8746
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrapyrroles and derivatives
Sub Class
Metallotetrapyrroles
Direct Parent
Metallotetrapyrroles
Alternative Parents
Diterpenoids / Aryl alkyl ketones / Fatty acid esters / Substituted pyrroles / Dicarboxylic acids and derivatives / 1,3-dicarbonyl compounds / Methyl esters / Heteroaromatic compounds / Azacyclic compounds / Organonitrogen compounds
show 4 more
Substituents
Metallotetrapyrrole skeleton / Diterpenoid / Aryl ketone / Aryl alkyl ketone / Fatty acid ester / Dicarboxylic acid or derivatives / Substituted pyrrole / 1,3-dicarbonyl compound / Fatty acyl / Methyl ester
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
methyl ester, bacteriochlorophyll (CHEBI:30033)

Targets

Kind
Protein
Organism
Prosthecochloris aestuarii
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Intermediary in the transfer of excitation energy from the chlorophyll to the reaction centers.
Gene Name
Not Available
Uniprot ID
P11741
Uniprot Name
Bacteriochlorophyll a protein
Molecular Weight
40276.145 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Chlorobium tepidum (strain ATCC 49652 / DSM 12025 / TLS)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Intermediary in the transfer of excitation energy from the chlorophyll to the reaction centers.
Gene Name
fmoA
Uniprot ID
Q46393
Uniprot Name
Bacteriochlorophyll a protein
Molecular Weight
40294.285 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:55