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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:38 UTC
HMDB IDHMDB0014481
Secondary Accession Numbers
  • HMDB14481
Metabolite Identification
Common NamePimecrolimus
DescriptionPimecrolimus, also known as ASM 981 or elidel, belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. Pimecrolimus is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753184
Synonyms
ValueSource
ASM 981HMDB
SDZ ASM 981HMDB
33-Epi-chloro-33-desoxyascomycinHMDB
ElidelHMDB
Novartis brand OF pimecrolimusHMDB
SDZ-ASM-981HMDB
PimecrolimusMeSH
Chemical FormulaC43H68ClNO11
Average Molecular Weight810.453
Monoisotopic Molecular Weight809.44808973
IUPAC Name(1R,9S,12S,13S,14S,17R,18Z,21S,23S,24R,25S,27R)-12-[(1E)-1-[(1R,3R,4S)-4-chloro-3-methoxycyclohexyl]prop-1-en-2-yl]-17-ethyl-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone
Traditional Nameelidel
CAS Registry Number137071-32-0
SMILES
[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@@]1([H])C(=O)O[C@@H]([C@@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@H](Cl)[C@@H](C1)OC
InChI Identifier
InChI=1S/C43H68ClNO11/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3/b24-18-,26-20+/t25-,27+,28-,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
InChI KeyKASDHRXLYQOAKZ-KDCWXYOMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolide lactams
Sub ClassNot Available
Direct ParentMacrolide lactams
Alternative Parents
Substituents
  • Macrolide lactam
  • Alpha-amino acid ester
  • Macrolide
  • Alpha-amino acid or derivatives
  • Cyclohexyl halide
  • Oxane
  • Piperidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Hemiacetal
  • Ketone
  • Lactam
  • Lactone
  • Secondary alcohol
  • Cyclic ketone
  • Organoheterocyclic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organohalogen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0015 g/LNot Available
LogP4.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP4.36ALOGPS
logP6.81ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)9.96ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area158.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity214.03 m³·mol⁻¹ChemAxon
Polarizability87.87 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-304.46830932474
DeepCCS[M+Na]+278.24230932474
AllCCS[M+H]+270.132859911
AllCCS[M+H-H2O]+269.532859911
AllCCS[M+NH4]+270.732859911
AllCCS[M+Na]+270.832859911
AllCCS[M-H]-260.232859911
AllCCS[M+Na-2H]-267.032859911
AllCCS[M+HCOO]-274.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pimecrolimus[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@@]1([H])C(=O)O[C@@H]([C@@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@H](Cl)[C@@H](C1)OC5933.1Standard polar33892256
Pimecrolimus[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@@]1([H])C(=O)O[C@@H]([C@@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@H](Cl)[C@@H](C1)OC4799.2Standard non polar33892256
Pimecrolimus[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N1CCCC[C@@]1([H])C(=O)O[C@@H]([C@@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)/C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]1CC[C@H](Cl)[C@@H](C1)OC5419.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pimecrolimus GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pimecrolimus GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pimecrolimus GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pimecrolimus GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 10V, Positive-QTOFsplash10-03dl-0200001930-f4bb642a4d4f486c209a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 20V, Positive-QTOFsplash10-0596-1600005910-9dd8c9e2bff41ccbfc122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 40V, Positive-QTOFsplash10-05fr-9200008700-0fe27d0204e5557d9f2b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 10V, Negative-QTOFsplash10-0a4i-0000000390-3929233ab0243446a3b22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 20V, Negative-QTOFsplash10-052f-0000000920-7452e58c70586e87e40a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 40V, Negative-QTOFsplash10-03dl-4000001900-5bee15aff2ef0290c7bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 10V, Negative-QTOFsplash10-0a4i-0000000190-f926d21ad4c14e2a5e9a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 20V, Negative-QTOFsplash10-0a4i-1000000960-0fca3bfc5ce1d40d5f702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 40V, Negative-QTOFsplash10-0532-1300008920-c6c7778a86de0fae977f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 10V, Positive-QTOFsplash10-03di-0200001790-ffc173ba0e1f13f4fdbe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 20V, Positive-QTOFsplash10-03di-0200000950-8f0c6efeed9be08a63e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pimecrolimus 40V, Positive-QTOFsplash10-0fai-3500000900-062c1f27c7506c5aa8032021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00337 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00337 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPimecrolimus
METLIN IDNot Available
PubChem Compound17753757
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Grassberger M, Baumruker T, Enz A, Hiestand P, Hultsch T, Kalthoff F, Schuler W, Schulz M, Werner FJ, Winiski A, Wolff B, Zenke G: A novel anti-inflammatory drug, SDZ ASM 981, for the treatment of skin diseases: in vitro pharmacology. Br J Dermatol. 1999 Aug;141(2):264-73. [PubMed:10468798 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Zollinger M, Waldmeier F, Hartmann S, Zenke G, Zimmerlin AG, Glaenzel U, Baldeck JP, Schweitzer A, Berthier S, Moenius T, Grassberger MA: Pimecrolimus: absorption, distribution, metabolism, and excretion in healthy volunteers after a single oral dose and supplementary investigations in vitro. Drug Metab Dispos. 2006 May;34(5):765-74. Epub 2006 Feb 7. [PubMed:16467136 ]
General function:
Involved in binding
Specific function:
Kinase subunit of both mTORC1 and mTORC2, which regulate cell growth and survival in response to nutrient and hormonal signals. mTORC1 is activated in response to growth factors or amino-acids. Amino-acid-signaling to mTORC1 is mediated by Rag GTPases, which cause amino-acid-induced relocalization of mTOR within the endomembrane system. Growth factor-stimulated mTORC1 activation involves AKT1-mediated phosphorylation of TSC1-TSC2, which leads to the activation of the RHEB GTPase that potently activates the protein kinase activity of mTORC1. Activated mTORC1 up-regulates protein synthesis by phosphorylating key regulators of mRNA translation and ribosome synthesis. mTORC1 phosphorylates EIF4EBP1 and releases it from inhibiting the elongation initiation factor 4E (eiF4E). mTORC1 phosphorylates and activates S6K1 at 'Thr-421', which then promotes protein synthesis by phosphorylating PDCD4 and targeting it for degradation. mTORC2 is also activated by growth factors, but seems to be nutrient- insensitive. mTORC2 seems to function upstream of Rho GTPases to regulate the actin cytoskeleton, probably by activating one or more Rho-type guanine nucleotide exchange factors. mTORC2 promotes the serum-induced formation of stress-fibers or F-actin. mTORC2 plays a critical role in AKT1 'Ser-473' phosphorylation, which may facilitate the phosphorylation of the activation loop of AKT1 on 'Thr-308' by PDK1 which is a prerequisite for full activation. mTORC2 regulates the phosphorylation of SGK1 at 'Ser-422'. mTORC2 also modulates the phosphorylation of PRKCA on 'Ser-657'
Gene Name:
MTOR
Uniprot ID:
P42345
Molecular weight:
288889.0
References
  1. Reitamo S, Remitz A, Kyllonen H, Saarikko J: Topical noncorticosteroid immunomodulation in the treatment of atopic dermatitis. Am J Clin Dermatol. 2002;3(6):381-8. [PubMed:12113647 ]
General function:
Involved in protein folding
Specific function:
May play a role in modulation of ryanodine receptor isoform-1 (RYR-1), a component of the calcium release channel of skeletal muscle sarcoplasmic reticulum. There are four molecules of FKBP12 per skeletal muscle RYR. PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptides
Gene Name:
FKBP1A
Uniprot ID:
P62942
Molecular weight:
11950.7
References
  1. Reitamo S, Remitz A, Kyllonen H, Saarikko J: Topical noncorticosteroid immunomodulation in the treatment of atopic dermatitis. Am J Clin Dermatol. 2002;3(6):381-8. [PubMed:12113647 ]