Home > Compound List > Compound details
104987-11-3 molecular structure
click picture or here to close

(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

ChemBase ID: 130465
Molecular Formular: C44H69NO12
Molecular Mass: 804.01816
Monoisotopic Mass: 803.48197665
SMILES and InChIs

SMILES:
O=C1C(=O)N2CCCC[C@H]2C(=O)O[C@@H](/C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(/C[C@@H](C[C@@H](OC)[C@H]2O[C@]1(O)[C@H](C)C[C@@H]2OC)C)\C)CC=C
Canonical SMILES:
C=CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@@H](OC)[C@H]2O[C@](O)([C@@H](C[C@@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@@H](C1)OC)O)/C)CCCC2
InChI:
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
InChIKey:
QJJXYPPXXYFBGM-LFZNUXCKSA-N

Cite this record

CBID:130465 http://www.chembase.cn/molecule-130465.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
IUPAC Traditional name
tacrolimus
Synonyms
Tacrolimus
CAS Number
104987-11-3
PubChem SID
162224744
PubChem CID
6473866
445643
ATC CODE
D11AH01
L04AD02
CHEMBL
1200738
Chemspider ID
4976056
DrugBank ID
DB00864
Unique Ingredient Identifier
Y5L2157C4J
Wikipedia Title
Tacrolimus

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.955601  H Acceptors 11 
H Donor LogD (pH = 5.5) 5.594105 
LogD (pH = 7.4) 5.5929146  Log P 5.59412 
Molar Refractivity 215.6203 cm3 Polarizability 84.94902 Å3
Polar Surface Area 178.36 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Pharmacology Properties Bioassay(PubChem)
Admin Routes
Topical, oral, iv expand Show data source
Bioavailability
20%, less after eating food rich in fat expand Show data source
Excretion
Mostly faecal expand Show data source
Half Life
11.3 h (range 3.5-40.6 h) expand Show data source
Metabolism
Hepatic CYP3A4 expand Show data source
Protein Bound
75-99% expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
    No data available
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle