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11011-38-4 molecular structure
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(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-{1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-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

ChemBase ID: 130532
Molecular Formular: C43H69NO12
Molecular Mass: 792.00746
Monoisotopic Mass: 791.48197665
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
Canonical SMILES:
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/C43H69NO12/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)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1
InChIKey:
ZDQSOHOQTUFQEM-IXLPKJJWSA-N

Cite this record

CBID:130532 http://www.chembase.cn/molecule-130532.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-{1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-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
(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-17-ethyl-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-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
IUPAC Traditional name
(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-{1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-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
ascomycin
Synonyms
17-ethyl-1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone
Ascomycin
Ascomycin from Streptomyces hygroscopicus var. ascomyceticus
CAS Number
11011-38-4
104987-12-4
MDL Number
MFCD06198665
PubChem SID
162224811
24890817
PubChem CID
5282071
6437370
CHEMBL
8597
Chemspider ID
4445297
Wikipedia Title
Ascomycin

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
A3835 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.955601  H Acceptors 11 
H Donor LogD (pH = 5.5) 5.453524 
LogD (pH = 7.4) 5.452334  Log P 5.4535394 
Molar Refractivity 210.9752 cm3 Polarizability 83.36068 Å3
Polar Surface Area 178.36 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Bioassay(PubChem)
RTECS
KD4185000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H312-H332 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
-20°C expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A3835 external link
Linkage
An FK506 analog with an ethyl rather than an allyl group at position 21.
Biochem/physiol Actions
Strong immunosuppressant; inhibits allogenic T-lymphocyte proliferation. It binds with high affinity to FKBP and inhibits calcineurin phosphatase in the nM range.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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