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103060-53-3 molecular structure
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(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-(1-carboxypropan-2-yl)-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2S)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid

ChemBase ID: 130517
Molecular Formular: C72H101N17O26
Molecular Mass: 1620.67064
Monoisotopic Mass: 1619.71036644
SMILES and InChIs

SMILES:
CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)NC1C(OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)CNC1=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)c1ccccc1N)C
Canonical SMILES:
NCCC[C@@H]1NC(=O)CNC(=O)C(NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc2c[nH]c3c2cccc3)NC(=O)CCCCCCCCC)CC(=O)N)CC(=O)O)C(C)OC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@H](NC1=O)CC(=O)O)C)CC(=O)O)CO)C(CC(=O)O)C)CC(=O)c1ccccc1N
InChI:
InChI=1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35?,36-,37?,43+,44+,45+,46+,47+,48+,49+,50-,60+,61?/m1/s1
InChIKey:
DOAKLVKFURWEDJ-OFNKPWESSA-N

Cite this record

CBID:130517 http://www.chembase.cn/molecule-130517.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-(1-carboxypropan-2-yl)-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2S)-3-carbamoyl-2-[(2S)-2-decanamido-3-(1H-indol-3-yl)propanamido]propanamido]propanoic acid
IUPAC Traditional name
daptomycin
Brand Name
Cubicin
Synonyms
Daptomycin
CAS Number
103060-53-3
PubChem SID
162224796
PubChem CID
16129629
ATC CODE
J01XX09
CHEMBL
508162
Chemspider ID
10482098
DrugBank ID
DB00080
KEGG ID
D01080
Unique Ingredient Identifier
NWQ5N31VKK
Wikipedia Title
Daptomycin

DATA SOURCES

DATA SOURCES

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.9766474  H Acceptors 27 
H Donor 22  LogD (pH = 5.5) -14.167885 
LogD (pH = 7.4) -18.900747  Log P -9.365402 
Molar Refractivity 393.5654 cm3 Polarizability 155.05566 Å3
Polar Surface Area 702.02 Å2 Rotatable Bonds 35 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Pharmacology Properties Bioassay(PubChem)
Admin Routes
Intravenous expand Show data source
Bioavailability
n/a expand Show data source
Excretion
Renal (78%; primarily as unchanged drug); Faeces (5.7%) expand Show data source
Half Life
7–11 hours (up to 28 hours in renal impairment) expand Show data source
Metabolism
Renal (speculative) expand Show data source
Protein Bound
90–95% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
B (US) expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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