(1'R,2S,4'S,5S,6R,12'S,13'S,20'R,21'R,24'S)-6-cyclohexyl-21',24'-dihydroxy-12'-{[(2S,4S,5S,6S)-5-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.14,8.020,24]pentacosane]-10',14',16',22'-tetraen-2'-one

• ChemBase ID: 154974
• Molecular Formular: C50H74O14
• Molecular Mass: 899.11416
• Monoisotopic Mass: 898.50785705
• SMILES: C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]2CC(C/C=C(/[C@H]1O[C@@H]1C[C@@H]([C@H]([C@@H](O1)C)O[C@@H]1C[C@@H]([C@H]([C@@H](O1)C)O)OC)OC)\C)O[C@]1(C2)C=C[C@@H]([C@H](O1)C1CCCCC1)C)O
• Canonical SMILES: CO[C@H]1C[C@H](O[C@H]([C@@H]1O[C@@H]1C[C@H](OC)[C@H]([C@@H](O1)C)O)C)O[C@H]1[C@@H](C)/C=C/C=C/2\CO[C@H]3[C@]2(O)[C@@H](C=C([C@H]3O)C)C(=O)O[C@H]2CC(C/C=C/1\C)O[C@]1(C2)C=C[C@@H]([C@H](O1)C1CCCCC1)C
• InChI: InChI=1S/C50H74O14/c1-27-13-12-16-34-26-57-47-42(51)30(4)21-37(50(34,47)54)48(53)60-36-22-35(63-49(25-36)20-19-29(3)45(64-49)33-14-10-9-11-15-33)18-17-28(2)44(27)61-41-24-39(56-8)46(32(6)59-41)62-40-23-38(55-7)43(52)31(5)58-40/h12-13,16-17,19-21,27,29,31-33,35-47,51-52,54H,9-11,14-15,18,22-26H2,1-8H3/t27-,29-,31-,32-,35?,36-,37-,38-,39-,40+,41+,42+,43-,44-,45-,46-,47+,49+,50+/m0/s1
• InChIKey: QLFZZSKTJWDQOS-HKZHLHRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'R,2S,4'S,5S,6R,12'S,13'S,20'R,21'R,24'S)-6-cyclohexyl-21',24'-dihydroxy-12'-{[(2S,4S,5S,6S)-5-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• IUPAC Traditional name: (1'R,2S,4'S,5S,6R,12'S,13'S,20'R,21'R,24'S)-6-cyclohexyl-21',24'-dihydroxy-12'-{[(2S,4S,5S,6S)-5-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1^4,^8.0^2^0,^2^4]pentacosane]-10',14',16',22'-tetraen-2'-one
• Synonyms: Doramectin; Doramectin synthetic; 25-Cyclohexyl-5-O-demethyl-25-de(1-methylpropyl)avermectin; Doramectin; 25-环己基-5-O-去甲基-25-去(1-甲基丙基)阿维菌素; 多拉克汀; 多拉克汀 合成的; 多拉克汀

Database IDs

• CAS Number: 117704-25-3
• MDL Number: MFCD00894747
• PubChem SID: 162249112; 24860745
• PubChem CID: 16212180

CALCULATED PROPERTIES

• Acid pKa: 12.467905
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 6.2738442
• LogD (pH = 7.4): 6.2738404
• Log P: 6.2738442
• Molar Refractivity: 238.5796 cm^3
• Polarizability: 94.7172 Å^3
• Polar Surface Area: 170.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-50/53
• Safety Statements: 33-45-60-61
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H410
• GHS Precautionary statements: P273-P301 + P310-P501
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%
• Grade: VETRANAL™, analytical standard
• Impurities: ≤5% water (Karl Fischer)
• Biological Source: from synthetic
• Empirical Formula (Hill Notation): C50H74O14

DETAILS

Sigma Aldrich - D6696

Application
Doramectin is commonly used in veterinary medicine for the treatment of parasites such as gastrointestinal roundworms, lungworms, eyeworms, grubs, sucking lice and mange mites. It is effective against Haemonchus spp., Ostertagia spp., Trichostrongylus spp., Cooperia spp., Oesophagostomum spp., Dyctiocaulus viviparus, Dermatobia hominis, Boophilus microplus, Psoroptes bovis, as well as other internal and external parasites1,2.
Biochem/physiol Actions
Doramectin is a derivative of ivermectin. It is thought to work like other macrocyclic lactones by opening glutamate-gated chloride channels in the nerve cells, causing paralysis.

Sigma Aldrich - 33993

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC