(1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29,31,33(45),34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrate hydrochloride

• ChemBase ID: 147609
• Molecular Formular: C66H78Cl3N9O25
• Molecular Mass: 1503.72982
• Monoisotopic Mass: 1501.41744208
• SMILES: C[C@H]1[C@H](C(C[C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc1c2cc3cc1Oc1ccc(cc1Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@@H]1c3ccc(c(c3)c3c(cc(cc3O)O)[C@@H](NC(=O)[C@H]([C@@H](c3ccc(c(c3)Cl)O2)O)NC1=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)CO)O)O)(C)N)O.O.Cl
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c3cc4cc2Oc2ccc(cc2Cl)[C@@H](O)[C@@H]2NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC(=O)[C@@H]([C@@H](c4ccc(O3)c(Cl)c4)O)NC(=O)[C@@H](CC(C)C)NC)c3ccc(c(c3)c3c(O)cc(cc3[C@@H](NC2=O)C(=O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@H](C(C1)(C)N)O.O.Cl
• InChI: InChI=1S/C66H75Cl2N9O24.ClH.H2O/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92;;/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95);1H;1H2/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66?;;/m0../s1
• InChIKey: ZMJRZOPYYSQOFX-ZQMWIOGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^3,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8(48),9,11,14,16,29,31,33(45),34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrate hydrochloride
• IUPAC Traditional name: (1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-(carbamoylmethyl)-47,49-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^3,^6.2^1^4,^1^7.1^8,^1^2.1^2^9,^3^3.0^1^0,^2^5.0^3^4,^3^9]pentaconta-3,5,8(48),9,11,14,16,29,31,33(45),34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrate hydrochloride
• Synonyms: Vancomycin hydrochloride hydrate; 万古霉素 盐酸盐 水合物

Database IDs

• CAS Number: 123409-00-7
• MDL Number: MFCD00151026
• PubChem SID: 162241796
• PubChem CID: 71311286

CALCULATED PROPERTIES

• Acid pKa: 2.9872115
• H Acceptors: 24
• H Donor: 19
• LogD (pH = 5.5): -6.39765
• LogD (pH = 7.4): -4.8581004
• Log P: -4.406618
• Molar Refractivity: 346.6085 cm^3
• Polarizability: 138.79524 Å^3
• Polar Surface Area: 530.49 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]21/D -28.5°, c = 1 in H2O

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C66H75Cl2N9O24 · HCl · xH2O

DETAILS

Sigma Aldrich - 861987

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Used as selective membrane mergers to study the functional determinants of synthetic vesicle fusion1Used as an antibiotic for a variety of different studies including:
• Impact to intestinal flora with prolonged exposure to antibiotics2
• Usefulness against antibiotic resistant bacterial strains3
• Transport of nanoparticles across phospholipid membranes4