(1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,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-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrochloride

• ChemBase ID: 179437
• Molecular Formular: C66H76Cl3N9O24
• Molecular Mass: 1485.71454
• Monoisotopic Mass: 1483.4068774
• SMILES: c1c2cc(c(c1)Oc1cc3cc(c1O[C@@H]1O[C@H](C([C@@H]([C@@H]1O[C@@H]1O[C@H]([C@H]([C@](C1)(N)C)O)C)O)O)CO)Oc1ccc(cc1Cl)[C@H](C(C(=O)N[C@H](C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(=O)N[C@H](c3c(c4cc1ccc4O)c(cc(c3)O)O)C(=O)O)[C@@H]2O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl.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([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](C1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@](C1)(C)N)O.Cl
• InChI: InChI=1S/C66H75Cl2N9O24.ClH/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/t24-,34+,35-,42+,44-,46?,47+,48-,49?,50?,51+,52+,53?,54-,56+,57+,65-,66-;/m0./s1
• InChIKey: LCTORFDMHNKUSG-YWXMBMLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,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-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrochloride
• IUPAC Traditional name: (1S,2R,18R,22S,25R,28R,40S)-48-{[(2S,3R,4S,6R)-3-{[(2S,4S,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-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid hydrochloride
• Synonyms: Lyphocin Deuterated; Meek Deuterated; Vancocin Deuterated Hydrochloride; Vancocine Deuterated Hydrochloride; Vancocyn Deuterated; Vancor Deuterated; Vancomycin Deuterated HydrochlorideDISCONTINUED; Lyphocin; Meek; Vancocin Hydrochloride; Vancocine Hydrochloride; Vancocyn; Vancor; Vancomycin Hydrochloride

Database IDs

• CAS Number: 1404-93-9
• PubChem SID: 164235347
• PubChem CID: 71752910

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

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >190°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V096500

Amphoteric glycopeptide antibiotic produced by Streptomyces orientalis discovered in soil. Inhibits bacterial cell wall synthesis by binding to peptidoglycan. Antibacterial.

Toronto Research Chemicals - V096502

Labelled Vancomycin (V096500). Amphoteric glycopeptide antibiotic produced by Streptomyces orientalis discovered in soil. Inhibits bacterial cell wall synthesis by binding to peptidoglycan. Antibacterial.

REFERENCES

• Marshall, F.J., et al.: J. Med. Chem., 8, 18 (1965)
• Cunha, B.A., et al.: Med. Clin. North Am., 79, 817 (1965)
• Li, L., et al.: Ther. Drug Monit., 17, 366 (1965)
• Marshall, F.J., et al.: J. Med. Chem., 8, 18 (1965)
• Cunha, B.A., et al.: Med. Clin. North Am., 79, 817 (1965)
• Li, L., et al.: Ther. Drug Monit., 17, 366 (1965)