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Basic Information
CAS No.: 1404-90-6
Name: Vancomycin
Article Data: 8
Molecular Structure:
Molecular Structure of 1404-90-6 (Vancomycin)
Formula: C66H75Cl2N9O24
Molecular Weight: 1449.27
Synonyms: 22H-8,11:18,21-Dietheno-23,36-(iminomethano)-13,16:31,35-dimetheno-1H,16H-[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylicacid, 3-(2-amino-2-oxoethyl)-44-[[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-a-L-lyxo-hexopyranosyl)-b-D-glucopyranosyl]oxy]-10,19-dichloro-2,3,4,5,6,7,23,24,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-[[4-methyl-2-(methylamino)-1-oxopentyl]amino]-2,5,24,38,39-pentaoxo-,[3S-[3R*,6S*(S*),7S*,22S*,23R*,26R*,36S*,38aS*]]-;Diatracin;Vancocin;VancocinCP;Vancocine;Vancoled;Vancoplus;
EINECS: 215-772-6
Density: 1.657 g/cm3
Appearance: Almost white powder
PSA: 530.49000
LogP: 4.73460
Synthetic route

UDP-vancosamine

101485-50-1

desvancosaminyl vancomycin

1404-90-6

vancomycin

Conditions
ConditionsYield
With tris(2-carboxyethyl)phosphine; glycosyltransferase GtfD; bovine serum albumin In glycerol at 37℃; for 1.5h; Enzymatic reaction;87%

C82H87Cl2N9O28

1404-90-6

vancomycin

Conditions
ConditionsYield
With ammonium bicarbonate; palladium on activated charcoal In acetic acid at 23℃; for 4h; Hydrogenolysis;81%
With ammonium formate; acetic acid; 10percent Pd/C In methanol at 23℃; for 4h;81%
216668-88-1

N,N'-dialloc-tri-O-allyl vancomycin allyl ester

1404-90-6

vancomycin

Conditions
ConditionsYield
With bis(triphenylphosphine)palladium(II) dichloride; tri-n-butyl-tin hydride In acetic acid; N,N-dimethyl-formamide for 0.166667h; Ambient temperature;78%

vancomycin - Nα,Nε-diacetyl-L-Lys-D-Ala-D-Ala - complex

A

24570-39-6

(R)-2-[(R)-2-((S)-2,6-Bis-acetylamino-hexanoylamino)-propionylamino]-propionic acid

B

1404-90-6

vancomycin

Conditions
ConditionsYield
With sodium citrate at 25℃; Equilibrium constant; pH 5.1;

vancomycin - Nα-(fluoresceinylthiocarbamoyl)-Nω-acetyl-L-Lys-D-Ala-D-Ala complex

A

1404-90-6

vancomycin

B

Nα-(fluoresceinylthiocarbamoyl)-Nω-acetyl-L-Lys-D-Ala-D-Ala

Conditions
ConditionsYield
With sodium citrate at 25℃; Equilibrium constant; pH 5.1;

N-Demethylvancomycin

(S)-adenosyl-L-methionine

(S)-adenosyl-L-methionine

1404-90-6

vancomycin

Conditions
ConditionsYield
With Tris-HCl buffer; N-methyltransferase at 25℃; for 24h; pH=7.5; Methylation; Enzymatic reaction;

C67H77Cl2N9O24

1404-90-6

vancomycin

Conditions
ConditionsYield
With lithium hydroxide; water In tetrahydrofuran at 0℃; for 0.333333h; Hydrolysis;
101485-50-1

desvancosaminyl vancomycin

755033-86-4

thymidine 5'-(3-amino-2,3,6-trideoxy-3C-methyl-β-L-lyxo-hexopyranosyl diphosphate)

1404-90-6

vancomycin

Conditions
ConditionsYield
With glycosyltransferase GtfD Enzyme kinetics; Further Variations:; Reagents;
1404-90-6

vancomycin

82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

C96H95Cl2N9O28

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water100%
87156-40-9

1-amino-2-azidoethane

1404-90-6

vancomycin

C68H79Cl2N13O23

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 0 - 23℃;100%
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History

   Vancomycin (CAS NO.1404-90-6) was first isolated by EC Kornfeld (working at Eli Lilly) from a soil sample collected from the interior jungles of Borneo by a missionary. The organism that produced it was eventually named Amycolatopsis orientalis.
   The compound was initially labelled compound 05865, but was eventually given the generic name, vancomycin (derived from the word "vanquished").In 1958 ,The rapid development of penicillin-resistance by staphylococci led to the compound being fast-tracked for approval by the FDA . Eli Lilly first marketed vancomycin hydrochloride under the trade name Vancocin.

Specification

The Vancomycin, with the CAS registry number 1404-90-6, has the systematic name of (1S,2R,18R,19R,22S,25R,28R,40S)-48-{[(2S,3R,4S,5S,6R)-3-{[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-22-(2-a mino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-{[(2R)-4-methyl-2-(methylamino)pentanoyl]amino}-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2~3,6~.2~14,17~ .1~8,12~.1~29,33~.0~10,25~.0~34,39~]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid (non-preferred name).

The physical properties of this chemical are as below: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 33; (7)#H bond donors: 21; (8)#Freely Rotating Bonds: 23; (9)Polar Surface Area: 530.49; (10)Index of Refraction: 1.735; (11)Molar Refractivity: 350.837 cm3; (12)Molar Volume: 874.685 cm3; (13)Polarizability: 139.083×10-24 cm3; (14)Surface Tension: 105.146 dyne/cm; (15)Density: 1.657 g/cm3; (16)Exact Mass: 1447.4302; (17)MonoIsotopic Mass: 1447.4302; (18)Topological Polar Surface Area: 531; (19)Heavy Atom Count: 101; (20)Complexity: 2960.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O) O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
(2)Isomeric SMILES: C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)(=O)O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
(3)InChI: InChI=1S/C66H75Cl2N9O24/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)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
(4)InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo intravenous 30mg/kg/20M-C (30mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

CARDIAC: OTHER CHANGES
Archives of Disease in Childhood. Vol. 73, Pg. F123, 1995.
infant TDLo intravenous 119mg/kg (119mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Toxicology, Clinical Toxicology. Vol. 34, Pg. 83, 1996.
 
infant TDLo intravenous 295mg/kg/3D-I (295mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 285, 1992.
 
man TDLo intravenous 15mg/kg/2H-C (15mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Pharmacotherpy. Vol. 33, Pg. 1043, 1999.
 
mouse LD50 intraperitoneal 1734mg/kg (1734mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 675, 1967.
mouse LD50 intravenous 430mg/kg (430mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 913, 1990.
 
mouse LD50 subcutaneous 5gm/kg (5000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 315, 1980.
women TDLo intravenous 15mg/kg/90M-C (15mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" New England Journal of Medicine. Vol. 313, Pg. 756, 1985.
 
women TDLo intravenous 170mg/kg/19D- (170mg/kg) BLOOD: AGRANULOCYTOSIS Canadian Medical Association Journal. Vol. 132, Pg. 39, 1985.
 
women TDLo multiple routes 30mg/kg/2D-I (30mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Annals of Internal Medicine. Vol. 115, Pg. 410, 1991.