Rifamycin S

HCID 6436726

Notes Reactions

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Basic information

CAS: 13553-79-2
Standard SMILES: CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C)c(O)c4c(c3C2=O)C(=O)C=C(NC(=O)/C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C4=O
InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N
Molecular formula: C37H45NO12
Average molar mass: 695.8 g/mol
Monoisotopic mass: 695.29417588

Overview

Rifamycin S is an organic molecular entity.

Names & identifiers

Preferred name: Rifamycin S
IUPAC: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate
English name: Rifamycin S
Molecular formula: C37H45NO12
Molecular weight: 695.75

Names & synonyms

Rifamycin S13553-79-21,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycinNSC 144130PI53N820JVDTXSID301043935[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetateNSC-144130((7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo(23.3.1.14,7.05,28)triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl) acetateRefChem:179427DTXCID601526374236-938-4

Show more names

rifamycin1007221,4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycinrifomycinsnci144-130Rifamycin S CRSRifaximin Impurity ERifamycin S USP/EP/BP

Rifomycin SMFCD06198807NCI 144-130Rifampicin SRifamycin, 1,4-dideoxy-1,4-dihydro-1,4-dioxo-Rafamycin SC37H45NO12EINECS 236-938-4

Database identifiers

CAS: 13553-79-2
PubChem CID: 6436726
DTXSID: DTXSID301043935
ChEMBL: CHEMBL236921
ChEBI: CHEBI:34948
UNII: PI53N820JV
EC Number: 236-938-4

Properties

Computed structural properties

XLogP: 4.1
Topological polar surface area: 195 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 12
Rotatable bonds: 3
Heavy atoms: 50
Formal charge: 0
Complexity: 1,480

Physicochemical properties

Melting point: 179 · 179-181°C (dec.)
alpha: 20 · D20 +476° (c = 0.1 in methanol)
Boiling point: 700.89 °C · 700.89°C (rough estimate)
Density: 1.2387 · 1.2387 (rough estimate)
refractive index: 1.663 · 1.6630 (estimate)
storage temp.: -20 °C · -20°C Freezer
solubility: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
form: Solid
pka: 3.85 · 3.85±0.70(Predicted)
color: Orange to Dark Orange
λmax: 390 nm · 390nm(MeOH)(lit.)
Merck: 14 · 14,8217
InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N
SMILES: C1[C@H](C)[C@H](O)[C@@H](C)[C@H](O)[C@H](C)[C@H](C(=O)OC)[C@@H](C)[C@H](OC)C=CO[C@]2(C)C(=O)C3C4C(=O)C=C(NC(=O)C(C)=CC=1)C(=O)C=4C(O)=C(C)C=3O2 |c:38,t:21,40|
FDA UNII: 53 N820JV · PI53N820JV
ATC code: 7 AA13,D06AX15,J04AB03,S01AA16,S02AA12 · A07AA13,D06AX15,J04AB03,S01AA16,S02AA12
UNSPSC Code: 51101500 · 51101500
NACRES: 41 · NA.41
Symbol(GHS): 8 · GHS08
Signal word: Warning
Hazard statements: 371 · H371
Precautionary statements: 501 · P501-P260-P270-P264-P308+P311-P405
target organs: Kidney
WGK Germany: 3 · WGK 3
RTECS: 1925000 · KD1925000
HS Code: 2941.9 · 2941.90.1050
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Oral · STOT RE 2 Oral
Toxicity: 50 in · LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P270, P273, P301+P317, P308+P316, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 16-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17133

Hazard Classes and CategoriesAcute Tox. 4 (40%)

Safety data

wgk: WGK 3
rtecs: KD1925000
hs_code: 2941.90.1050
Toxicity: LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)
Signal word: Warning
Symbol(GHS): GHS08
Storage Class: 11 - Combustible Solids
target organs: Kidney
Hazard statements: H371
REACH Registrations: Active
Hazard Classifications: STOT RE 2 Oral
Precautionary statements: P501-P260-P270-P264-P308+P311-P405