Rifamycin

Details

• Internal ID: 3925e865-1220-489a-818f-5a05ccc1e6cc
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
• SMILES (Canonical): CC1C=CC=C(C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C
• SMILES (Isomeric): C[C@H]1/C=C/C=C(\C(=O)NC2=CC(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C
• InChI: InChI=1S/C37H47NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,40-44H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
• InChI Key: HJYYPODYNSCCOU-ODRIEIDWSA-N
• Popularity: 1,787 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₇NO₁₂
• Molecular Weight: 697.80 g/mol
• Exact Mass: 697.30982593 g/mol
• Topological Polar Surface Area (TPSA): 201.00 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.75
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 2

Synonyms

• Rifamycin SV
• Rifocin
• Rifamicine SV
• Rifomycin SV
• Rifamicina
• Rifamycine
• Rifamycinum
• Rifocyn
• 6998-60-3
• UNII-DU69T8ZZPA
• Rifamycine [INN-French]
• Rifamycinum [INN-Latin]
• DU69T8ZZPA
• Rifamicina [INN-Spanish]
• EINECS 230-273-3
• Aemcolo
• CB-01-11
• M-14
• CHEBI:29673
• DTXSID1032014
• 6998-60-3 (free acid)
• 15105-92-7
• Rifamycin SV, an antibiotic produced by certain strains of Streptomyces mediterranei, or the same substance produced by any other means
• Rifamycine (INN-French)
• Rifamycinum (INN-Latin)
• Rifamicina (INN-Spanish)
• 2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione, 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate
• RIFAMYCIN SV (EP IMPURITY)
• RIFAMYCIN SV [EP IMPURITY]
• (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate
• [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
• 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(Epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2H)-dione 21-acetate
• RIFAXIMIN IMPURITY C (EP IMPURITY)
• RIFAXIMIN IMPURITY C [EP IMPURITY]
• RIFOMYCIN
• Tuborin
• rifamycin-sv
• NSC133100
• Rifamycin [USAN:INN:BAN:DCF]
• (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca(1,11,13)trienoimino)naphtho(2,1-b)furan-21-yl acetate
• (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate
• RIFAMYCIN [INN]
• Rifamycin (USAN/INN)
• RIFAMYCIN [USAN]
• RIFAMYCIN SV [MI]
• RIFAMYCIN [WHO-DD]
• 5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-1,11(2-H)-dione, 21-acetate
• SCHEMBL151824
• CHEMBL437765
• GTPL4570
• DTXCID9012014
• CHEBI:26580
• HY-B1907A
• A07AA13
• D06AX15
• J04AB03
• S02AA12
• HJYYPODYNSCCOU-ODRIEIDWSA-N
• (7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate
• BDBM50391000
• LMPK05000005
• AKOS024281286
• DB11753
• CS-0092130
• D02549
• SR-01000872597
• SR-01000872597-1
• (pentahydroxy-methoxy-heptamethyl-dioxo-[?]yl) acetate
• Q26270990
• (7S,11S,13S,17S,18S,12R,14R,15R,16R)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7 ,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1<4, 7>.0<5,28>]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate
• 2,7-(Epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2H)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2S,16S,17S,18R,19R,20R,21S,22R,23S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8536	85.36%
Caco-2	-	0.8472	84.72%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Plasma membrane	0.4312	43.12%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	+	0.7372	73.72%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9763	97.63%
P-glycoprotein inhibitior	-	0.8619	86.19%
P-glycoprotein substrate	+	0.7903	79.03%
CYP3A4 substrate	+	0.5889	58.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8986	89.86%
CYP3A4 inhibition	-	0.7487	74.87%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7637	76.37%
CYP inhibitory promiscuity	-	0.6615	66.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Danger	0.4575	45.75%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9125	91.25%
Skin irritation	-	0.8166	81.66%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	+	0.5299	52.99%
Human Ether-a-go-go-Related Gene inhibition	+	0.6549	65.49%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.8644	86.44%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7410	74.10%
Acute Oral Toxicity (c)	III	0.7013	70.13%
Estrogen receptor binding	+	0.8194	81.94%
Androgen receptor binding	+	0.8093	80.93%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7970	79.70%
Aromatase binding	+	0.6209	62.09%
PPAR gamma	+	0.7901	79.01%
Honey bee toxicity	-	0.7026	70.26%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9598	95.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.31%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.69%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.26%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	95.91%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.85%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.80%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.47%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.98%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.69%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	91.29%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.04%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.58%	96.38%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.34%	94.42%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.37%	96.77%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.20%	91.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.75%	91.07%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.26%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.89%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.55%	94.80%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.47%	91.03%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.32%	97.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.24%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.98%	97.28%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	82.55%	83.65%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.53%	85.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 6324616
• LOTUS: LTS0177559
• wikiData: Q26270990