2,15,17,29-tetrahydroxy-27-(4-iodophenylcarbamoylmethoxy)-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-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate; (rifamycin B)

ID: ALA307649

PubChem CID: 6507126

Max Phase: Preclinical

Molecular Formula: C45H53IN2O13

Molecular Weight: 956.82

Molecule Type: Small molecule

Associated Items:

Bioactivity Summary Target Summary Assay Summary

This compound is not in our inventory system

Names and Identifiers

Synonyms: Rifamycin B | CHEMBL307649|BHDJFLBHWKKNQU-FMAVLDMNSA-N

Canonical SMILES: COC1/C=C/OC2(C)Oc3c(C)c(O)c4c(O)c(cc(OCC(=O)Nc5ccc(I)cc5)c4c3C2=O)NC(=O)/C(C)=C\C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C

Standard InChI: InChI=1S/C45H53IN2O13/c1-21-11-10-12-22(2)44(56)48-30-19-32(58-20-33(50)47-29-15-13-28(46)14-16-29)34-35(40(30)54)39(53)26(6)42-36(34)43(55)45(8,61-42)59-18-17-31(57-9)23(3)41(60-27(7)49)25(5)38(52)24(4)37(21)51/h10-19,21,23-25,31,37-38,41,51-54H,20H2,1-9H3,(H,47,50)(H,48,56)/b11-10+,18-17+,22-12-

Standard InChI Key: BHDJFLBHWKKNQU-FMAVLDMNSA-N

Molfile:

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M  END

Associated Targets(non-human)

Escherichia coli (133304 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Enterococcus faecalis (29875 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Streptococcus pyogenes (16140 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Bacillus subtilis (32866 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mdr1a Multidrug resistance protein 1a (106 Activities)

Discover Target: Mdr1a

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Small molecule	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 956.82	Molecular Weight (Monoisotopic): 956.2592	AlogP: 6.67	#Rotatable Bonds: 6
Polar Surface Area: 219.41	Molecular Species: NEUTRAL	HBA: 13	HBD: 6
#RO5 Violations: 4	HBA (Lipinski): 15	HBD (Lipinski): 6	#RO5 Violations (Lipinski): 4
CX Acidic pKa: 7.09	CX Basic pKa: ┄	CX LogP: 6.16	CX LogD: 5.67
Aromatic Rings: 3	Heavy Atoms: 61	QED Weighted: 0.09	Np Likeness Score: 1.40

References

1. Bacchi A, Pelizzi G, Nebuloni M, Ferrari P.. (1998) Comprehensive study on structure-activity relationships of rifamycins: discussion of molecular and crystal structure and spectroscopic and thermochemical properties of rifamycin O., 41 (13): [PMID:9632365] [10.1021/jm970791o]
2. Lukovits I, Lopata A.. (1980) Decomposition of pharmacological activity indices into mutually independent components using principal component analysis., 23 (4): [PMID:7381845] [10.1021/jm00178a018]
3. Courtois A, Payen L, Vernhet L, de Vries EG, Guillouzo A, Fardel O.. (1999) Inhibition of multidrug resistance-associated protein (MRP) activity by rifampicin in human multidrug-resistant lung tumor cells., 139 (1): [PMID:10408915] [10.1016/s0304-3835(99)00024-5]
4. Fardel O, Lecureur V, Loyer P, Guillouzo A.. (1995) Rifampicin enhances anti-cancer drug accumulation and activity in multidrug-resistant cells., 49 (1): [PMID:7763306] [10.1016/0006-2952(95)00045-2]

2,15,17,29-tetrahydroxy-27-(4-iodophenylcarbamoylmethoxy)-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-1,3,5(28),9,19,21,25(29),26-octaen-13-yl acetate; (rifamycin B)

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Calculated Properties

References

Source