Erythromycin

Details

• Internal ID: 39f3588e-08cb-4aeb-8949-41f5494175e0
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Aminosaccharides > Aminoglycosides
• IUPAC Name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
• InChI: InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChI Key: ULGZDMOVFRHVEP-RWJQBGPGSA-N
• Popularity: 43,925 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₇NO₁₃
• Molecular Weight: 733.90 g/mol
• Exact Mass: 733.46124119 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 1.79
• H-Bond Acceptor: 14
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• 114-07-8
• Erythromycin A
• E-Mycin
• Abomacetin
• Erythromycinum
• Emgel
• Erymax
• Ilotycin
• Robimycin
• Torlamicina
• Eryderm
• Erythro-Statin
• E-Glades
• Ery-Tab
• Erythromycine
• Eritromicina
• Erycette
• Pantomicina
• Erygel
• Sansac
• E-Base
• Erythra-Derm
• Erythromycin base
• ERYC
• Erythrocin
• Dumotrycin
• Mephamycin
• Ermycin
• Eryacne
• Stiemycin
• Aknin
• Erycen
• Wemid
• R-P Mycin
• Eryc Sprinkles
• Theramycin Z
• Akne-Mycin
• E-Solve 2
• Ak-Mycin
• Erythromast 36
• T-Stat
• Erytrociclin
• Acneryne
• Endoeritrin
• Eritomicina
• Eryacnen
• Erydermer
• Eryhexal
• Erythroderm
• Iloticina
• Latotryd
• Lederpax
• Oftamolets
• Pantoderm
• Pantodrin
• Pharyngocin
• Primacine
• Proterytrin
• Stiemicyn
• Tiprocin
• Acnesol
• Derimer
• Deripil
• Emuvin
• Emycin
• Erecin
• Erisone
• Erymed
• Erysafe
• Erytab
• Erytop
• Inderm
• Mercina
• Romycin
• AustriaS
• Eros
• C-Solve-2
• Ery-maxin
• Erythro-Teva
• Sans-acne
• Erimycin-T
• Ery-Diolan
• Inderm Gel
• Del-Mycin
• Udima Ery Gel
• Aknederm Ery Gel
• Abboticin
• Emu-Ve
• Akne Cordes Losung
• Eryc 125
• Ilotycin T.S.
• Skid Gel E
• E-Mycin (base)
• Emu-V
• Ery-B
• Ery-Tab (base)
• E-Base (base)
• ERYC (base)
• erythromycin-A
• A/T/S
• Erythrogran
• Erythroguent
• Erythromid
• Propiocine
• Dotycin
• Erycinum
• Ilocaps
• PCE Dispertab (base)
• Erycin
• Kesso-Mycin
• Eryc-125
• Eryc-250
• Taimoxin-F
• erythro
• Oftalmolosa Cusi Eritromicina
• Eritrocina
• Staticin
• Retcin
• erthromycin
• Sentry AQ mardel maracyn
• Eritromicina [INN-Spanish]
• Erythromycine [INN-French]
• Erythromycinum [INN-Latin]
• Benzamycin
• CCRIS 9078
• DTXSID4022991
• UNII-63937KV33D
• CHEBI:42355
• HSDB 3074
• EM-A
• EINECS 204-040-1
• NSC 55929
• NSC-55929
• PCE (ERYTHROMYCIN)
• CHEMBL532
• 63937KV33D
• AI3-50138
• DTXCID102991
• J01FA01
• EC 204-040-1
• Erythromycin [USP:INN:BAN:JAN]
• MFCD00084654
• NSC55929
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-7,12,13-trihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
• ERY
• BENZAMYCIN COMPONENT ERYTHROMYCIN
• Erythromycin C-13
• Aknemycin
• ERYTHROMYCIN COMPONENT OF BENZAMYCIN
• Eritromicina (INN-Spanish)
• Erythromycine (INN-French)
• Erythromycinum (INN-Latin)
• 8HPH7ND0LN
• ERYTHROMYCIN (MART.)
• ERYTHROMYCIN [MART.]
• (3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)oxacyclotetradecane-2,10-dione
• Ilosone (estolate)
• ERYTHROMYCIN (USP-RS)
• ERYTHROMYCIN [USP-RS]
• N-Methylerythromycin A
• ERYTHROMYCIN (EP MONOGRAPH)
• Erythromycin (USP:INN:BAN:JAN)
• ERYTHROMYCIN [EP MONOGRAPH]
• ERYTHROMYCIN (USP MONOGRAPH)
• ERYTHROMYCIN [USP MONOGRAPH]
• Erythromycin, labeled with carbon-13
• Staticin (TN)
• Akne-mycin (TN)
• Erygel (TN)
• Eryc (TN)
• T-stat (TN)
• Pce (TN)
• SR-05000001618
• Enythromycin
• Spotex
• ErythromycinBase
• Gallimycin-36
• NCGC00094670-01
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
• CAS-114-07-8
• Prestwick_205
• 215031-94-0
• 82343-12-2
• Spectrum_000115
• Spectrum_000659
• ErythromycinBase Filmtab
• Erythro-100 Injection
• API E.M. Erythromycin
• Erythromycin Base Filmtab
• Prestwick3_000151
• Spectrum2_000759
• Spectrum2_001263
• Spectrum4_000538
• Spectrum5_001596
• UNII-8HPH7ND0LN
• ERYTHROMYCIN [MI]
• E0751
• Erythro-36, Erythro-Dry
• ERYTHROMYCIN [INN]
• ERYTHROMYCIN [JAN]
• ERYTHROMYCIN [HSDB]
• SCHEMBL2601
• API E.M ERYTHROMYCIN
• ERYTHROMYCIN [VANDF]
• BSPBio_000282
• BSPBio_002480
• KBioGR_001175
• KBioSS_000555
• KBioSS_001139
• MLS001066618
• BIDD:GT0017
• DivK1c_000294
• DivK1c_000397
• DivK1c_000702
• ERYTHROMYCIN [WHO-DD]
• ERYTHROMYCIN [WHO-IP]
• SPECTRUM1500280
• SPBio_000778
• SPBio_001226
• BPBio1_000312
• GTPL1456
• CHEBI:48923
• Erythromycin (JP17/USP/INN)
• HMS500O16
• KBio1_000294
• KBio1_000397
• KBio1_000702
• KBio2_000555
• KBio2_001139
• KBio2_003123
• KBio2_003707
• KBio2_005691
• KBio2_006275
• ERYTHROMYCIN [GREEN BOOK]
• NINDS_000294
• NINDS_000397
• NINDS_000702
• ERYTHROMYCIN [ORANGE BOOK]
• HMS1920M04
• HMS2091D05
• HMS2095O04
• HMS3712O04
• Pharmakon1600-01500280
• HY-B0220
• RKL10096
• Tox21_111311
• Tox21_111869
• Tox21_300515
• BDBM50344942
• CCG-38992
• LMPK04000006
• NSC756759
• ERYTHROMYCINUM [WHO-IP LATIN]
• Gallimycin Injection, Gallimycin-100
• AKOS015895249
• DB00199
• NSC-756759
• IDI1_000294
• IDI1_000397
• IDI1_000702
• SMP1_000119
• NCGC00179619-01
• NCGC00179619-02
• NCGC00179619-03
• NCGC00254234-01
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
• AC-12744
• AC-12901
• SMR000544946
• Erythromycin, potency: >=850 mug per mg
• Erythromycin, tested according to Ph.Eur.
• SBI-0051368.P003
• Erythromycin, N-demethyl-N-(methyl-11C)-
• Erythromycin 1000 microg/mL in Acetonitrile
• Erythromycin, meets USP testing specifications
• C01912
• D00140
• E-3250
• Erythromycin, plant cell culture tested, ~98%
• AB00051981_09
• AB00051981_10
• Erythromycin, Biotechnology Performance Certified
• Erythromycin estolate impurity, free erythromycin-
• Q213511
• SR-01000799155
• Erythromycin, Antibiotic for Culture Media Use Only
• Erythromycin, BioReagent, suitable for cell culture
• SR-01000799155-2
• SR-05000001618-1
• SR-05000001618-2
• BRD-K63550407-001-13-5
• BRD-K63550407-028-03-9
• Z2587996953
• Erythromycin A, British Pharmacopoeia (BP) Reference Standard
• Erythromycin A, European Pharmacopoeia (EP) Reference Standard
• Erythromycin, United States Pharmacopeia (USP) Reference Standard
• ERYTHROMYCIN ESTOLATE IMPURITY, FREE ERYTHROMYCIN [EP IMPURITY]
• ERYTHROMYCIN ESTOLATE IMPURITY, FREE ERYTHROMYCIN- [USP IMPURITY]
• Erythromycin, for microbiological assay, European Pharmacopoeia (EP) Reference Standard
• Erythromycin, Pharmaceutical Secondary Standard; Certified Reference Material
• (3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-.alpha.-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-4-(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyloxy)-14-ethyl-7,12,13-trihydroxy-6-[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyloxy]-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl]oxy}-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione (non-preferred name)
• [3R-(3R*,4S*,5S*,6R*,7R*,9R*,11R*,12R*,13S*,14R*)]-4-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy]-14-ethyl-7,12,13-trihydroxy-3,5,7,9,11,13-hexamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy]oxacyclotetradecane-2,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7859	78.59%
Caco-2	-	0.9372	93.72%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Lysosomes	0.6348	63.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8665	86.65%
P-glycoprotein inhibitior	+	0.7128	71.28%
P-glycoprotein substrate	+	0.9225	92.25%
CYP3A4 substrate	+	0.7340	73.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8938	89.38%
CYP3A4 inhibition	-	0.5744	57.44%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9074	90.74%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9391	93.91%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5441	54.41%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9132	91.32%
Skin irritation	-	0.7819	78.19%
Skin corrosion	-	0.9180	91.80%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7450	74.50%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.9376	93.76%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8450	84.50%
Acute Oral Toxicity (c)	III	0.7984	79.84%
Estrogen receptor binding	-	0.7769	77.69%
Androgen receptor binding	-	0.6632	66.32%
Thyroid receptor binding	-	0.7874	78.74%
Glucocorticoid receptor binding	+	0.7259	72.59%
Aromatase binding	+	0.6356	63.56%
PPAR gamma	+	0.7056	70.56%
Honey bee toxicity	-	0.5745	57.45%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.4056	40.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL240	Q12809	HERG	39 nM	IC50	via Super-PRED
CHEMBL2203	O43193	Motilin receptor	50.12 nM	EC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.37%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.16%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.44%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.38%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.52%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.47%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.40%	96.21%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	86.11%	82.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.05%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.05%	95.56%
CHEMBL2996	Q05655	Protein kinase C delta	85.68%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.74%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.59%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.12%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.10%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.05%	96.77%
CHEMBL233	P35372	Mu opioid receptor	83.92%	97.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.40%	89.00%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	83.32%	95.00%
CHEMBL255	P29275	Adenosine A2b receptor	81.02%	98.59%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.91%	94.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 12560
• LOTUS: LTS0126541
• wikiData: Q213511