Calcimycin

Details

• Internal ID: 0eb94cfa-f927-4518-93f3-18eb4b430a9d
• Taxonomy: Organoheterocyclic compounds > Benzoxazoles
• IUPAC Name: 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(CC(C(O2)C(C)C(=O)C3=CC=CN3)C)C)OC1CC4=NC5=C(O4)C=CC(=C5C(=O)O)NC
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@@H](C[C@H]([C@H](O2)[C@H](C)C(=O)C3=CC=CN3)C)C)O[C@@H]1CC4=NC5=C(O4)C=CC(=C5C(=O)O)NC
• InChI: InChI=1S/C29H37N3O6/c1-15-10-11-29(17(3)13-16(2)27(38-29)18(4)26(33)20-7-6-12-31-20)37-22(15)14-23-32-25-21(36-23)9-8-19(30-5)24(25)28(34)35/h6-9,12,15-18,22,27,30-31H,10-11,13-14H2,1-5H3,(H,34,35)/t15-,16-,17-,18-,22-,27+,29+/m1/s1
• InChI Key: HIYAVKIYRIFSCZ-CYEMHPAKSA-N
• Popularity: 17,844 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₇N₃O₆
• Molecular Weight: 523.60 g/mol
• Exact Mass: 523.26823591 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.53
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• 52665-69-7
• antibiotic A-23187
• Calcium ionophore III
• Calcimycin A23187
• rel-Calcimycin
• A23187
• A-23187
• UNII-37H9VM9WZL
• 37H9VM9WZL
• MLS001056783
• Calcium ionophore A23187
• SMR000326983
• A23187, free acid
• EINECS 258-084-1
• 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
• 79646-37-0
• SR-01000075434
• 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-((3,9,11-trimethyl-8-(1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl)-1,7-dioxaspiro(5.5)undec-2-yl)methyl)-, (6S-(6alpha(2S*,3S*),8beta(R*),9beta,11alpha))-
• A-23187;Antibiotic A-23187
• C29-H37-N3-O6
• 4-BENZOXAZOLECARBOXYLIC ACID, 5-(METHYLAMINO)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-TRIMETHYL-8-((1S)-1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIRO(5.5)UNDEC-2-YL)METHYL)-
• 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-
• CALCIMYCIN [MI]
• Lopac0_000317
• Calimycin;Antibiotic A-23187
• CHEMBL1256686
• DTXSID1040405
• SCHEMBL17390959
• BDBM44170
• CHEBI:107643
• cid_11957499
• HIYAVKIYRIFSCZ-CYEMHPAKSA-N
• HMS2231L17
• HMS3260P16
• HMS3267F15
• 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[3,9,11-trimethyl-8-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-, [6S-[6.alpha.(2S*,3S*),8.beta.(R*),9.beta.,11.alpha.]]-
• 4-Benzoxazolecarboxylic acid, 5-(methylamino)-2-[[3,9,11-trimethyl-8-[1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-, [6S-[6alpha(2S*,3S*),8beta(R*),9beta,11alpha]]-
• 5-(methylamino)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-((S)-1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl)-1,7-dioxaspiro[5.5]undecan-2-yl)methyl)benzo[d]oxazole-4-carboxylic acid
• Antibiotic A-23187A-23187
• HY-N6687
• Tox21_500317
• AKOS024456478
• CCG-204412
• LP00317
• SDCCGSBI-0050305.P002
• A23187; Calcium ionophore A23187
• NCGC00025064-02
• NCGC00025064-03
• NCGC00025064-04
• NCGC00025064-09
• NCGC00261002-01
• CS-0006888
• EU-0100317
• C 7522
• SR-01000597415
• Calcium Ionophore A23187, >=98% (TLC), powder
• Q3650244
• SR-01000075434-1
• SR-01000075434-5
• SR-01000597415-1
• BRD-K41431477-001-05-6
• Calcium ionophore III, Selectophore(TM), function tested
• 2-[[(2S,3R,5R,6S,8R,9R)-2-[(1S)-2-keto-1-methyl-2-(1H-pyrrol-2-yl)ethyl]-3,5,9-trimethyl-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-5-(methylamino)-1,3-benzoxazole-4-carboxylic acid
• 4-Benzoxazolecarboxylicacid,5-(methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-
• 5-(METHYLAMINO)-2-(((2R,3R,6S,8S,9R,11R)-3,9,11-TRIMETHYL-8-((1S)-1-METHYL-2-OXO-2-(1H-PYRROL-2-YL)ETHYL)-1,7-DIOXASPIRO(5.5)UNDEC-2-YL)METHYL)-4-BENZOXAZOLECARBOXYLIC ACID
• 5-(methylamino)-2-[[(2S,3R,5R,6S,8R,9R)-3,5,9-trimethyl-2-[(2S)-1-oxidanylidene-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid
• 5-(Methylamino)-2-[[2R,3R,6S,8S,9R,11R)-3,9,11-trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)-ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4-benzoxazolecarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6531	65.31%
Caco-2	-	0.7933	79.33%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Plasma membrane	0.5412	54.12%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.8606	86.06%
OATP1B3 inhibitior	+	0.9204	92.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7822	78.22%
BSEP inhibitior	+	0.9529	95.29%
P-glycoprotein inhibitior	-	0.8847	88.47%
P-glycoprotein substrate	+	0.7133	71.33%
CYP3A4 substrate	+	0.6837	68.37%
CYP2C9 substrate	+	0.8102	81.02%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.8063	80.63%
CYP2C8 inhibition	+	0.6839	68.39%
CYP inhibitory promiscuity	+	0.5358	53.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6337	63.37%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9349	93.49%
Skin irritation	-	0.8068	80.68%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6622	66.22%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5524	55.24%
skin sensitisation	-	0.8830	88.30%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.9034	90.34%
Acute Oral Toxicity (c)	III	0.6153	61.53%
Estrogen receptor binding	+	0.7805	78.05%
Androgen receptor binding	+	0.7480	74.80%
Thyroid receptor binding	+	0.6107	61.07%
Glucocorticoid receptor binding	+	0.8080	80.80%
Aromatase binding	+	0.7023	70.23%
PPAR gamma	+	0.5956	59.56%
Honey bee toxicity	-	0.8041	80.41%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9248	92.48%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	19952.6 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	35481.3 nM	Potency	via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293278	O75496	Geminin	1584.9 nM	Potency	via CMAUP
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	1074 nM	AC50	via CMAUP
CHEMBL5514	P42858	Huntingtin	891.3 nM; 891.3 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	35481.3 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM; 14125.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	15848.9 nM; 31622.8 nM; 22387.2 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	15.8 nM; 501.2 nM; 15.8 nM; 501.2 nM; 1258.9 nM; 15.8 nM	Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	290928.6 nM; 1122 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293298	Q01453	Peripheral myelin protein 22	6012 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	3162.3 nM; 2818.4 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3981.1 nM; 58047.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	2612.2 nM; 1468.9 nM; 2328.1 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	8912.5 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	6309.6 nM	Potency	via CMAUP
CHEMBL1741176	P17861	X-box-binding protein 1	1410 nM	IC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.89%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.57%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.64%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.64%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.98%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.24%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.60%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	86.67%	90.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.46%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.11%	93.56%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	83.03%	88.84%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.65%	82.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.16%	85.30%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.07%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.96%	94.23%
CHEMBL5028	O14672	ADAM10	81.75%	97.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.74%	92.88%

Plants that contains it

• Glehnia littoralis

Cross-Links

• PubChem: 11957499
• NPASS: NPC196449
• ChEMBL: CHEMBL1256686
• LOTUS: LTS0246487
• wikiData: Q3650244