Pyrindamycin A

Details

• Internal ID: fa9df903-410d-4324-8852-1bfe690f00db
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acid esters
• IUPAC Name: methyl (2R,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
• SMILES (Canonical): CC1(C(=O)C2=C3C(CN(C3=CC(=C2N1)O)C(=O)C4=CC5=CC(=C(C(=C5N4)OC)OC)OC)CCl)C(=O)OC
• SMILES (Isomeric): C[C@@]1(C(=O)C2=C3[C@@H](CN(C3=CC(=C2N1)O)C(=O)C4=CC5=CC(=C(C(=C5N4)OC)OC)OC)CCl)C(=O)OC
• InChI: InChI=1S/C26H26ClN3O8/c1-26(25(34)38-5)23(32)18-17-12(9-27)10-30(14(17)8-15(31)20(18)29-26)24(33)13-6-11-7-16(35-2)21(36-3)22(37-4)19(11)28-13/h6-8,12,28-29,31H,9-10H2,1-5H3/t12-,26-/m1/s1
• InChI Key: BOGFADYROAVVTF-MZHQLVBMSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆ClN₃O₈
• Molecular Weight: 544.00 g/mol
• Exact Mass: 543.1408425 g/mol
• Topological Polar Surface Area (TPSA): 139.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.42
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Duocarmycin C2
• 118292-36-7
• methyl (2R,8S)-8-(chloromethyl)-4-hydroxy-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-7,8-dihydro-3H-pyrrolo[3,2-e]indole-2-carboxylate
• BRN 4834144
• CHEMBL159088
• SCHEMBL19493132
• DTXSID00152093
• AKOS040735857
• Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 8-(chloromethyl)-1,2,3,6,7,8-hexahydro-4-hydroxy-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester, (2R-trans)-
• HY-12458
• CS-0011402

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5190	51.90%
Caco-2	-	0.7983	79.83%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4908	49.08%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8670	86.70%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9044	90.44%
BSEP inhibitior	+	0.9434	94.34%
P-glycoprotein inhibitior	+	0.6706	67.06%
P-glycoprotein substrate	+	0.5911	59.11%
CYP3A4 substrate	+	0.6817	68.17%
CYP2C9 substrate	-	0.5844	58.44%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.5586	55.86%
CYP2C9 inhibition	+	0.5177	51.77%
CYP2C19 inhibition	+	0.5368	53.68%
CYP2D6 inhibition	-	0.8343	83.43%
CYP1A2 inhibition	-	0.7410	74.10%
CYP2C8 inhibition	+	0.7061	70.61%
CYP inhibitory promiscuity	+	0.6839	68.39%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7600	76.00%
Carcinogenicity (trinary)	Non-required	0.4895	48.95%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9536	95.36%
Skin irritation	-	0.8084	80.84%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4876	48.76%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.9000	90.00%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7463	74.63%
Acute Oral Toxicity (c)	III	0.6573	65.73%
Estrogen receptor binding	+	0.7364	73.64%
Androgen receptor binding	+	0.7218	72.18%
Thyroid receptor binding	+	0.6248	62.48%
Glucocorticoid receptor binding	+	0.5868	58.68%
Aromatase binding	+	0.5802	58.02%
PPAR gamma	+	0.6690	66.90%
Honey bee toxicity	-	0.7743	77.43%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9072	90.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.73%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.41%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.16%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.46%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.67%	93.03%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.36%	91.03%
CHEMBL2581	P07339	Cathepsin D	92.09%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	91.34%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.01%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL2535	P11166	Glucose transporter	90.47%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	89.58%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL261	P00915	Carbonic anhydrase I	88.69%	96.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.62%	99.17%
CHEMBL230	P35354	Cyclooxygenase-2	87.45%	89.63%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.92%	85.14%
CHEMBL4208	P20618	Proteasome component C5	86.20%	90.00%
CHEMBL255	P29275	Adenosine A2b receptor	86.17%	98.59%
CHEMBL4302	P08183	P-glycoprotein 1	85.54%	92.98%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.93%	89.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.29%	93.99%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.27%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.22%	94.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.08%	98.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.84%	93.40%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.07%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.80%	97.28%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.08%	86.92%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.59%	96.90%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.46%	96.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.13%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 147252
• LOTUS: LTS0242977
• wikiData: Q75068199