Cryptophycin B

Details

• Internal ID: 133a02d3-290a-499c-957f-1ecd0a1a312b
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: (3S,6R,10R,13E,16S)-10-[(4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
• SMILES (Canonical): CC1CNC(=O)C(NC(=O)C=CCC(OC(=O)C(OC1=O)CC(C)C)C(C)C2C(O2)C3=CC=CC=C3)CC4=CC=C(C=C4)OC
• SMILES (Isomeric): C[C@@H]1CNC(=O)[C@H](NC(=O)/C=C/C[C@H](OC(=O)[C@@H](OC1=O)CC(C)C)[C@H](C)[C@@H]2[C@H](O2)C3=CC=CC=C3)CC4=CC=C(C=C4)OC
• InChI: InChI=1S/C35H44N2O8/c1-21(2)18-29-35(41)43-28(23(4)31-32(45-31)25-10-7-6-8-11-25)12-9-13-30(38)37-27(19-24-14-16-26(42-5)17-15-24)33(39)36-20-22(3)34(40)44-29/h6-11,13-17,21-23,27-29,31-32H,12,18-20H2,1-5H3,(H,36,39)(H,37,38)/b13-9+/t22-,23+,27-,28+,29+,31-,32-/m1/s1
• InChI Key: YFGZFQNBPSCWPN-FOLMERSESA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄N₂O₈
• Molecular Weight: 620.70 g/mol
• Exact Mass: 620.30976637 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.08
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• Cryptophycin 2
• NSC670038
• CHEMBL1975251
• ANTINEOPLASTIC-D670038
• DTXSID101333780
• NSC-670038
• (3S,6R,10R,13E,16S)-10-[(4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9215	92.15%
Caco-2	-	0.7940	79.40%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5644	56.44%
OATP2B1 inhibitior	+	0.5733	57.33%
OATP1B1 inhibitior	+	0.8592	85.92%
OATP1B3 inhibitior	+	0.9220	92.20%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9720	97.20%
P-glycoprotein inhibitior	+	0.9413	94.13%
P-glycoprotein substrate	+	0.7515	75.15%
CYP3A4 substrate	+	0.6866	68.66%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.8767	87.67%
CYP3A4 inhibition	-	0.5373	53.73%
CYP2C9 inhibition	-	0.8293	82.93%
CYP2C19 inhibition	-	0.7669	76.69%
CYP2D6 inhibition	-	0.8524	85.24%
CYP1A2 inhibition	-	0.8580	85.80%
CYP2C8 inhibition	+	0.6748	67.48%
CYP inhibitory promiscuity	-	0.8395	83.95%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5641	56.41%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.9389	93.89%
Skin irritation	-	0.7760	77.60%
Skin corrosion	-	0.9340	93.40%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8005	80.05%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.5988	59.88%
skin sensitisation	-	0.8632	86.32%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6027	60.27%
Acute Oral Toxicity (c)	III	0.6147	61.47%
Estrogen receptor binding	+	0.7684	76.84%
Androgen receptor binding	+	0.7367	73.67%
Thyroid receptor binding	+	0.5933	59.33%
Glucocorticoid receptor binding	+	0.7971	79.71%
Aromatase binding	+	0.5278	52.78%
PPAR gamma	+	0.7846	78.46%
Honey bee toxicity	-	0.7463	74.63%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9406	94.06%

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	97.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.96%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.63%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.24%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.87%	93.99%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.51%	85.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.67%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.50%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.43%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.39%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	88.14%	90.17%
CHEMBL4208	P20618	Proteasome component C5	87.93%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.68%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.30%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.14%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.95%	97.25%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.85%	92.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.34%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.14%	94.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.00%	96.09%
CHEMBL4349	Q02083	N-acylsphingosine-amidohydrolase	82.67%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.11%	97.14%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	81.07%	97.64%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.01%	95.89%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.83%	89.44%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.28%	93.00%

Plants that contains it

• Neurolaena lobata

Cross-Links

• PubChem: 5468424
• NPASS: NPC207675
• ChEMBL: CHEMBL1975251
• LOTUS: LTS0177130
• wikiData: Q77374023