Kahalalide F

Details

• Internal ID: 0c4fbbac-d81a-41d0-a66c-45c80efa30cd
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2R)-N-[(2S)-5-amino-1-[[(2R,3S)-1-[[(3S,6Z,9S,12R,15R,18R,19R)-9-benzyl-15-[(2S)-butan-2-yl]-6-ethylidene-19-methyl-2,5,8,11,14,17-hexaoxo-3,12-di(propan-2-yl)-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]-1-[(2R)-2-[[(2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2R)-3-methyl-2-(5-methylhexanoylamino)butanoyl]amino]butanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carboxamide
• SMILES (Canonical): CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(=CC)C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C(C(C)CC)NC(=O)C(CCCN)NC(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C(C(C)C)NC(=O)C(C(C)O)NC(=O)C(C(C)C)NC(=O)CCCC(C)C)C)C(C)C)CC3=CC=CC=C3)C(C)C
• SMILES (Isomeric): CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N/C(=C\C)/C(=O)N[C@H](C(=O)O[C@@H]([C@H](C(=O)N1)NC(=O)[C@@H]([C@@H](C)CC)NC(=O)[C@H](CCCN)NC(=O)[C@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](C(C)C)NC(=O)CCCC(C)C)C)C(C)C)CC3=CC=CC=C3)C(C)C
• InChI: InChI=1S/C75H124N14O16/c1-20-44(16)59(71(100)88-62-47(19)105-75(104)58(43(14)15)84-63(92)49(22-3)77-65(94)51(37-48-30-24-23-25-31-48)79-67(96)55(40(8)9)81-70(99)60(45(17)21-2)86-73(62)102)85-64(93)50(32-27-35-76)78-66(95)52-33-28-36-89(52)74(103)57(42(12)13)83-69(98)56(41(10)11)82-72(101)61(46(18)90)87-68(97)54(39(6)7)80-53(91)34-26-29-38(4)5/h22-25,30-31,38-47,50-52,54-62,90H,20-21,26-29,32-37,76H2,1-19H3,(H,77,94)(H,78,95)(H,79,96)(H,80,91)(H,81,99)(H,82,101)(H,83,98)(H,84,92)(H,85,93)(H,86,102)(H,87,97)(H,88,100)/b49-22-/t44-,45-,46+,47+,50-,51-,52+,54+,55+,56-,57+,58-,59+,60+,61-,62+/m0/s1
• InChI Key: RCGXNDQKCXNWLO-YUHQQKLOSA-N
• Popularity: 50 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₅H₁₂₄N₁₄O₁₆
• Molecular Weight: 1477.90 g/mol
• Exact Mass: 1476.93197392 g/mol
• Topological Polar Surface Area (TPSA): 442.00 Ų
• XlogP: 7.40
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 17
• H-Bond Donor: 14
• Rotatable Bonds: 33

Synonyms

• BQD6E2ZXEA
• UNII-BQD6E2ZXEA
• 149204-42-2
• pm-92102
• Kahalide F
• C75H124N14O16
• C75-H124-N14-O16
• KAHALALIDE F [MI]
• SCHEMBL60285
• CHEMBL513639
• DTXSID301031233
• NSC668814
• NSC-668814
• Q27274814
• 1-Oxa-4,10,13,16-pentaazacyclononadecane, cyclic peptide derivative
• L-Valine, N-(5-methyl-1-oxohexyl)-D-valyl-L-threonyl-L-valyl-D-valyl-D-prolyl-L-ornithyl-D-alloisoleucyl-D-allothreonyl-D-alloisoleucyl-D-valyl-L-phenylalanyl-(2Z)-2-amino-2-butenoly-(13.fwdarw.8)-lactone
• L-VALINE, N-(5-METHYL-1-OXOHEXYL)-D-VALYL-L-THREONYL-L-VALYL-D-VALYL-D-PROLYL-L-ORNITHYL-D-ALLOISOLEUCYL-D-ALLOTHREONYL-D-ALLOISOLEUCYL-D-VALYL-L-PHENYLALANYL-(2Z)-2-AMINO-2-BUTENOYL-, (13->8)-LACTONE
• Valine, N-(5-methyl-1-oxohexyl)valylthreonylvalylvalyl-D-prolyl-L-ornithyl-D-alloisoleucylthreonyl-D-alloisoleucylvalyl-L-phenylalanyl-(Z)-2,3-didehydro-2-aminobutanoyl-, rho-lactone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5698	56.98%
Caco-2	-	0.8628	86.28%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4956	49.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8195	81.95%
OATP1B3 inhibitior	+	0.9168	91.68%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9839	98.39%
P-glycoprotein inhibitior	+	0.7421	74.21%
P-glycoprotein substrate	+	0.8822	88.22%
CYP3A4 substrate	+	0.7471	74.71%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.8282	82.82%
CYP3A4 inhibition	-	0.5221	52.21%
CYP2C9 inhibition	-	0.8617	86.17%
CYP2C19 inhibition	-	0.8422	84.22%
CYP2D6 inhibition	-	0.9161	91.61%
CYP1A2 inhibition	-	0.8803	88.03%
CYP2C8 inhibition	+	0.7762	77.62%
CYP inhibitory promiscuity	-	0.9409	94.09%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.5650	56.50%
Eye corrosion	-	0.9875	98.75%
Eye irritation	-	0.8959	89.59%
Skin irritation	-	0.7651	76.51%
Skin corrosion	-	0.9126	91.26%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7245	72.45%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6552	65.52%
skin sensitisation	-	0.8542	85.42%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.5052	50.52%
Acute Oral Toxicity (c)	III	0.6019	60.19%
Estrogen receptor binding	+	0.6480	64.80%
Androgen receptor binding	+	0.6948	69.48%
Thyroid receptor binding	+	0.6958	69.58%
Glucocorticoid receptor binding	+	0.7860	78.60%
Aromatase binding	+	0.7605	76.05%
PPAR gamma	+	0.7936	79.36%
Honey bee toxicity	-	0.6796	67.96%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.8939	89.39%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.82%	98.95%
CHEMBL3837	P07711	Cathepsin L	99.39%	96.61%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	98.47%	98.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.21%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.01%	96.09%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	97.27%	97.64%
CHEMBL2514	O95665	Neurotensin receptor 2	97.07%	100.00%
CHEMBL230	P35354	Cyclooxygenase-2	96.80%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.65%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	96.59%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.50%	97.09%
CHEMBL4588	P22894	Matrix metalloproteinase 8	96.08%	94.66%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.85%	96.47%
CHEMBL5103	Q969S8	Histone deacetylase 10	95.62%	90.08%
CHEMBL2492	P36544	Neuronal acetylcholine receptor protein alpha-7 subunit	94.16%	88.42%
CHEMBL3359	P21462	Formyl peptide receptor 1	93.97%	93.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	93.90%	97.14%
CHEMBL333	P08253	Matrix metalloproteinase-2	93.88%	96.31%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	93.47%	82.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.72%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.51%	100.00%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	91.97%	97.50%
CHEMBL3310	Q96DB2	Histone deacetylase 11	91.76%	88.56%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	91.11%	95.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.84%	93.00%
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	90.33%	98.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.64%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.28%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.91%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.04%	95.89%
CHEMBL255	P29275	Adenosine A2b receptor	85.92%	98.59%
CHEMBL4072	P07858	Cathepsin B	85.61%	93.67%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	85.10%	96.03%
CHEMBL4581	P52732	Kinesin-like protein 1	84.95%	93.18%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.12%	82.69%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.11%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.87%	91.19%
CHEMBL1937	Q92769	Histone deacetylase 2	81.50%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.40%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.91%	95.89%

Plants that contains it

• Rheum australe

Cross-Links

• PubChem: 9898671
• NPASS: NPC7817