2-[(1R,2S,3R,6R,8S,9S,10R,11R,12S,13S)-11,12-dihydroxy-13-methoxycarbonyl-8-[(2S)-1-methoxy-1-oxopropan-2-yl]-9-methyl-3-(3-methylbut-2-enoyloxy)-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecan-9-yl]acetic acid

Details

• Internal ID: 4dbcd425-2b2b-431e-be3f-f9ad3f5e6d20
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: 2-[(1R,2S,3R,6R,8S,9S,10R,11R,12S,13S)-11,12-dihydroxy-13-methoxycarbonyl-8-[(2S)-1-methoxy-1-oxopropan-2-yl]-9-methyl-3-(3-methylbut-2-enoyloxy)-4-oxo-5,14-dioxatetracyclo[8.5.0.01,6.02,13]pentadecan-9-yl]acetic acid
• SMILES (Canonical): CC(C1CC2C34COC(C3C(C(=O)O2)OC(=O)C=C(C)C)(C(C(C4C1(C)CC(=O)O)O)O)C(=O)OC)C(=O)OC
• SMILES (Isomeric): C[C@@H]([C@@H]1C[C@@H]2[C@@]34CO[C@@]([C@@H]3[C@H](C(=O)O2)OC(=O)C=C(C)C)([C@H]([C@@H]([C@@H]4[C@@]1(C)CC(=O)O)O)O)C(=O)OC)C(=O)OC
• InChI: InChI=1S/C27H36O13/c1-11(2)7-16(30)40-18-20-26-10-38-27(20,24(35)37-6)21(32)17(31)19(26)25(4,9-15(28)29)13(12(3)22(33)36-5)8-14(26)39-23(18)34/h7,12-14,17-21,31-32H,8-10H2,1-6H3,(H,28,29)/t12-,13-,14+,17+,18+,19+,20+,21-,25-,26+,27-/m0/s1
• InChI Key: MOPJOSMHIBNYOK-OFEMSGAVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₆O₁₃
• Molecular Weight: 568.60 g/mol
• Exact Mass: 568.21559120 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9337	93.37%
Caco-2	-	0.7860	78.60%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7836	78.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8444	84.44%
OATP1B3 inhibitior	+	0.9531	95.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9589	95.89%
P-glycoprotein inhibitior	+	0.7325	73.25%
P-glycoprotein substrate	+	0.8494	84.94%
CYP3A4 substrate	+	0.6843	68.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8974	89.74%
CYP3A4 inhibition	-	0.7315	73.15%
CYP2C9 inhibition	-	0.8366	83.66%
CYP2C19 inhibition	-	0.8746	87.46%
CYP2D6 inhibition	-	0.9377	93.77%
CYP1A2 inhibition	-	0.8650	86.50%
CYP2C8 inhibition	+	0.4520	45.20%
CYP inhibitory promiscuity	-	0.9282	92.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5124	51.24%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9058	90.58%
Skin irritation	-	0.5717	57.17%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4690	46.90%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8459	84.59%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.6019	60.19%
Acute Oral Toxicity (c)	I	0.6339	63.39%
Estrogen receptor binding	+	0.8057	80.57%
Androgen receptor binding	+	0.6870	68.70%
Thyroid receptor binding	-	0.5051	50.51%
Glucocorticoid receptor binding	+	0.7620	76.20%
Aromatase binding	+	0.6922	69.22%
PPAR gamma	+	0.6836	68.36%
Honey bee toxicity	-	0.6014	60.14%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9829	98.29%

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	98.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.01%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	97.98%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.11%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.04%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	95.73%	98.03%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.66%	96.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	93.97%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.83%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.71%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	93.70%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	92.92%	97.79%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.85%	96.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.71%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.16%	96.77%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	91.36%	96.47%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.69%	95.71%
CHEMBL340	P08684	Cytochrome P450 3A4	88.72%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.72%	89.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	86.09%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL3776	Q14790	Caspase-8	85.80%	97.06%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.58%	94.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.88%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.84%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.85%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.71%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	82.37%	97.47%
CHEMBL5028	O14672	ADAM10	82.01%	97.50%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.51%	80.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.47%	97.09%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 70692363
• NPASS: NPC94509