Apoptolidin D

Details

• Internal ID: 4b35d1ea-e04a-473a-9d93-96bdaafe71d0
• Taxonomy: Phenylpropanoids and polyketides > Macrolides and analogues
• IUPAC Name: (3E,5E,7E,9R,10R,11E,13E,17S,18S,20S)-20-[(R)-[(2R,3R,4S,5R,6R)-2,4-dihydroxy-6-[(2R)-2-[(2R,4S,5S,6S)-4-hydroxy-5-[(2S,4R,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4,6-dimethyloxan-2-yl]oxy-3-methoxypropyl]-3,5-dimethyloxan-2-yl]-hydroxymethyl]-10-[(2R,3S,4S,5R,6S)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-18-methoxy-3,5,9,13-tetramethyl-1-oxacycloicosa-3,5,7,11,13-pentaen-2-one
• SMILES (Canonical): CC1C=CC=C(C=C(C(=O)OC(CC(C(CCC=C(C=CC1OC2C(C(C(C(O2)C)OC)O)O)C)O)OC)C(C3(C(C(C(C(O3)CC(COC)OC4CC(C(C(O4)C)OC5CC(C(C(O5)C)O)OC)(C)O)C)O)C)O)O)C)C
• SMILES (Isomeric): C[C@@H]1/C=C/C=C(/C=C(/C(=O)O[C@@H](C[C@@H]([C@H](CC/C=C(/C=C/[C@H]1O[C@H]2[C@H]([C@@H]([C@H]([C@@H](O2)C)OC)O)O)\C)O)OC)[C@H]([C@]3([C@@H]([C@H]([C@H]([C@H](O3)C[C@H](COC)O[C@H]4C[C@]([C@H]([C@@H](O4)C)O[C@H]5C[C@H]([C@@H]([C@H](O5)C)O)OC)(C)O)C)O)C)O)O)\C)\C
• InChI: InChI=1S/C57H94O21/c1-29-17-16-20-39(58)42(68-12)25-44(75-54(64)32(4)23-30(2)18-15-19-31(3)40(22-21-29)76-55-50(62)49(61)51(70-14)36(8)73-55)52(63)57(66)34(6)47(59)33(5)41(78-57)24-38(28-67-11)74-46-27-56(10,65)53(37(9)72-46)77-45-26-43(69-13)48(60)35(7)71-45/h15,17-19,21-23,31,33-53,55,58-63,65-66H,16,20,24-28H2,1-14H3/b19-15+,22-21+,29-17+,30-18+,32-23+/t31-,33+,34-,35-,36+,37+,38-,39+,40-,41-,42+,43-,44+,45+,46+,47+,48-,49+,50+,51+,52-,53+,55+,56+,57-/m1/s1
• InChI Key: ONVFWWCNSIUNAP-XPKGCDIMSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₉₄O₂₁
• Molecular Weight: 1115.30 g/mol
• Exact Mass: 1114.62876000 g/mol
• Topological Polar Surface Area (TPSA): 290.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 21
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6402	64.02%
Caco-2	-	0.8680	86.80%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8261	82.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8168	81.68%
OATP1B3 inhibitior	+	0.8610	86.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9793	97.93%
P-glycoprotein inhibitior	+	0.7459	74.59%
P-glycoprotein substrate	+	0.8374	83.74%
CYP3A4 substrate	+	0.7518	75.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8808	88.08%
CYP3A4 inhibition	-	0.9612	96.12%
CYP2C9 inhibition	-	0.8867	88.67%
CYP2C19 inhibition	-	0.8792	87.92%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9244	92.44%
CYP2C8 inhibition	+	0.7920	79.20%
CYP inhibitory promiscuity	-	0.9785	97.85%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6844	68.44%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9005	90.05%
Skin irritation	-	0.6403	64.03%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8167	81.67%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8572	85.72%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6132	61.32%
Acute Oral Toxicity (c)	III	0.4877	48.77%
Estrogen receptor binding	+	0.8314	83.14%
Androgen receptor binding	+	0.7035	70.35%
Thyroid receptor binding	+	0.7057	70.57%
Glucocorticoid receptor binding	+	0.8338	83.38%
Aromatase binding	+	0.6265	62.65%
PPAR gamma	+	0.8419	84.19%
Honey bee toxicity	-	0.6005	60.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8794	87.94%

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	99.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.85%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.64%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.96%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.00%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.52%	97.36%
CHEMBL2581	P07339	Cathepsin D	95.25%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.97%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	93.93%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.41%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.67%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.92%	97.14%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	90.64%	97.33%
CHEMBL226	P30542	Adenosine A1 receptor	90.30%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.10%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	89.04%	97.05%
CHEMBL3401	O75469	Pregnane X receptor	89.02%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.52%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.24%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.10%	93.03%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.95%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.05%	89.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.66%	91.24%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.80%	96.47%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.34%	91.71%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.76%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.21%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 102470238
• LOTUS: LTS0243066
• wikiData: Q77511933