methyl (1S,1'S,2'R,3S,3'S,5S,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-8'-methoxy-1,7'-dimethyl-11'-oxo-12'-propan-2-ylspiro[2,6-dioxabicyclo[3.1.0]hexane-3,6'-4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane]-5-carboxylate

Details

• Internal ID: 434c6d6a-da70-43f4-861d-6e890c872000
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: methyl (1S,1'S,2'R,3S,3'S,5S,5'R,7'R,8'S,9'S,12'R)-2',12'-dihydroxy-8'-methoxy-1,7'-dimethyl-11'-oxo-12'-propan-2-ylspiro[2,6-dioxabicyclo[3.1.0]hexane-3,6'-4,10-dioxatetracyclo[7.2.1.02,7.03,5]dodecane]-5-carboxylate
• SMILES (Canonical): CC(C)C1(C2C(C3(C4(CC5(C(O4)(O5)C)C(=O)OC)C6C(C3(C1C(=O)O2)O)O6)C)OC)O
• SMILES (Isomeric): CC(C)[C@@]1([C@@H]2[C@H]([C@]3([C@@]4(C[C@]5([C@@](O4)(O5)C)C(=O)OC)[C@H]6[C@@H]([C@]3([C@H]1C(=O)O2)O)O6)C)OC)O
• InChI: InChI=1S/C21H28O10/c1-8(2)20(24)9-14(22)29-12(20)10(26-5)16(3)18(11-13(28-11)21(9,16)25)7-19(15(23)27-6)17(4,30-18)31-19/h8-13,24-25H,7H2,1-6H3/t9-,10+,11+,12-,13-,16-,17-,18+,19+,20+,21-/m0/s1
• InChI Key: NOGWISBIQAZXPI-NPKSLNFFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₁₀
• Molecular Weight: 440.40 g/mol
• Exact Mass: 440.16824709 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7894	78.94%
Caco-2	-	0.6668	66.68%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5826	58.26%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.9604	96.04%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7028	70.28%
P-glycoprotein inhibitior	-	0.5514	55.14%
P-glycoprotein substrate	-	0.5487	54.87%
CYP3A4 substrate	+	0.6616	66.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.5936	59.36%
CYP2C9 inhibition	-	0.8652	86.52%
CYP2C19 inhibition	-	0.8476	84.76%
CYP2D6 inhibition	-	0.8920	89.20%
CYP1A2 inhibition	-	0.9089	90.89%
CYP2C8 inhibition	-	0.8138	81.38%
CYP inhibitory promiscuity	-	0.8926	89.26%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5040	50.40%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.8703	87.03%
Skin irritation	-	0.7287	72.87%
Skin corrosion	-	0.8823	88.23%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6298	62.98%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8304	83.04%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.8989	89.89%
Acute Oral Toxicity (c)	III	0.3659	36.59%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.7592	75.92%
Thyroid receptor binding	+	0.6502	65.02%
Glucocorticoid receptor binding	+	0.5726	57.26%
Aromatase binding	+	0.6980	69.80%
PPAR gamma	+	0.7231	72.31%
Honey bee toxicity	-	0.8136	81.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.7035	70.35%

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	97.95%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.80%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.59%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.68%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.98%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	89.32%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.96%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.76%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.11%	91.07%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.54%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.07%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.86%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.55%	92.62%
CHEMBL2581	P07339	Cathepsin D	82.50%	98.95%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.15%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	81.91%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.14%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.13%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.89%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	80.57%	96.77%

Plants that contains it

• Picrodendron baccatum

Cross-Links

• PubChem: 101606233
• LOTUS: LTS0087303
• wikiData: Q105182577