[(1R,2S,2'S,3R,3'aR,4R,4'R,5R,5'aS,6R,7S,9R,9'aS,9'bS)-4,5-diacetyloxy-3,4'-dihydroxy-7'-methoxy-2',3,5'a,6,6',9,9'b-heptamethyl-8',10-dioxospiro[11-oxatricyclo[7.2.1.01,6]dodecane-2,3'-2,3a,4,5,9,9a-hexahydro-1H-cyclopenta[a]naphthalene]-7-yl] acetate

Details

• Internal ID: bbca629c-6f3b-482e-91a3-24fadafd5270
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,2S,2'S,3R,3'aR,4R,4'R,5R,5'aS,6R,7S,9R,9'aS,9'bS)-4,5-diacetyloxy-3,4'-dihydroxy-7'-methoxy-2',3,5'a,6,6',9,9'b-heptamethyl-8',10-dioxospiro[11-oxatricyclo[7.2.1.01,6]dodecane-2,3'-2,3a,4,5,9,9a-hexahydro-1H-cyclopenta[a]naphthalene]-7-yl] acetate
• SMILES (Canonical): CC1CC2(C3CC(=O)C(=C(C3(CC(C2C14C(C(C(C5(C46CC(CC5OC(=O)C)(C(=O)O6)C)C)OC(=O)C)OC(=O)C)(C)O)O)C)C)OC)C
• SMILES (Isomeric): C[C@H]1C[C@]2([C@@H]3CC(=O)C(=C([C@]3(C[C@H]([C@H]2[C@]14[C@@]([C@@H]([C@@H]([C@@]5([C@]46C[C@@](C[C@@H]5OC(=O)C)(C(=O)O6)C)C)OC(=O)C)OC(=O)C)(C)O)O)C)C)OC)C
• InChI: InChI=1S/C37H52O12/c1-17-13-33(8)24-12-22(41)26(45-11)18(2)32(24,7)14-23(42)27(33)37(17)35(10,44)29(48-21(5)40)28(47-20(4)39)34(9)25(46-19(3)38)15-31(6)16-36(34,37)49-30(31)43/h17,23-25,27-29,42,44H,12-16H2,1-11H3/t17-,23+,24+,25-,27+,28-,29+,31+,32+,33-,34+,35-,36+,37-/m0/s1
• InChI Key: VHDPYIUOLKMMCD-YMXNCCJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₂O₁₂
• Molecular Weight: 688.80 g/mol
• Exact Mass: 688.34587709 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.58
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9843	98.43%
Caco-2	-	0.8199	81.99%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6047	60.47%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8546	85.46%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9580	95.80%
P-glycoprotein inhibitior	+	0.7861	78.61%
P-glycoprotein substrate	+	0.5462	54.62%
CYP3A4 substrate	+	0.7157	71.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8894	88.94%
CYP3A4 inhibition	-	0.5596	55.96%
CYP2C9 inhibition	-	0.8593	85.93%
CYP2C19 inhibition	-	0.8471	84.71%
CYP2D6 inhibition	-	0.9502	95.02%
CYP1A2 inhibition	-	0.7225	72.25%
CYP2C8 inhibition	+	0.6519	65.19%
CYP inhibitory promiscuity	-	0.9106	91.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4439	44.39%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8934	89.34%
Skin irritation	+	0.4950	49.50%
Skin corrosion	-	0.9343	93.43%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5074	50.74%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5973	59.73%
skin sensitisation	-	0.8309	83.09%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.6113	61.13%
Acute Oral Toxicity (c)	I	0.4950	49.50%
Estrogen receptor binding	+	0.7282	72.82%
Androgen receptor binding	+	0.7506	75.06%
Thyroid receptor binding	+	0.5345	53.45%
Glucocorticoid receptor binding	+	0.7467	74.67%
Aromatase binding	+	0.7277	72.77%
PPAR gamma	+	0.6998	69.98%
Honey bee toxicity	-	0.6691	66.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9888	98.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.07%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.56%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.60%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.69%	96.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.61%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.27%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.45%	95.56%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	89.11%	85.30%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.79%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.86%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.69%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.69%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.47%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.15%	94.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.67%	82.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.53%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.50%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.21%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.88%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.40%	97.09%
CHEMBL5028	O14672	ADAM10	82.34%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.45%	100.00%
CHEMBL2535	P11166	Glucose transporter	80.70%	98.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.00%	93.00%

Plants that contains it

• Ruptiliocarpon caracolito

Cross-Links

• PubChem: 162954912
• LOTUS: LTS0231229
• wikiData: Q105286328