dimethyl (1S,2S,3S,4S,5S,12R)-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadeca-6,8-diene-2,4-dicarboxylate

Details

• Internal ID: 09d02827-26dc-458c-b2ad-726a06ebb8bf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: dimethyl (1S,2S,3S,4S,5S,12R)-5-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.01,9.03,8]pentadeca-6,8-diene-2,4-dicarboxylate
• SMILES (Canonical): CC1(C(C=CC2=C3CCC4CC3(CC4=C)C(C21)C(=O)OC)O)C(=O)OC
• SMILES (Isomeric): C[C@]1([C@H](C=CC2=C3CC[C@@H]4C[C@]3(CC4=C)[C@H]([C@@H]21)C(=O)OC)O)C(=O)OC
• InChI: InChI=1S/C21H26O5/c1-11-9-21-10-12(11)5-7-14(21)13-6-8-15(22)20(2,19(24)26-4)16(13)17(21)18(23)25-3/h6,8,12,15-17,22H,1,5,7,9-10H2,2-4H3/t12-,15+,16-,17-,20-,21+/m1/s1
• InChI Key: GPTWGKVTHRFAFX-VKCRYBOWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.17802393 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.5862	58.62%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7953	79.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8825	88.25%
OATP1B3 inhibitior	+	0.9037	90.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.8183	81.83%
P-glycoprotein inhibitior	-	0.6684	66.84%
P-glycoprotein substrate	-	0.6055	60.55%
CYP3A4 substrate	+	0.6915	69.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.8142	81.42%
CYP2C9 inhibition	-	0.7931	79.31%
CYP2C19 inhibition	-	0.8630	86.30%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.6198	61.98%
CYP2C8 inhibition	+	0.5141	51.41%
CYP inhibitory promiscuity	-	0.9172	91.72%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9363	93.63%
Carcinogenicity (trinary)	Non-required	0.5848	58.48%
Eye corrosion	-	0.9786	97.86%
Eye irritation	-	0.9737	97.37%
Skin irritation	-	0.6008	60.08%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7594	75.94%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7392	73.92%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6457	64.57%
Acute Oral Toxicity (c)	III	0.3855	38.55%
Estrogen receptor binding	+	0.7112	71.12%
Androgen receptor binding	+	0.6094	60.94%
Thyroid receptor binding	+	0.5989	59.89%
Glucocorticoid receptor binding	+	0.7821	78.21%
Aromatase binding	+	0.5295	52.95%
PPAR gamma	-	0.4868	48.68%
Honey bee toxicity	-	0.7180	71.80%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9952	99.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	89.57%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.44%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.99%	99.23%
CHEMBL2581	P07339	Cathepsin D	85.26%	98.95%
CHEMBL2243	O00519	Anandamide amidohydrolase	85.25%	97.53%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.52%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	82.69%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.25%	85.14%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 145643046
• LOTUS: LTS0122491
• wikiData: Q105015183