(1R,2S,4S,5R,9S,10S,13R,15R)-15-acetyloxy-5,9-dimethyl-2-[(Z)-2-methylbut-2-enoyl]oxy-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Details

• Internal ID: a9bcec6f-c45a-439a-b1dc-a732ba77680a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1R,2S,4S,5R,9S,10S,13R,15R)-15-acetyloxy-5,9-dimethyl-2-[(Z)-2-methylbut-2-enoyl]oxy-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2C(CCCC2(C)C(=O)O)(C3C14CC(CC3)C(=C)C4OC(=O)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@H]2[C@@](CCC[C@@]2(C)C(=O)O)([C@H]3[C@]14C[C@@H](CC3)C(=C)[C@H]4OC(=O)C)C
• InChI: InChI=1S/C27H38O6/c1-7-15(2)23(29)33-21-13-20-25(5,11-8-12-26(20,6)24(30)31)19-10-9-18-14-27(19,21)22(16(18)3)32-17(4)28/h7,18-22H,3,8-14H2,1-2,4-6H3,(H,30,31)/b15-7-/t18-,19+,20+,21+,22-,25+,26-,27-/m1/s1
• InChI Key: SFZBVMQDIRVKBD-AWPIIFSRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₈O₆
• Molecular Weight: 458.60 g/mol
• Exact Mass: 458.26683893 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 5.07
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9889	98.89%
Caco-2	+	0.4921	49.21%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7892	78.92%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8298	82.98%
OATP1B3 inhibitior	-	0.3664	36.64%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.7124	71.24%
BSEP inhibitior	+	0.8249	82.49%
P-glycoprotein inhibitior	+	0.6692	66.92%
P-glycoprotein substrate	-	0.6405	64.05%
CYP3A4 substrate	+	0.6800	68.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9041	90.41%
CYP3A4 inhibition	-	0.7912	79.12%
CYP2C9 inhibition	-	0.7593	75.93%
CYP2C19 inhibition	-	0.8063	80.63%
CYP2D6 inhibition	-	0.9653	96.53%
CYP1A2 inhibition	+	0.5144	51.44%
CYP2C8 inhibition	+	0.5469	54.69%
CYP inhibitory promiscuity	-	0.9475	94.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5950	59.50%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.8572	85.72%
Skin irritation	+	0.6367	63.67%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7700	77.00%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.7774	77.74%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6859	68.59%
Acute Oral Toxicity (c)	III	0.3048	30.48%
Estrogen receptor binding	+	0.8338	83.38%
Androgen receptor binding	+	0.6406	64.06%
Thyroid receptor binding	+	0.5886	58.86%
Glucocorticoid receptor binding	+	0.7827	78.27%
Aromatase binding	+	0.7390	73.90%
PPAR gamma	+	0.6575	65.75%
Honey bee toxicity	-	0.7499	74.99%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5155	51.55%
Fish aquatic toxicity	+	1.0000	100.00%

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	93.34%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.87%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	91.52%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.49%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.09%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.77%	96.38%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.98%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.42%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.80%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.12%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.89%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.63%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	83.55%	90.17%
CHEMBL2581	P07339	Cathepsin D	83.46%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.43%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.97%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.27%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.49%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.80%	100.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.26%	91.07%

Plants that contains it

• Thapsia gummifera

Cross-Links

• PubChem: 101277270
• LOTUS: LTS0088136
• wikiData: Q105252161