(16S)-9,12beta,16-Trihydroxy-17-[(E)-2-methyl-2-butenoyloxy]kauran-19-oic acid

Details

• Internal ID: daf0652c-3917-45ef-b7a6-b8c8368054fb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1S,4S,5S,9R,10S,12R,13S,14S)-10,12,14-trihydroxy-5,9-dimethyl-14-[[(E)-2-methylbut-2-enoyl]oxymethyl]tetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OCC1(CC23CCC4C(CCCC4(C2(CC(C1C3)O)O)C)(C)C(=O)O)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)OC[C@@]1(C[C@@]23CC[C@@H]4[C@@](CCC[C@]4([C@@]2(C[C@H]([C@@H]1C3)O)O)C)(C)C(=O)O)O
• InChI: InChI=1S/C25H38O7/c1-5-15(2)19(27)32-14-24(30)13-23-10-7-18-21(3,20(28)29)8-6-9-22(18,4)25(23,31)12-17(26)16(24)11-23/h5,16-18,26,30-31H,6-14H2,1-4H3,(H,28,29)/b15-5+/t16-,17+,18+,21-,22+,23-,24+,25+/m0/s1
• InChI Key: IGZHPMRMPWASLT-DYISRMJYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₈O₇
• Molecular Weight: 450.60 g/mol
• Exact Mass: 450.26175355 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9717	97.17%
Caco-2	-	0.5739	57.39%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8049	80.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8625	86.25%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7329	73.29%
BSEP inhibitior	+	0.9011	90.11%
P-glycoprotein inhibitior	-	0.6535	65.35%
P-glycoprotein substrate	-	0.6330	63.30%
CYP3A4 substrate	+	0.7127	71.27%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.9015	90.15%
CYP3A4 inhibition	-	0.9101	91.01%
CYP2C9 inhibition	-	0.7202	72.02%
CYP2C19 inhibition	-	0.8846	88.46%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9083	90.83%
CYP2C8 inhibition	+	0.4494	44.94%
CYP inhibitory promiscuity	-	0.9092	90.92%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7102	71.02%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.9454	94.54%
Skin irritation	+	0.6309	63.09%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4302	43.02%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6342	63.42%
skin sensitisation	-	0.9235	92.35%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5754	57.54%
Acute Oral Toxicity (c)	III	0.4464	44.64%
Estrogen receptor binding	+	0.8399	83.99%
Androgen receptor binding	+	0.7159	71.59%
Thyroid receptor binding	+	0.5530	55.30%
Glucocorticoid receptor binding	+	0.6684	66.84%
Aromatase binding	+	0.7605	76.05%
PPAR gamma	+	0.5387	53.87%
Honey bee toxicity	-	0.7637	76.37%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6055	60.55%
Fish aquatic toxicity	+	0.9937	99.37%

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	97.28%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.66%	95.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.01%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.67%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.98%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.61%	93.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.01%	82.69%
CHEMBL1937	Q92769	Histone deacetylase 2	86.64%	94.75%
CHEMBL221	P23219	Cyclooxygenase-1	86.52%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.39%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.18%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.41%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.19%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.33%	97.09%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.29%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.81%	96.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.40%	91.07%
CHEMBL226	P30542	Adenosine A1 receptor	80.92%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.91%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.64%	95.56%
CHEMBL2664	P23526	Adenosylhomocysteinase	80.47%	86.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.37%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.08%	89.34%

Plants that contains it

• Asparagus cochinchinensis

Cross-Links

• PubChem: 102056179
• NPASS: NPC93950