Methyl 16alpha,17-dihydroxy-ent-kauran-19-oate

Details

• Internal ID: 7140f752-6ec9-4287-a20a-352062f36594
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: methyl (1S,4S,5R,9S,10R,13R,14R)-14-hydroxy-14-(hydroxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC12CCCC(C1CCC34C2CCC(C3)C(C4)(CO)O)(C)C(=O)OC
• SMILES (Isomeric): C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@H](C3)[C@](C4)(CO)O)(C)C(=O)OC
• InChI: InChI=1S/C21H34O4/c1-18-8-4-9-19(2,17(23)25-3)15(18)7-10-20-11-14(5-6-16(18)20)21(24,12-20)13-22/h14-16,22,24H,4-13H2,1-3H3/t14-,15+,16+,18-,19-,20+,21+/m1/s1
• InChI Key: CZYWWRRSTIZTFL-SJIZYOMUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.50 g/mol
• Exact Mass: 350.24570956 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Methyl 16alpha,17-dihydroxy-ent-kauran-19-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9632	96.32%
Caco-2	+	0.7087	70.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7501	75.01%
OATP2B1 inhibitior	-	0.8620	86.20%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.8201	82.01%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7792	77.92%
BSEP inhibitior	+	0.6095	60.95%
P-glycoprotein inhibitior	-	0.8433	84.33%
P-glycoprotein substrate	-	0.6406	64.06%
CYP3A4 substrate	+	0.6805	68.05%
CYP2C9 substrate	-	0.5928	59.28%
CYP2D6 substrate	-	0.8317	83.17%
CYP3A4 inhibition	-	0.8615	86.15%
CYP2C9 inhibition	-	0.7057	70.57%
CYP2C19 inhibition	-	0.8299	82.99%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	-	0.7584	75.84%
CYP2C8 inhibition	-	0.8104	81.04%
CYP inhibitory promiscuity	-	0.9685	96.85%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7643	76.43%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9627	96.27%
Skin irritation	-	0.6602	66.02%
Skin corrosion	-	0.9648	96.48%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5649	56.49%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7677	76.77%
skin sensitisation	-	0.8972	89.72%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.7961	79.61%
Acute Oral Toxicity (c)	III	0.5954	59.54%
Estrogen receptor binding	+	0.8495	84.95%
Androgen receptor binding	+	0.5843	58.43%
Thyroid receptor binding	+	0.6174	61.74%
Glucocorticoid receptor binding	+	0.8091	80.91%
Aromatase binding	+	0.7591	75.91%
PPAR gamma	-	0.6477	64.77%
Honey bee toxicity	-	0.8211	82.11%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8960	89.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.04%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.72%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.57%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.52%	96.38%
CHEMBL233	P35372	Mu opioid receptor	90.29%	97.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.26%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.78%	91.07%
CHEMBL4040	P28482	MAP kinase ERK2	89.76%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.04%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.77%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.60%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.58%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.43%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.29%	91.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.84%	91.03%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.44%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.14%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	83.75%	91.19%
CHEMBL2581	P07339	Cathepsin D	83.13%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.74%	82.69%
CHEMBL4072	P07858	Cathepsin B	81.93%	93.67%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.66%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	80.97%	95.36%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.93%	100.00%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	80.68%	88.81%
CHEMBL1075317	P61964	WD repeat-containing protein 5	80.65%	96.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.06%	92.50%

Plants that contains it

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Curcuma aeruginosa
• Delphinium giraldii
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Helianthus debilis
• Juniperus scopulorum
• Lasianthaea podocephala
• Lupinus cosentinii
• Melampodium leucanthum
• Myrica pensylvanica
• Neopallasia pectinata
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Stellaria media
• Tephroseris kirilowii
• Tephroseris palustris

Cross-Links

• PubChem: 46233487
• NPASS: NPC199965
• ChEMBL: CHEMBL598159
• LOTUS: LTS0247430
• wikiData: Q104973272