(4R)-17-Acetoxykauran-18-oic acid

Details

• Internal ID: 37dad4dd-54cb-41cc-b889-93cedf70eb91
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1S,4S,5R,9S,10R,13R,14S)-14-(acetyloxymethyl)-5,9-dimethyltetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• SMILES (Canonical): CC(=O)OCC1CC23CCC4C(C2CCC1C3)(CCCC4(C)C(=O)O)C
• SMILES (Isomeric): CC(=O)OC[C@H]1C[C@@]23CC[C@H]4[C@]([C@@H]2CC[C@@H]1C3)(CCC[C@@]4(C)C(=O)O)C
• InChI: InChI=1S/C22H34O4/c1-14(23)26-13-16-12-22-10-7-17-20(2,18(22)6-5-15(16)11-22)8-4-9-21(17,3)19(24)25/h15-18H,4-13H2,1-3H3,(H,24,25)/t15-,16-,17+,18+,20-,21-,22+/m1/s1
• InChI Key: DPBCVQQQIVNUMJ-BDTXQGIKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.50 g/mol
• Exact Mass: 362.24570956 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9832	98.32%
Caco-2	+	0.6455	64.55%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7449	74.49%
OATP2B1 inhibitior	-	0.8661	86.61%
OATP1B1 inhibitior	+	0.8573	85.73%
OATP1B3 inhibitior	+	0.9099	90.99%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7364	73.64%
BSEP inhibitior	+	0.7715	77.15%
P-glycoprotein inhibitior	-	0.6512	65.12%
P-glycoprotein substrate	-	0.7302	73.02%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	0.5865	58.65%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8516	85.16%
CYP2C9 inhibition	-	0.5623	56.23%
CYP2C19 inhibition	-	0.7792	77.92%
CYP2D6 inhibition	-	0.9453	94.53%
CYP1A2 inhibition	-	0.7736	77.36%
CYP2C8 inhibition	-	0.6810	68.10%
CYP inhibitory promiscuity	-	0.8673	86.73%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6648	66.48%
Eye corrosion	-	0.9659	96.59%
Eye irritation	-	0.8966	89.66%
Skin irritation	-	0.8166	81.66%
Skin corrosion	-	0.9803	98.03%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4599	45.99%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.6476	64.76%
skin sensitisation	-	0.7852	78.52%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5947	59.47%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6983	69.83%
Acute Oral Toxicity (c)	III	0.6823	68.23%
Estrogen receptor binding	+	0.8661	86.61%
Androgen receptor binding	-	0.4908	49.08%
Thyroid receptor binding	+	0.6360	63.60%
Glucocorticoid receptor binding	+	0.8191	81.91%
Aromatase binding	+	0.6271	62.71%
PPAR gamma	-	0.5128	51.28%
Honey bee toxicity	-	0.8634	86.34%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.01%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.83%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.81%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.47%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.82%	91.11%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.27%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.29%	96.61%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.64%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.70%	91.19%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.55%	93.04%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.16%	96.77%
CHEMBL5255	O00206	Toll-like receptor 4	82.69%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.04%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.23%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.83%	95.89%

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
• 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: 102425890
• NPASS: NPC145727
• LOTUS: LTS0085787
• wikiData: Q104986378