(2R,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methyl-3-methylideneheptanoic acid

Details

• Internal ID: 14cc1eb7-4551-4af1-86e7-9c0ee700d3e1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• IUPAC Name: (2R,6R)-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]-2-methyl-3-methylideneheptanoic acid
• SMILES (Canonical): CC(CCC(=C)C(C)C(=O)O)C1CCC2(C1(CCC34C2CCC5C3(C4)CCC(C5(C)C)O)C)C
• SMILES (Isomeric): C[C@H](CCC(=C)[C@@H](C)C(=O)O)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)CC[C@@H](C5(C)C)O)C)C
• InChI: InChI=1S/C31H50O3/c1-19(21(3)26(33)34)8-9-20(2)22-12-14-29(7)24-11-10-23-27(4,5)25(32)13-15-30(23)18-31(24,30)17-16-28(22,29)6/h20-25,32H,1,8-18H2,2-7H3,(H,33,34)/t20-,21-,22-,23+,24+,25+,28-,29+,30-,31+/m1/s1
• InChI Key: FCQSIIVNJCMJLB-SRBJWBKWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.37599545 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 9.20
• Atomic LogP (AlogP): 7.48
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 13878-93-8
• CHEMBL3926423

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	-	0.6967	69.67%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7434	74.34%
OATP2B1 inhibitior	-	0.5614	56.14%
OATP1B1 inhibitior	+	0.8815	88.15%
OATP1B3 inhibitior	+	0.7974	79.74%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6809	68.09%
P-glycoprotein inhibitior	-	0.5683	56.83%
P-glycoprotein substrate	-	0.7267	72.67%
CYP3A4 substrate	+	0.6450	64.50%
CYP2C9 substrate	-	0.6653	66.53%
CYP2D6 substrate	-	0.8408	84.08%
CYP3A4 inhibition	-	0.7880	78.80%
CYP2C9 inhibition	-	0.7842	78.42%
CYP2C19 inhibition	-	0.8429	84.29%
CYP2D6 inhibition	-	0.9492	94.92%
CYP1A2 inhibition	-	0.8827	88.27%
CYP2C8 inhibition	-	0.7014	70.14%
CYP inhibitory promiscuity	-	0.7847	78.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6617	66.17%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.9260	92.60%
Skin irritation	+	0.5727	57.27%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.7965	79.65%
Human Ether-a-go-go-Related Gene inhibition	-	0.4830	48.30%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.6968	69.68%
skin sensitisation	-	0.5772	57.72%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8617	86.17%
Acute Oral Toxicity (c)	I	0.4877	48.77%
Estrogen receptor binding	+	0.7045	70.45%
Androgen receptor binding	+	0.7704	77.04%
Thyroid receptor binding	+	0.6368	63.68%
Glucocorticoid receptor binding	+	0.7480	74.80%
Aromatase binding	+	0.7419	74.19%
PPAR gamma	+	0.6576	65.76%
Honey bee toxicity	-	0.7756	77.56%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.20%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.54%	97.25%
CHEMBL2581	P07339	Cathepsin D	92.69%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.33%	93.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.29%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.83%	90.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.72%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.89%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.77%	95.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.41%	93.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.34%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.97%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.91%	91.19%
CHEMBL237	P41145	Kappa opioid receptor	85.10%	98.10%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.57%	96.47%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.17%	90.24%
CHEMBL2514	O95665	Neurotensin receptor 2	83.74%	100.00%
CHEMBL233	P35372	Mu opioid receptor	83.53%	97.93%
CHEMBL4040	P28482	MAP kinase ERK2	82.37%	83.82%
CHEMBL220	P22303	Acetylcholinesterase	82.18%	94.45%
CHEMBL3837	P07711	Cathepsin L	81.80%	96.61%
CHEMBL4246	P42680	Tyrosine-protein kinase TEC	81.73%	82.05%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.52%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.63%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.27%	95.56%

Plants that contains it

• Aconitum burnatii
• Alseodaphne paludosa
• Annona impressivenia
• Bersama yangambiensis
• Caloncoba echinata
• Castanopsis sclerophylla
• Conocephalum japonicum
• Cordylanthus kingii
• Croton cascarilloides
• Disynaphia halimifolia
• Eragrostis viscosa
• Forsteronia refracta
• Fridericia chica
• Grewia mollis
• Gymnocarpium robertianum
• Heliotropium floridum
• Heterotheca grandiflora
• Hovenia acerba
• Juglans nigra
• Kaempferia marginata
• Kaunia saltensis
• Mangifera indica
• Nauclea officinalis
• Ruta pinnata
• Salvia dorrii
• Sophora flavescens var. flavescens
• Stevia polycephala
• Teucrium cubense
• Thymus piperella
• Trichilia rubescens
• Uraria picta

Cross-Links

• PubChem: 101286241
• NPASS: NPC166825