Phytuberin

Details

• Internal ID: 52216e78-feb7-4621-8144-e79975e5b6c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(3aR,5aS,8R,9aR)-3a,5a-dimethyl-6,7,8,9-tetrahydro-5H-furo[2,3-i][2]benzofuran-8-yl]propan-2-yl acetate
• SMILES (Canonical): CC(=O)OC(C)(C)C1CCC2(COC3(C2(C1)OC=C3)C)C
• SMILES (Isomeric): CC(=O)OC(C)(C)[C@@H]1CC[C@]2(CO[C@]3([C@]2(C1)OC=C3)C)C
• InChI: InChI=1S/C17H26O4/c1-12(18)21-14(2,3)13-6-7-15(4)11-20-16(5)8-9-19-17(15,16)10-13/h8-9,13H,6-7,10-11H2,1-5H3/t13-,15+,16-,17-/m1/s1
• InChI Key: YARAJYKHRCCDLG-XLNGHYISSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• 37209-50-0
• RR00OUQ5B6
• 2-[(3aR,5aS,8R,9aR)-3a,5a-dimethyl-6,7,8,9-tetrahydro-5H-furo[2,3-i][2]benzofuran-8-yl]propan-2-yl acetate
• (-)-Phytuberin
• AC1L9CQ2
• UNII-RR00OUQ5B6
• CHEBI:8196
• SCHEMBL5912276
• DTXSID10958386
• C09709
• Q27107914
• 2-(3a,5a-Dimethyl-5,5a,6,7,8,9-hexahydro-3aH-furo[3,2-c][2]benzofuran-8-yl)propan-2-yl acetate
• 2-[(3aR,5aS,8R,9aR)-3a,5a-dimethyl-5,5a,6,7,8,9-hexahydro-3aH-furo[3,2-c][2]benzofuran-8-yl]propan-2-yl acetate
• 3AH-FURO(3,2-C)ISOBENZOFURAN-8-METHANOL, 5,5A,6,7,8,9-HEXAHYDRO-.ALPHA.,.ALPHA.,3A,5A-TETRAMETHYL-, 8-ACETATE, (3AR,5AS,8R,9AR)-
• 7H-Furo(3,2-c)benzofuran-8-methanol, 3a,5,5a,6,8,9-hexahydro-alpha,alpha,3a,5a-tetramethyl-, acetate, (3aR,5aS,8S,9aR)-
• 7H-Furo(3,2-c)benzofuran-8-methanol, 3a,5,5a,6,8,9-hexahydro-alpha,alpha,3a,5a-tetramethyl-, acetate, (3aR-(3aalpha,5abeta,8beta,9aR*))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9883	98.83%
Caco-2	+	0.7985	79.85%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6690	66.90%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.9216	92.16%
OATP1B3 inhibitior	+	0.9055	90.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6112	61.12%
P-glycoprotein inhibitior	-	0.8328	83.28%
P-glycoprotein substrate	-	0.8229	82.29%
CYP3A4 substrate	+	0.6601	66.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.8352	83.52%
CYP2C9 inhibition	-	0.7495	74.95%
CYP2C19 inhibition	-	0.7654	76.54%
CYP2D6 inhibition	-	0.9211	92.11%
CYP1A2 inhibition	-	0.7663	76.63%
CYP2C8 inhibition	+	0.4579	45.79%
CYP inhibitory promiscuity	-	0.8327	83.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.5380	53.80%
Eye corrosion	-	0.9656	96.56%
Eye irritation	-	0.8851	88.51%
Skin irritation	-	0.7997	79.97%
Skin corrosion	-	0.9589	95.89%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4503	45.03%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6394	63.94%
skin sensitisation	-	0.7447	74.47%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.6889	68.89%
Mitochondrial toxicity	-	0.7000	70.00%
Nephrotoxicity	+	0.7099	70.99%
Acute Oral Toxicity (c)	III	0.6568	65.68%
Estrogen receptor binding	+	0.6933	69.33%
Androgen receptor binding	+	0.6377	63.77%
Thyroid receptor binding	+	0.6427	64.27%
Glucocorticoid receptor binding	+	0.5962	59.62%
Aromatase binding	+	0.7010	70.10%
PPAR gamma	-	0.6264	62.64%
Honey bee toxicity	-	0.7472	74.72%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9716	97.16%

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	96.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.02%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.99%	94.45%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	91.34%	95.71%
CHEMBL2581	P07339	Cathepsin D	87.70%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.35%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.34%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.87%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.84%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.59%	97.09%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	85.50%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.30%	89.05%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.34%	86.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.74%	97.28%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.70%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.44%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.09%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.62%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.43%	89.50%

Plants that contains it

• Nicotiana tabacum
• Nicotiana undulata
• Solanum lycopersicum
• Solanum tuberosum

Cross-Links

• PubChem: 442387
• NPASS: NPC64261
• LOTUS: LTS0200535
• wikiData: Q27107914