3-O-Acetylpinobanksin

Details

• Internal ID: 45acbeda-b090-42ca-86d3-d63be51d0cd7
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: [(2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H](OC2=CC(=CC(=C2C1=O)O)O)C3=CC=CC=C3
• InChI: InChI=1S/C17H14O6/c1-9(18)22-17-15(21)14-12(20)7-11(19)8-13(14)23-16(17)10-5-3-2-4-6-10/h2-8,16-17,19-20H,1H3/t16-,17+/m1/s1
• InChI Key: BJYHZSNSMVEQEH-SJORKVTESA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₆
• Molecular Weight: 314.29 g/mol
• Exact Mass: 314.07903816 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 52117-69-8
• Pinobanksin 3-acetate
• Pinobanksin-3-acetate
• Pinobanksin 3-O-acetate
• Pinobanksin acetate
• [(2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] acetate
• CHEBI:80490
• (2R-trans)-3-(Acetyloxy)-2,3-dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzo pyran-4-one
• 4H-1-Benzopyran-4-one, 3-(acetyloxy)-2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2R-trans)-
• (2R,3R)-5,7-Dihydroxy-4-oxo-2-phenylchroman-3-yl acetate
• (2R-trans)-3-(Acetyloxy)-2,3-dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one
• 3-Acetylpinobanksin
• SCHEMBL2438615
• 3-O-Acetylpinobanksin; Pinobanksin 3-O-acetate; Pinobanksin 3-acetate
• CHEMBL1094265
• (2R,3R)-pinobanksin 3-acetate
• DTXSID80200127
• HY-N1854
• AKOS030553614
• MS-24604
• CS-0017723
• E87108
• Q27149541
• [(2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-chroman-3-yl] acetate
• 4H-1-Benzopyran-4-one,3-(acetyloxy)-2,3-dihydro-5,7-dihydroxy-2-phenyl-,(2R,3R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8836	88.36%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7004	70.04%
OATP2B1 inhibitior	-	0.8659	86.59%
OATP1B1 inhibitior	+	0.8941	89.41%
OATP1B3 inhibitior	+	0.8411	84.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5530	55.30%
P-glycoprotein inhibitior	-	0.6448	64.48%
P-glycoprotein substrate	-	0.9315	93.15%
CYP3A4 substrate	+	0.5178	51.78%
CYP2C9 substrate	+	0.6023	60.23%
CYP2D6 substrate	-	0.8604	86.04%
CYP3A4 inhibition	-	0.8163	81.63%
CYP2C9 inhibition	+	0.5998	59.98%
CYP2C19 inhibition	-	0.7940	79.40%
CYP2D6 inhibition	-	0.9477	94.77%
CYP1A2 inhibition	-	0.5973	59.73%
CYP2C8 inhibition	+	0.5357	53.57%
CYP inhibitory promiscuity	-	0.5615	56.15%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6321	63.21%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.6332	63.32%
Skin irritation	-	0.6434	64.34%
Skin corrosion	-	0.9282	92.82%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5455	54.55%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.9351	93.51%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.7202	72.02%
Acute Oral Toxicity (c)	III	0.6473	64.73%
Estrogen receptor binding	+	0.7642	76.42%
Androgen receptor binding	+	0.7166	71.66%
Thyroid receptor binding	-	0.6605	66.05%
Glucocorticoid receptor binding	+	0.6291	62.91%
Aromatase binding	-	0.6303	63.03%
PPAR gamma	+	0.6360	63.60%
Honey bee toxicity	-	0.8692	86.92%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9641	96.41%

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	98.87%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.79%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.40%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.18%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.11%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.72%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.27%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	90.79%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.22%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	84.32%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.33%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.26%	99.17%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.86%	94.08%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.18%	99.15%

Plants that contains it

• Anodendron affine
• Cedrela salvadorensis
• Galium latoramosum
• Garcinia gummi-gutta
• Greyia flanaganii
• Hertia cheirifolia
• Licaria chrysophylla
• Lychnophora pohlii
• Lychnophora staavioides
• Ormosia hosiei
• Ornithoglossum viride
• Ozothamnus stirlingii
• Petasites radiatus
• Pinus armandii
• Populus cathayana
• Populus deltoides
• Populus suaveolens
• Populus yunnanensis
• Schizanthus tricolor
• Sphaeranthus confertifolius
• Xerochrysum viscosum

Cross-Links

• PubChem: 148556
• NPASS: NPC153724
• LOTUS: LTS0086670
• wikiData: Q27149541