Farrerol

Details

• Internal ID: 909eaaf9-0076-4553-84a6-8128c5913b62
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C(=O)CC(O2)C3=CC=C(C=C3)O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C)O
• InChI: InChI=1S/C17H16O5/c1-8-15(20)9(2)17-14(16(8)21)12(19)7-13(22-17)10-3-5-11(18)6-4-10/h3-6,13,18,20-21H,7H2,1-2H3/t13-/m0/s1
• InChI Key: DYHOLQACRGJEHX-ZDUSSCGKSA-N
• Popularity: 52 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.13
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• CHEBI:67897
• CHEMBL507611
• (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydrochromen-4-one
• (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-4-benzopyrone
• (2~{S})-2-(4-hydroxyphenyl)-6,8-dimethyl-5,7-bis(oxidanyl)-2,3-dihydrochromen-4-one
• AC1L9CQK
• 6,8-DIMETHYL-4',5,7-TRIHYDROXYFLAVANONE
• Farrerol, >=98% (HPLC)
• DTXSID40947026
• HY-N0344
• s9552
• ZINC04098306
• AKOS015896732
• AC-34143
• CS-0008902
• C09734
• Q27104948
• (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethylchroman-4-one
• (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-chroman-4-one
• 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethyl-2,3-dihydro-4H-1-benzopyran-4-one
• JXY

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9385	93.85%
Caco-2	+	0.7245	72.45%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8009	80.09%
OATP2B1 inhibitior	-	0.5912	59.12%
OATP1B1 inhibitior	+	0.7937	79.37%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7659	76.59%
P-glycoprotein inhibitior	-	0.8511	85.11%
P-glycoprotein substrate	-	0.9113	91.13%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.7974	79.74%
CYP2D6 substrate	-	0.7747	77.47%
CYP3A4 inhibition	+	0.8649	86.49%
CYP2C9 inhibition	+	0.8644	86.44%
CYP2C19 inhibition	+	0.8207	82.07%
CYP2D6 inhibition	-	0.7188	71.88%
CYP1A2 inhibition	+	0.9147	91.47%
CYP2C8 inhibition	-	0.6602	66.02%
CYP inhibitory promiscuity	+	0.7428	74.28%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6527	65.27%
Eye corrosion	-	0.9920	99.20%
Eye irritation	+	0.7797	77.97%
Skin irritation	-	0.6422	64.22%
Skin corrosion	-	0.9271	92.71%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5673	56.73%
Micronuclear	+	0.8559	85.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8933	89.33%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6529	65.29%
Acute Oral Toxicity (c)	III	0.3665	36.65%
Estrogen receptor binding	+	0.8024	80.24%
Androgen receptor binding	+	0.6507	65.07%
Thyroid receptor binding	+	0.6648	66.48%
Glucocorticoid receptor binding	+	0.8212	82.12%
Aromatase binding	-	0.4847	48.47%
PPAR gamma	+	0.7127	71.27%
Honey bee toxicity	-	0.9200	92.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8897	88.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.85%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.53%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.35%	99.23%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	86.64%	85.11%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.56%	90.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.09%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.69%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.09%	96.09%

Plants that contains it

• Asparagus officinalis
• Astragalus dissectus
• Cheniella glauca
• Hildegardia barteri
• Justicia adhatoda
• Ocotea minarum
• Pancratium maritimum
• Rhododendron dauricum
• Rhododendron farrerae
• Rhododendron ferrugineum
• Rhododendron spinuliferum
• Wikstroemia canescens

Cross-Links

• PubChem: 442396
• NPASS: NPC167624
• LOTUS: LTS0016330
• wikiData: Q27104948