Rawsonol

Details

• Internal ID: 7c54b4b2-656f-449a-b7a8-e69842220774
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 6-bromo-4-[[3-bromo-5-[[4-bromo-2,3-dihydroxy-6-(methoxymethyl)phenyl]methyl]-2-hydroxyphenyl]methyl]-3-[(3-bromo-4-hydroxyphenyl)methyl]benzene-1,2-diol
• SMILES (Canonical): COCC1=CC(=C(C(=C1CC2=CC(=C(C(=C2)Br)O)CC3=CC(=C(C(=C3CC4=CC(=C(C=C4)O)Br)O)O)Br)O)O)Br
• SMILES (Isomeric): COCC1=CC(=C(C(=C1CC2=CC(=C(C(=C2)Br)O)CC3=CC(=C(C(=C3CC4=CC(=C(C=C4)O)Br)O)O)Br)O)O)Br
• InChI: InChI=1S/C29H24Br4O7/c1-40-12-17-11-23(33)29(39)27(37)19(17)6-14-4-16(25(35)21(31)8-14)9-15-10-22(32)28(38)26(36)18(15)5-13-2-3-24(34)20(30)7-13/h2-4,7-8,10-11,34-39H,5-6,9,12H2,1H3
• InChI Key: KCFBHVMAGOSSRA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₄Br₄O₇
• Molecular Weight: 804.10 g/mol
• Exact Mass: 803.82145 g/mol
• Topological Polar Surface Area (TPSA): 131.00 Ų
• XlogP: 8.00
• Atomic LogP (AlogP): 7.89
• H-Bond Acceptor: 7
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• 125111-69-5
• 1,2-Benzenediol, 6-bromo-3-((3-bromo-5-((5-bromo-2-((3-bromo-4-hydroxyphenyl)methyl)-3,4-dihydroxyphenyl)methyl)-4-hydroxyphenyl)methyl)-4-(methoxymethyl)-
• 6-bromo-3-(3-bromo-4-hydroxybenzyl)-4-(3-bromo-5-(4-bromo-2,3-dihydroxy-6-(methoxymethyl)benzyl)-2-hydroxybenzyl)benzene-1,2-diol
• D0Y6DJ
• 6-bromo-4-[[3-bromo-5-[[4-bromo-2,3-dihydroxy-6-(methoxymethyl)phenyl]methyl]-2-hydroxyphenyl]methyl]-3-[(3-bromo-4-hydroxyphenyl)methyl]benzene-1,2-diol
• CHEMBL518631
• SCHEMBL1151771
• DTXSID00154658
• AKOS040747355

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9443	94.43%
Caco-2	-	0.8290	82.90%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8841	88.41%
OATP2B1 inhibitior	+	0.5779	57.79%
OATP1B1 inhibitior	+	0.8679	86.79%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9343	93.43%
P-glycoprotein inhibitior	+	0.7296	72.96%
P-glycoprotein substrate	-	0.7452	74.52%
CYP3A4 substrate	+	0.5332	53.32%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	+	0.3530	35.30%
CYP3A4 inhibition	-	0.5251	52.51%
CYP2C9 inhibition	+	0.5282	52.82%
CYP2C19 inhibition	+	0.5419	54.19%
CYP2D6 inhibition	-	0.7938	79.38%
CYP1A2 inhibition	+	0.6724	67.24%
CYP2C8 inhibition	+	0.8541	85.41%
CYP inhibitory promiscuity	-	0.5789	57.89%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7178	71.78%
Carcinogenicity (trinary)	Non-required	0.5425	54.25%
Eye corrosion	-	0.9756	97.56%
Eye irritation	-	0.8317	83.17%
Skin irritation	-	0.8119	81.19%
Skin corrosion	-	0.9566	95.66%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9572	95.72%
Micronuclear	-	0.6426	64.26%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7541	75.41%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8970	89.70%
Acute Oral Toxicity (c)	III	0.6661	66.61%
Estrogen receptor binding	+	0.9143	91.43%
Androgen receptor binding	+	0.8674	86.74%
Thyroid receptor binding	+	0.6594	65.94%
Glucocorticoid receptor binding	+	0.7550	75.50%
Aromatase binding	+	0.6533	65.33%
PPAR gamma	+	0.8110	81.10%
Honey bee toxicity	-	0.7271	72.71%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5151	51.51%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.53%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.41%	95.17%
CHEMBL2581	P07339	Cathepsin D	94.36%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.10%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.90%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.96%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.92%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.49%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.12%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	87.42%	83.57%
CHEMBL4208	P20618	Proteasome component C5	86.11%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.44%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.86%	95.89%
CHEMBL3194	P02766	Transthyretin	82.84%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.40%	96.95%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	80.24%	97.23%

Plants that contains it

• Gypothamnium pinifolium

Cross-Links

• PubChem: 180306
• NPASS: NPC7398
• ChEMBL: CHEMBL518631
• LOTUS: LTS0262332
• wikiData: Q104990516