Hawaiienol B

Details

• Internal ID: 979e4129-64d2-431b-937c-36b5a8ea567e
• Taxonomy: Benzenoids > Phenol ethers > Anisoles
• IUPAC Name: (1S,3R,4R,5R,6S)-3,5,6-trihydroxy-1-methoxy-3,6-bis(4-methoxyphenyl)-7-oxabicyclo[2.2.1]heptan-2-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2(C(C3C(C(=O)C2(O3)OC)(C4=CC=C(C=C4)OC)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)[C@@]2([C@@H]([C@@H]3[C@@](C(=O)[C@]2(O3)OC)(C4=CC=C(C=C4)OC)O)O)O
• InChI: InChI=1S/C21H22O8/c1-26-14-8-4-12(5-9-14)19(24)17-16(22)20(25,21(28-3,29-17)18(19)23)13-6-10-15(27-2)11-7-13/h4-11,16-17,22,24-25H,1-3H3/t16-,17-,19-,20+,21-/m1/s1
• InChI Key: JXZNGXLFMMDPFT-YCXYWVQESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₈
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.13146766 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8789	87.89%
Caco-2	-	0.5808	58.08%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6891	68.91%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9199	91.99%
OATP1B3 inhibitior	+	0.8149	81.49%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8044	80.44%
P-glycoprotein inhibitior	+	0.5793	57.93%
P-glycoprotein substrate	-	0.8446	84.46%
CYP3A4 substrate	+	0.5780	57.80%
CYP2C9 substrate	-	0.8015	80.15%
CYP2D6 substrate	-	0.8091	80.91%
CYP3A4 inhibition	+	0.5825	58.25%
CYP2C9 inhibition	-	0.8736	87.36%
CYP2C19 inhibition	-	0.8388	83.88%
CYP2D6 inhibition	-	0.9161	91.61%
CYP1A2 inhibition	-	0.9298	92.98%
CYP2C8 inhibition	-	0.8641	86.41%
CYP inhibitory promiscuity	-	0.5432	54.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.3534	35.34%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.7659	76.59%
Skin irritation	-	0.7902	79.02%
Skin corrosion	-	0.9525	95.25%
Ames mutagenesis	+	0.6030	60.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.5205	52.05%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.5738	57.38%
skin sensitisation	-	0.9019	90.19%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4726	47.26%
Acute Oral Toxicity (c)	III	0.5935	59.35%
Estrogen receptor binding	+	0.8201	82.01%
Androgen receptor binding	+	0.8224	82.24%
Thyroid receptor binding	+	0.6683	66.83%
Glucocorticoid receptor binding	+	0.6431	64.31%
Aromatase binding	+	0.7540	75.40%
PPAR gamma	+	0.6136	61.36%
Honey bee toxicity	-	0.9240	92.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9631	96.31%

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	96.19%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.99%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.23%	94.00%
CHEMBL2581	P07339	Cathepsin D	86.42%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.83%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.54%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.63%	95.89%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.64%	93.99%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.89%	92.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.23%	94.08%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139590078
• LOTUS: LTS0158280
• wikiData: Q105136874