(2S)-2-[(3Z)-4,8-dimethylnona-3,7-dienyl]-8-hydroxy-3-methylidene-4H-chromene-6-carboxylic acid

Details

• Internal ID: 17eace82-d4d2-409a-b5ac-32524816afd7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (2S)-2-[(3Z)-4,8-dimethylnona-3,7-dienyl]-8-hydroxy-3-methylidene-4H-chromene-6-carboxylic acid
• SMILES (Canonical): CC(=CCCC(=CCCC1C(=C)CC2=C(O1)C(=CC(=C2)C(=O)O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C\CC[C@H]1C(=C)CC2=C(O1)C(=CC(=C2)C(=O)O)O)/C)C
• InChI: InChI=1S/C22H28O4/c1-14(2)7-5-8-15(3)9-6-10-20-16(4)11-17-12-18(22(24)25)13-19(23)21(17)26-20/h7,9,12-13,20,23H,4-6,8,10-11H2,1-3H3,(H,24,25)/b15-9-/t20-/m0/s1
• InChI Key: XBOKPWYVDNVFMX-WKSDAVQWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₄
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.19875937 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 5.42
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9594	95.94%
Caco-2	-	0.5647	56.47%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7006	70.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8691	86.91%
OATP1B3 inhibitior	+	0.8897	88.97%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6727	67.27%
P-glycoprotein inhibitior	-	0.4301	43.01%
P-glycoprotein substrate	-	0.7337	73.37%
CYP3A4 substrate	+	0.5536	55.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.6417	64.17%
CYP2C9 inhibition	-	0.6700	67.00%
CYP2C19 inhibition	+	0.6186	61.86%
CYP2D6 inhibition	-	0.7827	78.27%
CYP1A2 inhibition	+	0.7677	76.77%
CYP2C8 inhibition	-	0.7122	71.22%
CYP inhibitory promiscuity	-	0.6067	60.67%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7477	74.77%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.7574	75.74%
Skin irritation	-	0.6659	66.59%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.5908	59.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.5224	52.24%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7149	71.49%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6296	62.96%
Acute Oral Toxicity (c)	III	0.5614	56.14%
Estrogen receptor binding	+	0.5640	56.40%
Androgen receptor binding	+	0.5750	57.50%
Thyroid receptor binding	+	0.6160	61.60%
Glucocorticoid receptor binding	+	0.5878	58.78%
Aromatase binding	+	0.6990	69.90%
PPAR gamma	+	0.8303	83.03%
Honey bee toxicity	-	0.8546	85.46%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
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	95.74%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	93.66%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.46%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	88.29%	91.19%
CHEMBL2581	P07339	Cathepsin D	87.26%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.22%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.28%	89.34%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.28%	95.56%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	85.10%	92.08%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.29%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.29%	89.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.18%	97.21%

Plants that contains it

• Piper auritum

Cross-Links

• PubChem: 163194624
• LOTUS: LTS0187012
• wikiData: Q105324610