Deoxyfrenolicin

Details

• Internal ID: e396ff37-fd02-451e-bb4b-dae097f6e410
• Taxonomy: Phenylpropanoids and polyketides > Isochromanequinones > Benzoisochromanequinones
• IUPAC Name: 2-[(1R,3S)-9-hydroxy-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
• SMILES (Canonical): CCCC1C2=C(CC(O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O
• SMILES (Isomeric): CCC[C@@H]1C2=C(C[C@H](O1)CC(=O)O)C(=O)C3=C(C2=O)C(=CC=C3)O
• InChI: InChI=1S/C18H18O6/c1-2-4-13-16-11(7-9(24-13)8-14(20)21)17(22)10-5-3-6-12(19)15(10)18(16)23/h3,5-6,9,13,19H,2,4,7-8H2,1H3,(H,20,21)/t9-,13+/m0/s1
• InChI Key: XWXZEYLPRXYHQC-TVQRCGJNSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.30 g/mol
• Exact Mass: 330.11033829 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• 10023-11-7
• L0RG5J840S
• 2-[(1R,3S)-9-hydroxy-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
• DTXSID90143036
• 2-((1R,3S)-9-hydroxy-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo(g)isochromen-3-yl)acetic acid
• RefChem:131951
• DTXCID4065527
• 1H-Naphtho[2,3-c]pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-, (1R,3S)-
• UNII-L0RG5J840S
• CHEMBL444165
• orb3023118
• BDBM29510
• HY-N14134
• TN9939
• 1H-Naphtho[2,3-c]pyran-3-aceticacid, 3,4,5,10-tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-, (1R,3S)-
• Q27282560
• [(1R,3S)-9-Hydroxy-5,10-dioxo-1-propyl-3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid
• 1H-Naphtho(2,3-c)pyran-3-acetic acid, 3,4,5,10-tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-, (1R-trans)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9745	97.45%
Caco-2	+	0.6164	61.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7361	73.61%
OATP2B1 inhibitior	-	0.5846	58.46%
OATP1B1 inhibitior	+	0.8950	89.50%
OATP1B3 inhibitior	+	0.9713	97.13%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7877	78.77%
P-glycoprotein inhibitior	-	0.7998	79.98%
P-glycoprotein substrate	-	0.5801	58.01%
CYP3A4 substrate	+	0.5060	50.60%
CYP2C9 substrate	-	0.5851	58.51%
CYP2D6 substrate	-	0.8913	89.13%
CYP3A4 inhibition	+	0.6777	67.77%
CYP2C9 inhibition	-	0.6561	65.61%
CYP2C19 inhibition	-	0.5784	57.84%
CYP2D6 inhibition	-	0.7605	76.05%
CYP1A2 inhibition	-	0.5535	55.35%
CYP2C8 inhibition	-	0.6628	66.28%
CYP inhibitory promiscuity	-	0.6697	66.97%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.6831	68.31%
Skin irritation	-	0.6909	69.09%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6466	64.66%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.6605	66.05%
skin sensitisation	-	0.7415	74.15%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6457	64.57%
Acute Oral Toxicity (c)	III	0.3465	34.65%
Estrogen receptor binding	+	0.5946	59.46%
Androgen receptor binding	+	0.7176	71.76%
Thyroid receptor binding	-	0.6513	65.13%
Glucocorticoid receptor binding	+	0.6862	68.62%
Aromatase binding	-	0.7133	71.33%
PPAR gamma	+	0.6538	65.38%
Honey bee toxicity	-	0.9642	96.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9778	97.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.66%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.09%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.07%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.25%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	93.01%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.78%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.89%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.75%	93.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.89%	96.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.65%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.13%	89.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 3084051
• LOTUS: LTS0126388
• wikiData: Q27282560