2-[(1R,3S)-3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl]acetic acid

Details

• Internal ID: a26caa25-c41f-415f-809d-addc01b9b99d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: 2-[(1R,3S)-3-hydroxy-2,2,3-trimethyl-4-oxocyclopentyl]acetic acid
• SMILES (Canonical): CC1(C(CC(=O)C1(C)O)CC(=O)O)C
• SMILES (Isomeric): C[C@]1(C(=O)C[C@@H](C1(C)C)CC(=O)O)O
• InChI: InChI=1S/C10H16O4/c1-9(2)6(5-8(12)13)4-7(11)10(9,3)14/h6,14H,4-5H2,1-3H3,(H,12,13)/t6-,10-/m1/s1
• InChI Key: OBFKTGKIOIHLFK-LHLIQPBNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23 g/mol
• Exact Mass: 200.10485899 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.83
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9223	92.23%
Caco-2	+	0.6247	62.47%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7907	79.07%
OATP2B1 inhibitior	-	0.8437	84.37%
OATP1B1 inhibitior	+	0.9326	93.26%
OATP1B3 inhibitior	+	0.9450	94.50%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9331	93.31%
P-glycoprotein inhibitior	-	0.9755	97.55%
P-glycoprotein substrate	-	0.9152	91.52%
CYP3A4 substrate	-	0.6151	61.51%
CYP2C9 substrate	-	0.6211	62.11%
CYP2D6 substrate	-	0.8870	88.70%
CYP3A4 inhibition	-	0.9346	93.46%
CYP2C9 inhibition	-	0.9466	94.66%
CYP2C19 inhibition	-	0.9490	94.90%
CYP2D6 inhibition	-	0.9585	95.85%
CYP1A2 inhibition	-	0.9646	96.46%
CYP2C8 inhibition	-	0.9748	97.48%
CYP inhibitory promiscuity	-	0.9830	98.30%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7313	73.13%
Eye corrosion	-	0.9418	94.18%
Eye irritation	+	0.5975	59.75%
Skin irritation	-	0.5797	57.97%
Skin corrosion	-	0.8221	82.21%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7406	74.06%
Micronuclear	-	0.7441	74.41%
Hepatotoxicity	+	0.6110	61.10%
skin sensitisation	-	0.5808	58.08%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7503	75.03%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5714	57.14%
Acute Oral Toxicity (c)	III	0.6000	60.00%
Estrogen receptor binding	-	0.7188	71.88%
Androgen receptor binding	-	0.6216	62.16%
Thyroid receptor binding	-	0.8462	84.62%
Glucocorticoid receptor binding	-	0.7197	71.97%
Aromatase binding	-	0.7007	70.07%
PPAR gamma	-	0.8645	86.45%
Honey bee toxicity	-	0.9727	97.27%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.7843	78.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.27%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.74%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.90%	85.14%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	85.30%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.55%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.11%	95.56%

Plants that contains it

• Curcuma longa
• Salvia officinalis

Cross-Links

• PubChem: 163056253
• LOTUS: LTS0157764
• wikiData: Q105027333