(1R,4aS,6S,7R,7aS)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 0f438c23-334c-473b-ac68-7c2f50340d2b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: (1R,4aS,6S,7R,7aS)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H](C[C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O)O
• InChI: InChI=1S/C10H14O5/c1-4-7(11)2-5-6(9(12)13)3-15-10(14)8(4)5/h3-5,7-8,10-11,14H,2H2,1H3,(H,12,13)/t4-,5+,7-,8+,10+/m0/s1
• InChI Key: AFGLVJBHCHBOML-KHFPWOERSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.21 g/mol
• Exact Mass: 214.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.06
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• (1R)-1,4aalpha,5,6,7,7aalpha-Hexahydro-1alpha,6alpha-dihydroxy-7alpha-methylcyclopenta[c]pyran-4-carboxylic acid
• (1R,4aS,6S,7R,7aS)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	-	0.8464	84.64%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5308	53.08%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.7061	70.61%
OATP1B3 inhibitior	+	0.9772	97.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9863	98.63%
P-glycoprotein inhibitior	-	0.9740	97.40%
P-glycoprotein substrate	-	0.9057	90.57%
CYP3A4 substrate	-	0.5749	57.49%
CYP2C9 substrate	-	0.6126	61.26%
CYP2D6 substrate	-	0.8739	87.39%
CYP3A4 inhibition	-	0.8665	86.65%
CYP2C9 inhibition	-	0.8961	89.61%
CYP2C19 inhibition	-	0.8653	86.53%
CYP2D6 inhibition	-	0.9303	93.03%
CYP1A2 inhibition	-	0.6830	68.30%
CYP2C8 inhibition	-	0.8863	88.63%
CYP inhibitory promiscuity	-	0.8896	88.96%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9638	96.38%
Carcinogenicity (trinary)	Non-required	0.5059	50.59%
Eye corrosion	-	0.9702	97.02%
Eye irritation	-	0.6677	66.77%
Skin irritation	+	0.5808	58.08%
Skin corrosion	-	0.8650	86.50%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7699	76.99%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7579	75.79%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.7697	76.97%
Acute Oral Toxicity (c)	I	0.4096	40.96%
Estrogen receptor binding	-	0.6576	65.76%
Androgen receptor binding	-	0.6482	64.82%
Thyroid receptor binding	-	0.6183	61.83%
Glucocorticoid receptor binding	-	0.5600	56.00%
Aromatase binding	-	0.8771	87.71%
PPAR gamma	-	0.8208	82.08%
Honey bee toxicity	-	0.9512	95.12%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.7187	71.87%

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	93.07%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.04%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.53%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.29%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.75%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.60%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.66%	91.11%
CHEMBL4208	P20618	Proteasome component C5	81.49%	90.00%

Plants that contains it

• Euphorbia hirta
• Flacourtia indica
• Tripterospermum japonicum

Cross-Links

• PubChem: 25026155
• NPASS: NPC21601
• LOTUS: LTS0112872
• wikiData: Q104911167