(1R,2R,4S,9S,10S,13S,15S,16R)-2,15,16-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-7-en-6-one

Details

• Internal ID: 9cc801c2-ff38-4315-80d1-8fdfd8234b0d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1R,2R,4S,9S,10S,13S,15S,16R)-2,15,16-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-7-en-6-one
• SMILES (Canonical): CC1(C2CC(C34C(C2(C=CC1=O)C)CCC(C3O)C(=C)C4O)O)C
• SMILES (Isomeric): C[C@@]12C=CC(=O)C([C@H]1C[C@H]([C@]34[C@H]2CC[C@H]([C@H]3O)C(=C)[C@@H]4O)O)(C)C
• InChI: InChI=1S/C20H28O4/c1-10-11-5-6-12-19(4)8-7-14(21)18(2,3)13(19)9-15(22)20(12,16(10)23)17(11)24/h7-8,11-13,15-17,22-24H,1,5-6,9H2,2-4H3/t11-,12-,13+,15+,16-,17+,19-,20-/m0/s1
• InChI Key: CLQZWQHSQOTGBA-OHMGPRHDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.84
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	-	0.5877	58.77%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5697	56.97%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8682	86.82%
OATP1B3 inhibitior	-	0.2421	24.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.8408	84.08%
P-glycoprotein inhibitior	-	0.8144	81.44%
P-glycoprotein substrate	-	0.7494	74.94%
CYP3A4 substrate	+	0.6214	62.14%
CYP2C9 substrate	-	0.8160	81.60%
CYP2D6 substrate	-	0.8551	85.51%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.7438	74.38%
CYP2C19 inhibition	-	0.7885	78.85%
CYP2D6 inhibition	-	0.9259	92.59%
CYP1A2 inhibition	-	0.8166	81.66%
CYP2C8 inhibition	-	0.7163	71.63%
CYP inhibitory promiscuity	-	0.8259	82.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6203	62.03%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9573	95.73%
Skin irritation	+	0.5323	53.23%
Skin corrosion	-	0.9208	92.08%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4941	49.41%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.6291	62.91%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7005	70.05%
Acute Oral Toxicity (c)	I	0.5726	57.26%
Estrogen receptor binding	+	0.7739	77.39%
Androgen receptor binding	+	0.5267	52.67%
Thyroid receptor binding	+	0.6689	66.89%
Glucocorticoid receptor binding	+	0.7286	72.86%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9803	98.03%

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	92.72%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.89%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	87.71%	90.17%
CHEMBL1937	Q92769	Histone deacetylase 2	87.63%	94.75%
CHEMBL2581	P07339	Cathepsin D	87.46%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.41%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.68%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.67%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.00%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.54%	97.25%

Plants that contains it

• Isodon liangshanicus

Cross-Links

• PubChem: 162898137
• LOTUS: LTS0169490
• wikiData: Q104963838