12S-hydroxyandrographolide

Details

• Internal ID: ff81f7d0-7329-4241-af37-b9e5ed9640ab
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: (4S)-3-[(1R)-2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-4-hydroxyoxolan-2-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CC(C3C(COC3=O)O)O)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2C[C@H](C3[C@@H](COC3=O)O)O)(C)CO)O
• InChI: InChI=1S/C20H32O6/c1-11-4-5-15-19(2,7-6-16(24)20(15,3)10-21)12(11)8-13(22)17-14(23)9-26-18(17)25/h12-17,21-24H,1,4-10H2,2-3H3/t12-,13-,14-,15+,16-,17?,19+,20+/m1/s1
• InChI Key: NLYQWYLWLQBMPF-BRQCOXQQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₆
• Molecular Weight: 368.50 g/mol
• Exact Mass: 368.21988874 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.01
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• CHEMBL518455
• 869593-50-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9401	94.01%
Caco-2	-	0.5600	56.00%
Blood Brain Barrier	+	0.6777	67.77%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7024	70.24%
OATP2B1 inhibitior	-	0.8658	86.58%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5338	53.38%
BSEP inhibitior	+	0.5883	58.83%
P-glycoprotein inhibitior	-	0.7522	75.22%
P-glycoprotein substrate	-	0.7122	71.22%
CYP3A4 substrate	+	0.6670	66.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8062	80.62%
CYP inhibitory promiscuity	-	0.8964	89.64%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5856	58.56%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9019	90.19%
Skin irritation	+	0.5319	53.19%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5849	58.49%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7351	73.51%
skin sensitisation	-	0.9081	90.81%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.5328	53.28%
Estrogen receptor binding	+	0.8225	82.25%
Androgen receptor binding	+	0.7367	73.67%
Thyroid receptor binding	+	0.7184	71.84%
Glucocorticoid receptor binding	+	0.8015	80.15%
Aromatase binding	+	0.6983	69.83%
PPAR gamma	-	0.5176	51.76%
Honey bee toxicity	-	0.8017	80.17%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
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
CHEMBL4040	P28482	MAP kinase ERK2	96.15%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.97%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.59%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.46%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.37%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.95%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.64%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.76%	97.25%
CHEMBL2581	P07339	Cathepsin D	85.38%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.83%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.63%	86.33%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	81.58%	89.34%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.54%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.60%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.01%	85.14%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44575259
• NPASS: NPC157910