(Z)-2-[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]ethyl]-4-hydroxybut-2-enoic acid

Details

• Internal ID: 758f0cbc-14d4-49b5-ad14-e15b69073621
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (Z)-2-[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]ethyl]-4-hydroxybut-2-enoic acid
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CCC(=CCO)C(=O)O)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CC/C(=C/CO)/C(=O)O)(C)CO)O
• InChI: InChI=1S/C20H32O5/c1-13-4-7-16-19(2,10-8-17(23)20(16,3)12-22)15(13)6-5-14(9-11-21)18(24)25/h9,15-17,21-23H,1,4-8,10-12H2,2-3H3,(H,24,25)/b14-9-/t15-,16+,17-,19+,20+/m1/s1
• InChI Key: SSCXIOHKJCIXKI-KWKBPYNPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9580	95.80%
Caco-2	+	0.6463	64.63%
Blood Brain Barrier	+	0.6027	60.27%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7317	73.17%
OATP2B1 inhibitior	-	0.8655	86.55%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.8104	81.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5608	56.08%
BSEP inhibitior	-	0.4717	47.17%
P-glycoprotein inhibitior	-	0.7881	78.81%
P-glycoprotein substrate	-	0.7911	79.11%
CYP3A4 substrate	+	0.6421	64.21%
CYP2C9 substrate	-	0.8058	80.58%
CYP2D6 substrate	-	0.9065	90.65%
CYP3A4 inhibition	-	0.8514	85.14%
CYP2C9 inhibition	-	0.8890	88.90%
CYP2C19 inhibition	-	0.8852	88.52%
CYP2D6 inhibition	-	0.9244	92.44%
CYP1A2 inhibition	-	0.8936	89.36%
CYP2C8 inhibition	-	0.6332	63.32%
CYP inhibitory promiscuity	-	0.9302	93.02%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6932	69.32%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8348	83.48%
Skin irritation	-	0.5952	59.52%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4093	40.93%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.7726	77.26%
skin sensitisation	-	0.8436	84.36%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.6996	69.96%
Acute Oral Toxicity (c)	III	0.6637	66.37%
Estrogen receptor binding	+	0.6555	65.55%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.7402	74.02%
Glucocorticoid receptor binding	+	0.7985	79.85%
Aromatase binding	+	0.6798	67.98%
PPAR gamma	+	0.5550	55.50%
Honey bee toxicity	-	0.8781	87.81%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9898	98.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	92.40%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.52%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.64%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.10%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.69%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.46%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.57%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.04%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.69%	100.00%
CHEMBL5028	O14672	ADAM10	80.36%	97.50%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44577209
• NPASS: NPC104560
• ChEMBL: CHEMBL511768
• LOTUS: LTS0046372
• wikiData: Q105259598