orthosiphol I

Details

• Internal ID: fd04a3bc-dc01-4113-a9df-9fcc70ab918d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-2,3-diacetyloxy-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1C(C(C2CC(C3(C(C2(C1OC(=O)C4=CC=CC=C4)C)C(=O)CC(C3=O)(C)C=C)O)O)(C)C)OC(=O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@]2([C@@H](C[C@H]([C@@]3([C@@H]2C(=O)C[C@](C3=O)(C)C=C)O)O)C([C@@H]1OC(=O)C)(C)C)C)OC(=O)C4=CC=CC=C4
• InChI: InChI=1S/C31H38O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(35)31(23,38)27(29)37)28(4,5)24(40-17(3)33)22(39-16(2)32)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,20-25,35,38H,1,14-15H2,2-7H3/t20-,21+,22-,23+,24+,25-,29-,30-,31-/m0/s1
• InChI Key: RJWRSVTYTNSBOB-FYEHOKTBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₀
• Molecular Weight: 570.60 g/mol
• Exact Mass: 570.24649740 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• CHEMBL465222

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9808	98.08%
Caco-2	-	0.7795	77.95%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6899	68.99%
OATP2B1 inhibitior	-	0.8548	85.48%
OATP1B1 inhibitior	+	0.8459	84.59%
OATP1B3 inhibitior	+	0.8578	85.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9545	95.45%
P-glycoprotein inhibitior	+	0.7799	77.99%
P-glycoprotein substrate	-	0.6487	64.87%
CYP3A4 substrate	+	0.6762	67.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	+	0.5986	59.86%
CYP2C9 inhibition	-	0.8744	87.44%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.9330	93.30%
CYP1A2 inhibition	-	0.7153	71.53%
CYP2C8 inhibition	+	0.6119	61.19%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5910	59.10%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.9048	90.48%
Skin irritation	-	0.6323	63.23%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7234	72.34%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5447	54.47%
skin sensitisation	-	0.6694	66.94%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6150	61.50%
Acute Oral Toxicity (c)	III	0.6083	60.83%
Estrogen receptor binding	+	0.7365	73.65%
Androgen receptor binding	+	0.6950	69.50%
Thyroid receptor binding	+	0.5987	59.87%
Glucocorticoid receptor binding	+	0.7304	73.04%
Aromatase binding	+	0.6303	63.03%
PPAR gamma	+	0.6479	64.79%
Honey bee toxicity	-	0.6169	61.69%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.61%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.33%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.42%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	94.24%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.44%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.04%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	91.57%	91.19%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.23%	94.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.57%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.44%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.01%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.55%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.96%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.81%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.46%	93.00%
CHEMBL5028	O14672	ADAM10	81.03%	97.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.83%	89.34%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.39%	93.03%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.34%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.13%	94.08%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Dryopteris expansa
• Dryopteris filix-mas
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Gentiana olivieri
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus var. aristatus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10674582
• NPASS: NPC161239
• LOTUS: LTS0106500
• wikiData: Q105030775