orthosiphol T

Details

• Internal ID: be20558a-57ad-41e3-9b7f-89666c79e824
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6-acetyloxy-5-benzoyloxy-2-ethenyl-7,10,10a-trihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1C(C(C2CC(C3(C(C2(C1OC(=O)C4=CC=CC=C4)C)C(CC(C3=O)(C)C=C)OC(=O)C5=CC=CC=C5)O)O)(C)C)O
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@@H]([C@]2([C@@H](C[C@H]([C@@]3([C@@H]2[C@@H](C[C@](C3=O)(C)C=C)OC(=O)C4=CC=CC=C4)O)O)C([C@@H]1O)(C)C)C)OC(=O)C5=CC=CC=C5
• InChI: InChI=1S/C36H42O10/c1-7-34(5)19-23(45-30(40)21-14-10-8-11-15-21)27-35(6)24(18-25(38)36(27,43)32(34)42)33(3,4)28(39)26(44-20(2)37)29(35)46-31(41)22-16-12-9-13-17-22/h7-17,23-29,38-39,43H,1,18-19H2,2-6H3/t23-,24+,25-,26+,27-,28-,29+,34+,35+,36+/m1/s1
• InChI Key: JSXWPPDJFPNHQS-KXWDHPLKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₂O₁₀
• Molecular Weight: 634.70 g/mol
• Exact Mass: 634.27779753 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• CHEMBL510297

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9776	97.76%
Caco-2	-	0.8180	81.80%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6899	68.99%
OATP2B1 inhibitior	-	0.8568	85.68%
OATP1B1 inhibitior	+	0.8739	87.39%
OATP1B3 inhibitior	+	0.8634	86.34%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9743	97.43%
P-glycoprotein inhibitior	+	0.8081	80.81%
P-glycoprotein substrate	-	0.6063	60.63%
CYP3A4 substrate	+	0.6651	66.51%
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	+	0.6187	61.87%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9443	94.43%
Carcinogenicity (trinary)	Non-required	0.5910	59.10%
Eye corrosion	-	0.9933	99.33%
Eye irritation	-	0.9099	90.99%
Skin irritation	-	0.6857	68.57%
Skin corrosion	-	0.9218	92.18%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8053	80.53%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.6931	69.31%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4820	48.20%
Acute Oral Toxicity (c)	III	0.6083	60.83%
Estrogen receptor binding	+	0.7443	74.43%
Androgen receptor binding	+	0.6834	68.34%
Thyroid receptor binding	+	0.6323	63.23%
Glucocorticoid receptor binding	+	0.7232	72.32%
Aromatase binding	+	0.6126	61.26%
PPAR gamma	+	0.6781	67.81%
Honey bee toxicity	-	0.6872	68.72%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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
CHEMBL221	P23219	Cyclooxygenase-1	98.73%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	97.91%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.93%	98.95%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.22%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.83%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.19%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	92.14%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.63%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.57%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.61%	99.23%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	86.91%	97.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.62%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.14%	82.69%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.00%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.87%	93.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.76%	96.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.61%	94.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.54%	91.07%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.53%	83.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	82.45%	97.53%
CHEMBL4208	P20618	Proteasome component C5	80.16%	90.00%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 11082749
• NPASS: NPC304876
• ChEMBL: CHEMBL510297
• LOTUS: LTS0212566
• wikiData: Q104399601