Orthosiphol K

Details

• Internal ID: 64cb4257-1182-4fd7-98fe-91a449ef89ac
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-10-acetyloxy-5-benzoyloxy-2-ethenyl-6,7,10a-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)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(C)C=C)O)C)OC(=O)C5=CC=CC=C5)O)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3OC(=O)C4=CC=CC=C4)(C)C=C)O)([C@H]([C@H]([C@H](C2(C)C)O)O)OC(=O)C5=CC=CC=C5)C
• 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(44-20(2)37)36(27,43)32(34)42)33(3,4)28(39)26(38)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: XZOHHNDEJRVJSL-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

• CHEMBL474466

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9710	97.10%
Caco-2	-	0.8101	81.01%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7294	72.94%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8882	88.82%
OATP1B3 inhibitior	+	0.8402	84.02%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9499	94.99%
P-glycoprotein inhibitior	+	0.8051	80.51%
P-glycoprotein substrate	-	0.6056	60.56%
CYP3A4 substrate	+	0.6718	67.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	+	0.5401	54.01%
CYP2C9 inhibition	-	0.8464	84.64%
CYP2C19 inhibition	-	0.8405	84.05%
CYP2D6 inhibition	-	0.9329	93.29%
CYP1A2 inhibition	-	0.6552	65.52%
CYP2C8 inhibition	+	0.6972	69.72%
CYP inhibitory promiscuity	-	0.9385	93.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5733	57.33%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.9059	90.59%
Skin irritation	-	0.7103	71.03%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7576	75.76%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.6966	69.66%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6449	64.49%
Acute Oral Toxicity (c)	III	0.6312	63.12%
Estrogen receptor binding	+	0.7250	72.50%
Androgen receptor binding	+	0.6624	66.24%
Thyroid receptor binding	+	0.6163	61.63%
Glucocorticoid receptor binding	+	0.7445	74.45%
Aromatase binding	+	0.6023	60.23%
PPAR gamma	+	0.6829	68.29%
Honey bee toxicity	-	0.6859	68.59%
Biodegradation	-	0.8500	85.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.79%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	95.73%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.08%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.84%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.76%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	91.29%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.12%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	89.94%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.67%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.51%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.90%	94.08%
CHEMBL2535	P11166	Glucose transporter	86.13%	98.75%
CHEMBL240	Q12809	HERG	85.36%	89.76%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.30%	95.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.54%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.14%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.77%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.53%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.45%	82.69%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.32%	85.14%
CHEMBL5028	O14672	ADAM10	82.30%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.41%	91.07%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.67%	97.53%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.62%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.33%	95.89%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Catoferia spicata
• 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: 10054824
• NPASS: NPC249471
• LOTUS: LTS0067212
• wikiData: Q104399595