Orthosiphol X

Details

• Internal ID: 2f5047ad-8eb1-410b-a5e5-71e08c2b50dd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-3-acetyloxy-4-benzoyloxy-7-ethenyl-5,8a,9-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-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)O)O)O)(C)C)OC(=O)C5=CC=CC=C5
• 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)O)O)O)C([C@@H]1OC(=O)C4=CC=CC=C4)(C)C)C)OC(=O)C5=CC=CC=C5
• InChI: InChI=1S/C36H42O10/c1-7-34(5)19-23(38)27-35(6)24(18-25(39)36(27,43)32(34)42)33(3,4)28(45-30(40)21-14-10-8-11-15-21)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: ADVJBOBFOAHJLA-KXWDHPLKSA-N
• Popularity: 2 references 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

• 7-O-deacetylorthosiphol O
• CHEMBL445290

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9532	95.32%
Caco-2	-	0.8242	82.42%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6253	62.53%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.8597	85.97%
OATP1B3 inhibitior	+	0.8861	88.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9759	97.59%
P-glycoprotein inhibitior	+	0.7990	79.90%
P-glycoprotein substrate	-	0.6233	62.33%
CYP3A4 substrate	+	0.6775	67.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8702	87.02%
CYP3A4 inhibition	+	0.6630	66.30%
CYP2C9 inhibition	-	0.8643	86.43%
CYP2C19 inhibition	-	0.8646	86.46%
CYP2D6 inhibition	-	0.9228	92.28%
CYP1A2 inhibition	-	0.7859	78.59%
CYP2C8 inhibition	+	0.6070	60.70%
CYP inhibitory promiscuity	-	0.9500	95.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6166	61.66%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.6892	68.92%
Skin corrosion	-	0.9183	91.83%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8536	85.36%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5390	53.90%
skin sensitisation	-	0.7094	70.94%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7471	74.71%
Acute Oral Toxicity (c)	III	0.6386	63.86%
Estrogen receptor binding	+	0.7481	74.81%
Androgen receptor binding	+	0.6872	68.72%
Thyroid receptor binding	+	0.6279	62.79%
Glucocorticoid receptor binding	+	0.7133	71.33%
Aromatase binding	+	0.5971	59.71%
PPAR gamma	+	0.6905	69.05%
Honey bee toxicity	-	0.6788	67.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	99.27%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	98.04%	90.17%
CHEMBL240	Q12809	HERG	97.58%	89.76%
CHEMBL2581	P07339	Cathepsin D	96.17%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.07%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.30%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	93.09%	91.19%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	92.28%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.12%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.42%	95.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.81%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.22%	96.95%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.15%	94.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.16%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.47%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.22%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.76%	93.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.22%	97.21%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.87%	83.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.34%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.71%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.66%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.59%	89.00%
CHEMBL5028	O14672	ADAM10	80.32%	97.50%

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: 10054823
• NPASS: NPC158333
• ChEMBL: CHEMBL445290
• LOTUS: LTS0137788
• wikiData: Q104399605