orthosiphol J

Details

• Internal ID: b527ac63-af8c-4f04-9e08-11bfe9d8ae58
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-2,3,9-triacetyloxy-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3=O)(C)C=C)O)C)OC(=O)C4=CC=CC=C4)OC(=O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@]([C@H]([C@H]([C@H](C2(C)C)OC(=O)C)OC(=O)C)OC(=O)C3=CC=CC=C3)([C@@H]4[C@@]1(C(=O)[C@@](CC4=O)(C)C=C)O)C
• InChI: InChI=1S/C33H40O11/c1-9-31(7)16-21(37)25-32(8)22(15-23(41-17(2)34)33(25,40)29(31)39)30(5,6)26(43-19(4)36)24(42-18(3)35)27(32)44-28(38)20-13-11-10-12-14-20/h9-14,22-27,40H,1,15-16H2,2-8H3/t22-,23+,24-,25+,26+,27-,31-,32-,33-/m0/s1
• InChI Key: HOFNFIRZXJMXPW-LEWITGLZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₁
• Molecular Weight: 612.70 g/mol
• Exact Mass: 612.25706209 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.15
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• CHEMBL502992
• SCHEMBL12566525

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.7851	78.51%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7216	72.16%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.8470	84.70%
OATP1B3 inhibitior	+	0.8279	82.79%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9629	96.29%
P-glycoprotein inhibitior	+	0.8546	85.46%
P-glycoprotein substrate	-	0.6518	65.18%
CYP3A4 substrate	+	0.6751	67.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	+	0.6594	65.94%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	-	0.7975	79.75%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.6569	65.69%
CYP2C8 inhibition	+	0.6374	63.74%
CYP inhibitory promiscuity	-	0.9225	92.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5616	56.16%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8940	89.40%
Skin irritation	-	0.6378	63.78%
Skin corrosion	-	0.9285	92.85%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6444	64.44%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.6318	63.18%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6055	60.55%
Acute Oral Toxicity (c)	III	0.6264	62.64%
Estrogen receptor binding	+	0.7785	77.85%
Androgen receptor binding	+	0.6868	68.68%
Thyroid receptor binding	+	0.6450	64.50%
Glucocorticoid receptor binding	+	0.7786	77.86%
Aromatase binding	+	0.6503	65.03%
PPAR gamma	+	0.6996	69.96%
Honey bee toxicity	-	0.6267	62.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	99.30%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.25%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.95%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.29%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.92%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	90.29%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.35%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.34%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.35%	94.62%
CHEMBL5028	O14672	ADAM10	84.94%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.36%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.61%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.06%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.04%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.72%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.28%	83.00%

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: 10438744
• NPASS: NPC112216
• LOTUS: LTS0255291
• wikiData: Q105031250