Orthosiphol Z

Details

• Internal ID: 9969ec1b-087c-4c3c-a1b2-21f4d833c723
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(4aR,4bR,7R,8aR,9R,10aR)-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-2,5,8-trioxo-6,9,10,10a-tetrahydro-4bH-phenanthren-3-yl] acetate
• SMILES (Canonical): CC(=O)OC1=CC2(C(CC(C3(C2C(=O)CC(C3=O)(C)C=C)O)O)C(C1=O)(C)C)C
• SMILES (Isomeric): CC(=O)OC1=C[C@]2([C@@H](C[C@H]([C@@]3([C@@H]2C(=O)C[C@](C3=O)(C)C=C)O)O)C(C1=O)(C)C)C
• InChI: InChI=1S/C22H28O7/c1-7-20(5)9-12(24)16-21(6)10-13(29-11(2)23)17(26)19(3,4)14(21)8-15(25)22(16,28)18(20)27/h7,10,14-16,25,28H,1,8-9H2,2-6H3/t14-,15+,16+,20-,21-,22-/m0/s1
• InChI Key: BPJCFHARVKYGQI-XFRCGTSASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.18350323 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.51
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9807	98.07%
Caco-2	-	0.6191	61.91%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7212	72.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8792	87.92%
OATP1B3 inhibitior	+	0.8594	85.94%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5612	56.12%
P-glycoprotein inhibitior	-	0.6800	68.00%
P-glycoprotein substrate	-	0.7524	75.24%
CYP3A4 substrate	+	0.6355	63.55%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8919	89.19%
CYP3A4 inhibition	-	0.5642	56.42%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.8509	85.09%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.8208	82.08%
CYP2C8 inhibition	-	0.6917	69.17%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.5992	59.92%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9450	94.50%
Skin irritation	-	0.5812	58.12%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3887	38.87%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5360	53.60%
skin sensitisation	-	0.6238	62.38%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.7229	72.29%
Acute Oral Toxicity (c)	III	0.5385	53.85%
Estrogen receptor binding	+	0.6327	63.27%
Androgen receptor binding	+	0.6914	69.14%
Thyroid receptor binding	+	0.5511	55.11%
Glucocorticoid receptor binding	+	0.6482	64.82%
Aromatase binding	+	0.6031	60.31%
PPAR gamma	+	0.5566	55.66%
Honey bee toxicity	-	0.5899	58.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9951	99.51%

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	95.86%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.23%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.27%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	91.49%	91.19%
CHEMBL1951	P21397	Monoamine oxidase A	90.79%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.17%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.53%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.22%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.11%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.50%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.21%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.78%	91.24%

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: 11090752
• NPASS: NPC82847
• LOTUS: LTS0172232
• wikiData: Q104942447