Orthosiphol Y

Details

• Internal ID: 586b5381-67aa-4094-aa1b-8e4ef81bb39f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(4aR,4bS,5R,7R,8aR,9R,10aR)-3-acetyloxy-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-2,8-dioxo-4b,5,6,9,10,10a-hexahydrophenanthren-9-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C(=CC2(C3C1(C(=O)C(CC3O)(C)C=C)O)C)OC(=O)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@](C=C(C(=O)C2(C)C)OC(=O)C)([C@@H]3[C@@]1(C(=O)[C@@](C[C@H]3O)(C)C=C)O)C
• InChI: InChI=1S/C24H32O8/c1-8-22(6)10-14(27)18-23(7)11-15(31-12(2)25)19(28)21(4,5)16(23)9-17(32-13(3)26)24(18,30)20(22)29/h8,11,14,16-18,27,30H,1,9-10H2,2-7H3/t14-,16+,17-,18-,22+,23+,24+/m1/s1
• InChI Key: HPYXDZBUORPUPP-FBZJSPOMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₈
• Molecular Weight: 448.50 g/mol
• Exact Mass: 448.20971797 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 11-debenzoyloxyorthosiphol D
• CHEMBL523730

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9750	97.50%
Caco-2	-	0.6642	66.42%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6503	65.03%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.8667	86.67%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6054	60.54%
P-glycoprotein inhibitior	-	0.4372	43.72%
P-glycoprotein substrate	-	0.7293	72.93%
CYP3A4 substrate	+	0.6572	65.72%
CYP2C9 substrate	-	0.8074	80.74%
CYP2D6 substrate	-	0.8948	89.48%
CYP3A4 inhibition	-	0.5059	50.59%
CYP2C9 inhibition	-	0.8770	87.70%
CYP2C19 inhibition	-	0.8720	87.20%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.8832	88.32%
CYP2C8 inhibition	-	0.6191	61.91%
CYP inhibitory promiscuity	-	0.9206	92.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6197	61.97%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9310	93.10%
Skin irritation	-	0.5780	57.80%
Skin corrosion	-	0.9207	92.07%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5423	54.23%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5339	53.39%
skin sensitisation	-	0.6236	62.36%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6631	66.31%
Acute Oral Toxicity (c)	III	0.5347	53.47%
Estrogen receptor binding	+	0.7670	76.70%
Androgen receptor binding	+	0.6669	66.69%
Thyroid receptor binding	+	0.6072	60.72%
Glucocorticoid receptor binding	+	0.6866	68.66%
Aromatase binding	+	0.5645	56.45%
PPAR gamma	+	0.6292	62.92%
Honey bee toxicity	-	0.5647	56.47%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9930	99.30%

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	96.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.42%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.92%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	93.13%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.23%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.68%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.64%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.42%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.03%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.20%	100.00%
CHEMBL2581	P07339	Cathepsin D	84.94%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.84%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.28%	85.14%

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: 11144807
• NPASS: NPC198539
• ChEMBL: CHEMBL523730
• LOTUS: LTS0014813
• wikiData: Q104399607