Orthosiphol W

Details

• Internal ID: 318989ba-073f-4a72-a21b-013f49a9e7db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-3,9-diacetyloxy-7-ethenyl-2,5,8a-trihydroxy-1,1,4a,7-tetramethyl-8-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3O)(C)C=C)O)C)OC(=O)C4=CC=CC=C4)OC(=O)C)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]3O)(C)C=C)O)([C@H]([C@H]([C@H](C2(C)C)O)OC(=O)C)OC(=O)C4=CC=CC=C4)C
• InChI: InChI=1S/C31H40O10/c1-8-29(6)15-19(34)23-30(7)20(14-21(39-16(2)32)31(23,38)27(29)37)28(4,5)24(35)22(40-17(3)33)25(30)41-26(36)18-12-10-9-11-13-18/h8-13,19-25,34-35,38H,1,14-15H2,2-7H3/t19-,20+,21-,22+,23-,24-,25+,29+,30+,31+/m1/s1
• InChI Key: LOZCNNJQVGZXFP-SRHIYTGZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₀O₁₀
• Molecular Weight: 572.60 g/mol
• Exact Mass: 572.26214747 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 3-O-deacetylorthosiphol U
• CHEMBL448016

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9747	97.47%
Caco-2	-	0.8054	80.54%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6136	61.36%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8611	86.11%
OATP1B3 inhibitior	+	0.8738	87.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9033	90.33%
P-glycoprotein inhibitior	+	0.7285	72.85%
P-glycoprotein substrate	-	0.6554	65.54%
CYP3A4 substrate	+	0.6716	67.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.6826	68.26%
CYP2C9 inhibition	-	0.8353	83.53%
CYP2C19 inhibition	-	0.8534	85.34%
CYP2D6 inhibition	-	0.9163	91.63%
CYP1A2 inhibition	-	0.8074	80.74%
CYP2C8 inhibition	+	0.6579	65.79%
CYP inhibitory promiscuity	-	0.9192	91.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6160	61.60%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9103	91.03%
Skin irritation	-	0.6303	63.03%
Skin corrosion	-	0.9149	91.49%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6460	64.60%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5610	56.10%
skin sensitisation	-	0.6681	66.81%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4722	47.22%
Acute Oral Toxicity (c)	III	0.6228	62.28%
Estrogen receptor binding	+	0.7350	73.50%
Androgen receptor binding	+	0.6459	64.59%
Thyroid receptor binding	+	0.6112	61.12%
Glucocorticoid receptor binding	+	0.6946	69.46%
Aromatase binding	+	0.6427	64.27%
PPAR gamma	+	0.6528	65.28%
Honey bee toxicity	-	0.7018	70.18%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9967	99.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.18%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	95.99%	90.17%
CHEMBL1951	P21397	Monoamine oxidase A	95.79%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.65%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.48%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.56%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.36%	85.14%
CHEMBL240	Q12809	HERG	91.95%	89.76%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.95%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	91.37%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.96%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.49%	82.69%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.09%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.51%	94.08%
CHEMBL5028	O14672	ADAM10	84.90%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.99%	89.00%
CHEMBL4208	P20618	Proteasome component C5	82.31%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.25%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.19%	93.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.08%	83.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.33%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.55%	95.89%

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: 11071897
• NPASS: NPC60509
• LOTUS: LTS0157201
• wikiData: Q104399604