orthosiphol O

Details

• Internal ID: e915aa9b-3572-4a7a-a8d7-8c10a5b47b1d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-3,9-diacetyloxy-4-benzoyloxy-7-ethenyl-5,8a-dihydroxy-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)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3O)(C)C=C)O)C)OC(=O)C4=CC=CC=C4)OC(=O)C)OC(=O)C5=CC=CC=C5)(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)OC(=O)C4=CC=CC=C4)OC(=O)C)OC(=O)C5=CC=CC=C5)C
• InChI: InChI=1S/C38H44O11/c1-8-36(6)20-25(41)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(48-32(42)23-15-11-9-12-16-23)28(47-22(3)40)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1
• InChI Key: MTXOFPKHBDQARM-OFUWLHILSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₁
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.28836222 g/mol
• Topological Polar Surface Area (TPSA): 163.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.24
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• CHEMBL500763
• [(2S,3S,4R,4aS,4bS,5R,7R,8aR,9R,10aS)-3,9-diacetyloxy-4-benzoyloxy-7-ethenyl-5,8a-dihydroxy-1,1,4a,7-tetramethyl-8-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-2-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9715	97.15%
Caco-2	-	0.8217	82.17%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6136	61.36%
OATP2B1 inhibitior	-	0.8593	85.93%
OATP1B1 inhibitior	+	0.8599	85.99%
OATP1B3 inhibitior	+	0.8734	87.34%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9791	97.91%
P-glycoprotein inhibitior	+	0.8317	83.17%
P-glycoprotein substrate	-	0.6304	63.04%
CYP3A4 substrate	+	0.6810	68.10%
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	+	0.6454	64.54%
CYP inhibitory promiscuity	-	0.9192	91.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6160	61.60%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9048	90.48%
Skin irritation	-	0.6835	68.35%
Skin corrosion	-	0.9223	92.23%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7822	78.22%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5015	50.15%
skin sensitisation	-	0.6918	69.18%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6488	64.88%
Acute Oral Toxicity (c)	III	0.6228	62.28%
Estrogen receptor binding	+	0.7703	77.03%
Androgen receptor binding	+	0.6856	68.56%
Thyroid receptor binding	+	0.6496	64.96%
Glucocorticoid receptor binding	+	0.7375	73.75%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.7314	73.14%
Honey bee toxicity	-	0.6864	68.64%
Biodegradation	-	0.7500	75.00%
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	98.15%	91.49%
CHEMBL240	Q12809	HERG	96.66%	89.76%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.53%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	96.43%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.13%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	92.55%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.32%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.27%	82.69%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.62%	94.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.70%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.59%	94.08%
CHEMBL5028	O14672	ADAM10	85.30%	97.50%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.46%	83.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.39%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.10%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.08%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.69%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.36%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.07%	90.00%

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: 10032464
• NPASS: NPC242262
• ChEMBL: CHEMBL500763
• LOTUS: LTS0144629
• wikiData: Q104399599