Orthosiphol M

Details

• Internal ID: e90fb142-d41b-4790-9309-e58a04335bf8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-3,9-diacetyloxy-7-ethenyl-2,8a-dihydroxy-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)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@]([C@H]([C@H]([C@H](C2(C)C)O)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/C31H38O10/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/h8-13,20-25,35,38H,1,14-15H2,2-7H3/t20-,21+,22-,23+,24+,25-,29-,30-,31-/m0/s1
• InChI Key: GTEFXIUCQAABAV-FYEHOKTBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₈O₁₀
• Molecular Weight: 570.60 g/mol
• Exact Mass: 570.24649740 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 10
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• CHEMBL450421
• SCHEMBL15941241

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	-	0.7881	78.81%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7196	71.96%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8478	84.78%
OATP1B3 inhibitior	+	0.8123	81.23%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9344	93.44%
P-glycoprotein inhibitior	+	0.7841	78.41%
P-glycoprotein substrate	-	0.6815	68.15%
CYP3A4 substrate	+	0.6630	66.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.5260	52.60%
CYP2C9 inhibition	-	0.8244	82.44%
CYP2C19 inhibition	-	0.8391	83.91%
CYP2D6 inhibition	-	0.9267	92.67%
CYP1A2 inhibition	-	0.6953	69.53%
CYP2C8 inhibition	+	0.6390	63.90%
CYP inhibitory promiscuity	-	0.9041	90.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5696	56.96%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9042	90.42%
Skin irritation	-	0.6513	65.13%
Skin corrosion	-	0.9250	92.50%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4491	44.91%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.6463	64.63%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5177	51.77%
Acute Oral Toxicity (c)	III	0.6242	62.42%
Estrogen receptor binding	+	0.7387	73.87%
Androgen receptor binding	+	0.6806	68.06%
Thyroid receptor binding	+	0.6212	62.12%
Glucocorticoid receptor binding	+	0.7469	74.69%
Aromatase binding	+	0.6515	65.15%
PPAR gamma	+	0.6243	62.43%
Honey bee toxicity	-	0.6442	64.42%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
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	98.45%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.77%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.41%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.52%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	89.18%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.29%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.96%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.32%	94.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.73%	91.07%
CHEMBL5028	O14672	ADAM10	84.52%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.04%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.26%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.95%	97.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.66%	94.08%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.13%	93.03%

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: 10030927
• NPASS: NPC198455
• LOTUS: LTS0072336
• wikiData: Q104399596