orthosiphol D

Details

• Internal ID: 33d26787-348e-42d0-98ac-0383783bf8ce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2R,4R,4aS,4bR,8aR,10R,10aR)-6,10-diacetyloxy-2-ethenyl-10a-hydroxy-2,4b,8,8-tetramethyl-1,7-dioxo-3,4,4a,8a,9,10-hexahydrophenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C(=CC2(C3C1(C(=O)C(CC3OC(=O)C4=CC=CC=C4)(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]3OC(=O)C4=CC=CC=C4)(C)C=C)O)C
• InChI: InChI=1S/C31H36O9/c1-8-29(6)15-20(40-26(35)19-12-10-9-11-13-19)24-30(7)16-21(38-17(2)32)25(34)28(4,5)22(30)14-23(39-18(3)33)31(24,37)27(29)36/h8-13,16,20,22-24,37H,1,14-15H2,2-7H3/t20-,22+,23-,24-,29+,30+,31+/m1/s1
• InChI Key: LSZJDNYREMWISO-FHGPSSOVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₆O₉
• Molecular Weight: 552.60 g/mol
• Exact Mass: 552.23593272 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.74
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• CHEMBL448572
• SCHEMBL12566539

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	-	0.7456	74.56%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7477	74.77%
OATP2B1 inhibitior	-	0.7127	71.27%
OATP1B1 inhibitior	+	0.8736	87.36%
OATP1B3 inhibitior	-	0.2273	22.73%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9678	96.78%
P-glycoprotein inhibitior	+	0.8587	85.87%
P-glycoprotein substrate	-	0.5969	59.69%
CYP3A4 substrate	+	0.6846	68.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8895	88.95%
CYP3A4 inhibition	+	0.5360	53.60%
CYP2C9 inhibition	-	0.7662	76.62%
CYP2C19 inhibition	-	0.7499	74.99%
CYP2D6 inhibition	-	0.9260	92.60%
CYP1A2 inhibition	-	0.6363	63.63%
CYP2C8 inhibition	+	0.7085	70.85%
CYP inhibitory promiscuity	-	0.8737	87.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9643	96.43%
Carcinogenicity (trinary)	Non-required	0.5622	56.22%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8989	89.89%
Skin irritation	-	0.6224	62.24%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6712	67.12%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5853	58.53%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6850	68.50%
Acute Oral Toxicity (c)	III	0.5930	59.30%
Estrogen receptor binding	+	0.7765	77.65%
Androgen receptor binding	+	0.6819	68.19%
Thyroid receptor binding	+	0.6663	66.63%
Glucocorticoid receptor binding	+	0.7853	78.53%
Aromatase binding	+	0.5968	59.68%
PPAR gamma	+	0.7098	70.98%
Honey bee toxicity	-	0.6543	65.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
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
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.54%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	95.39%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.10%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.13%	91.11%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.49%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	93.32%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.97%	95.56%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	92.70%	97.53%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.65%	94.62%
CHEMBL340	P08684	Cytochrome P450 3A4	92.46%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.77%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.84%	99.23%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.79%	94.23%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.92%	95.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.73%	82.69%
CHEMBL5028	O14672	ADAM10	85.08%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.35%	96.95%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.13%	83.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.83%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.59%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.40%	100.00%

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: 44583689
• NPASS: NPC306799
• ChEMBL: CHEMBL448572
• LOTUS: LTS0267895
• wikiData: Q104399588