orthosiphonone A

Details

• Internal ID: 6ea219ad-064a-4b8c-ad5f-5c6c998457ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-3,9-diacetyloxy-4-benzoyloxy-7-ethenyl-8a-hydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-2-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)OC(=O)C5=CC=CC=C5)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@]([C@H]([C@H]([C@H](C2(C)C)OC(=O)C3=CC=CC=C3)OC(=O)C)OC(=O)C4=CC=CC=C4)([C@@H]5[C@@]1(C(=O)[C@@](CC5=O)(C)C=C)O)C
• InChI: InChI=1S/C38H42O11/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/h8-18,26-31,45H,1,19-20H2,2-7H3/t26-,27+,28-,29+,30+,31-,36-,37-,38-/m0/s1
• InChI Key: VGFQEWWZGREADO-WFHOPHNXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₂O₁₁
• Molecular Weight: 674.70 g/mol
• Exact Mass: 674.27271215 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.45
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• CHEMBL447412
• SCHEMBL12566535
• DTXSID801100279
• (2R,4aR,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-Bis(acetyloxy)-5,7-bis(benzoyloxy)-2-ethenyldodecahydro-10a-hydroxy-2,4b,8,8-tetramethyl-1,4-phenanthrenedione
• 237417-08-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9870	98.70%
Caco-2	-	0.8131	81.31%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7216	72.16%
OATP2B1 inhibitior	-	0.8599	85.99%
OATP1B1 inhibitior	+	0.8467	84.67%
OATP1B3 inhibitior	+	0.8419	84.19%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9845	98.45%
P-glycoprotein inhibitior	+	0.8657	86.57%
P-glycoprotein substrate	-	0.6534	65.34%
CYP3A4 substrate	+	0.6729	67.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	+	0.6594	65.94%
CYP2C9 inhibition	-	0.7904	79.04%
CYP2C19 inhibition	-	0.7975	79.75%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.6569	65.69%
CYP2C8 inhibition	+	0.6248	62.48%
CYP inhibitory promiscuity	-	0.9225	92.25%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.5616	56.16%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.6934	69.34%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7120	71.20%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.6596	65.96%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6082	60.82%
Acute Oral Toxicity (c)	III	0.6264	62.64%
Estrogen receptor binding	+	0.7721	77.21%
Androgen receptor binding	+	0.7094	70.94%
Thyroid receptor binding	+	0.6723	67.23%
Glucocorticoid receptor binding	+	0.7791	77.91%
Aromatase binding	+	0.6088	60.88%
PPAR gamma	+	0.7263	72.63%
Honey bee toxicity	-	0.6283	62.83%
Biodegradation	-	0.7750	77.50%
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	99.33%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.15%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.95%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.08%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.29%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.92%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	90.29%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.73%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.34%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.35%	94.62%
CHEMBL5028	O14672	ADAM10	84.94%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.60%	82.69%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.61%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.06%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.04%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.72%	99.23%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.28%	83.00%

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: 10439492
• NPASS: NPC77719
• ChEMBL: CHEMBL447412
• LOTUS: LTS0019028
• wikiData: Q104399614