orthosiphonone C

Details

• Internal ID: 2c706f76-7f79-4739-97e6-d16df27490c8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-9-acetyloxy-7-ethenyl-2,4,8a-trihydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-3-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(CC3=O)(C)C=C)O)C)O)OC(=O)C4=CC=CC=C4)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)C3=CC=CC=C3)O)([C@@H]4[C@@]1(C(=O)[C@@](CC4=O)(C)C=C)O)C
• InChI: InChI=1S/C29H36O9/c1-7-27(5)14-17(31)21-28(6)18(13-19(37-15(2)30)29(21,36)25(27)35)26(3,4)22(32)20(23(28)33)38-24(34)16-11-9-8-10-12-16/h7-12,18-23,32-33,36H,1,13-14H2,2-6H3/t18-,19+,20-,21+,22+,23-,27-,28-,29-/m0/s1
• InChI Key: HJGHLDCCNKXCAO-SKLQCFIISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₉
• Molecular Weight: 528.60 g/mol
• Exact Mass: 528.23593272 g/mol
• Topological Polar Surface Area (TPSA): 147.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.01
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• CHEMBL464115
• [(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-9-acetyloxy-7-ethenyl-2,4,8a-trihydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-3-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9671	96.71%
Caco-2	-	0.7958	79.58%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6693	66.93%
OATP2B1 inhibitior	-	0.8564	85.64%
OATP1B1 inhibitior	+	0.8593	85.93%
OATP1B3 inhibitior	+	0.8471	84.71%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8490	84.90%
P-glycoprotein inhibitior	+	0.6416	64.16%
P-glycoprotein substrate	-	0.7009	70.09%
CYP3A4 substrate	+	0.6641	66.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.6316	63.16%
CYP2C9 inhibition	-	0.8026	80.26%
CYP2C19 inhibition	-	0.8550	85.50%
CYP2D6 inhibition	-	0.9137	91.37%
CYP1A2 inhibition	-	0.7521	75.21%
CYP2C8 inhibition	+	0.6245	62.45%
CYP inhibitory promiscuity	-	0.8753	87.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6049	60.49%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9209	92.09%
Skin irritation	-	0.6577	65.77%
Skin corrosion	-	0.9211	92.11%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3697	36.97%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.6675	66.75%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4792	47.92%
Acute Oral Toxicity (c)	III	0.6515	65.15%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.6622	66.22%
Thyroid receptor binding	+	0.6035	60.35%
Glucocorticoid receptor binding	+	0.6660	66.60%
Aromatase binding	+	0.6350	63.50%
PPAR gamma	+	0.6320	63.20%
Honey bee toxicity	-	0.6813	68.13%
Biodegradation	-	0.8000	80.00%
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	99.24%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.79%	86.33%
CHEMBL2581	P07339	Cathepsin D	93.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.70%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.33%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.37%	94.08%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.01%	99.23%
CHEMBL5028	O14672	ADAM10	86.49%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.74%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.28%	89.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.39%	83.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.15%	91.07%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.30%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.19%	97.09%

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: 11226314
• NPASS: NPC165260
• LOTUS: LTS0132733
• wikiData: Q105029231