secoorthosiphol B

Details

• Internal ID: 7809e1f3-90eb-4c7f-8177-04dd7d44fb75
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: 2-[(1S,2R,4R,4aR,6R,8R,8aS)-4-acetyloxy-8-benzoyloxy-6-ethenyl-4a-hydroxy-2-(1-methoxy-2-methyl-1-oxopropan-2-yl)-1,6-dimethyl-5-oxo-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]acetic acid
• SMILES (Canonical): CC(=O)OC1CC(C(C2C1(C(=O)C(CC2OC(=O)C3=CC=CC=C3)(C)C=C)O)(C)CC(=O)O)C(C)(C)C(=O)OC
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@H]([C@]([C@@H]2[C@@]1(C(=O)[C@@](C[C@H]2OC(=O)C3=CC=CC=C3)(C)C=C)O)(C)CC(=O)O)C(C)(C)C(=O)OC
• InChI: InChI=1S/C30H38O10/c1-8-28(5)15-19(40-24(34)18-12-10-9-11-13-18)23-29(6,16-22(32)33)20(27(3,4)26(36)38-7)14-21(39-17(2)31)30(23,37)25(28)35/h8-13,19-21,23,37H,1,14-16H2,2-7H3,(H,32,33)/t19-,20+,21-,23-,28+,29+,30+/m1/s1
• InChI Key: ZNOSNEAHXFOXRY-KKKLMDDUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₈O₁₀
• Molecular Weight: 558.60 g/mol
• Exact Mass: 558.24649740 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.36
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

• CHEMBL510190

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	-	0.7245	72.45%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7274	72.74%
OATP2B1 inhibitior	-	0.8534	85.34%
OATP1B1 inhibitior	+	0.8559	85.59%
OATP1B3 inhibitior	-	0.2605	26.05%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8615	86.15%
P-glycoprotein inhibitior	+	0.8207	82.07%
P-glycoprotein substrate	+	0.5771	57.71%
CYP3A4 substrate	+	0.7044	70.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8934	89.34%
CYP3A4 inhibition	+	0.6920	69.20%
CYP2C9 inhibition	-	0.8255	82.55%
CYP2C19 inhibition	-	0.7439	74.39%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.7654	76.54%
CYP2C8 inhibition	+	0.7504	75.04%
CYP inhibitory promiscuity	-	0.9426	94.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6889	68.89%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8984	89.84%
Skin irritation	-	0.6491	64.91%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7435	74.35%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7827	78.27%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6079	60.79%
Acute Oral Toxicity (c)	I	0.3684	36.84%
Estrogen receptor binding	+	0.7258	72.58%
Androgen receptor binding	+	0.6595	65.95%
Thyroid receptor binding	+	0.6170	61.70%
Glucocorticoid receptor binding	+	0.7432	74.32%
Aromatase binding	+	0.6038	60.38%
PPAR gamma	+	0.6462	64.62%
Honey bee toxicity	-	0.6886	68.86%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.87%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.65%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.45%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.35%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.23%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	92.90%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.99%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.79%	96.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.56%	91.07%
CHEMBL340	P08684	Cytochrome P450 3A4	88.21%	91.19%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.81%	94.08%
CHEMBL2996	Q05655	Protein kinase C delta	87.61%	97.79%
CHEMBL5028	O14672	ADAM10	87.02%	97.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.09%	94.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.58%	97.14%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	84.63%	81.29%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.49%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.23%	97.25%
CHEMBL2535	P11166	Glucose transporter	83.10%	98.75%
CHEMBL4208	P20618	Proteasome component C5	81.45%	90.00%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	81.19%	94.97%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Catoferia spicata
• 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: 15548728
• NPASS: NPC127857
• LOTUS: LTS0060901
• wikiData: Q104399616