(Z)-2-(hydroxymethyl)-4-[(1S,2S,8S,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]but-2-enoic acid

Details

• Internal ID: 79ba53c6-3555-46be-a584-07a804127d24
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (Z)-2-(hydroxymethyl)-4-[(1S,2S,8S,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]but-2-enoic acid
• SMILES (Canonical): CC(=CCCC1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)OC45C6CC(C=C4C3=O)C(=O)C5(OC6(C)C)CC=C(CO)C(=O)O)O)C)C
• SMILES (Isomeric): CC(=CCC[C@]1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)O[C@@]45[C@H]6C[C@@H](C=C4C3=O)C(=O)[C@@]5(OC6(C)C)C/C=C(/CO)\C(=O)O)O)C)C
• InChI: InChI=1S/C38H44O9/c1-20(2)9-8-14-36(7)15-13-24-29(40)28-30(41)26-17-23-18-27-35(5,6)47-37(33(23)42,16-12-22(19-39)34(43)44)38(26,27)46-32(28)25(31(24)45-36)11-10-21(3)4/h9-10,12-13,15,17,23,27,39-40H,8,11,14,16,18-19H2,1-7H3,(H,43,44)/b22-12-/t23-,27+,36+,37+,38-/m1/s1
• InChI Key: MNNVIONVHRRQPF-IPAPZNLXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₉
• Molecular Weight: 644.70 g/mol
• Exact Mass: 644.29853298 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 6.21
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9600	96.00%
Caco-2	-	0.8125	81.25%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8127	81.27%
OATP2B1 inhibitior	-	0.7177	71.77%
OATP1B1 inhibitior	-	0.5298	52.98%
OATP1B3 inhibitior	+	0.8047	80.47%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5614	56.14%
BSEP inhibitior	+	0.9953	99.53%
P-glycoprotein inhibitior	+	0.8359	83.59%
P-glycoprotein substrate	+	0.6728	67.28%
CYP3A4 substrate	+	0.7099	70.99%
CYP2C9 substrate	-	0.8043	80.43%
CYP2D6 substrate	-	0.8694	86.94%
CYP3A4 inhibition	-	0.7268	72.68%
CYP2C9 inhibition	-	0.6815	68.15%
CYP2C19 inhibition	-	0.8053	80.53%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	-	0.6469	64.69%
CYP2C8 inhibition	+	0.7307	73.07%
CYP inhibitory promiscuity	-	0.7678	76.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5060	50.60%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9051	90.51%
Skin irritation	-	0.6234	62.34%
Skin corrosion	-	0.9337	93.37%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4335	43.35%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8805	88.05%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9217	92.17%
Acute Oral Toxicity (c)	III	0.5621	56.21%
Estrogen receptor binding	+	0.8223	82.23%
Androgen receptor binding	+	0.7597	75.97%
Thyroid receptor binding	+	0.6454	64.54%
Glucocorticoid receptor binding	+	0.8377	83.77%
Aromatase binding	+	0.7301	73.01%
PPAR gamma	+	0.7435	74.35%
Honey bee toxicity	-	0.6987	69.87%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9956	99.56%

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	99.57%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.02%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.15%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	90.74%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.10%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.55%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.51%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.46%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.14%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.88%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.44%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.35%	94.75%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	84.83%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.33%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.17%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.90%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	80.96%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.11%	96.00%

Plants that contains it

• Callitriche stagnalis
• Croton discolor
• Eclipta prostrata
• Fragaria chiloensis
• Garcinia hanburyi
• Hemionitis glauca
• Millettia extensa
• Rhizomnium pseudopunctatum
• Ruscus hypoglossum
• Salix babylonica
• Scrophularia glabrata
• Toxicodendron radicans
• Vernonanthura discolor
• Wrightia coccinea

Cross-Links

• PubChem: 102402042
• NPASS: NPC271086
• LOTUS: LTS0028581
• wikiData: Q105168496