(8S)-4',9,9'-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone

Details

• Internal ID: 44522ad0-9ab3-429f-9246-9d979148ed84
• Taxonomy: Benzenoids > Indanes > Indanones > Indanediones
• IUPAC Name: (8S)-4',9,9'-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone
• SMILES (Canonical): CC=CC=CC1=CC2=CC3=C(C(=C2C(=O)N1)O)C4(CC3)C(=O)C5=C(C6=C(C(=C5C4=O)O)C(=O)C(=CC6=O)OC)O
• SMILES (Isomeric): C/C=C/C=C/C1=CC2=CC3=C(C(=C2C(=O)N1)O)[C@@]4(CC3)C(=O)C5=C(C6=C(C(=C5C4=O)O)C(=O)C(=CC6=O)OC)O
• InChI: InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,34-36H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+/t30-/m0/s1
• InChI Key: BZONSJUONOFNNP-MHSJTTIKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₁NO₉
• Molecular Weight: 539.50 g/mol
• Exact Mass: 539.12163125 g/mol
• Topological Polar Surface Area (TPSA): 167.00 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9366	93.66%
Caco-2	-	0.8826	88.26%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6923	69.23%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8513	85.13%
OATP1B3 inhibitior	+	0.9563	95.63%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8072	80.72%
BSEP inhibitior	+	0.9548	95.48%
P-glycoprotein inhibitior	+	0.6927	69.27%
P-glycoprotein substrate	-	0.5481	54.81%
CYP3A4 substrate	+	0.6565	65.65%
CYP2C9 substrate	+	0.6060	60.60%
CYP2D6 substrate	-	0.8714	87.14%
CYP3A4 inhibition	-	0.8920	89.20%
CYP2C9 inhibition	-	0.7307	73.07%
CYP2C19 inhibition	-	0.7058	70.58%
CYP2D6 inhibition	-	0.8653	86.53%
CYP1A2 inhibition	+	0.5733	57.33%
CYP2C8 inhibition	+	0.6451	64.51%
CYP inhibitory promiscuity	+	0.5876	58.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5116	51.16%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.8165	81.65%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	+	0.5046	50.46%
Human Ether-a-go-go-Related Gene inhibition	+	0.6508	65.08%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.5585	55.85%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4772	47.72%
Acute Oral Toxicity (c)	III	0.4648	46.48%
Estrogen receptor binding	+	0.7981	79.81%
Androgen receptor binding	+	0.6996	69.96%
Thyroid receptor binding	+	0.5254	52.54%
Glucocorticoid receptor binding	+	0.7822	78.22%
Aromatase binding	+	0.5696	56.96%
PPAR gamma	+	0.7366	73.66%
Honey bee toxicity	-	0.7471	74.71%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.6945	69.45%

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	98.85%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.35%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.99%	93.99%
CHEMBL1937	Q92769	Histone deacetylase 2	96.77%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.84%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	94.04%	89.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.40%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.29%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	92.25%	91.03%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.93%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.66%	96.09%
CHEMBL284	P27487	Dipeptidyl peptidase IV	91.63%	95.69%
CHEMBL2535	P11166	Glucose transporter	91.63%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.13%	94.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	90.08%	92.68%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.04%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.20%	99.23%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.13%	91.71%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	88.95%	91.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.45%	89.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	86.81%	81.14%
CHEMBL2581	P07339	Cathepsin D	86.17%	98.95%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.04%	98.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.89%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.24%	97.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.09%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.24%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.20%	91.07%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.83%	89.34%

Plants that contains it

• Aglaia spectabilis
• Clibadium pentaneuron
• Coespeletia thyrsiformis f. marcanoi
• Croton bonplandianus
• Croton californicus
• Culcitium canescens
• Cymbopogon nardus
• Dendrobium rotundatum
• Malva verticillata
• Nolina erumpens
• Petasites paradoxus
• Philotheca fitzgeraldii
• Piptolepis leptospermoides
• Ratibida latipalearis
• Toxicodendron succedaneum
• Weddellina squamulosa

Cross-Links

• PubChem: 9937086
• NPASS: NPC289905
• ChEMBL: CHEMBL256952
• LOTUS: LTS0102969
• wikiData: Q27292813