5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione

Details

• Internal ID: f8d67958-230e-4151-97aa-69c81303f0e3
• Taxonomy: Benzenoids > Pyrenes > Benzopyrenes
• IUPAC Name: 5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
• SMILES (Canonical): CC1=CC(=C2C3=C4C5=C(C(=CC(=C5C2=O)O)O)C6=C7C4=C8C(=C13)C(=CC(=C8C(=O)C7=C(C=C6O)O)O)C)O
• SMILES (Isomeric): CC1=CC(=C2C3=C4C5=C(C(=CC(=C5C2=O)O)O)C6=C7C4=C8C(=C13)C(=CC(=C8C(=O)C7=C(C=C6O)O)O)C)O
• InChI: InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
• InChI Key: BTXNYTINYBABQR-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₁₆O₈
• Molecular Weight: 504.40 g/mol
• Exact Mass: 504.08451746 g/mol
• Topological Polar Surface Area (TPSA): 156.00 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 5.08
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9808	98.08%
Caco-2	-	0.5675	56.75%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8031	80.31%
OATP2B1 inhibitior	+	0.5848	58.48%
OATP1B1 inhibitior	+	0.9578	95.78%
OATP1B3 inhibitior	+	0.9358	93.58%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.5721	57.21%
P-glycoprotein inhibitior	-	0.7771	77.71%
P-glycoprotein substrate	-	0.9774	97.74%
CYP3A4 substrate	-	0.6930	69.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	+	0.5153	51.53%
CYP2C9 inhibition	+	0.8024	80.24%
CYP2C19 inhibition	-	0.6248	62.48%
CYP2D6 inhibition	-	0.5855	58.55%
CYP1A2 inhibition	+	0.8896	88.96%
CYP2C8 inhibition	-	0.9674	96.74%
CYP inhibitory promiscuity	-	0.6006	60.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8020	80.20%
Carcinogenicity (trinary)	Non-required	0.6808	68.08%
Eye corrosion	-	0.9886	98.86%
Eye irritation	+	0.8573	85.73%
Skin irritation	-	0.5638	56.38%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.8064	80.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.3804	38.04%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.7552	75.52%
skin sensitisation	-	0.8617	86.17%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.5949	59.49%
Acute Oral Toxicity (c)	III	0.7500	75.00%
Estrogen receptor binding	+	0.8877	88.77%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	-	0.5205	52.05%
Glucocorticoid receptor binding	+	0.7502	75.02%
Aromatase binding	-	0.7455	74.55%
PPAR gamma	+	0.7811	78.11%
Honey bee toxicity	-	0.9674	96.74%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9716	97.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	8912.5 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	22387.2 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	14125.4 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	562.3 nM; 354.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	19952.6 nM	Potency	via CMAUP
CHEMBL1800	P34998	Corticotropin releasing factor receptor 1	300 nM; 300 nM	IC50; IC50	PMID: 20408551; PMID: 20408551
CHEMBL340	P08684	Cytochrome P450 3A4	8700 nM	IC50	PMID: 20408551
CHEMBL234	P35462	Dopamine D3 receptor	34.5 nM	Ki	PMID: 20408551
CHEMBL1293224	P10636	Microtubule-associated protein tau	14125.4 nM; 17782.8 nM; 14125.4 nM; 4466.8 nM; 4466.8 nM	Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	17782.8 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	12589.3 nM; 1778.3 nM; 14125.4 nM; 1778.3 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.66%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.72%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.38%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.13%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.02%	93.99%
CHEMBL1951	P21397	Monoamine oxidase A	83.95%	91.49%
CHEMBL4208	P20618	Proteasome component C5	82.57%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.49%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.71%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.34%	94.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.17%	93.65%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.40%	93.40%

Plants that contains it

• Hypericum perforatum

Cross-Links

• PubChem: 5281051
• NPASS: NPC227841
• ChEMBL: CHEMBL286494