(1S,8S,9S)-3,6-dihydroxy-15-methyl-9-(3-methylbut-2-enyl)tetracyclo[6.5.3.01,9.02,7]hexadeca-2,4,6,11,15-pentaene-10,13-dione

Details

• Internal ID: deed3885-0eec-4cbe-896b-70680be2d6b9
• Taxonomy: Benzenoids > Fluorenes
• IUPAC Name: (1S,8S,9S)-3,6-dihydroxy-15-methyl-9-(3-methylbut-2-enyl)tetracyclo[6.5.3.01,9.02,7]hexadeca-2,4,6,11,15-pentaene-10,13-dione
• SMILES (Canonical): CC1=CC2C3=C(C=CC(=C3C4(C1)C2(C(=O)C=CC4=O)CC=C(C)C)O)O
• SMILES (Isomeric): CC1=C[C@H]2C3=C(C=CC(=C3[C@@]4(C1)[C@]2(C(=O)C=CC4=O)CC=C(C)C)O)O
• InChI: InChI=1S/C22H22O4/c1-12(2)8-9-21-14-10-13(3)11-22(21,18(26)7-6-17(21)25)20-16(24)5-4-15(23)19(14)20/h4-8,10,14,23-24H,9,11H2,1-3H3/t14-,21+,22-/m0/s1
• InChI Key: PDQBHONFOHDGLI-CUJSYCCXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₄
• Molecular Weight: 350.40 g/mol
• Exact Mass: 350.15180918 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.5402	54.02%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8238	82.38%
OATP2B1 inhibitior	-	0.7190	71.90%
OATP1B1 inhibitior	+	0.9191	91.91%
OATP1B3 inhibitior	+	0.9091	90.91%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5480	54.80%
P-glycoprotein inhibitior	-	0.6895	68.95%
P-glycoprotein substrate	-	0.6410	64.10%
CYP3A4 substrate	+	0.5982	59.82%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.7986	79.86%
CYP3A4 inhibition	-	0.6105	61.05%
CYP2C9 inhibition	+	0.7391	73.91%
CYP2C19 inhibition	+	0.6359	63.59%
CYP2D6 inhibition	-	0.7187	71.87%
CYP1A2 inhibition	+	0.6913	69.13%
CYP2C8 inhibition	-	0.7517	75.17%
CYP inhibitory promiscuity	+	0.8189	81.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8423	84.23%
Carcinogenicity (trinary)	Non-required	0.6126	61.26%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.6403	64.03%
Skin irritation	-	0.6260	62.60%
Skin corrosion	-	0.9147	91.47%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5993	59.93%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5158	51.58%
skin sensitisation	-	0.6272	62.72%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7430	74.30%
Acute Oral Toxicity (c)	III	0.6180	61.80%
Estrogen receptor binding	+	0.6254	62.54%
Androgen receptor binding	+	0.6882	68.82%
Thyroid receptor binding	+	0.5396	53.96%
Glucocorticoid receptor binding	+	0.7927	79.27%
Aromatase binding	-	0.6127	61.27%
PPAR gamma	+	0.7663	76.63%
Honey bee toxicity	-	0.8909	89.09%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	97.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.71%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.30%	93.40%
CHEMBL1937	Q92769	Histone deacetylase 2	90.78%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.55%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.43%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	86.79%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.89%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.25%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.92%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.02%	97.09%

Plants that contains it

• Diospyros sylvatica

Cross-Links

• PubChem: 162898619
• LOTUS: LTS0166132
• wikiData: Q105206676