(4bS,7S,8aS)-7-ethenyl-3-hydroxy-4b,7-dimethyl-5,6,8,8a,9,10-hexahydrophenanthrene-1-carboxylic acid

Details

• Internal ID: acbd0e87-cf6a-4b09-bc17-16227e7b24ed
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: (4bS,7S,8aS)-7-ethenyl-3-hydroxy-4b,7-dimethyl-5,6,8,8a,9,10-hexahydrophenanthrene-1-carboxylic acid
• SMILES (Canonical): CC1(CCC2(C(C1)CCC3=C(C=C(C=C32)O)C(=O)O)C)C=C
• SMILES (Isomeric): C[C@@]1(CC[C@]2([C@H](C1)CCC3=C(C=C(C=C32)O)C(=O)O)C)C=C
• InChI: InChI=1S/C19H24O3/c1-4-18(2)7-8-19(3)12(11-18)5-6-14-15(17(21)22)9-13(20)10-16(14)19/h4,9-10,12,20H,1,5-8,11H2,2-3H3,(H,21,22)/t12-,18-,19-/m0/s1
• InChI Key: HINQPZSXRLXOFR-NXXSPTCGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.40 g/mol
• Exact Mass: 300.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 4.29
• H-Bond Acceptor: 2
• 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	+	0.9958	99.58%
Caco-2	+	0.7785	77.85%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7637	76.37%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8947	89.47%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.8120	81.20%
P-glycoprotein inhibitior	-	0.8954	89.54%
P-glycoprotein substrate	-	0.8281	82.81%
CYP3A4 substrate	+	0.5513	55.13%
CYP2C9 substrate	-	0.6177	61.77%
CYP2D6 substrate	-	0.8884	88.84%
CYP3A4 inhibition	-	0.7208	72.08%
CYP2C9 inhibition	-	0.8486	84.86%
CYP2C19 inhibition	-	0.7348	73.48%
CYP2D6 inhibition	-	0.8756	87.56%
CYP1A2 inhibition	+	0.5699	56.99%
CYP2C8 inhibition	+	0.6392	63.92%
CYP inhibitory promiscuity	-	0.8050	80.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8611	86.11%
Carcinogenicity (trinary)	Non-required	0.5583	55.83%
Eye corrosion	-	0.9859	98.59%
Eye irritation	+	0.5627	56.27%
Skin irritation	-	0.5738	57.38%
Skin corrosion	-	0.9358	93.58%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7586	75.86%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5420	54.20%
skin sensitisation	-	0.7135	71.35%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7170	71.70%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6334	63.34%
Acute Oral Toxicity (c)	III	0.7757	77.57%
Estrogen receptor binding	-	0.5482	54.82%
Androgen receptor binding	-	0.5964	59.64%
Thyroid receptor binding	+	0.7067	70.67%
Glucocorticoid receptor binding	+	0.7784	77.84%
Aromatase binding	+	0.5627	56.27%
PPAR gamma	+	0.5698	56.98%
Honey bee toxicity	-	0.8535	85.35%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
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	96.80%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.46%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.59%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.70%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.34%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.88%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.90%	97.09%
CHEMBL233	P35372	Mu opioid receptor	82.58%	97.93%
CHEMBL2581	P07339	Cathepsin D	81.03%	98.95%
CHEMBL4208	P20618	Proteasome component C5	80.75%	90.00%

Plants that contains it

• Dryopteris maximowiczii

Cross-Links

• PubChem: 21637593
• LOTUS: LTS0033919
• wikiData: Q105028925