4,5,12-Trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one

Details

• Internal ID: 0df5850c-6d86-42f6-9489-4d4987dcd0dc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids
• IUPAC Name: 4,5,12-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
• SMILES (Canonical): CC1CC2(C(C2(C)C)C3C=C(CC4(C1(C3=O)C=C(C4O)C)O)CO)O
• SMILES (Isomeric): CC1CC2(C(C2(C)C)C3C=C(CC4(C1(C3=O)C=C(C4O)C)O)CO)O
• InChI: InChI=1S/C20H28O5/c1-10-6-18-11(2)7-19(24)14(17(19,3)4)13(16(18)23)5-12(9-21)8-20(18,25)15(10)22/h5-6,11,13-15,21-22,24-25H,7-9H2,1-4H3
• InChI Key: WUWIUEURLHJKBN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 98.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9869	98.69%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5885	58.85%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6322	63.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8567	85.67%
BSEP inhibitior	-	0.8730	87.30%
P-glycoprotein inhibitior	-	0.8881	88.81%
P-glycoprotein substrate	-	0.5194	51.94%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	-	0.8214	82.14%
CYP2D6 substrate	-	0.8218	82.18%
CYP3A4 inhibition	-	0.8088	80.88%
CYP2C9 inhibition	-	0.6687	66.87%
CYP2C19 inhibition	-	0.8139	81.39%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.7524	75.24%
CYP2C8 inhibition	-	0.8487	84.87%
CYP inhibitory promiscuity	-	0.9313	93.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6630	66.30%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9398	93.98%
Skin irritation	-	0.6431	64.31%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5308	53.08%
Human Ether-a-go-go-Related Gene inhibition	-	0.6566	65.66%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5725	57.25%
skin sensitisation	-	0.7612	76.12%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5453	54.53%
Acute Oral Toxicity (c)	III	0.4766	47.66%
Estrogen receptor binding	+	0.6142	61.42%
Androgen receptor binding	+	0.6818	68.18%
Thyroid receptor binding	+	0.6225	62.25%
Glucocorticoid receptor binding	+	0.7109	71.09%
Aromatase binding	+	0.5811	58.11%
PPAR gamma	-	0.6526	65.26%
Honey bee toxicity	-	0.8773	87.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9200	92.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2996	Q05655	Protein kinase C delta	94.95%	97.79%
CHEMBL299	P17252	Protein kinase C alpha	91.55%	98.03%
CHEMBL2581	P07339	Cathepsin D	91.53%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.29%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.06%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.69%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.61%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.99%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.93%	97.09%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	85.87%	86.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.21%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	83.95%	90.17%

Plants that contains it

• Mabea excelsa

Cross-Links

• PubChem: 162886567
• LOTUS: LTS0239091
• wikiData: Q105313358