(1R)-2-[(1aR,3aR,4R,5R,7aS,7bS)-4-(hydroxymethyl)-5,7a,7b-trimethyl-2,3,3a,5,6,7-hexahydro-1aH-naphtho[1,2-b]oxiren-4-yl]-1-(furan-3-yl)ethanol

Details

• Internal ID: 13363fd1-5687-4f9e-96d1-61c7adceecd9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1R)-2-[(1aR,3aR,4R,5R,7aS,7bS)-4-(hydroxymethyl)-5,7a,7b-trimethyl-2,3,3a,5,6,7-hexahydro-1aH-naphtho[1,2-b]oxiren-4-yl]-1-(furan-3-yl)ethanol
• SMILES (Canonical): CC1CCC2(C(C1(CC(C3=COC=C3)O)CO)CCC4C2(O4)C)C
• SMILES (Isomeric): C[C@@H]1CC[C@]2([C@@H]([C@]1(C[C@H](C3=COC=C3)O)CO)CC[C@@H]4[C@]2(O4)C)C
• InChI: InChI=1S/C20H30O4/c1-13-6-8-18(2)16(4-5-17-19(18,3)24-17)20(13,12-21)10-15(22)14-7-9-23-11-14/h7,9,11,13,15-17,21-22H,4-6,8,10,12H2,1-3H3/t13-,15-,16+,17-,18+,19-,20-/m1/s1
• InChI Key: PZYXVRLXODTTQL-NHGVGGNESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 66.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.69
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9772	97.72%
Caco-2	+	0.6471	64.71%
Blood Brain Barrier	+	0.6385	63.85%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4882	48.82%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.7888	78.88%
OATP1B3 inhibitior	+	0.9224	92.24%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6893	68.93%
BSEP inhibitior	-	0.7011	70.11%
P-glycoprotein inhibitior	-	0.8568	85.68%
P-glycoprotein substrate	-	0.6657	66.57%
CYP3A4 substrate	+	0.5957	59.57%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.7024	70.24%
CYP3A4 inhibition	+	0.5322	53.22%
CYP2C9 inhibition	-	0.6841	68.41%
CYP2C19 inhibition	-	0.7330	73.30%
CYP2D6 inhibition	-	0.9108	91.08%
CYP1A2 inhibition	-	0.7582	75.82%
CYP2C8 inhibition	+	0.4655	46.55%
CYP inhibitory promiscuity	-	0.7815	78.15%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5554	55.54%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9903	99.03%
Skin irritation	-	0.7341	73.41%
Skin corrosion	-	0.9472	94.72%
Ames mutagenesis	-	0.7011	70.11%
Human Ether-a-go-go-Related Gene inhibition	+	0.7115	71.15%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6560	65.60%
skin sensitisation	-	0.8488	84.88%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8416	84.16%
Acute Oral Toxicity (c)	III	0.5008	50.08%
Estrogen receptor binding	+	0.9020	90.20%
Androgen receptor binding	+	0.5927	59.27%
Thyroid receptor binding	+	0.6942	69.42%
Glucocorticoid receptor binding	+	0.7440	74.40%
Aromatase binding	+	0.7488	74.88%
PPAR gamma	-	0.5751	57.51%
Honey bee toxicity	-	0.8085	80.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9448	94.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.33%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.96%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.17%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.43%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.67%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.04%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	88.43%	90.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.33%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.18%	90.24%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.72%	95.56%
CHEMBL5555	O00767	Acyl-CoA desaturase	80.42%	97.50%

Plants that contains it

• Microglossa pyrrhopappa

Cross-Links

• PubChem: 14707149
• LOTUS: LTS0272185
• wikiData: Q105217194