methyl (1S,4S,5R,9S,10R,12S,13R)-13-(acetyloxymethyl)-13-hydroxy-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylate

Details

• Internal ID: 79d7a819-f338-43eb-a61b-762df3174dce
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
• IUPAC Name: methyl (1S,4S,5R,9S,10R,12S,13R)-13-(acetyloxymethyl)-13-hydroxy-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadecane-5-carboxylate
• SMILES (Canonical): CC(=O)OCC1(CC23CCC1CC2C4(CCCC(C4CC3)(C)C(=O)OC)C)O
• SMILES (Isomeric): CC(=O)OC[C@]1(C[C@]23CC[C@H]1C[C@H]2[C@@]4(CCC[C@@]([C@H]4CC3)(C)C(=O)OC)C)O
• InChI: InChI=1S/C23H36O5/c1-15(24)28-14-23(26)13-22-10-6-16(23)12-18(22)20(2)8-5-9-21(3,19(25)27-4)17(20)7-11-22/h16-18,26H,5-14H2,1-4H3/t16-,17-,18-,20+,21+,22+,23-/m0/s1
• InChI Key: GQLZUIXFOJYYHD-IWWSQFKYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.25627424 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9814	98.14%
Caco-2	+	0.6591	65.91%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8832	88.32%
OATP2B1 inhibitior	-	0.8666	86.66%
OATP1B1 inhibitior	+	0.9017	90.17%
OATP1B3 inhibitior	+	0.8906	89.06%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6864	68.64%
BSEP inhibitior	+	0.7852	78.52%
P-glycoprotein inhibitior	-	0.5349	53.49%
P-glycoprotein substrate	-	0.5781	57.81%
CYP3A4 substrate	+	0.6834	68.34%
CYP2C9 substrate	+	0.5528	55.28%
CYP2D6 substrate	-	0.8538	85.38%
CYP3A4 inhibition	-	0.7480	74.80%
CYP2C9 inhibition	-	0.8064	80.64%
CYP2C19 inhibition	-	0.8689	86.89%
CYP2D6 inhibition	-	0.9666	96.66%
CYP1A2 inhibition	-	0.8380	83.80%
CYP2C8 inhibition	-	0.6782	67.82%
CYP inhibitory promiscuity	-	0.9730	97.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7393	73.93%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9269	92.69%
Skin irritation	-	0.7008	70.08%
Skin corrosion	-	0.9739	97.39%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3837	38.37%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7454	74.54%
skin sensitisation	-	0.8983	89.83%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6828	68.28%
Acute Oral Toxicity (c)	III	0.6381	63.81%
Estrogen receptor binding	+	0.8799	87.99%
Androgen receptor binding	+	0.6471	64.71%
Thyroid receptor binding	+	0.6020	60.20%
Glucocorticoid receptor binding	+	0.8294	82.94%
Aromatase binding	+	0.7015	70.15%
PPAR gamma	+	0.5365	53.65%
Honey bee toxicity	-	0.7604	76.04%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9401	94.01%

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	99.21%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	97.66%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.29%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	95.50%	82.69%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	90.69%	91.65%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.87%	94.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.18%	96.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.00%	91.07%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.65%	91.11%
CHEMBL299	P17252	Protein kinase C alpha	87.65%	98.03%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.45%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.45%	94.45%
CHEMBL268	P43235	Cathepsin K	86.14%	96.85%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.56%	94.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.99%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.33%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	84.14%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.71%	91.24%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.48%	97.09%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.38%	97.50%
CHEMBL5028	O14672	ADAM10	83.15%	97.50%
CHEMBL233	P35372	Mu opioid receptor	82.22%	97.93%
CHEMBL238	Q01959	Dopamine transporter	82.14%	95.88%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.10%	96.77%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.92%	89.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.87%	91.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.47%	91.19%
CHEMBL2581	P07339	Cathepsin D	80.48%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.06%	100.00%

Plants that contains it

• Alstonia angustiloba
• Amphiachyris dracunculoides
• Annona cherimola
• Baccharis grandicapitulata
• Beesia calthifolia
• Boschniakia rossica
• Botrychium ternatum
• Bursera kerberi
• Clerodendrum trichotomum
• Clinacanthus nutans
• Crotalaria stolzii
• Curcuma aeruginosa
• Delphinium giraldii
• Eucalyptus albens
• Euonymus fortunei
• Euploca racemosa
• Hedysarum gmelinii
• Helenium integrifolium
• Juniperus scopulorum
• Lasianthaea podocephala
• Lupinus cosentinii
• Melampodium leucanthum
• Myrica pensylvanica
• Neopallasia pectinata
• Papaver pseudocanescens
• Pellacalyx axillaris
• Peperomia filiformis
• Phlomis crinita
• Psidium acutangulum
• Pyrolirion flavum
• Renealmia alpinia
• Rhododendron mucronulatum
• Seseli libanotis
• Sideritis dasygnaphala
• Stellaria media
• Tephroseris kirilowii
• Tephroseris palustris

Cross-Links

• PubChem: 25006927
• NPASS: NPC264870