[(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-4-isopropenyl-2,13,15-trimethyl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate

Details

• Internal ID: 63dc60ba-b6ae-4c03-85e7-0bd2bbb9e68d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Rhamnofolane and daphnane diterpenoids
• IUPAC Name: [(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-2,13,15-trimethyl-4-prop-1-en-2-yl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate
• SMILES (Canonical): CC1CCCCCCCC23OC4C5C6C(O6)(C(C7(C(C1C(C7OC(=O)C8=CC=CC=C8)C)C5(O2)C(CC4(O3)C(=C)C)C)O)O)CO
• SMILES (Isomeric): C[C@H]1CCCCCCCC23O[C@@H]4[C@@H]5[C@H]6[C@](O6)([C@H]([C@]7([C@@H]([C@@H]1[C@@H]([C@@H]7OC(=O)C8=CC=CC=C8)C)[C@@]5(O2)[C@@H](C[C@@]4(O3)C(=C)C)C)O)O)CO
• InChI: InChI=1S/C37H50O9/c1-20(2)33-18-22(4)37-26-29(33)44-35(45-33,46-37)17-13-8-6-7-10-14-21(3)25-23(5)28(42-31(39)24-15-11-9-12-16-24)36(41,27(25)37)32(40)34(19-38)30(26)43-34/h9,11-12,15-16,21-23,25-30,32,38,40-41H,1,6-8,10,13-14,17-19H2,2-5H3/t21-,22+,23-,25-,26+,27+,28-,29+,30-,32+,33+,34-,35?,36+,37+/m0/s1
• InChI Key: IAPHKDDUYAWCMB-BLZWUUDBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₅₀O₉
• Molecular Weight: 638.80 g/mol
• Exact Mass: 638.34548317 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 4.52
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• Pimelea factor P2
• CHEMBL507954
• [(1R,2R,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15S,25R)-10,11-dihydroxy-9-(hydroxymethyl)-4-isopropenyl-2,13,15-trimethyl-8,24,26,27-tetraoxaheptacyclo[12.10.1.14,23.15,23.01,6.07,9.011,25]heptacosan-12-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8750	87.50%
Caco-2	-	0.8218	82.18%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7258	72.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8287	82.87%
OATP1B3 inhibitior	+	0.9118	91.18%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9370	93.70%
P-glycoprotein inhibitior	+	0.6431	64.31%
P-glycoprotein substrate	+	0.5671	56.71%
CYP3A4 substrate	+	0.7114	71.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8339	83.39%
CYP3A4 inhibition	-	0.6811	68.11%
CYP2C9 inhibition	-	0.7303	73.03%
CYP2C19 inhibition	-	0.7631	76.31%
CYP2D6 inhibition	-	0.9073	90.73%
CYP1A2 inhibition	-	0.7331	73.31%
CYP2C8 inhibition	+	0.7903	79.03%
CYP inhibitory promiscuity	-	0.7861	78.61%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6422	64.22%
Eye corrosion	-	0.9856	98.56%
Eye irritation	-	0.9169	91.69%
Skin irritation	-	0.6314	63.14%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.6940	69.40%
Human Ether-a-go-go-Related Gene inhibition	+	0.7226	72.26%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5680	56.80%
skin sensitisation	-	0.8607	86.07%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6963	69.63%
Acute Oral Toxicity (c)	I	0.3848	38.48%
Estrogen receptor binding	+	0.7588	75.88%
Androgen receptor binding	+	0.7478	74.78%
Thyroid receptor binding	+	0.5158	51.58%
Glucocorticoid receptor binding	+	0.5960	59.60%
Aromatase binding	+	0.7294	72.94%
PPAR gamma	+	0.6858	68.58%
Honey bee toxicity	-	0.8114	81.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	96.05%	90.17%
CHEMBL2581	P07339	Cathepsin D	95.02%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.44%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.94%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.63%	86.33%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	93.54%	94.08%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	92.17%	94.62%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	91.05%	83.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	89.56%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.70%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.11%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.90%	97.09%
CHEMBL2535	P11166	Glucose transporter	84.96%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.71%	97.14%
CHEMBL5028	O14672	ADAM10	84.19%	97.50%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.23%	89.44%
CHEMBL2996	Q05655	Protein kinase C delta	82.92%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.81%	92.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.84%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.51%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	81.37%	91.49%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.21%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.14%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.05%	93.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.81%	91.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.72%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.66%	100.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	80.43%	94.23%

Plants that contains it

• Daphne genkwa

Cross-Links

• PubChem: 44559301
• NPASS: NPC475548
• ChEMBL: CHEMBL507954
• LOTUS: LTS0276274
• wikiData: Q105036216