Pyripyropene A

Details

• Internal ID: 416f1729-900d-4fc3-9247-d6fde694a06f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 1-hydroxysteroids
• IUPAC Name: [(1S,2S,5S,6R,7R,9S,10S,18R)-5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl acetate
• InChI: InChI=1S/C31H37NO10/c1-16(33)38-15-30(5)22-13-24(40-18(3)35)31(6)27(29(22,4)10-9-23(30)39-17(2)34)26(36)25-21(42-31)12-20(41-28(25)37)19-8-7-11-32-14-19/h7-8,11-12,14,22-24,26-27,36H,9-10,13,15H2,1-6H3/t22-,23+,24+,26+,27-,29+,30+,31-/m1/s1
• InChI Key: PMMQOFWSZRQWEV-RVTXXDJVSA-N
• Popularity: 40 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₇NO₁₀
• Molecular Weight: 583.60 g/mol
• Exact Mass: 583.24174638 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.76
• H-Bond Acceptor: 11
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 147444-03-9
• EKX655RQH9
• [(1S,2S,5S,6R,7R,9S,10S,18R)-5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo[8.8.0.02,7.012,17]octadeca-12(17),13-dien-6-yl]methyl acetate
• CHEBI:64695
• DTXSID601017602
• FO 1289A
• FO-1289A
• ((1S,2S,5S,6R,7R,9S,10S,18R)-5,9-diacetyloxy-18-hydroxy-2,6,10-trimethyl-16-oxo-14-pyridin-3-yl-11,15-dioxatetracyclo(8.8.0.02,7.012,17)octadeca-12(17),13-dien-6-yl)methyl acetate
• RefChem:177779
• DTXCID501475786
• CHEMBL4518651
• (+)-Pyripyropene A
• (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(acetoxymethyl)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,6-diyl diacetate
• (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[(acetyloxy)methyl]-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl diacetate
• (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(Acetoxymethyl)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromene-3,6-diyl diacetate
• SCHEMBL106356
• MEGxm0_000331
• orb1708776
• SCHEMBL31376280
• ACon0_000398
• ACon1_001711
• BDBM50611411
• AKOS027320855
• NCGC00180218-01
• NCGC00180218-02!
• HY-117832
• CS-0068214
• G91508
• T12592
• P983692
• Q27133384
• (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,6-Bis(acetyloxy)-4-[(acetyloxy)methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-11-one
• 2H,11H-Naphtho(2,1-b)pyrano(3,4-e)pyran-11-one, 1,3,4,4a,5,6a,12,12a,12b-decahydro-4-((acetyloxy)methyl)-3,6-bis(acetyloxy)-12-hydroxy-9-(3-pyridinyl)-4,6a,12b-trimethyl-
• 2H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-11-one, 3,6-bis(acetyloxy)-4-[(acetyloxy)methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-9-(3-pyridinyl)-, (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-
• 7T8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8807	88.07%
Caco-2	-	0.7963	79.63%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8551	85.51%
OATP2B1 inhibitior	-	0.7184	71.84%
OATP1B1 inhibitior	+	0.8684	86.84%
OATP1B3 inhibitior	+	0.8500	85.00%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9955	99.55%
P-glycoprotein inhibitior	+	0.8187	81.87%
P-glycoprotein substrate	+	0.5196	51.96%
CYP3A4 substrate	+	0.6952	69.52%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8451	84.51%
CYP3A4 inhibition	-	0.5605	56.05%
CYP2C9 inhibition	-	0.8401	84.01%
CYP2C19 inhibition	-	0.7895	78.95%
CYP2D6 inhibition	-	0.9559	95.59%
CYP1A2 inhibition	-	0.5946	59.46%
CYP2C8 inhibition	+	0.8485	84.85%
CYP inhibitory promiscuity	-	0.5995	59.95%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6423	64.23%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.8589	85.89%
Skin corrosion	-	0.9641	96.41%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8160	81.60%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5669	56.69%
skin sensitisation	-	0.9188	91.88%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.8486	84.86%
Acute Oral Toxicity (c)	III	0.4712	47.12%
Estrogen receptor binding	+	0.8333	83.33%
Androgen receptor binding	+	0.7096	70.96%
Thyroid receptor binding	+	0.6036	60.36%
Glucocorticoid receptor binding	+	0.7689	76.89%
Aromatase binding	+	0.7376	73.76%
PPAR gamma	+	0.7580	75.80%
Honey bee toxicity	-	0.7155	71.55%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9736	97.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4465	O75908	Acyl coenzyme A:cholesterol acyltransferase 2	179 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.25%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.85%	86.33%
CHEMBL2581	P07339	Cathepsin D	94.57%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.05%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.59%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.59%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.96%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.53%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.19%	97.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.00%	81.11%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	87.27%	91.65%
CHEMBL5028	O14672	ADAM10	87.13%	97.50%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	86.85%	85.30%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.00%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.07%	97.28%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.12%	94.62%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.50%	97.53%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.38%	92.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.76%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.38%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11828024
• LOTUS: LTS0200539
• wikiData: Q27133384