Pravastatin

Details

• Internal ID: aa1b298a-6dd0-438c-83bb-7b0b7ea8d872
• Taxonomy: Organic acids and derivatives > Hydroxy acids and derivatives > Medium-chain hydroxy acids and derivatives
• IUPAC Name: (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• InChI: InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
• InChI Key: TUZYXOIXSAXUGO-PZAWKZKUSA-N
• Popularity: 12,725 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆O₇
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.24610348 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.44
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 10

Synonyms

• 81093-37-0
• Pravastatinum
• Pravastatina
• Pravastatine
• Eptastatin
• Pravachol
• Pravator
• Pravastatin acid
• Pravastatinum [Latin]
• CCRIS 7557
• UNII-KXO2KT9N0G
• KXO2KT9N0G
• Pravastatin (INN)
• (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• CHEBI:63618
• C10AA03
• CHEMBL1144
• (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
• DTXSID6023498
• HSDB 8368
• Pravastatine [French]
• Pravastatina [Spanish]
• (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• Pravastatinum (Latin)
• PRAVASTATIN [INN]
• Pravastatin [INN:BAN]
• (betaR,deltaR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-beta,delta,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic acid
• 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-((2S)-2-methyl-1-oxobutoxy)-, (betaR,deltaR,1S,2S,6S,8S,8aR)-
• 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, (1S-(1alpha(betas*,deltas*),2alpha,6alpha,8beta(R*),8aalpha))-
• Mevalothin
• Pravator (TN)
• (+)-(3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acid
• Pravastatin-3H
• (+)-(3R,5R)-3,5-dihydroxy-7-((1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-(((S)-2-methylbutyryl)oxy)-1,2,6,7,8,8a-hexahydro-1-naphthyl)heptanoic acid
• (3R,5R)-3,5-dihydroxy-7-((1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-(((2S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid
• 3beta-Hydroxycompactin
• KS-5015
• PRAVASTATIN [VANDF]
• SCHEMBL1117
• PRAVASTATIN [WHO-DD]
• BIDD:GT0773
• PRAVASTATIN [EMA EPAR]
• DTXCID003498
• GTPL2953
• BDBM20688
• TUZYXOIXSAXUGO-PZAWKZKUSA-N
• HMS3715P11
• HY-B0165
• 1,4-Butanedisulfonicaciddisodiumsalt
• LMFA05000695
• s5713
• AKOS015895229
• CCG-221195
• DB00175
• NCGC00188962-01
• NCGC00188962-02
• 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-, (1S-(1alpha(betaS*,deltaS*),2alpha,6alpha,8beta(R*),8aalpha))-1-Naphthaleneheptanoic acid
• C01844
• D08410
• H12037
• EN300-6481366
• A840039
• SR-01000781259
• Q1240093
• SR-01000781259-2
• BRD-K60511616-236-01-4
• BRD-K60511616-236-02-2
• BRD-K60511616-236-08-9
• (1S-(1alpha(betaS*,deltaS*),2alpha,6alpha,8beta(R*),8aalpha))-1,2,6,7,8,8a-Hexahydro-beta,!d,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthaleneheptanoic Acid
• (3R,5R)-3,5-dihydroxy-7-((1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-((S)-2-methylbutanoyloxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid
• (3R,5R)-3,5-dihydroxy-7-[(1S,2S,6S,8S)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
• 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-.beta.,.delta.,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-, (.beta.R,.delta,R,1S,2S,6S,8S,8aR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	-	0.6499	64.99%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7797	77.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8427	84.27%
OATP1B3 inhibitior	+	0.8895	88.95%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.4584	45.84%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.9343	93.43%
CYP3A4 substrate	+	0.7484	74.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8872	88.72%
CYP3A4 inhibition	+	0.6571	65.71%
CYP2C9 inhibition	-	0.8909	89.09%
CYP2C19 inhibition	-	0.8513	85.13%
CYP2D6 inhibition	-	0.8903	89.03%
CYP1A2 inhibition	-	0.8952	89.52%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.7992	79.92%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.7165	71.65%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.9751	97.51%
Skin irritation	-	0.5217	52.17%
Skin corrosion	-	0.9442	94.42%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7402	74.02%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.9250	92.50%
skin sensitisation	-	0.8323	83.23%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.9316	93.16%
Acute Oral Toxicity (c)	III	0.3559	35.59%
Estrogen receptor binding	+	0.7313	73.13%
Androgen receptor binding	+	0.8240	82.40%
Thyroid receptor binding	-	0.5291	52.91%
Glucocorticoid receptor binding	+	0.7549	75.49%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.8545	85.45%
Honey bee toxicity	-	0.8024	80.24%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL402	P04035	HMG-CoA reductase	400 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.97%	96.09%
CHEMBL2581	P07339	Cathepsin D	98.07%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	97.30%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.56%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.82%	97.25%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	88.15%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.97%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.72%	94.08%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.22%	93.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.90%	94.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.76%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.43%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.25%	96.37%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.78%	94.97%
CHEMBL226	P30542	Adenosine A1 receptor	82.70%	95.93%
CHEMBL3776	Q14790	Caspase-8	81.43%	97.06%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.65%	89.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.30%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.14%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.08%	96.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54687
• LOTUS: LTS0227130
• wikiData: Q1240093