Prostratin

Details

• Internal ID: 45701ce4-a44d-4fe4-8f67-efbf894c5e8b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Tigliane and ingenane diterpenoids > Phorbol esters
• IUPAC Name: [(1R,2S,6R,10S,11R,13S,15R)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-13-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] acetate
• SMILES (Canonical): CC1CC2(C(C2(C)C)C3C1(C4C=C(C(=O)C4(CC(=C3)CO)O)C)O)OC(=O)C
• SMILES (Isomeric): C[C@@H]1C[C@@]2([C@@H](C2(C)C)[C@H]3[C@]1([C@@H]4C=C(C(=O)[C@]4(CC(=C3)CO)O)C)O)OC(=O)C
• InChI: InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1
• InChI Key: BOJKFRKNLSCGHY-HXGSDTCMSA-N
• Popularity: 144 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.50 g/mol
• Exact Mass: 390.20423867 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 60857-08-1
• 12-Deoxyphorbol-13-acetate
• 12-Deoxyphorbol 13-acetate
• CHEBI:69818
• (1aR,1bS,4aR,7aS,7bR,8R,9aS)-9a-(Acetyloxy)-1,1a,1b,4,4a,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one
• Stillingia Factor S7
• KO94U6DIQ6
• [dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] acetate
• NSC-623310
• (1AR,1BS,4AR,7AS,7BR,8R,9AS)-9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE
• NSC 623310; SA 101A; Stillingia factor S7
• SCHEMBL344837
• CHEMBL170518
• Prostratin, >=98% (HPLC)
• SA-101A
• BOJKFRKNLSCGHY-HXGSDTCMSA-N
• HMS3648K03
• BDBM50368315
• K-101A
• 13-O-ACETYL-12-DEOXYPHORBOL
• AKOS027250797
• CCG-208192
• SMP2_000144
• 12-deoxyphorbol-13-acetate (prostratin)
• MS-26507
• HY-107421
• CS-0028449
• C20197
• SR-01000946228
• Q3270742
• SR-01000946228-1
• BRD-K91145395-001-01-9
• 4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate
• 5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE, 9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-, (1AR,1BS,4AR,7AS,7BR,8R,9AS)-
• 5H-CYCLOPROPA(3,4)BENZ(1,2-E)AZULEN-5-ONE, 9A-(ACETYLOXY)-1,1A,1B,4,4A,7A,7B,8,9,9A-DECAHYDRO-4A,7B-DIHYDROXY-3-(HYDROXYMETHYL)-1,1,6,8-TETRAMETHYL-, (1AR-(1A.ALPHA.,1B.BETA.,4A.BETA.,7A.ALPHA.,7B.ALPHA.,8.ALPHA.,9A.ALPHA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9706	97.06%
Caco-2	-	0.6349	63.49%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6860	68.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8975	89.75%
OATP1B3 inhibitior	+	0.9136	91.36%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8843	88.43%
BSEP inhibitior	-	0.7331	73.31%
P-glycoprotein inhibitior	-	0.8503	85.03%
P-glycoprotein substrate	-	0.5996	59.96%
CYP3A4 substrate	+	0.6607	66.07%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.8032	80.32%
CYP2C9 inhibition	+	0.5158	51.58%
CYP2C19 inhibition	-	0.8923	89.23%
CYP2D6 inhibition	-	0.9309	93.09%
CYP1A2 inhibition	-	0.8593	85.93%
CYP2C8 inhibition	-	0.6676	66.76%
CYP inhibitory promiscuity	-	0.8402	84.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6786	67.86%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9073	90.73%
Skin irritation	-	0.6419	64.19%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4464	44.64%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6225	62.25%
skin sensitisation	-	0.7873	78.73%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.5702	57.02%
Acute Oral Toxicity (c)	III	0.5479	54.79%
Estrogen receptor binding	+	0.7236	72.36%
Androgen receptor binding	+	0.6825	68.25%
Thyroid receptor binding	+	0.6865	68.65%
Glucocorticoid receptor binding	+	0.7016	70.16%
Aromatase binding	+	0.7608	76.08%
PPAR gamma	+	0.5186	51.86%
Honey bee toxicity	-	0.8113	81.13%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9561	95.61%

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	97.35%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.38%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.95%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.47%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	85.97%	97.79%
CHEMBL1937	Q92769	Histone deacetylase 2	84.50%	94.75%
CHEMBL4794	Q8NER1	Vanilloid receptor	84.48%	98.97%
CHEMBL4208	P20618	Proteasome component C5	84.07%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.49%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.43%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.84%	100.00%

Plants that contains it

• Euphorbia caerulescens
• Euphorbia cornigera
• Euphorbia ebracteolata
• Euphorbia fischeri
• Euphorbia fischeriana
• Homalanthus nutans
• Trigonostemon howii

Cross-Links

• PubChem: 454217
• NPASS: NPC153036
• ChEMBL: CHEMBL170518
• LOTUS: LTS0196273
• wikiData: Q3270742