prostaglandin D2

Details

• Internal ID: 4b570753-e2f6-4a42-9124-4c5fc48442e7
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
• IUPAC Name: (Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
• SMILES (Canonical): CCCCCC(C=CC1C(C(CC1=O)O)CC=CCCCC(=O)O)O
• SMILES (Isomeric): CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
• InChI Key: BHMBVRSPMRCCGG-OUTUXVNYSA-N
• Popularity: 3,688 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 12

Synonyms

• PGD2
• 41598-07-6
• 11-Dehydroprostaglandin F2-alpha
• 11-Dehydroprostaglandin F2alpha
• BRN 2170623
• (5Z,13E,15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate
• RXY07S6CZ2
• (Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
• CHEBI:15555
• (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate
• 9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoic acid
• [3H]prostaglandin D2
• UNII-RXY07S6CZ2
• (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
• [3H]-PGD2
• 11-Dehydroprostaglandin F2 alpha
• prosta-glandin d2
• [3H]11-dehydroprostaglandin F2-alpha
• PGD2 (Prostaglandin D2)
• BSPBio_001486
• PG2
• BML1-F05
• GTPL1881
• GTPL1891
• SCHEMBL2508829
• CHEMBL1235252
• BDBM21544
• DTXSID30897162
• BHMBVRSPMRCCGG-OUTUXVNYSA-N
• HMS1361K08
• HMS1791K08
• HMS1989K08
• HMS3402K08
• HMS3648M03
• (5E,13E)-9,15-DIHYDROXY-11-OXOPROSTA-5,13-DIEN-1-OIC ACID
• LMFA03010004
• AKOS032954030
• Prostaglandin D2, >=95%, synthetic
• Prostaglandin D2, cell culture tested
• DB02056
• IDI1_033956
• Prosta-5,13-dien-1-oic acid, 9,15-dihydroxy-11-oxo-, (5Z,9-alpha,13E,15S)-
• NCGC00161284-01
• NCGC00161284-02
• NCGC00161284-03
• MS-25470
• HY-101988
• CS-0022427
• C00696
• 9S,15S-dihydroxy-11-oxo-5Z,13E-prostadienoate
• Q419750
• SR-01000946237
• SR-01000946237-1
• 9alpha,15S-dihydroxy-11-oxo-prosta-5Z,13E-dien-1-oic acid
• E8965369-341A-46F4-8677-2CEB4F9432BA
• (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoate
• (5Z,13E)-(15S)-9,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
• (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoate
• (5Z,13E)-(15S)-9a,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid
• (5Z,13E,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoate
• (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oate
• (5z,13e)-(15s)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
• (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoic acid
• (5Z,13E,15S)-9-alpha,15-dihydroxy-11-oxoprosta-5,13-dienoic acid
• (5Z,13E,15S)-9a,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
• (5Z,13E,15S)-9alpha,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
• (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oate
• (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oate
• (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxo-prosta-5,13-dien-1-oic acid
• (5Z,9alpha,13E,15S)-9,15-dihydroxy-11-oxoprosta-5,13-dien-1-oic acid
• (5Z,9-alpha,13E,15S)-9,15-dihydroxy-11-oxo-Prosta-5,13-dien-1-oic acid
• 9,15- DIHYDROXY-11-OXO-PROSTA-5,13-DIEN-1-OIC ACID, (5Z,9-.ALPHA.,13E,15S)
• (5Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9681	96.81%
Caco-2	-	0.7987	79.87%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8162	81.62%
OATP2B1 inhibitior	-	0.8565	85.65%
OATP1B1 inhibitior	+	0.7594	75.94%
OATP1B3 inhibitior	+	0.9430	94.30%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.4586	45.86%
P-glycoprotein inhibitior	-	0.7826	78.26%
P-glycoprotein substrate	-	0.6413	64.13%
CYP3A4 substrate	+	0.5848	58.48%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9502	95.02%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.8327	83.27%
CYP inhibitory promiscuity	-	0.9725	97.25%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7224	72.24%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9488	94.88%
Skin irritation	+	0.5568	55.68%
Skin corrosion	-	0.8674	86.74%
Ames mutagenesis	-	0.8978	89.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6411	64.11%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.8351	83.51%
skin sensitisation	-	0.8636	86.36%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8575	85.75%
Acute Oral Toxicity (c)	III	0.6983	69.83%
Estrogen receptor binding	+	0.8285	82.85%
Androgen receptor binding	+	0.6198	61.98%
Thyroid receptor binding	-	0.5885	58.85%
Glucocorticoid receptor binding	+	0.8002	80.02%
Aromatase binding	-	0.7513	75.13%
PPAR gamma	+	0.6464	64.64%
Honey bee toxicity	-	0.9326	93.26%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9878	98.78%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5071	Q9Y5Y4	G protein-coupled receptor 44	7 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.54%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	97.20%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.11%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.04%	93.56%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	88.98%	96.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.04%	97.25%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	86.85%	92.08%
CHEMBL1781	P11387	DNA topoisomerase I	86.72%	97.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.63%	85.14%
CHEMBL299	P17252	Protein kinase C alpha	86.48%	98.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.81%	90.71%
CHEMBL5255	O00206	Toll-like receptor 4	83.68%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.15%	100.00%
CHEMBL1881	P43116	Prostanoid EP2 receptor	81.92%	93.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.73%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.63%	91.19%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.07%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.80%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.72%	95.56%
CHEMBL1902	P62942	FK506-binding protein 1A	80.68%	97.05%
CHEMBL230	P35354	Cyclooxygenase-2	80.60%	89.63%

Plants that contains it

• Larix sibirica

Cross-Links

• PubChem: 448457
• LOTUS: LTS0276317
• wikiData: Q419750