Genipin

Details

• Internal ID: 913ccb7d-2f3f-4423-9302-e4d2b85cd91c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• SMILES (Canonical): COC(=O)C1=COC(C2C1CC=C2CO)O
• SMILES (Isomeric): COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
• InChI: InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1
• InChI Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N
• Popularity: 2,206 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₅
• Molecular Weight: 226.23 g/mol
• Exact Mass: 226.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 6902-77-8
• (+)-Genipin
• A3V2NE52YG
• methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• DTXSID30894999
• methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
• RefChem:142877
• DTXCID601324556
• 636-196-5
• 1,4a,5,7a-Tetrahydro-1-hydroxy-7-(hydroxymethyl)-cyclopenta(c)pyran-4-carboxylic acid methyl ester
• MFCD00888600
• CHEBI:5298
• ST080860
• C09780
• methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate
• (1R,4aS,7aS)-methyl 1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• Methyl (1S,2R,6S)-2-Hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
• AC1L9CSN
• UNII-A3V2NE52YG
• Genipin (Standard)
• SureCN34249
• SCHEMBL34249
• MLS006010198
• CHEMBL459016
• orb1306097
• GLXC-06545
• HMS3261H13
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R-(1.ALPHA.,4A.ALPHA.,7A.ALPHA.))-
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER
• EX-A4263
• Tox21_500516
• BDBM50565452
• Genipin, >=98% (HPLC), powder
• HY-17389R
• s2412
• AKOS015851487
• AC-8847
• BCP9000722
• CCG-221820
• FG30976
• LP00516
• SDCCGSBI-0633724.P001
• NCGC00186010-01
• NCGC00186010-03
• NCGC00186010-10
• NCGC00261201-01
• AS-18947
• HY-17389
• SMR001456266
• SY015025
• G0458
• NS00097440
• AB01566854_01
• EN300-7409283
• 902G778
• F809725
• Q1463401
• BRD-K28824103-001-02-8
• BRD-K28824103-001-04-4
• Genipin is known as an aglycone dervied from Geniposide.
• Z2044761865
• (1R,4aS,7aS)-1-Hydroxy-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
• 1202641-87-9
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R,4AS,7AS)-
• Cyclopenta(c)pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester
• Cyclopenta[c]pyran-4-carboxylic acid, 1,4a,5,7a-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methylester, (1R,4aS,7aS)-
• methyl (4aS,7aS,1R)-1-hydroxy-7-(hydroxymethyl)-1,5,4a,7a-tetrahydro-4aH-cyclo penta[1,2-d]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9471	94.71%
Caco-2	-	0.7653	76.53%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6292	62.92%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8717	87.17%
OATP1B3 inhibitior	+	0.9638	96.38%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9476	94.76%
P-glycoprotein inhibitior	-	0.9723	97.23%
P-glycoprotein substrate	-	0.7874	78.74%
CYP3A4 substrate	+	0.5405	54.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8463	84.63%
CYP3A4 inhibition	-	0.7608	76.08%
CYP2C9 inhibition	-	0.8319	83.19%
CYP2C19 inhibition	-	0.7691	76.91%
CYP2D6 inhibition	-	0.8858	88.58%
CYP1A2 inhibition	-	0.5396	53.96%
CYP2C8 inhibition	-	0.7684	76.84%
CYP inhibitory promiscuity	-	0.6513	65.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.7068	70.68%
Eye corrosion	-	0.9263	92.63%
Eye irritation	-	0.8722	87.22%
Skin irritation	-	0.7534	75.34%
Skin corrosion	-	0.9553	95.53%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6414	64.14%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5932	59.32%
skin sensitisation	-	0.8248	82.48%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7772	77.72%
Acute Oral Toxicity (c)	III	0.5546	55.46%
Estrogen receptor binding	-	0.6984	69.84%
Androgen receptor binding	-	0.6068	60.68%
Thyroid receptor binding	-	0.6319	63.19%
Glucocorticoid receptor binding	-	0.5171	51.71%
Aromatase binding	-	0.6827	68.27%
PPAR gamma	-	0.8232	82.32%
Honey bee toxicity	-	0.9291	92.91%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8323	83.23%

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	96.94%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.05%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	90.70%	83.82%
CHEMBL4208	P20618	Proteasome component C5	85.03%	90.00%
CHEMBL2581	P07339	Cathepsin D	84.89%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.12%	97.09%
CHEMBL5028	O14672	ADAM10	81.70%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.10%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.54%	86.92%

Plants that contains it

• Apodytes dimidiata
• Eucommia ulmoides
• Gardenia jasminoides
• Garrya elliptica
• Genipa americana
• Rothmannia globosa

Cross-Links

• PubChem: 442424
• NPASS: NPC211455
• ChEMBL: CHEMBL459016
• LOTUS: LTS0216206
• wikiData: Q1463401