Crocetin gentiobiosylglucosyl ester

Details

• Internal ID: 31d38a22-7e8b-4fa4-8d71-a311cae6ec5d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 1-O-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 16-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• SMILES (Canonical): CC(=CC=CC=C(C)C=CC=C(C)C(=O)OC1C(C(C(C(O1)COC2C(C(C(C(O2)CO)O)O)O)O)O)O)C=CC=C(C)C(=O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)O)/C=C/C=C(\C)/C(=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C38H54O19/c1-18(11-7-13-20(3)34(50)56-37-32(48)29(45)26(42)23(16-40)54-37)9-5-6-10-19(2)12-8-14-21(4)35(51)57-38-33(49)30(46)27(43)24(55-38)17-52-36-31(47)28(44)25(41)22(15-39)53-36/h5-14,22-33,36-49H,15-17H2,1-4H3/b6-5+,11-7+,12-8+,18-9+,19-10+,20-13+,21-14+/t22-,23-,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,36-,37+,38+/m1/s1
• InChI Key: CZSBHMFVVLYIQQ-DRVLGOCHSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₄O₁₉
• Molecular Weight: 814.80 g/mol
• Exact Mass: 814.32592949 g/mol
• Topological Polar Surface Area (TPSA): 312.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -3.05
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 15

Synonyms

• crocetin gentiobiosylglucosyl ester
• ZF2MOD2N6Y
• Crocin 2
• DTXSID80856143
• All-trans-crocetin beta-D-gentiobiosyl-beta-D-glucosyl ester
• trans-Crocetin (beta-D-glucosyl)-(beta-D-gentiobiosyl) ester
• beta-D-Glucopyranose, 6-o-beta-D-glucopyranosyl-, 1-((2E,4E,6E,8E,10E,12E,14E)-beta-D-glucopyranosyl 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate)
• RefChem:1082262
• DTXCID301511479
• Crocin II
• tricrocin
• beta-D-gentiobiosyl beta-D-glucosyl crocetin
• 1-[(2E,4E,6E,8E,10E,12E,14E)-b-D-glucopyranosyl 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate] 6-O-b-D-glucopyranosyl-b-D-Glucopyranose
• 1-O-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 16-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• trans-crocetin (beta-D-glucosyl)(beta-D-gentibiosyl) ester
• trans-crocetin (beta-D-glucosyl)-(beta-D-gentibiosyl) ester
• CrocinII
• (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• 1-[(2E,4E,6E,8E,10E,12E,14E)-beta-D-glucopyranosyl 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate] 6-O-beta-D-glucopyranosyl-beta-D-glucopyranose
• UNII-ZF2MOD2N6Y
• C38H54O19
• MFCD11111454
• Crocin II (Standard)
• orb1303760
• CHEMBL2311863
• SCHEMBL15726728
• CHEBI:62771
• HY-N0698R
• HMS3887O09
• HY-N0698
• MSK14868
• s9232
• AKOS030530137
• CCG-270508
• OC09382
• AC-34859
• AS-75256
• CS-0009715
• C17513
• Q27132166
• trans-Crocetin (beta-D-glucosyl) (beta-D-gentibiosyl) ester
• ALL-TRANS-CROCETIN .BETA.-D-GENTIOBIOSYL-.BETA.-D-GLUCOSYL ESTER
• TRANS-CROCETIN (.BETA.-D-GLUCOSYL)-(.BETA.-D-GENTIOBIOSYL) ESTER
• .BETA.-D-GLUCOPYRANOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-, 1-((2E,4E,6E,8E,10E,12E,14E)-.BETA.-D-GLUCOPYRANOSYL 2,6,11,15-TETRAMETHYL-2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOATE)
• Crocetingentiobiosylglucosyl ester;Tricrocin;Crocin 2;?-D-Glucopyranose 6-O-?-D-glucopyranosyl-1-[(2E,4E,6E,8E,10E,12E,14E)-?-D-gluc opyranosyl 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate]
• O1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] O16-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8451	84.51%
Caco-2	-	0.8617	86.17%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	0.5723	57.23%
OATP1B1 inhibitior	+	0.8403	84.03%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9065	90.65%
P-glycoprotein inhibitior	+	0.7337	73.37%
P-glycoprotein substrate	-	0.8970	89.70%
CYP3A4 substrate	+	0.6050	60.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.9295	92.95%
CYP2C9 inhibition	-	0.9011	90.11%
CYP2C19 inhibition	-	0.9032	90.32%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.9389	93.89%
CYP2C8 inhibition	-	0.7973	79.73%
CYP inhibitory promiscuity	-	0.8758	87.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9063	90.63%
Skin irritation	-	0.8195	81.95%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.8354	83.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7444	74.44%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8841	88.41%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6016	60.16%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	+	0.7873	78.73%
Androgen receptor binding	-	0.5574	55.74%
Thyroid receptor binding	+	0.5902	59.02%
Glucocorticoid receptor binding	+	0.7237	72.37%
Aromatase binding	+	0.6053	60.53%
PPAR gamma	+	0.7490	74.90%
Honey bee toxicity	-	0.7597	75.97%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7555	75.55%
Fish aquatic toxicity	-	0.3838	38.38%

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	95.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.31%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	91.66%	94.73%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.51%	96.95%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	87.36%	97.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.04%	99.17%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.65%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.58%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.49%	98.75%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.12%	94.80%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.70%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.53%	94.33%
CHEMBL2581	P07339	Cathepsin D	80.43%	98.95%

Plants that contains it

• Crocus sativus
• Gardenia jasminoides

Cross-Links

• PubChem: 9940690
• NPASS: NPC285588
• LOTUS: LTS0215875
• wikiData: Q27132166