Crocin

Details

• Internal ID: 6c7dc8a6-834e-4849-bcdd-d3f3cd4dcc2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: bis[(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)COC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)O[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CO[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)CO)/C)/C)/C=C/C=C(/C(=O)O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO[C@@H]4O[C@@H]([C@H]([C@@H]([C@H]4O)O)O)CO)\C
• InChI: InChI=1S/C44H64O24/c1-19(11-7-13-21(3)39(59)67-43-37(57)33(53)29(49)25(65-43)17-61-41-35(55)31(51)27(47)23(15-45)63-41)9-5-6-10-20(2)12-8-14-22(4)40(60)68-44-38(58)34(54)30(50)26(66-44)18-62-42-36(56)32(52)28(48)24(16-46)64-42/h5-14,23-38,41-58H,15-18H2,1-4H3/b6-5+,11-7+,12-8+,19-9+,20-10+,21-13+,22-14+/t23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37-,38-,41-,42-,43+,44+/m1/s1
• InChI Key: SEBIKDIMAPSUBY-RTJKDTQDSA-N
• Popularity: 679 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₄H₆₄O₂₄
• Molecular Weight: 977.00 g/mol
• Exact Mass: 976.37875290 g/mol
• Topological Polar Surface Area (TPSA): 391.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -5.23
• H-Bond Acceptor: 24
• H-Bond Donor: 14
• Rotatable Bonds: 18

Synonyms

• 42553-65-1
• Crocine
• Crocin 1
• alpha-Crocin
• Crocin A
• Crocetin bis(gentiobiosyl) ester
• crocetin di-gentiobiose ester
• DTXSID7046172
• 877GWI46C2
• trans-Crocetin di(beta-D-gentiobiosyl) ester
• all-trans-Crocetin di-beta-D-gentiobiosyl ester
• DTXCID201457
• bis[(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
• 39465-00-4
• 8,8'-Diapo-psi,psi-carotenedioic acid, bis(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl) ester
• beta-D-Glucopyranose, 6-O-beta-D-glucopyranosyl-, 1,1'-((2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate)
• bis(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• bis((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
• bis(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)methyl)oxan-2-yl (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• RefChem:919204
• 254-465-1
• 255-881-6
• Crocin I
• Gardenia Yellow
• 94238-00-3
• crocin-1
• Saffron
• .alpha.-crocin
• Crocetin digentiobiose ester
• crocetin digentiobioside
• CHEMBL446785
• 11012-59-2
• NCGC00160471-01
• Bis(6-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl) 8,8'-diapo-psi,psi-carotenedioate
• (2E,4E,6E,8E,10E,12E,14E)-Bis((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) 2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• CCRIS 678
• CCRIS 7705
• EINECS 255-881-6
• BRN 6473367
• UNII-F32BA2H92Z
• UNII-877GWI46C2
• Crocin-I
• HSDB 8211
• Natural red 1
• EINECS 254-465-1
• Natural yellow 19
• CROCIN [WHO-DD]
• Crocin - microscopy grade
• F32BA2H92Z
• orb1301900
• SCHEMBL1463936
• CHEBI:79068
• MSK2444
• bis(beta-D-gentiobiosyl) crocetin
• HMS3887O07
• Crocetin Di(Beta-Gentiobiosyl)Ester
• HY-N0697
• crocetin di-beta-D-gentiobiose ester
• Tox21_111837
• BDBM50260195
• s9511
• AKOS015896765
• DB11874
• OC08286
• NCGC00160471-02
• 8,8'-Diapo-.psi.,.psi.-carotenedioic acid, bis(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl) ester
• DA-72400
• FC158408
• FS-10544
• CROCETIN DI-GENTIOBIOSE ESTER [MI]
• CAS-42553-65-1
• C.I. 75100
• CS-0009714
• trans-crocetin bis(beta-D-gentiobiosyl) ester
• C08589
• Q424767
• TRANS-CROCETIN DI(.BETA.-D-GENTIOBIOSYL) ESTER
• ALL-TRANS-CROCETIN DI-.BETA.-D-GENTIOBIOSYL ESTER
• (2E,4E,6E,8E,10E,12E,14E)-Bis((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)2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• .BETA.-D-GLUCOPYRANOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-, 1,1'-((2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-TETRAMETHYL-2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOATE)
• Bis(6-O-?-D-Glucopyranosyl-?-D-glucopyranosyl) 8,8'-diapo-?-?-carotenedioic acid ester;Crocetin digentiobiose ester
• bis[(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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8451	84.51%
Caco-2	-	0.8600	86.00%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	0.8562	85.62%
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	+	0.9421	94.21%
P-glycoprotein inhibitior	+	0.7375	73.75%
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	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9012	90.12%
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	+	0.7367	73.67%
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	+	0.7708	77.08%
Androgen receptor binding	+	0.5417	54.17%
Thyroid receptor binding	+	0.6079	60.79%
Glucocorticoid receptor binding	+	0.7320	73.20%
Aromatase binding	+	0.6299	62.99%
PPAR gamma	+	0.7682	76.82%
Honey bee toxicity	-	0.7597	75.97%
Biodegradation	-	0.8500	85.00%
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

• Buddleja officinalis
• Crocus sativus
• Crocus vernus
• Gardenia jasminoides

Cross-Links

• PubChem: 5281233
• NPASS: NPC110072
• LOTUS: LTS0243166
• wikiData: Q424767