Dicrocin

Details

• Internal ID: 026b0b9e-6a88-464f-ba9d-46a87cb24fc0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)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)CO)O)O)O)C=CC=C(C)C(=O)OC2C(C(C(C(O2)CO)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)/C)/C=C/C=C(/C(=O)O[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)CO)\C
• InChI: InChI=1S/C32H44O14/c1-17(11-7-13-19(3)29(41)45-31-27(39)25(37)23(35)21(15-33)43-31)9-5-6-10-18(2)12-8-14-20(4)30(42)46-32-28(40)26(38)24(36)22(16-34)44-32/h5-14,21-28,31-40H,15-16H2,1-4H3/b6-5+,11-7+,12-8+,17-9+,18-10+,19-13+,20-14+/t21-,22-,23-,24-,25+,26+,27-,28-,31+,32+/m1/s1
• InChI Key: QBZWPZHDUZGTLS-IIDMIUPYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₁₄
• Molecular Weight: 652.70 g/mol
• Exact Mass: 652.27310607 g/mol
• Topological Polar Surface Area (TPSA): 233.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

• Crocin IV
• crocetin diglucosyl ester
• Crocetin diglucopyranoside
• 57710-64-2
• bis(beta-D-glucosyl) crocetin
• all-trans-crocetin di(beta-D-glucosyl) ester
• UNII-8PF1UU481E
• 8PF1UU481E
• crocetin di(beta-D-glucopyranosyl) ester
• trans-crocetin di(beta-D-glucosyl) ester
• trans-Crocetin di-(beta-D-glucosyl) ester
• bis[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• beta-D-Glucopyranose, 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-(hydroxymethyl)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
• CHEBI:62768
• DTXSID001312682
• HY-N9371
• MS-30971
• CS-0159554
• C19868
• TRANS-CROCETIN DI-(.BETA.-D-GLUCOSYL) ESTER
• Q27132162
• ALL-TRANS-CROCETIN DI(.BETA.-D-GLUCOSYL) ESTER
• .BETA.-D-GLUCOPYRANOSE, 1,1'-((2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-TETRAMETHYL-2,4,6,8,10,12,14-HEXADECAHEPTAENEDIOATE)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8451	84.51%
Caco-2	-	0.8464	84.64%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	0.5670	56.70%
OATP1B1 inhibitior	+	0.8373	83.73%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8241	82.41%
P-glycoprotein inhibitior	+	0.7284	72.84%
P-glycoprotein substrate	-	0.9428	94.28%
CYP3A4 substrate	+	0.5699	56.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8723	87.23%
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	-	0.8758	87.58%
CYP inhibitory promiscuity	-	0.8758	87.58%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6766	67.66%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.8195	81.95%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6452	64.52%
Micronuclear	-	0.6641	66.41%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.8841	88.41%
Respiratory toxicity	-	0.7111	71.11%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.5558	55.58%
Acute Oral Toxicity (c)	III	0.5725	57.25%
Estrogen receptor binding	+	0.7625	76.25%
Androgen receptor binding	-	0.5883	58.83%
Thyroid receptor binding	+	0.5978	59.78%
Glucocorticoid receptor binding	+	0.6555	65.55%
Aromatase binding	+	0.5516	55.16%
PPAR gamma	+	0.7147	71.47%
Honey bee toxicity	-	0.7652	76.52%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7755	77.55%
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	94.75%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.78%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	90.61%	94.73%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.98%	97.47%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.47%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.61%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.69%	89.00%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.98%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.67%	96.47%
CHEMBL2581	P07339	Cathepsin D	80.71%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.58%	86.92%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.27%	94.33%

Plants that contains it

• Crocus sativus
• Gardenia jasminoides

Cross-Links

• PubChem: 25244294
• NPASS: NPC55553
• LOTUS: LTS0028360
• wikiData: Q27132162