Crocetin(2-)

Details

• Internal ID: 28d70e7a-0e65-4b25-b775-3a7ef5c74911
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Acyclic diterpenoids
• IUPAC Name: (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)[O-])C=CC=C(C)C(=O)[O-]
• SMILES (Isomeric): C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)[O-])/C)/C)/C=C/C=C(/C(=O)[O-])\C
• InChI: InChI=1S/C20H24O4/c1-15(11-7-13-17(3)19(21)22)9-5-6-10-16(2)12-8-14-18(4)20(23)24/h5-14H,1-4H3,(H,21,22)(H,23,24)/p-2/b6-5+,11-7+,12-8+,15-9+,16-10+,17-13+,18-14+
• InChI Key: PANKHBYNKQNAHN-MQQNZMFNSA-L
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₄-₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.15180918 g/mol
• Topological Polar Surface Area (TPSA): 80.30 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 1.94
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• (2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethylhexadeca-2,4,6,8,10,12,14-heptaenedioate
• crocetin dianion
• 8,8'-diapocarotenedioate
• CHEBI:62767
• 8,8'-diapo-8,8'-carotenedioate
• 8,8'-diapo-psi,psi-carotenedioate
• 8,8'-diapocarotene-8,8'-dioate
• Q27132161

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9291	92.91%
Caco-2	+	0.7806	78.06%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7096	70.96%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.8890	88.90%
OATP1B3 inhibitior	+	0.9550	95.50%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9198	91.98%
P-glycoprotein inhibitior	-	0.6287	62.87%
P-glycoprotein substrate	-	0.9648	96.48%
CYP3A4 substrate	-	0.5932	59.32%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	-	0.8920	89.20%
CYP3A4 inhibition	-	0.9158	91.58%
CYP2C9 inhibition	-	0.8898	88.98%
CYP2C19 inhibition	-	0.9236	92.36%
CYP2D6 inhibition	-	0.9279	92.79%
CYP1A2 inhibition	-	0.9322	93.22%
CYP2C8 inhibition	-	0.9697	96.97%
CYP inhibitory promiscuity	-	0.9231	92.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.6491	64.91%
Carcinogenicity (trinary)	Non-required	0.6748	67.48%
Eye corrosion	+	0.7781	77.81%
Eye irritation	+	0.7379	73.79%
Skin irritation	+	0.6729	67.29%
Skin corrosion	+	0.5747	57.47%
Ames mutagenesis	-	0.5391	53.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.6824	68.24%
skin sensitisation	+	0.5733	57.33%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	-	0.7556	75.56%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	+	0.7780	77.80%
Acute Oral Toxicity (c)	III	0.6432	64.32%
Estrogen receptor binding	+	0.9076	90.76%
Androgen receptor binding	-	0.8213	82.13%
Thyroid receptor binding	+	0.6818	68.18%
Glucocorticoid receptor binding	+	0.5703	57.03%
Aromatase binding	+	0.7782	77.82%
PPAR gamma	+	0.8364	83.64%
Honey bee toxicity	-	0.8673	86.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9429	94.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	86.05%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.61%	96.09%

Plants that contains it

• Crocus sativus
• Gardenia jasminoides

Cross-Links

• PubChem: 25244519
• NPASS: NPC43061