Bixin

Details

• Internal ID: f82734d7-9440-435d-a7cf-e76f4967d1a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Acyclic diterpenoids
• IUPAC Name: (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
• InChI: InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
• InChI Key: RAFGELQLHMBRHD-SLEZCNMESA-N
• Popularity: 884 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₄
• Molecular Weight: 394.50 g/mol
• Exact Mass: 394.21440943 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 7.50
• Atomic LogP (AlogP): 5.81
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 10

Synonyms

• 6983-79-5
• (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
• DTXSID1024629
• Methyl (9-cis)-hydrogen-6,6'-diapo-psi,psi-carotenedioate
• 9L7T4VB66G
• Annatto (E 160b)
• E160b
• CHEBI:3136
• DTXCID304535
• 2,4,6,8,10,12,14,16,18-Eicosanonaenedioic acid, 4,8,13,17-tetramethyl-, monomethyl ester, (2E,4Z,6E,8E,10E,12E,14E,16E,18E)-
• RefChem:29838
• 230-248-7
• cis-Bixin
• 20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
• Isobixin
• Stable bixin
• 6'-methyl hydrogen 9'-Z-6,6'-diapocarotene-6,6'-dioate
• 6'-methyl hydrogen 9'-cis-6,6'-diapocarotene-6,6'-dioate
• C25H30O4
• alpha-Bixin
• EINECS 230-248-7
• UNII-9L7T4VB66G
• CCRIS 9384
• a-Bixin
• (9-cis)-6,6'-diapo-?,?-carotenedioic acid 6-methyl ester; a-Bixin; Bixinol
• BIXINS CIS-FORM
• .ALPHA.-BIXIN
• BIXIN [MART.]
• BIXINS CIS-FORM [MI]
• orb1710247
• orb3140792
• SCHEMBL9939959
• CHEMBL1172615
• 6-Methyl hydrogen (9Z)-6,6'-diapocarotene-6,6'-dioate
• HMS6018A15
• 2,4,6,8,10,12,14,16,18-Eicosanonaenedioic acid,4,8,13,17-tetramethyl-, monomethyl ester,(2E,4Z,6E,8E,10E,12E,14E,16E,18E)-
• Bixin, >=95.0% (HPLC)
• HY-N6884
• Tox21_303095
• MSK157564
• AKOS040732608
• FB31050
• NCGC00257045-01
• MS-26633
• CAS-6983-79-5
• CS-0100483
• C08582
• T10554
• Q424572
• 6,6'-DIAPO-.PSI.,.PSI.-CAROTENEDIOIC ACID, 6-METHYL ESTER, 9-CIS-
• (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxo-icosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
• 2,4,6,8,10,12,14,16,18-EICOSANONAENEDIOIC ACID, 4,8,13,17-TETRAMETHYL-, 1-METHYL ESTER, (2E,4Z,6E,8E,10E,12E,14E,16E,18E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9559	95.59%
Caco-2	-	0.5159	51.59%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7732	77.32%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.9142	91.42%
OATP1B3 inhibitior	+	0.9488	94.88%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9839	98.39%
P-glycoprotein inhibitior	+	0.6944	69.44%
P-glycoprotein substrate	-	0.9353	93.53%
CYP3A4 substrate	-	0.5341	53.41%
CYP2C9 substrate	-	0.5872	58.72%
CYP2D6 substrate	-	0.9088	90.88%
CYP3A4 inhibition	-	0.9369	93.69%
CYP2C9 inhibition	-	0.9293	92.93%
CYP2C19 inhibition	-	0.9406	94.06%
CYP2D6 inhibition	-	0.9398	93.98%
CYP1A2 inhibition	-	0.9625	96.25%
CYP2C8 inhibition	-	0.9265	92.65%
CYP inhibitory promiscuity	-	0.9497	94.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	+	0.5966	59.66%
Carcinogenicity (trinary)	Non-required	0.6934	69.34%
Eye corrosion	-	0.5753	57.53%
Eye irritation	-	0.8143	81.43%
Skin irritation	-	0.5549	55.49%
Skin corrosion	-	0.7781	77.81%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8838	88.38%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7138	71.38%
skin sensitisation	+	0.7431	74.31%
Respiratory toxicity	-	0.8222	82.22%
Reproductive toxicity	-	0.8556	85.56%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	+	0.7433	74.33%
Acute Oral Toxicity (c)	III	0.5194	51.94%
Estrogen receptor binding	+	0.8856	88.56%
Androgen receptor binding	+	0.5797	57.97%
Thyroid receptor binding	+	0.6472	64.72%
Glucocorticoid receptor binding	+	0.6167	61.67%
Aromatase binding	+	0.7021	70.21%
PPAR gamma	+	0.7286	72.86%
Honey bee toxicity	-	0.8520	85.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.8524	85.24%

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	99.47%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.69%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.73%	95.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.08%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.84%	94.45%

Plants that contains it

• Bixa orellana

Cross-Links

• PubChem: 5281226
• LOTUS: LTS0117455
• wikiData: Q424572