Capsorubin

Details

• Internal ID: 03fb2da5-7f78-42aa-a501-6b4270042737
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-bis[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
• SMILES (Canonical): CC(=CC=CC=C(C)C=CC=C(C)C=CC(=O)C1(CC(CC1(C)C)O)C)C=CC=C(C)C=CC(=O)C2(CC(CC2(C)C)O)C
• SMILES (Isomeric): C/C(=C\C=C\C=C(\C=C\C=C(\C=C\C(=O)[C@]1(C(C[C@@H](C1)O)(C)C)C)/C)/C)/C=C/C=C(/C=C/C(=O)[C@]2(C(C[C@@H](C2)O)(C)C)C)\C
• InChI: InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-23-35(43)39(9)27-33(41)25-37(39,5)6)15-11-12-16-30(2)18-14-20-32(4)22-24-36(44)40(10)28-34(42)26-38(40,7)8/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,39-,40-/m0/s1
• InChI Key: GVOIABOMXKDDGU-YUURSNASSA-N
• Popularity: 413 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₆O₄
• Molecular Weight: 600.90 g/mol
• Exact Mass: 600.41786026 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 10.30
• Atomic LogP (AlogP): 9.07
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 12

Synonyms

• 470-38-2
• all-trans-capsorubin
• 805VAB3L0H
• EINECS 207-425-2
• (3S,3'S,5R,5'R)-3,3'-DIHYDROXY-.KAPPA.,.KAPPA.-CAROTENE-6,6'-DIONE
• (3S,3'S,5R,5'R)-3,3'-Dihydroxy-kappa,kappa-carotene-6,6'-dione
• (2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-Bis((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
• E160 (Capsorubin)
• UNII-805VAB3L0H
• SCHEMBL115586
• CAPSORUBIN, ALL-TRANS-
• CHEBI:3378
• DTXSID901018116
• C40H56O4
• LMPR01070048
• AKOS040754968
• 3,3'-Dihydroxy-k,k-carotene-6,6'-dione
• C08585
• Q15633290
• (3S,5R,3'S,5'R)-3,3'-dihydroxy-kappa,kappa-carotene-6,6'-dione
• .KAPPA.,.KAPPA.-CAROTENE-6,6'-DIONE, 3,3'-DIHYDROXY-, (3S,3'S,5R,5'R)-
• 2,4,6,8,10,12,14,16,18-EICOSANONAENE-1,20-DIONE, 1,20-BIS(4-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-, (1R,1R,4S,4S)-(ALL-E)-
• 28368-02-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.8092	80.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7277	72.77%
OATP2B1 inhibitior	+	0.5735	57.35%
OATP1B1 inhibitior	+	0.9443	94.43%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9939	99.39%
P-glycoprotein inhibitior	+	0.7816	78.16%
P-glycoprotein substrate	-	0.8264	82.64%
CYP3A4 substrate	+	0.5913	59.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8511	85.11%
CYP3A4 inhibition	-	0.8582	85.82%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.9156	91.56%
CYP2D6 inhibition	-	0.9390	93.90%
CYP1A2 inhibition	-	0.9154	91.54%
CYP2C8 inhibition	-	0.9478	94.78%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7944	79.44%
Carcinogenicity (trinary)	Non-required	0.6062	60.62%
Eye corrosion	-	0.9731	97.31%
Eye irritation	-	0.9082	90.82%
Skin irritation	+	0.5208	52.08%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.5008	50.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6650	66.50%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6296	62.96%
skin sensitisation	+	0.6377	63.77%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	+	0.6286	62.86%
Acute Oral Toxicity (c)	III	0.4769	47.69%
Estrogen receptor binding	+	0.7955	79.55%
Androgen receptor binding	+	0.7193	71.93%
Thyroid receptor binding	+	0.7040	70.40%
Glucocorticoid receptor binding	+	0.7607	76.07%
Aromatase binding	-	0.4851	48.51%
PPAR gamma	+	0.7235	72.35%
Honey bee toxicity	-	0.8137	81.37%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9733	97.33%

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	95.25%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.71%	91.11%
CHEMBL1870	P28702	Retinoid X receptor beta	81.88%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.86%	94.45%
CHEMBL2581	P07339	Cathepsin D	81.41%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.20%	91.07%
CHEMBL2061	P19793	Retinoid X receptor alpha	80.49%	91.67%

Plants that contains it

• Capsicum annuum
• Lilium pumilum

Cross-Links

• PubChem: 5281229
• NPASS: NPC150641
• LOTUS: LTS0027442
• wikiData: Q15633290