Biliverdin

Details

• Internal ID: 6e932d36-f3b4-42a4-b84f-4a9b813bb855
• Taxonomy: Organoheterocyclic compounds > Tetrapyrroles and derivatives > Bilirubins
• IUPAC Name: 3-[(2Z,5Z)-2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid
• SMILES (Canonical): CC1=C(C(=CC2=C(C(=C(N2)C=C3C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)NC1=CC4=NC(=O)C(=C4C)C=C)CCC(=O)O
• SMILES (Isomeric): CC\1=C(/C(=C/C2=C(C(=C(N2)/C=C\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/N/C1=C\C4=NC(=O)C(=C4C)C=C)CCC(=O)O
• InChI: InChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)/b24-13-,27-14-,28-15-
• InChI Key: RCNSAJSGRJSBKK-NSQVQWHSSA-N
• Popularity: 4,036 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₄N₄O₆
• Molecular Weight: 582.60 g/mol
• Exact Mass: 582.24783482 g/mol
• Topological Polar Surface Area (TPSA): 161.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 4
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• biliverdine
• Biliverdine Ix Alpha
• Biliverdin IX alpha
• uteroverdine
• Biliverdin IX
• dehydrobilirubin
• Oocyan
• 114-25-0
• 21H-Biline-8,12-dipropanoic acid, 3,18-diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-
• O9MIA842K9
• CHEBI:17033
• 1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenone
• 8,12-bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbilin-1(19)(21H,24H)-dione
• Biliverdine dihydrochloride
• NSC 62793
• UNII-O9MIA842K9
• NSC-62793
• Protobiliverdin IX
• EINECS 204-042-2
• Biliverdin IXalpha; Biliverdine (VAN)
• BILIVERDINE [MI]
• SCHEMBL51428
• CHEMBL455477
• SCHEMBL20503445
• SCHEMBL24582034
• CHEBI:188102
• Biline-8,12-dipropionic acid, 1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-
• DB02073
• HY-135005A
• 1,19,22,24-tetrahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid
• 3,18-Diethenyl-1,19,22,24-tetrahydro-2,7,13,17-tetrametyl-1,19-dioxo-21H-biline-8,12-dipropanoic Acid
• 3-[(2Z,5Z)-2-[[3-(2-carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxopyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene]-5-[(4-ethenyl-3-methyl-5-oxopyrrol-2-yl)methylidene]-4-methylpyrrol-3-yl]propanoic acid
• CS-0226051
• 55482-27-4
• C00500
• 4,5-DI(2-CARBOXYETHYL)-1,3,6,7-TETRAMETHYL-2,8-DIVINYLBILATRIENE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6817	68.17%
Caco-2	-	0.9210	92.10%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7116	71.16%
OATP2B1 inhibitior	-	0.7096	70.96%
OATP1B1 inhibitior	+	0.8114	81.14%
OATP1B3 inhibitior	-	0.2317	23.17%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8322	83.22%
BSEP inhibitior	+	0.8998	89.98%
P-glycoprotein inhibitior	+	0.7740	77.40%
P-glycoprotein substrate	+	0.6844	68.44%
CYP3A4 substrate	+	0.6481	64.81%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.9061	90.61%
CYP3A4 inhibition	-	0.7609	76.09%
CYP2C9 inhibition	+	0.5484	54.84%
CYP2C19 inhibition	-	0.7778	77.78%
CYP2D6 inhibition	-	0.8604	86.04%
CYP1A2 inhibition	+	0.5357	53.57%
CYP2C8 inhibition	+	0.4772	47.72%
CYP inhibitory promiscuity	-	0.8270	82.70%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9053	90.53%
Carcinogenicity (trinary)	Non-required	0.5932	59.32%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9021	90.21%
Skin irritation	-	0.7726	77.26%
Skin corrosion	-	0.9239	92.39%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3846	38.46%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8270	82.70%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.8584	85.84%
Acute Oral Toxicity (c)	III	0.5846	58.46%
Estrogen receptor binding	+	0.8115	81.15%
Androgen receptor binding	+	0.7503	75.03%
Thyroid receptor binding	+	0.6559	65.59%
Glucocorticoid receptor binding	+	0.6432	64.32%
Aromatase binding	+	0.6321	63.21%
PPAR gamma	+	0.6674	66.74%
Honey bee toxicity	-	0.8535	85.35%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.9386	93.86%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.01%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.27%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.09%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	92.02%	89.34%
CHEMBL221	P23219	Cyclooxygenase-1	90.99%	90.17%
CHEMBL4070	P19784	Casein kinase II alpha (prime)	88.78%	91.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.26%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.94%	96.09%
CHEMBL255	P29275	Adenosine A2b receptor	87.45%	98.59%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.37%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.23%	91.11%
CHEMBL2185	Q96GD4	Serine/threonine-protein kinase Aurora-B	84.49%	96.80%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	83.84%	95.70%
CHEMBL5979	P05186	Alkaline phosphatase, tissue-nonspecific isozyme	83.00%	85.40%
CHEMBL1255126	O15151	Protein Mdm4	82.02%	90.20%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.33%	93.00%

Plants that contains it

• Allanblackia gabonensis
• Allanblackia stuhlmannii
• Garcinia multiflora

Cross-Links

• PubChem: 5280353
• LOTUS: LTS0061463
• wikiData: Q27134492