gamma-Rubromycin

Details

• Internal ID: 2a4cbd16-3f1c-4318-8881-15ab8e893e92
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Pyranochromenes
• IUPAC Name: methyl (2S)-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• SMILES (Canonical): COC1=CC(=O)C2=C(C1=O)C(=C3C(=C2O)CC4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O
• SMILES (Isomeric): COC1=CC(=O)C2=C(C1=O)C(=C3C(=C2O)C[C@@]4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O
• InChI: InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1
• InChI Key: CKLKRRFSZZUFKT-SANMLTNESA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₁₈O₁₂
• Molecular Weight: 522.40 g/mol
• Exact Mass: 522.07982601 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 27267-71-6
• methyl (2S)-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate
• .gamma.-Rubromycin
• DTXSID90181716
• AT25340
• J-016717
• (S)-4,4',9,9'-Tetrahydro-5',8',10-trihydroxy-7'-methoxy-4',9',9-trioxospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid methyl ester
• methyl (2S)-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxo-spiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f]benzofuran]-7-carboxylate
• Methyl 4,9,10'-trihydroxy-7-methoxy-5,8,9'-trioxo-4',5,8,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[4,3-g]chromene]-7'-carboxylate
• Spiro[benzol[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphthol[2,3-b]furan]-7-carboxylic acid, 4,5',8',0-tetrahydro-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxo-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9040	90.40%
Caco-2	-	0.7867	78.67%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8615	86.15%
OATP2B1 inhibitior	-	0.7138	71.38%
OATP1B1 inhibitior	+	0.8477	84.77%
OATP1B3 inhibitior	+	0.9031	90.31%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7321	73.21%
BSEP inhibitior	+	0.7126	71.26%
P-glycoprotein inhibitior	+	0.6904	69.04%
P-glycoprotein substrate	-	0.5509	55.09%
CYP3A4 substrate	+	0.6744	67.44%
CYP2C9 substrate	+	0.6393	63.93%
CYP2D6 substrate	-	0.8730	87.30%
CYP3A4 inhibition	-	0.7069	70.69%
CYP2C9 inhibition	-	0.7075	70.75%
CYP2C19 inhibition	-	0.5640	56.40%
CYP2D6 inhibition	-	0.8141	81.41%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.6668	66.68%
CYP inhibitory promiscuity	-	0.6669	66.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.5949	59.49%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.8799	87.99%
Skin irritation	-	0.7667	76.67%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7794	77.94%
Micronuclear	+	0.5459	54.59%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8230	82.30%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6219	62.19%
Acute Oral Toxicity (c)	I	0.5082	50.82%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	+	0.7427	74.27%
Thyroid receptor binding	-	0.5429	54.29%
Glucocorticoid receptor binding	+	0.8467	84.67%
Aromatase binding	+	0.7305	73.05%
PPAR gamma	+	0.6718	67.18%
Honey bee toxicity	-	0.7771	77.71%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9797	97.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2916	O14746	Telomerase reverse transcriptase	3000 nM	IC50	DOI: 10.1039/C0MD00241K

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.64%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.47%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.22%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.24%	94.00%
CHEMBL2535	P11166	Glucose transporter	93.82%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.59%	93.99%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.39%	95.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.35%	86.33%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	90.06%	94.42%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.93%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.88%	96.67%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.46%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.54%	96.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	84.89%	80.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.68%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.13%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.60%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.37%	93.04%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.88%	85.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.48%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.28%	90.71%

Plants that contains it

• Allium ampeloprasum
• Artemisia gmelinii
• Drimia altissima
• Helenium amarum
• Scutellaria viscidula
• Senecio retrorsus
• Taxus wallichiana

Cross-Links

• PubChem: 5464075
• NPASS: NPC174486
• ChEMBL: CHEMBL3347482
• LOTUS: LTS0187550
• wikiData: Q72506858