Resistomycin

Details

• Internal ID: 85b72f5e-5972-4d2f-a3b0-fa517e04a801
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthrols
• IUPAC Name: 6,10,14,19-tetrahydroxy-4,9,9-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(19),3,5,7,10,13,15,17-octaene-2,12-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(C3=C4C5=C2C1=C(C=C5C(C(=C4C(=O)C=C3O)O)(C)C)O)O
• SMILES (Isomeric): CC1=CC(=O)C2=C(C3=C4C5=C2C1=C(C=C5C(C(=C4C(=O)C=C3O)O)(C)C)O)O
• InChI: InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,24-25,27-28H,1-3H3
• InChI Key: MJKDGCARCYPVQG-UHFFFAOYSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₆O₆
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.09468823 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 0

Synonyms

• Heliomycin
• Geliomycin
• 20004-62-0
• Itamycin
• Croceomycin
• Antibiotic A 3733A
• 11029-70-2
• A 3733A
• DTXSID4046101
• X-340
• CHEBI:29671
• Heliomycin; Geliomycin; Itamycin
• 7N3A092A5X
• 2H-Benzo(cd)pyrene-2,6(1H)-dione, 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-
• NCGC00160275-02
• Heliomycin [INN]
• DTXCID2026101
• Geliomitsin
• 2,4,10,14-tetrahydroxy-7,7,12-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(18),2,4,8,10,12,14,16-octaene-6,19-dione
• CAS-20004-62-0
• BRN 2187224
• UNII-7N3A092A5X
• 6,10,14,19-tetrahydroxy-4,9,9-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(19),3,5,7,10,13,15,17-octaene-2,12-dione
• Heliomycin (Salt/Mix)
• RESISTOMYCIN [MI]
• 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-2H-benzo[cd]pyrene-2,6(1H)-dione
• HELIOMYCIN [WHO-DD]
• 4-08-00-03704 (Beilstein Handbook Reference)
• ANTIBIOTIC A-3733A
• SCHEMBL2134180
• CHEMBL1320139
• ABLACSIRCKEUOB-UHFFFAOYSA-N
• NP285
• Tox21_111753
• AKOS000715231
• Tox21_111753_1
• NCGC00160275-01
• NCGC00160275-03
• NCGC00160672-01
• SR-01000318568
• J-012937
• SR-01000318568-1
• BRD-K64517075-001-01-9
• Q27110219
• 1,2-Dihydro-1,1,9-trimethyl-3,5,7,10-tetrahydroxy-6H-benzo[c,d]pyrene-2,6-dione
• 2H-Benzo[cf]pyrene-2,6(1H)-dione,3,5,7,10-tetrahydroxy-1,1,9-trimethyl-
• 3,5,7,10-tetrahydroxy-1,1,9-trimethyl-2H-benzo(c,d)pyrene-2,6(1H)-dione
• 3,5,7,10-TETRAHYDROXY-1,1,9-TRIMETHYL-2H-BENZO(CF)PYRENE-2,6(1H)-DIONE
• 3,5,7,10-Tetrahydroxy-1,1,9-trimethyl-2H-benzo[cd]pyrene-2,6(1H)-dione #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.6191	61.91%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8480	84.80%
OATP2B1 inhibitior	-	0.5588	55.88%
OATP1B1 inhibitior	+	0.8160	81.60%
OATP1B3 inhibitior	+	0.8816	88.16%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.8018	80.18%
P-glycoprotein inhibitior	-	0.8522	85.22%
P-glycoprotein substrate	-	0.8068	80.68%
CYP3A4 substrate	+	0.6282	62.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8716	87.16%
CYP3A4 inhibition	-	0.7710	77.10%
CYP2C9 inhibition	+	0.8864	88.64%
CYP2C19 inhibition	+	0.5586	55.86%
CYP2D6 inhibition	-	0.7858	78.58%
CYP1A2 inhibition	+	0.8207	82.07%
CYP2C8 inhibition	-	0.7291	72.91%
CYP inhibitory promiscuity	+	0.8009	80.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9265	92.65%
Carcinogenicity (trinary)	Non-required	0.5673	56.73%
Eye corrosion	-	0.9921	99.21%
Eye irritation	+	0.7025	70.25%
Skin irritation	-	0.6544	65.44%
Skin corrosion	-	0.9233	92.33%
Ames mutagenesis	+	0.5646	56.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5574	55.74%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.5779	57.79%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5537	55.37%
Acute Oral Toxicity (c)	III	0.6827	68.27%
Estrogen receptor binding	+	0.8809	88.09%
Androgen receptor binding	-	0.5144	51.44%
Thyroid receptor binding	+	0.5378	53.78%
Glucocorticoid receptor binding	+	0.8563	85.63%
Aromatase binding	-	0.7203	72.03%
PPAR gamma	+	0.8013	80.13%
Honey bee toxicity	-	0.8359	83.59%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.10%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.10%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.81%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.27%	93.99%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.59%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.49%	95.64%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	84.02%	91.49%
CHEMBL4208	P20618	Proteasome component C5	83.26%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	82.25%	94.73%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.11%	92.68%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.54%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.84%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.80%	93.40%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.13%	96.67%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.06%	96.21%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 135430323
• LOTUS: LTS0041861
• wikiData: Q27110219