Rottlerin

Details

• Internal ID: 2ec286f4-5206-4187-95e2-86c5c12e4d9e
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
• SMILES (Canonical): CC1=C(C(=C(C(=C1O)C(=O)C)O)CC2=C(C(=C3C(=C2O)C=CC(O3)(C)C)C(=O)C=CC4=CC=CC=C4)O)O
• SMILES (Isomeric): CC1=C(C(=C(C(=C1O)C(=O)C)O)CC2=C(C(=C3C(=C2O)C=CC(O3)(C)C)C(=O)/C=C/C4=CC=CC=C4)O)O
• InChI: InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+
• InChI Key: DEZFNHCVIZBHBI-ZHACJKMWSA-N
• Popularity: 1,059 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₈O₈
• Molecular Weight: 516.50 g/mol
• Exact Mass: 516.17841785 g/mol
• Topological Polar Surface Area (TPSA): 145.00 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.40
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• Mallotoxin
• 82-08-6
• Kamalin
• NSC 56346
• NSC 94525
• C30H28O8
• EINECS 201-395-4
• UNII-E29LP3ZMUH
• E29LP3ZMUH
• (E)-1-(6-((3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one
• BRN 0070757
• CHEMBL34241
• BMK1-F10
• CHEBI:8899
• NSC56346
• NSC94525
• NSC-56346
• NSC-94525
• R 5648
• (E)-1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
• (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
• 1-[6-(3-Acetyl-2,4,6-trihydroxy-5-methyl-benzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenyl-propenone
• 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-3-phenylprop-2-en-1-one
• 5-18-05-00695 (Beilstein Handbook Reference)
• (2E)-1-[6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl]-3-phenylprop-2-en-1-one
• 3'-[(8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone
• 5,7-dihydroxy-2,2-dimethyl-6-(2,4,6-trihydroxy-3-methyl-5-acetylbenzyl)-8-cinnamoyl-1,2-chromene
• Acetophenone, 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-
• SR-01000076106
• 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
• (2E)-1-(6-(3-ACETYL-2,4,6-TRIHYDROXY-5-METHYLBENZYL)-5,7-DIHYDROXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-PHENYLPROP-2-EN-1-ONE
• (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
• 2-Propen-1-one, 1-(6-((3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl)-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl)-3-phenyl-, (E)-
• 2-Propen-1-one, 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-, (E)-
• Mallotoxin; NSC 56346; NSC 94525
• MFCD00017361
• R5648 (Rottlerin)
• ROTTLERIN [MI]
• NSC 94525Mallotoxin
• BiomolKI_000058
• BiomolKI2_000064
• D0R1JI
• Lopac0_001052
• BSPBio_001080
• MLS003370622
• SCHEMBL148175
• GTPL2611
• SCHEMBL1537089
• BCBcMAP01_000019
• CHEBI:92065
• Rottlerin - CAS 82-08-6
• DTXSID30231502
• HMS1362F21
• HMS1792F21
• HMS1990F21
• HMS3263C06
• HMS3403F21
• 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
• Tox21_501052
• BDBM50126829
• CCG-36482
• HB0561
• LMPK12120428
• AKOS024282482
• LP01052
• SDCCGSBI-0051022.P002
• IDI1_002135
• NCGC00025228-02
• NCGC00025228-03
• NCGC00025228-04
• NCGC00025228-05
• NCGC00025228-06
• NCGC00025228-07
• NCGC00025228-08
• NCGC00025228-09
• NCGC00025228-10
• NCGC00025228-11
• NCGC00025228-12
• NCGC00025228-19
• NCGC00261737-01
• HY-18980
• MS-29589
• SMR000058242
• CS-0014823
• EU-0101052
• S7862
• F88130
• Q7370686
• SR-01000076106-2
• SR-01000076106-3
• SR-01000076106-6
• BRD-K03816923-001-03-9
• BRD-K39256324-001-01-5
• Z2583131081
• (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methyl-phenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-chromen-8-yl]-3-phenyl-prop-2-en-1-one
• (E)-1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-on
• (E)-1-[6-[(3-Acetyl-2,4,6-trihydroxy-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one
• 1-(6-(3-acetyl-2,4,6-trihydroxy-5-methylbenzyl)-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl)-3-phenylprop-2-en-1-one
• 3'-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl)-2',4',6'-trihydroxy-5'-methyl-acetophenone
• 6-(3-Acetyl-2,4,6-trihydroxy-5-methylbenzyl)-2,2-dimethyl-8-(3-phenylpropenoyl)-2H-1-benzopyran-5,7-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9633	96.33%
Caco-2	-	0.8155	81.55%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7080	70.80%
OATP2B1 inhibitior	+	0.5684	56.84%
OATP1B1 inhibitior	+	0.7262	72.62%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9771	97.71%
P-glycoprotein inhibitior	+	0.7288	72.88%
P-glycoprotein substrate	-	0.6377	63.77%
CYP3A4 substrate	+	0.6034	60.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.7030	70.30%
CYP2C9 inhibition	+	0.6898	68.98%
CYP2C19 inhibition	-	0.6109	61.09%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7303	73.03%
CYP inhibitory promiscuity	+	0.5728	57.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6482	64.82%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.7428	74.28%
Skin irritation	-	0.7567	75.67%
Skin corrosion	-	0.9164	91.64%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8916	89.16%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.5948	59.48%
skin sensitisation	-	0.7344	73.44%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8476	84.76%
Acute Oral Toxicity (c)	III	0.6144	61.44%
Estrogen receptor binding	+	0.9125	91.25%
Androgen receptor binding	+	0.7671	76.71%
Thyroid receptor binding	+	0.6460	64.60%
Glucocorticoid receptor binding	+	0.8223	82.23%
Aromatase binding	+	0.6147	61.47%
PPAR gamma	+	0.8165	81.65%
Honey bee toxicity	-	0.8629	86.29%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5251	52.51%
Fish aquatic toxicity	+	0.9870	98.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM; 25118.9 nM; 17782.8 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM; 39810.7 nM; 39810.7 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL1293237	P54132	Bloom syndrome protein	31622.8 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2392	P06746	DNA polymerase beta	22387.2 nM	Potency	via CMAUP
CHEMBL1293278	O75496	Geminin	3981.1 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	39810.7 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2208	P49137	MAP kinase-activated protein kinase 2	5400 nM	IC50	PMID: 10998351
CHEMBL3094	Q8IW41	MAP kinase-activated protein kinase 5	1900 nM; 1900 nM	IC50; IC50	PMID: 10998351; PMID: 12672248
CHEMBL1293224	P10636	Microtubule-associated protein tau	17782.8 nM; 11220.2 nM; 15848.9 nM; 12589.3 nM; 17782.8 nM; 15848.9 nM; 17782.8 nM; 12589.3 nM	Potency; Potency; Potency; Potency; Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	1000 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	794.3 nM	Potency	via Super-PRED
CHEMBL1293298	Q01453	Peripheral myelin protein 22	47754.8 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	5011.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2996	Q05655	Protein kinase C delta	3000 nM	IC50	PMID: 12672248
CHEMBL1293232	Q16637	Survival motor neuron protein	11220.2 nM; 11220.2 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	44668.4 nM; 17782.8 nM; 7079.5 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.77%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.49%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.94%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.40%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.12%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.79%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.24%	95.56%
CHEMBL4208	P20618	Proteasome component C5	84.53%	90.00%
CHEMBL5028	O14672	ADAM10	83.00%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.38%	93.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.37%	89.67%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	80.27%	90.93%

Plants that contains it

• Adina racemosa
• Baileya multiradiata
• Eupatorium hyssopifolium
• Mallotus philippensis
• Maytenus horrida
• Miconia myriantha
• Onoseris lopezii
• Picea breweriana
• Populus grandidentata
• Symphyotrichum subulatum
• Virola elongata

Cross-Links

• PubChem: 5281847
• NPASS: NPC257236
• ChEMBL: CHEMBL34241
• LOTUS: LTS0082918
• wikiData: Q7370686