Isodiospyrin

Details

• Internal ID: 1fd705fc-5939-4b0b-9902-3fe9cdbc26a7
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC2=C(C(=O)C=CC2=O)C(=C1C3=C4C(=O)C=CC(=O)C4=C(C=C3C)O)O
• SMILES (Isomeric): CC1=CC2=C(C(=O)C=CC2=O)C(=C1C3=C4C(=O)C=CC(=O)C4=C(C=C3C)O)O
• InChI: InChI=1S/C22H14O6/c1-9-7-11-12(23)3-4-13(24)19(11)22(28)18(9)17-10(2)8-16(27)20-14(25)5-6-15(26)21(17)20/h3-8,27-28H,1-2H3
• InChI Key: OEEOHKZVBKYMBA-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₄O₆
• Molecular Weight: 374.30 g/mol
• Exact Mass: 374.07903816 g/mol
• Topological Polar Surface Area (TPSA): 109.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.25
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 20175-84-2
• Isoldiospyrin
• rac-Isodiospyrin
• 89475-33-2
• C22H14O6
• NSC208731
• 5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxonaphthalen-1-yl)-7-methylnaphthalene-1,4-dione
• CHEBI:6002
• NSC 208731
• [1,2'-Binaphthalene]-5,5',8,8'-tetrone, 1',4-dihydroxy-2,3'-dimethyl-, (-)-
• 5-hydroxy-6-(4-hydroxy-2-methyl-5,8-dioxo-1-naphthyl)-7-methyl-naphthalene-1,4-dione
• [1,2'-Binaphthalene]-5,5',8,8'-tetrone, 1',4-dihydroxy-2,3'-dimethyl-, (R)- (8CI); (1R)-1',4-Dihydroxy-2,3'-dimethyl[1,2'-binaphthalene]-5,5',8,8'-tetrone; (-)-Isodiospyrin
• (1,2'-Binaphthalene)-5,5',8,8'-tetrone, 1',4-dihydroxy-2,3'-dimethyl-, (-)-
• CHEMBL1992900
• BDBM93040
• DTXSID90174007
• OEEOHKZVBKYMBA-UHFFFAOYSA-N
• HY-N3488
• AKOS030533948
• CS-O-01697
• NSC-208731
• NCI60_001744
• CS-0024366
• Q27106975
• 5,5'-Dihydroxy-7,7'-dimethyl-6,8'-bi[1,4-naphthoquinone]
• [1,5',8,8'-tetrone, 1',4-dihydroxy-2,3'-dimethyl-, (-)-
• 1',4-dihydroxy-2,3'-dimethyl-(1,2'-binaphthalene)-5,5',8,8'-tetrone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9958	99.58%
Caco-2	-	0.6077	60.77%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8971	89.71%
OATP2B1 inhibitior	-	0.5643	56.43%
OATP1B1 inhibitior	+	0.8856	88.56%
OATP1B3 inhibitior	+	0.9170	91.70%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5760	57.60%
P-glycoprotein inhibitior	-	0.8556	85.56%
P-glycoprotein substrate	-	0.9308	93.08%
CYP3A4 substrate	-	0.5244	52.44%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.8665	86.65%
CYP3A4 inhibition	-	0.6475	64.75%
CYP2C9 inhibition	+	0.9411	94.11%
CYP2C19 inhibition	+	0.6023	60.23%
CYP2D6 inhibition	-	0.7762	77.62%
CYP1A2 inhibition	+	0.8847	88.47%
CYP2C8 inhibition	-	0.8957	89.57%
CYP inhibitory promiscuity	+	0.6427	64.27%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8109	81.09%
Carcinogenicity (trinary)	Non-required	0.5203	52.03%
Eye corrosion	-	0.9953	99.53%
Eye irritation	-	0.5642	56.42%
Skin irritation	-	0.5303	53.03%
Skin corrosion	-	0.9296	92.96%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6378	63.78%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.7552	75.52%
skin sensitisation	-	0.7756	77.56%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	-	0.6523	65.23%
Acute Oral Toxicity (c)	III	0.5532	55.32%
Estrogen receptor binding	+	0.7432	74.32%
Androgen receptor binding	+	0.6515	65.15%
Thyroid receptor binding	-	0.8257	82.57%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6939	69.39%
PPAR gamma	+	0.6060	60.60%
Honey bee toxicity	-	0.9766	97.66%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9974	99.74%

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	95.36%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.63%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.82%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.22%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.88%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.49%	89.00%
CHEMBL4208	P20618	Proteasome component C5	88.16%	90.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	86.21%	96.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.65%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	83.50%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.84%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.40%	93.03%

Plants that contains it

• Actinidia polygama
• Diospyros abyssinica
• Diospyros argentea
• Diospyros batocana
• Diospyros chamaethamnus
• Diospyros chloroxylon
• Diospyros ferrea
• Diospyros lotus
• Diospyros loureiroana subsp. loureiroana
• Diospyros maritima
• Diospyros mespiliformis
• Diospyros morrisiana
• Diospyros paniculata
• Diospyros piscatoria
• Diospyros sylvatica
• Diospyros verrucosa
• Diospyros virginiana
• Diospyros zombensis
• Euclea divinorum
• Euclea natalensis
• Nepeta cataria

Cross-Links

• PubChem: 99298
• NPASS: NPC50924
• LOTUS: LTS0120039
• wikiData: Q27106975