Diospyrin

Details

• Internal ID: 6b6d313f-cd69-4963-9022-e640e725a46f
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5-hydroxy-6-(5-hydroxy-7-methyl-1,4-dioxonaphthalen-2-yl)-7-methylnaphthalene-1,4-dione
• SMILES (Canonical): CC1=CC2=C(C(=C1)O)C(=O)C=C(C2=O)C3=C(C4=C(C=C3C)C(=O)C=CC4=O)O
• SMILES (Isomeric): CC1=CC2=C(C(=C1)O)C(=O)C=C(C2=O)C3=C(C4=C(C=C3C)C(=O)C=CC4=O)O
• InChI: InChI=1S/C22H14O6/c1-9-5-12-19(16(25)6-9)17(26)8-13(21(12)27)18-10(2)7-11-14(23)3-4-15(24)20(11)22(18)28/h3-8,25,28H,1-2H3
• InChI Key: WRFTYMHHWSAKSK-UHFFFAOYSA-N
• Popularity: 43 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): 3.11
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Euclein
• 28164-57-0
• O0IQZ8B2R7
• CHEBI:4633
• NSC-208730
• 1',5-Dihydroxy-3',7-dimethyl-(2,2'-binaphthalene)-1,4,5',8'-tetrone
• [2,2'-Binaphthalene]-1,4,5',8'-tetrone, 1',5-dihydroxy-3',7-dimethyl-
• (2,2'-BINAPHTHALENE)-1,4,5',8'-TETRONE, 1',5-DIHYDROXY-3',7-DIMETHYL-
• UNII-O0IQZ8B2R7
• CCRIS 7335
• NSC 208730
• BRN 1297556
• 5-hydroxy-6-(5-hydroxy-7-methyl-1,4-dioxonaphthalen-2-yl)-7-methylnaphthalene-1,4-dione
• CHEMBL242550
• SCHEMBL24684659
• BDBM93038
• DTXSID30182429
• WRFTYMHHWSAKSK-UHFFFAOYSA-N
• NSC208730
• 5,5'-Dihydroxy 7,7'-binaphthoquinone
• Q27106425
• [2,4,5',8'-tetrone, 1',5-dihydroxy-3',7-dimethyl-
• 1',5-dihydroxy-3',7-dimethyl-2,2'-binaphthalene-1,4,5',8'-tetrone
• 5-hydroxy-2-(1-hydroxy-3-methyl-5,8-dioxo-2-naphthyl)-7-methyl-naphthalene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9968	99.68%
Caco-2	+	0.5295	52.95%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.9018	90.18%
OATP2B1 inhibitior	+	0.5693	56.93%
OATP1B1 inhibitior	+	0.8767	87.67%
OATP1B3 inhibitior	+	0.9148	91.48%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4859	48.59%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.8416	84.16%
CYP3A4 substrate	+	0.5568	55.68%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.8665	86.65%
CYP3A4 inhibition	-	0.7006	70.06%
CYP2C9 inhibition	+	0.9592	95.92%
CYP2C19 inhibition	+	0.7766	77.66%
CYP2D6 inhibition	-	0.7041	70.41%
CYP1A2 inhibition	+	0.9159	91.59%
CYP2C8 inhibition	-	0.7739	77.39%
CYP inhibitory promiscuity	+	0.8403	84.03%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8088	80.88%
Carcinogenicity (trinary)	Non-required	0.5102	51.02%
Eye corrosion	-	0.9965	99.65%
Eye irritation	+	0.5350	53.50%
Skin irritation	-	0.5908	59.08%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5981	59.81%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.7357	73.57%
skin sensitisation	-	0.6582	65.82%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6863	68.63%
Acute Oral Toxicity (c)	III	0.4962	49.62%
Estrogen receptor binding	+	0.8110	81.10%
Androgen receptor binding	+	0.6478	64.78%
Thyroid receptor binding	-	0.8091	80.91%
Glucocorticoid receptor binding	+	0.6991	69.91%
Aromatase binding	-	0.7117	71.17%
PPAR gamma	+	0.5644	56.44%
Honey bee toxicity	-	0.9406	94.06%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
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
CHEMBL1951	P21397	Monoamine oxidase A	98.37%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.48%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.52%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.61%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.15%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	89.09%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.38%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.94%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.16%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.13%	93.03%

Plants that contains it

• Diospyros abyssinica
• Diospyros batocana
• Diospyros chamaethamnus
• Diospyros chloroxylon
• Diospyros ebenum
• Diospyros mannii
• Diospyros mespiliformis
• Diospyros montana
• Diospyros piscatoria
• Diospyros sylvatica
• Diospyros virginiana
• Euclea natalensis
• Euclea pseudebenus

Cross-Links

• PubChem: 308140
• LOTUS: LTS0037015
• wikiData: Q27106425