5,6,8-Trihydroxy-2,3-dimethyl-9-(5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)benzo[g]chromen-4-one

Details

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Internal ID 50d3c874-d363-4a22-ae00-37f1814c8082
Taxonomy Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
IUPAC Name 4,5,6-trihydroxy-2,3-dimethyl-9-(5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)benzo[g]chromen-8-one
SMILES (Canonical) CC1C(OC2=C(C1=O)C(=C3C(=C2)C(=C(C=C3O)O)C4=C5C=C6C(=C(C(=C(O6)C)C)O)C(=C5C(=CC4=O)O)O)O)C
SMILES (Isomeric) CC1C(OC2=C(C1=O)C(=C3C(=C2)C(=C(C=C3O)O)C4=C5C=C6C(=C(C(=C(O6)C)C)O)C(=C5C(=CC4=O)O)O)O)C
InChI InChI=1S/C30H24O10/c1-9-11(3)39-19-5-13-21(15(31)7-17(33)23(13)29(37)25(19)27(9)35)22-14-6-20-26(28(36)10(2)12(4)40-20)30(38)24(14)18(34)8-16(22)32/h5-9,11,31,33-34,36-38H,1-4H3
InChI Key BDIZPQDFMHMOFZ-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C30H24O10
Molecular Weight 544.50 g/mol
Exact Mass 544.13694696 g/mol
Topological Polar Surface Area (TPSA) 174.00 Ų
XlogP 3.10
Atomic LogP (AlogP) 5.22
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 1

Synonyms

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[9,9'-Bi-4H-naphtho[2,3-b]pyran]-4,4'-dione, 2,3-dihydro-5,5',6,6',8,8'-hexahydroxy-2,2',3,3'-tetramethyl-, stereoisomer
5,6,8-trihydroxy-2,3-dimethyl-9-(5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)benzo[g]chromen-4-one
DTXSID60910914
[9,9'-Bi-4H-naphtho[2,3-b]pyran]-4,4'-dione, 2,3-dihydro-5,5',6,6',8,8'-hexahydroxy-2,2',3,3'-tetramethyl-
5,5',6,6',8,8'-Hexahydroxy-2,2',3,3'-tetramethyl-2,3-dihydro-4H,4'H-[9,9'-binaphtho[2,3-b]pyran]-4,4'-dione

2D Structure

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2D Structure of 5,6,8-Trihydroxy-2,3-dimethyl-9-(5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl)benzo[g]chromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9374 93.74%
Caco-2 - 0.7223 72.23%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability - 0.5429 54.29%
Subcellular localzation Mitochondria 0.8155 81.55%
OATP2B1 inhibitior - 0.5616 56.16%
OATP1B1 inhibitior + 0.8020 80.20%
OATP1B3 inhibitior + 0.8148 81.48%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.6622 66.22%
P-glycoprotein inhibitior + 0.6030 60.30%
P-glycoprotein substrate + 0.5204 52.04%
CYP3A4 substrate + 0.6055 60.55%
CYP2C9 substrate - 0.5582 55.82%
CYP2D6 substrate - 0.8354 83.54%
CYP3A4 inhibition - 0.6075 60.75%
CYP2C9 inhibition + 0.5294 52.94%
CYP2C19 inhibition - 0.7532 75.32%
CYP2D6 inhibition - 0.9366 93.66%
CYP1A2 inhibition + 0.7158 71.58%
CYP2C8 inhibition + 0.4574 45.74%
CYP inhibitory promiscuity - 0.5104 51.04%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6214 62.14%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.8794 87.94%
Skin irritation - 0.6689 66.89%
Skin corrosion - 0.9397 93.97%
Ames mutagenesis - 0.5100 51.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7277 72.77%
Micronuclear + 0.8600 86.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.9184 91.84%
Respiratory toxicity + 0.5889 58.89%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.5375 53.75%
Nephrotoxicity - 0.8220 82.20%
Acute Oral Toxicity (c) III 0.6349 63.49%
Estrogen receptor binding + 0.8761 87.61%
Androgen receptor binding + 0.7246 72.46%
Thyroid receptor binding + 0.5961 59.61%
Glucocorticoid receptor binding + 0.7555 75.55%
Aromatase binding + 0.5709 57.09%
PPAR gamma + 0.5860 58.60%
Honey bee toxicity - 0.8615 86.15%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9489 94.89%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 98.75% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 97.05% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 93.30% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.21% 95.56%
CHEMBL3401 O75469 Pregnane X receptor 89.96% 94.73%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.18% 94.00%
CHEMBL5409 Q8TDU6 G-protein coupled bile acid receptor 1 87.93% 93.65%
CHEMBL2581 P07339 Cathepsin D 85.44% 98.95%
CHEMBL3194 P02766 Transthyretin 84.76% 90.71%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.11% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 81.63% 86.33%
CHEMBL3192 Q9BY41 Histone deacetylase 8 81.13% 93.99%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 80.18% 90.93%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Phyllolobium chinense

Cross-Links

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PubChem 176099
LOTUS LTS0161388
wikiData Q105224545