methyl (3S,4S)-3,4,6-trihydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate

Details

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Internal ID 14c085c5-573a-4c9b-9eb7-edf39e900661
Taxonomy Organoheterocyclic compounds > Naphthopyrans
IUPAC Name methyl (3S,4S)-3,4,6-trihydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate
SMILES (Canonical) CC1(C(C(C2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)O)O)C
SMILES (Isomeric) CC1([C@H]([C@H](C2=C(O1)C3=CC=CC=C3C(=C2C(=O)OC)O)O)O)C
InChI InChI=1S/C17H18O6/c1-17(2)15(20)13(19)10-11(16(21)22-3)12(18)8-6-4-5-7-9(8)14(10)23-17/h4-7,13,15,18-20H,1-3H3/t13-,15-/m0/s1
InChI Key ZNHMFNWRNCFYHA-ZFWWWQNUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C17H18O6
Molecular Weight 318.32 g/mol
Exact Mass 318.11033829 g/mol
Topological Polar Surface Area (TPSA) 96.20 Ų
XlogP 2.10
Atomic LogP (AlogP) 1.90
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl (3S,4S)-3,4,6-trihydroxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9158 91.58%
Caco-2 - 0.6825 68.25%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability + 0.6143 61.43%
Subcellular localzation Mitochondria 0.7301 73.01%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7851 78.51%
OATP1B3 inhibitior + 0.9527 95.27%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior - 0.7350 73.50%
P-glycoprotein inhibitior - 0.7584 75.84%
P-glycoprotein substrate - 0.7479 74.79%
CYP3A4 substrate + 0.6504 65.04%
CYP2C9 substrate - 0.8038 80.38%
CYP2D6 substrate - 0.8316 83.16%
CYP3A4 inhibition - 0.8474 84.74%
CYP2C9 inhibition - 0.9635 96.35%
CYP2C19 inhibition - 0.8171 81.71%
CYP2D6 inhibition - 0.8988 89.88%
CYP1A2 inhibition + 0.5729 57.29%
CYP2C8 inhibition + 0.5781 57.81%
CYP inhibitory promiscuity - 0.8393 83.93%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5655 56.55%
Eye corrosion - 0.9863 98.63%
Eye irritation - 0.8015 80.15%
Skin irritation - 0.7687 76.87%
Skin corrosion - 0.9572 95.72%
Ames mutagenesis + 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition - 0.7000 70.00%
Micronuclear + 0.7000 70.00%
Hepatotoxicity - 0.6875 68.75%
skin sensitisation - 0.9129 91.29%
Respiratory toxicity + 0.5778 57.78%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.5718 57.18%
Acute Oral Toxicity (c) III 0.6384 63.84%
Estrogen receptor binding + 0.6965 69.65%
Androgen receptor binding - 0.4850 48.50%
Thyroid receptor binding + 0.5776 57.76%
Glucocorticoid receptor binding + 0.8843 88.43%
Aromatase binding + 0.6801 68.01%
PPAR gamma + 0.8295 82.95%
Honey bee toxicity - 0.8646 86.46%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity + 0.9572 95.72%

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 99.29% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.21% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.45% 95.56%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 88.65% 95.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.62% 99.23%
CHEMBL1951 P21397 Monoamine oxidase A 84.51% 91.49%
CHEMBL221 P23219 Cyclooxygenase-1 84.16% 90.17%
CHEMBL2581 P07339 Cathepsin D 83.56% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.18% 89.00%
CHEMBL5028 O14672 ADAM10 82.13% 97.50%
CHEMBL340 P08684 Cytochrome P450 3A4 80.98% 91.19%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.57% 94.45%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 80.47% 92.62%

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.
Dolichopentas longiflora

Cross-Links

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PubChem 25145889
LOTUS LTS0141817
wikiData Q105380070