Sigmoidin D

Details

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Internal ID 42ce4e5f-81d1-4d97-af72-594cf9c2793c
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
IUPAC Name (2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
SMILES (Canonical) CC1(C(CC2=C(O1)C(=CC(=C2)C3CC(=O)C4=C(C=C(C=C4O3)O)O)O)O)C
SMILES (Isomeric) CC1([C@H](CC2=C(O1)C(=CC(=C2)[C@@H]3CC(=O)C4=C(C=C(C=C4O3)O)O)O)O)C
InChI InChI=1S/C20H20O7/c1-20(2)17(25)5-10-3-9(4-14(24)19(10)27-20)15-8-13(23)18-12(22)6-11(21)7-16(18)26-15/h3-4,6-7,15,17,21-22,24-25H,5,8H2,1-2H3/t15-,17-/m0/s1
InChI Key ASQDBJSRWIDYKK-RDJZCZTQSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C20H20O7
Molecular Weight 372.40 g/mol
Exact Mass 372.12090297 g/mol
Topological Polar Surface Area (TPSA) 116.00 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.58
H-Bond Acceptor 7
H-Bond Donor 4
Rotatable Bonds 1

Synonyms

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Sigmoidin-D
106533-44-2
CHEMBL516331
(2S)-2-[(3S)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
DTXSID60147642
CHEBI:186854
BDBM50274968
(2,6'-Bi-4H-1-Benzopyran)-4-one, 2,2',3,3'-tetrahydro-3',5,7,8'-tetrahydroxy-2',2'-dimethyl-, (S-(R*,R*))-

2D Structure

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2D Structure of Sigmoidin D

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9638 96.38%
Caco-2 - 0.6052 60.52%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.6608 66.08%
OATP2B1 inhibitior - 0.5745 57.45%
OATP1B1 inhibitior + 0.9191 91.91%
OATP1B3 inhibitior + 0.9534 95.34%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.6899 68.99%
P-glycoprotein inhibitior - 0.7512 75.12%
P-glycoprotein substrate - 0.7571 75.71%
CYP3A4 substrate + 0.6316 63.16%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7610 76.10%
CYP3A4 inhibition + 0.5597 55.97%
CYP2C9 inhibition - 0.6392 63.92%
CYP2C19 inhibition - 0.6956 69.56%
CYP2D6 inhibition - 0.7516 75.16%
CYP1A2 inhibition - 0.6019 60.19%
CYP2C8 inhibition - 0.6098 60.98%
CYP inhibitory promiscuity - 0.7252 72.52%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6154 61.54%
Eye corrosion - 0.9923 99.23%
Eye irritation - 0.7606 76.06%
Skin irritation - 0.6987 69.87%
Skin corrosion - 0.9033 90.33%
Ames mutagenesis - 0.5400 54.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4804 48.04%
Micronuclear + 0.5559 55.59%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.8369 83.69%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity + 0.6623 66.23%
Acute Oral Toxicity (c) III 0.6506 65.06%
Estrogen receptor binding + 0.8314 83.14%
Androgen receptor binding + 0.6411 64.11%
Thyroid receptor binding - 0.5058 50.58%
Glucocorticoid receptor binding + 0.7466 74.66%
Aromatase binding + 0.5242 52.42%
PPAR gamma + 0.8230 82.30%
Honey bee toxicity - 0.7734 77.34%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.9008 90.08%

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 99.22% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 97.53% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.81% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.19% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.98% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 92.59% 89.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.96% 99.23%
CHEMBL1929 P47989 Xanthine dehydrogenase 90.78% 96.12%
CHEMBL236 P41143 Delta opioid receptor 90.00% 99.35%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 88.47% 85.11%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 87.60% 93.40%
CHEMBL4208 P20618 Proteasome component C5 87.45% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.41% 97.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 87.25% 96.38%
CHEMBL2581 P07339 Cathepsin D 86.82% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 85.83% 100.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.91% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.36% 86.33%
CHEMBL2964 P36507 Dual specificity mitogen-activated protein kinase kinase 2 82.97% 80.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.49% 95.89%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 81.99% 90.71%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.61% 93.04%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.50% 94.00%

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.
Erythrina abyssinica
Erythrina abyssinica
Erythrina sigmoidea
Erythrina variegata

Cross-Links

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PubChem 129362
NPASS NPC174953
LOTUS LTS0093367
wikiData Q83013020