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(5aS,10aR)-2-[(1R,5S,6R)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8-trihydroxy-5a-(3-methylbut-2-enyl)-10aH-[1]benzofuro[3,2-b]chromen-11-one

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 8b251c22-a771-487d-8574-1444e287c30f
Taxonomy Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
IUPAC Name (5aS,10aR)-2-[(1R,5S,6R)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8-trihydroxy-5a-(3-methylbut-2-enyl)-10aH-[1]benzofuro[3,2-b]chromen-11-one
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C45H44O11/c1-21(2)6-9-27-32(48)13-11-28(40(27)51)41(52)37-29(26-10-7-24(46)18-33(26)49)16-23(5)17-30(37)38-34(50)20-36-39(42(38)53)43(54)44-45(56-36,15-14-22(3)4)31-12-8-25(47)19-35(31)55-44/h6-8,10-14,17-20,29-30,37,44,46-51,53H,9,15-16H2,1-5H3/t29-,30-,37-,44+,45+/m1/s1
InChI Key GCSSGYKMPPFQLH-KDJZGPCZSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C45H44O11
Molecular Weight 760.80 g/mol
Exact Mass 760.28836222 g/mol
Topological Polar Surface Area (TPSA) 194.00 Ų
XlogP 9.00
Atomic LogP (AlogP) 8.44
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (5aS,10aR)-2-[(1R,5S,6R)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8-trihydroxy-5a-(3-methylbut-2-enyl)-10aH-[1]benzofuro[3,2-b]chromen-11-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9815 98.15%
Caco-2 - 0.8608 86.08%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6838 68.38%
OATP2B1 inhibitior + 0.5747 57.47%
OATP1B1 inhibitior + 0.8057 80.57%
OATP1B3 inhibitior + 0.9206 92.06%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.9569 95.69%
P-glycoprotein inhibitior + 0.8194 81.94%
P-glycoprotein substrate + 0.7255 72.55%
CYP3A4 substrate + 0.7112 71.12%
CYP2C9 substrate + 0.5973 59.73%
CYP2D6 substrate - 0.7963 79.63%
CYP3A4 inhibition - 0.6766 67.66%
CYP2C9 inhibition + 0.7416 74.16%
CYP2C19 inhibition + 0.5761 57.61%
CYP2D6 inhibition - 0.8326 83.26%
CYP1A2 inhibition - 0.6264 62.64%
CYP2C8 inhibition + 0.8017 80.17%
CYP inhibitory promiscuity + 0.7447 74.47%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.5202 52.02%
Eye corrosion - 0.9905 99.05%
Eye irritation - 0.9045 90.45%
Skin irritation - 0.7261 72.61%
Skin corrosion - 0.9066 90.66%
Ames mutagenesis + 0.6500 65.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7962 79.62%
Micronuclear - 0.5400 54.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.7812 78.12%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.7541 75.41%
Acute Oral Toxicity (c) I 0.4773 47.73%
Estrogen receptor binding + 0.8378 83.78%
Androgen receptor binding + 0.7697 76.97%
Thyroid receptor binding + 0.5674 56.74%
Glucocorticoid receptor binding + 0.8061 80.61%
Aromatase binding + 0.6280 62.80%
PPAR gamma + 0.7487 74.87%
Honey bee toxicity - 0.7105 71.05%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9947 99.47%

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 99.62% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.36% 85.14%
CHEMBL2581 P07339 Cathepsin D 97.98% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.70% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.46% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.55% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 93.22% 89.00%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 92.95% 93.40%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 91.62% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.44% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 90.03% 94.73%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 89.90% 99.15%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 89.85% 95.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.62% 99.23%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 87.50% 85.00%
CHEMBL217 P14416 Dopamine D2 receptor 86.83% 95.62%
CHEMBL4208 P20618 Proteasome component C5 86.26% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.46% 95.89%
CHEMBL340 P08684 Cytochrome P450 3A4 85.38% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 84.89% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.62% 100.00%
CHEMBL2535 P11166 Glucose transporter 83.04% 98.75%
CHEMBL1929 P47989 Xanthine dehydrogenase 81.83% 96.12%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.74% 96.95%
CHEMBL3038469 P24941 CDK2/Cyclin A 81.63% 91.38%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 81.09% 90.93%
CHEMBL3359 P21462 Formyl peptide receptor 1 80.71% 93.56%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.29% 94.80%

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.
Morus nigra

Cross-Links

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PubChem 90681447
LOTUS LTS0257645
wikiData Q105006450