PlantaeDB Logo
Login Sign-up

Usararotenoid C

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

Top
Internal ID b6de7536-187e-48f4-886c-c1aa97af6b57
Taxonomy Phenylpropanoids and polyketides > Isoflavonoids > Rotenoids > Rotenones
IUPAC Name (1S,13R)-1-hydroxy-17-methoxy-16-(3-methylbut-2-enyl)-5,7,11,14-tetraoxapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaen-21-one
SMILES (Canonical) CC(=CCC1=C(C=CC2=C1OC3COC4=CC5=C(C=C4C3(C2=O)O)OCO5)OC)C
SMILES (Isomeric) CC(=CCC1=C(C=CC2=C1O[C@@H]3COC4=CC5=C(C=C4[C@]3(C2=O)O)OCO5)OC)C
InChI InChI=1S/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s1
InChI Key ZFSLOJRJABHMTL-OFNKIYASSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C23H22O7
Molecular Weight 410.40 g/mol
Exact Mass 410.13655304 g/mol
Topological Polar Surface Area (TPSA) 83.40 Ų
XlogP 3.80
Atomic LogP (AlogP) 3.16
H-Bond Acceptor 7
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

Top
CHEMBL3758287
NCGC00385810-01!
(6aR,12aS)-2,3-Methylenedioxy-9-methoxy-8-(3,3-dimethylallyl)-12a-hydroxyrotenoid
(6aR,12aS)-12a-hydroxy-9-methoxy-8-(3-methylbut-2-en-1-yl)-6a,12a-dihydrochromeno[2,3-c][1,3]dioxolo[4,5-g]chromen-12(6H)-one
1,3-dioxolo[6,7][1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one, 6a,12a-dihydro-12a-hydroxy-9-methoxy-8-(3-methyl-2-butenyl)-, (6aR,12aS)-
InChI=1/C23H22O7/c1-12(2)4-5-13-16(26-3)7-6-14-21(13)30-20-10-27-17-9-19-18(28-11-29-19)8-15(17)23(20,25)22(14)24/h4,6-9,20,25H,5,10-11H2,1-3H3/t20-,23+/m1/s

2D Structure

Top
2D Structure of Usararotenoid C

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9829 98.29%
Caco-2 + 0.6954 69.54%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6143 61.43%
Subcellular localzation Mitochondria 0.7427 74.27%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9211 92.11%
OATP1B3 inhibitior + 0.8880 88.80%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.9210 92.10%
P-glycoprotein inhibitior + 0.8382 83.82%
P-glycoprotein substrate - 0.5365 53.65%
CYP3A4 substrate + 0.6420 64.20%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7723 77.23%
CYP3A4 inhibition + 0.6105 61.05%
CYP2C9 inhibition - 0.5590 55.90%
CYP2C19 inhibition + 0.7178 71.78%
CYP2D6 inhibition - 0.8238 82.38%
CYP1A2 inhibition - 0.5722 57.22%
CYP2C8 inhibition - 0.6281 62.81%
CYP inhibitory promiscuity + 0.6017 60.17%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5599 55.99%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.7594 75.94%
Skin irritation - 0.7836 78.36%
Skin corrosion - 0.9428 94.28%
Ames mutagenesis - 0.5600 56.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5394 53.94%
Micronuclear - 0.5500 55.00%
Hepatotoxicity + 0.5376 53.76%
skin sensitisation - 0.6870 68.70%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity + 0.4620 46.20%
Acute Oral Toxicity (c) III 0.3938 39.38%
Estrogen receptor binding + 0.9126 91.26%
Androgen receptor binding + 0.6005 60.05%
Thyroid receptor binding + 0.6594 65.94%
Glucocorticoid receptor binding + 0.8536 85.36%
Aromatase binding + 0.6314 63.14%
PPAR gamma + 0.9126 91.26%
Honey bee toxicity - 0.7277 72.77%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6300 63.00%
Fish aquatic toxicity + 0.9776 97.76%

Targets

Top

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 98.07% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 94.79% 91.49%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.62% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.30% 94.45%
CHEMBL2581 P07339 Cathepsin D 93.19% 98.95%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 91.28% 92.62%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 90.23% 96.09%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 89.85% 94.80%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 88.87% 96.77%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.86% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 88.68% 96.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 88.48% 100.00%
CHEMBL4208 P20618 Proteasome component C5 87.70% 90.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 86.77% 85.14%
CHEMBL3922 P50579 Methionine aminopeptidase 2 86.60% 97.28%
CHEMBL3137262 O60341 LSD1/CoREST complex 86.37% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.63% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.52% 95.89%
CHEMBL2413 P32246 C-C chemokine receptor type 1 84.57% 89.50%
CHEMBL3492 P49721 Proteasome Macropain subunit 83.56% 90.24%
CHEMBL340 P08684 Cytochrome P450 3A4 83.52% 91.19%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 82.39% 89.62%

Plants that contains it

Top
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.
Millettia usaramensis

Cross-Links

Top
PubChem 641748
LOTUS LTS0222222
wikiData Q105374650