alpha-Methyl-n-butylshikonin

Details

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Internal ID e20f9b7e-a547-4f87-9c5b-7e61c569e1e2
Taxonomy Benzenoids > Naphthalenes > Naphthoquinones
IUPAC Name 3-butyl-5,8-dihydroxy-3-[(1S)-1-hydroxy-4-methylpent-3-enyl]-2-methyl-2H-naphthalene-1,4-dione
SMILES (Canonical) CCCCC1(C(C(=O)C2=C(C=CC(=C2C1=O)O)O)C)C(CC=C(C)C)O
SMILES (Isomeric) CCCCC1(C(C(=O)C2=C(C=CC(=C2C1=O)O)O)C)[C@H](CC=C(C)C)O
InChI InChI=1S/C21H28O5/c1-5-6-11-21(16(24)10-7-12(2)3)13(4)19(25)17-14(22)8-9-15(23)18(17)20(21)26/h7-9,13,16,22-24H,5-6,10-11H2,1-4H3/t13?,16-,21?/m0/s1
InChI Key KSMHEQVLYHYYNO-ZRKSEFCZSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C21H28O5
Molecular Weight 360.40 g/mol
Exact Mass 360.19367399 g/mol
Topological Polar Surface Area (TPSA) 94.80 Ų
XlogP 5.30
Atomic LogP (AlogP) 4.01
H-Bond Acceptor 5
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of alpha-Methyl-n-butylshikonin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 1.0000 100.00%
Caco-2 + 0.7852 78.52%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.8521 85.21%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8572 85.72%
OATP1B3 inhibitior + 0.8666 86.66%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.6031 60.31%
P-glycoprotein inhibitior - 0.8169 81.69%
P-glycoprotein substrate - 0.6217 62.17%
CYP3A4 substrate + 0.5449 54.49%
CYP2C9 substrate - 0.7853 78.53%
CYP2D6 substrate - 0.8270 82.70%
CYP3A4 inhibition + 0.5819 58.19%
CYP2C9 inhibition - 0.7342 73.42%
CYP2C19 inhibition - 0.6194 61.94%
CYP2D6 inhibition - 0.9088 90.88%
CYP1A2 inhibition - 0.5286 52.86%
CYP2C8 inhibition - 0.7262 72.62%
CYP inhibitory promiscuity - 0.6207 62.07%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8811 88.11%
Carcinogenicity (trinary) Non-required 0.6595 65.95%
Eye corrosion - 0.9945 99.45%
Eye irritation - 0.8502 85.02%
Skin irritation - 0.6082 60.82%
Skin corrosion - 0.9511 95.11%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5898 58.98%
Micronuclear - 0.8700 87.00%
Hepatotoxicity + 0.5875 58.75%
skin sensitisation - 0.6998 69.98%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.9170 91.70%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity - 0.5628 56.28%
Acute Oral Toxicity (c) III 0.3911 39.11%
Estrogen receptor binding - 0.4764 47.64%
Androgen receptor binding + 0.6108 61.08%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.8044 80.44%
Aromatase binding - 0.5401 54.01%
PPAR gamma + 0.7519 75.19%
Honey bee toxicity - 0.9257 92.57%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5500 55.00%
Fish aquatic toxicity + 1.0000 100.00%

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
CHEMBL2581 P07339 Cathepsin D 98.52% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.07% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.84% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.15% 94.45%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.30% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.05% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.72% 89.00%
CHEMBL3401 O75469 Pregnane X receptor 86.49% 94.73%
CHEMBL1907605 P24864 Cyclin-dependent kinase 2/cyclin E1 85.87% 92.88%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.14% 99.23%
CHEMBL221 P23219 Cyclooxygenase-1 85.05% 90.17%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.12% 93.56%
CHEMBL299 P17252 Protein kinase C alpha 83.86% 98.03%
CHEMBL4224 P49759 Dual specificty protein kinase CLK1 83.23% 85.30%
CHEMBL3038469 P24941 CDK2/Cyclin A 83.11% 91.38%
CHEMBL255 P29275 Adenosine A2b receptor 83.08% 98.59%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.49% 86.33%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.46% 96.90%

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.
Arnebia euchroma
Lithospermum erythrorhizon

Cross-Links

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PubChem 139246677
LOTUS LTS0062254
wikiData Q104393176