[(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R)-2,12,14-triacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.03,7]heptadec-10-en-16-yl] acetate

Details

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Internal ID b5d60cd8-462d-4951-bc9e-4921cd8eb05d
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
IUPAC Name [(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R)-2,12,14-triacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.03,7]heptadec-10-en-16-yl] acetate
SMILES (Canonical) CC1C(=O)OC2C1(C(C3C(=C)C(CC(C3(C(C=CC(=C)C2Cl)OC(=O)C)C)OC(=O)C)OC(=O)C)OC(=O)C)O
SMILES (Isomeric) C[C@H]1C(=O)O[C@@H]2[C@@]1([C@H]([C@H]3C(=C)[C@@H](C[C@@H]([C@@]3([C@H](/C=C\C(=C)[C@@H]2Cl)OC(=O)C)C)OC(=O)C)OC(=O)C)OC(=O)C)O
InChI InChI=1S/C28H35ClO11/c1-12-9-10-20(37-16(5)31)27(8)21(38-17(6)32)11-19(36-15(4)30)13(2)22(27)24(39-18(7)33)28(35)14(3)26(34)40-25(28)23(12)29/h9-10,14,19-25,35H,1-2,11H2,3-8H3/b10-9-/t14-,19+,20-,21-,22+,23-,24-,25-,27-,28+/m0/s1
InChI Key HHJDPMYEUWMJAG-CFZOEGMGSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H35ClO11
Molecular Weight 583.00 g/mol
Exact Mass 582.1867896 g/mol
Topological Polar Surface Area (TPSA) 152.00 Ų
XlogP 1.80
Atomic LogP (AlogP) 2.32
H-Bond Acceptor 11
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(1S,2S,3R,4R,7R,8S,10Z,12S,13R,14S,16R)-2,12,14-triacetyloxy-8-chloro-3-hydroxy-4,13-dimethyl-9,17-dimethylidene-5-oxo-6-oxatricyclo[11.4.0.03,7]heptadec-10-en-16-yl] acetate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9902 99.02%
Caco-2 - 0.7599 75.99%
Blood Brain Barrier + 0.7250 72.50%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.5751 57.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8476 84.76%
OATP1B3 inhibitior + 0.8231 82.31%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8060 80.60%
P-glycoprotein inhibitior + 0.7893 78.93%
P-glycoprotein substrate + 0.5280 52.80%
CYP3A4 substrate + 0.6980 69.80%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8935 89.35%
CYP3A4 inhibition - 0.7069 70.69%
CYP2C9 inhibition - 0.9145 91.45%
CYP2C19 inhibition - 0.8578 85.78%
CYP2D6 inhibition - 0.9391 93.91%
CYP1A2 inhibition - 0.7758 77.58%
CYP2C8 inhibition + 0.5706 57.06%
CYP inhibitory promiscuity - 0.8803 88.03%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.8401 84.01%
Carcinogenicity (trinary) Danger 0.5158 51.58%
Eye corrosion - 0.9769 97.69%
Eye irritation - 0.8941 89.41%
Skin irritation - 0.5788 57.88%
Skin corrosion - 0.8447 84.47%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3756 37.56%
Micronuclear - 0.6541 65.41%
Hepatotoxicity - 0.5144 51.44%
skin sensitisation - 0.6821 68.21%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.7625 76.25%
Nephrotoxicity + 0.6768 67.68%
Acute Oral Toxicity (c) III 0.5455 54.55%
Estrogen receptor binding + 0.7463 74.63%
Androgen receptor binding + 0.6804 68.04%
Thyroid receptor binding + 0.5843 58.43%
Glucocorticoid receptor binding + 0.7448 74.48%
Aromatase binding + 0.5965 59.65%
PPAR gamma + 0.7542 75.42%
Honey bee toxicity - 0.5272 52.72%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9883 98.83%

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 96.72% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.90% 97.25%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 93.78% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.17% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 91.28% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.02% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 89.29% 91.19%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.71% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 83.64% 95.50%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 82.73% 94.80%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.56% 97.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.03% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 80.96% 94.00%
CHEMBL2581 P07339 Cathepsin D 80.88% 98.95%
CHEMBL4208 P20618 Proteasome component C5 80.69% 90.00%

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.
Anisomeles indica

Cross-Links

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PubChem 46850440
NPASS NPC77957
LOTUS LTS0062533
wikiData Q105028315