[(1R,2S,3S,5R,8R,9S,11S,13R,14S,16S,17R,18S)-2-acetyloxy-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-3-yl] benzoate

Details

Top
Internal ID be10a5ee-d3fd-49bc-820c-5d3b5c0b7120
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids > Hetisine-type diterpenoid alkaloids
IUPAC Name [(1R,2S,3S,5R,8R,9S,11S,13R,14S,16S,17R,18S)-2-acetyloxy-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-3-yl] benzoate
SMILES (Canonical) CC(=O)OC1C(CC2(CN3C4C2C15C3C6CC7CC5(C6(C4)C(C7=C)O)O)C)OC(=O)C8=CC=CC=C8
SMILES (Isomeric) CC(=O)O[C@@H]1[C@H](C[C@]2(CN3[C@@H]4[C@H]2[C@@]15[C@H]3[C@H]6C[C@H]7C[C@@]5([C@]6(C4)[C@@H](C7=C)O)O)C)OC(=O)C8=CC=CC=C8
InChI InChI=1S/C29H33NO6/c1-14-17-9-18-22-29-21-19(11-27(18,23(14)32)28(29,34)10-17)30(22)13-26(21,3)12-20(24(29)35-15(2)31)36-25(33)16-7-5-4-6-8-16/h4-8,17-24,32,34H,1,9-13H2,2-3H3/t17-,18+,19-,20-,21+,22+,23+,24+,26-,27-,28-,29+/m0/s1
InChI Key UHHNHGRRAVEXIE-UYHAKKBPSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C29H33NO6
Molecular Weight 491.60 g/mol
Exact Mass 491.23078777 g/mol
Topological Polar Surface Area (TPSA) 96.30 Ų
XlogP 2.10
Atomic LogP (AlogP) 2.31
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of [(1R,2S,3S,5R,8R,9S,11S,13R,14S,16S,17R,18S)-2-acetyloxy-13,18-dihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.01,8.05,17.07,16.09,14.014,18]nonadecan-3-yl] benzoate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8849 88.49%
Caco-2 - 0.7468 74.68%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.5009 50.09%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8957 89.57%
OATP1B3 inhibitior + 0.9408 94.08%
MATE1 inhibitior - 0.9020 90.20%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6590 65.90%
P-glycoprotein inhibitior - 0.6469 64.69%
P-glycoprotein substrate + 0.6044 60.44%
CYP3A4 substrate + 0.7066 70.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7509 75.09%
CYP3A4 inhibition - 0.9588 95.88%
CYP2C9 inhibition - 0.8748 87.48%
CYP2C19 inhibition - 0.8618 86.18%
CYP2D6 inhibition - 0.9185 91.85%
CYP1A2 inhibition - 0.9026 90.26%
CYP2C8 inhibition + 0.6536 65.36%
CYP inhibitory promiscuity - 0.8920 89.20%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4697 46.97%
Eye corrosion - 0.9875 98.75%
Eye irritation - 0.9516 95.16%
Skin irritation - 0.7405 74.05%
Skin corrosion - 0.9301 93.01%
Ames mutagenesis - 0.6128 61.28%
Human Ether-a-go-go-Related Gene inhibition + 0.7621 76.21%
Micronuclear + 0.6300 63.00%
Hepatotoxicity - 0.5302 53.02%
skin sensitisation - 0.8387 83.87%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.9667 96.67%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.6402 64.02%
Acute Oral Toxicity (c) III 0.4956 49.56%
Estrogen receptor binding + 0.7600 76.00%
Androgen receptor binding + 0.7371 73.71%
Thyroid receptor binding - 0.5000 50.00%
Glucocorticoid receptor binding + 0.6691 66.91%
Aromatase binding + 0.6556 65.56%
PPAR gamma + 0.6231 62.31%
Honey bee toxicity - 0.7604 76.04%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9809 98.09%

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
CHEMBL2581 P07339 Cathepsin D 96.48% 98.95%
CHEMBL4040 P28482 MAP kinase ERK2 96.31% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.38% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.87% 86.33%
CHEMBL221 P23219 Cyclooxygenase-1 90.11% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 88.08% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.08% 95.56%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 85.50% 91.07%
CHEMBL4208 P20618 Proteasome component C5 85.26% 90.00%
CHEMBL5028 O14672 ADAM10 84.32% 97.50%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 82.22% 91.11%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 82.20% 97.14%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.79% 93.00%
CHEMBL2996 Q05655 Protein kinase C delta 81.66% 97.79%
CHEMBL340 P08684 Cytochrome P450 3A4 80.57% 91.19%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 80.31% 83.00%

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.
Carthamus tinctorius

Cross-Links

Top
PubChem 163025038
LOTUS LTS0188156
wikiData Q105152551