(1R,3S,5R,8R,9S,11S,14R,17R,18R)-3-hydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.01,8.05,17.09,14.014,18]nonadecane-10,16-dione

Details

Top
Internal ID 4b426d6c-4181-4591-ae01-230eeffb27cd
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Villanovane, atisane, trachylobane or helvifulvane diterpenoids > Atisane diterpenoids
IUPAC Name (1R,3S,5R,8R,9S,11S,14R,17R,18R)-3-hydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.01,8.05,17.09,14.014,18]nonadecane-10,16-dione
SMILES (Canonical) CC12CC(CC34C1C(=O)CC56C3CC(C(=C)C5)C(=O)C6C4N(C2)C)O
SMILES (Isomeric) C[C@@]12C[C@@H](C[C@]34[C@@H]1C(=O)C[C@@]56[C@H]3C[C@@H](C(=C)C5)C(=O)[C@@H]6[C@H]4N(C2)C)O
InChI InChI=1S/C21H27NO3/c1-10-5-20-8-13(24)17-19(2)6-11(23)7-21(17)14(20)4-12(10)16(25)15(20)18(21)22(3)9-19/h11-12,14-15,17-18,23H,1,4-9H2,2-3H3/t11-,12-,14+,15+,17+,18+,19-,20+,21+/m0/s1
InChI Key NCYSDVOIDBHHIO-WLOIPTGQSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C21H27NO3
Molecular Weight 341.40 g/mol
Exact Mass 341.19909372 g/mol
Topological Polar Surface Area (TPSA) 57.60 Ų
XlogP 0.70
Atomic LogP (AlogP) 1.82
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 0

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1R,3S,5R,8R,9S,11S,14R,17R,18R)-3-hydroxy-5,7-dimethyl-12-methylidene-7-azahexacyclo[9.6.2.01,8.05,17.09,14.014,18]nonadecane-10,16-dione

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9465 94.65%
Caco-2 + 0.7443 74.43%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability + 0.6286 62.86%
Subcellular localzation Mitochondria 0.5491 54.91%
OATP2B1 inhibitior - 0.8635 86.35%
OATP1B1 inhibitior + 0.8823 88.23%
OATP1B3 inhibitior + 0.9471 94.71%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7000 70.00%
BSEP inhibitior - 0.7801 78.01%
P-glycoprotein inhibitior - 0.7990 79.90%
P-glycoprotein substrate - 0.5314 53.14%
CYP3A4 substrate + 0.6649 66.49%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.3658 36.58%
CYP3A4 inhibition - 0.7798 77.98%
CYP2C9 inhibition - 0.8363 83.63%
CYP2C19 inhibition - 0.8264 82.64%
CYP2D6 inhibition - 0.8644 86.44%
CYP1A2 inhibition - 0.8008 80.08%
CYP2C8 inhibition - 0.8155 81.55%
CYP inhibitory promiscuity - 0.9523 95.23%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9800 98.00%
Carcinogenicity (trinary) Non-required 0.5337 53.37%
Eye corrosion - 0.9845 98.45%
Eye irritation - 0.9407 94.07%
Skin irritation - 0.7497 74.97%
Skin corrosion - 0.9082 90.82%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4059 40.59%
Micronuclear - 0.5500 55.00%
Hepatotoxicity - 0.5875 58.75%
skin sensitisation - 0.8169 81.69%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.9750 97.50%
Nephrotoxicity + 0.6067 60.67%
Acute Oral Toxicity (c) III 0.6157 61.57%
Estrogen receptor binding + 0.7778 77.78%
Androgen receptor binding + 0.7278 72.78%
Thyroid receptor binding + 0.7185 71.85%
Glucocorticoid receptor binding + 0.8428 84.28%
Aromatase binding + 0.7338 73.38%
PPAR gamma - 0.6208 62.08%
Honey bee toxicity - 0.7985 79.85%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.7942 79.42%

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
CHEMBL253 P34972 Cannabinoid CB2 receptor 96.20% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.74% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 89.73% 83.82%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.31% 95.56%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 89.00% 96.77%
CHEMBL2581 P07339 Cathepsin D 85.07% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.08% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.28% 89.00%
CHEMBL4026 P40763 Signal transducer and activator of transcription 3 81.17% 82.69%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.16% 94.45%

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.
Aconitum episcopale
Delphinium albiflorum

Cross-Links

Top
PubChem 101685134
LOTUS LTS0168193
wikiData Q105177443