Nagilactone C

Details

• Internal ID: 158f1682-d843-43a5-8ce7-f9e83956b20d
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,2S,4R,5R,6R,9S,10R,17R)-5,10-dihydroxy-1,6-dimethyl-12-propan-2-yl-3,8,13-trioxapentacyclo[7.7.1.02,4.06,17.011,16]heptadeca-11,15-diene-7,14-dione
• SMILES (Canonical): CC(C)C1=C2C(C3C4C(C(C5C(C4(C2=CC(=O)O1)C)O5)O)(C(=O)O3)C)O
• SMILES (Isomeric): CC(C)C1=C2[C@H]([C@@H]3[C@H]4[C@]([C@H]([C@@H]5[C@H]([C@@]4(C2=CC(=O)O1)C)O5)O)(C(=O)O3)C)O
• InChI: InChI=1S/C19H22O7/c1-6(2)11-9-7(5-8(20)24-11)18(3)14-12(10(9)21)26-17(23)19(14,4)15(22)13-16(18)25-13/h5-6,10,12-16,21-22H,1-4H3/t10-,12-,13-,14-,15+,16-,18-,19-/m1/s1
• InChI Key: DGNOPGIIPQKNHD-RSKPZANQSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₇
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.13655304 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.76
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 24338-53-2
• NSC 117884
• NSC 211500
• NSC-117884
• NagilactoneC
• NSC211500
• NSC-211500
• 38MVA8L9PT
• CHEMBL487996
• DTXSID401019971
• C19H22O7
• NSC117884
• dihydroxy-isopropyl-dimethyl-[?]dione
• AKOS040762092
• Podolactone B, 7, 8-deepoxy-8,14-didehydro-15,16-dideoxy-7-hydroxy-, (7.beta.)-
• (1aR,2R,2aR,4aS,4bR,5R,9bS,9cS)-1a,2,2a,4a,4b,5,9b,9c-Octahydro-2,5-dihydroxy-2a,9b-dimethyl-6-(1-methylethyl)-3H,8H-furo[2',3',4':4,5]oxireno[7,8]naphtho[2,1-c]pyran-3,8-dione
• (1S,2S,4R,5R,6R,9S,10R,17R)-5,10-dihydroxy-1,6-dimethyl-12-propan-2-yl-3,8,13-trioxapentacyclo[7.7.1.02,4.06,17.011,16]heptadeca-11,15-diene-7,14-dione
• 3H,8H-Furo[2',3',4':4,5]oxireno[7,8]naphtho[2,1-c]pyran-3,8-dione, 1a,2,2a,4a,4b,5,9b,9c-octahydro-2,5-dihydroxy-2a,9b-dimethyl-6-(1-methylethyl)-, (1aR,2R,2aR,4aS,4bR,5R,9bS,9cS)-
• 3H,8H-Furo[2',3',4':4,5]oxireno[7,8]naphtho[2,1-c]pyran-3,8-dione, 1aalpha,2,2a,4abeta,4bbeta,5,9b,9calpha-octahydro-2alpha,5alpha-dihydroxy-6-isopropyl-2abeta,9balpha-dimethyl- (8CI) Podolactone B, 7,8-deepoxy-8,14-didehydro-15,16-dideoxy-7-hydroxy-, (1alpha,2alpha,7beta)-
• 3J2
• Podolactone B, 7,8-deepoxy-8,14-didehydro-15,16-dideoxy-7-hydroxy-, (1alpha,2alpha,7beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9501	95.01%
Caco-2	-	0.6790	67.90%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7572	75.72%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8834	88.34%
OATP1B3 inhibitior	+	0.9022	90.22%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8703	87.03%
P-glycoprotein inhibitior	-	0.5956	59.56%
P-glycoprotein substrate	-	0.6399	63.99%
CYP3A4 substrate	+	0.5623	56.23%
CYP2C9 substrate	-	0.6040	60.40%
CYP2D6 substrate	-	0.8597	85.97%
CYP3A4 inhibition	-	0.8296	82.96%
CYP2C9 inhibition	-	0.6482	64.82%
CYP2C19 inhibition	-	0.7231	72.31%
CYP2D6 inhibition	-	0.9110	91.10%
CYP1A2 inhibition	-	0.8373	83.73%
CYP2C8 inhibition	-	0.8420	84.20%
CYP inhibitory promiscuity	-	0.8428	84.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4562	45.62%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.6848	68.48%
Skin corrosion	-	0.8993	89.93%
Ames mutagenesis	-	0.5337	53.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7838	78.38%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.6158	61.58%
skin sensitisation	-	0.7746	77.46%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6661	66.61%
Acute Oral Toxicity (c)	III	0.4607	46.07%
Estrogen receptor binding	+	0.5924	59.24%
Androgen receptor binding	+	0.6285	62.85%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4843	48.43%
Aromatase binding	-	0.5262	52.62%
PPAR gamma	+	0.7076	70.76%
Honey bee toxicity	-	0.8183	81.83%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9626	96.26%

Targets

Proven Targets:

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	94.92%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	89.78%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	89.67%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.65%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.64%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.32%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.18%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.95%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.31%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.56%	96.09%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.72%	85.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.55%	85.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.16%	91.07%

Plants that contains it

• Fissistigma oldhamii
• Ileostylus micranthus
• Lycium chinense
• Nageia nagi
• Podocarpus fasciculus
• Podocarpus purdieanus
• Podocarpus sellowii

Cross-Links

• PubChem: 72505
• NPASS: NPC108581
• LOTUS: LTS0190428
• wikiData: Q76005848