Viridicatumtoxin

Details

• Internal ID: 652a3bc9-0953-465d-9cba-52f3ad4e48ec
• Taxonomy: Phenylpropanoids and polyketides > Tetracyclines
• IUPAC Name: (3'S,4'S,6S,9'S)-3',4',8',9',12',14'-hexahydroxy-16'-methoxy-1,5,5-trimethyl-6',10'-dioxospiro[cyclohexene-6,18'-pentacyclo[11.6.1.02,11.04,9.017,20]icosa-1(20),2(11),7,12,14,16-hexaene]-7'-carboxamide
• SMILES (Canonical): CC1=CCCC(C12CC3=C4C2=C(C=C(C4=C(C5=C3C(C6(CC(=O)C(=C(C6(C5=O)O)O)C(=O)N)O)O)O)O)OC)(C)C
• SMILES (Isomeric): CC1=CCCC([C@@]12CC3=C4C2=C(C=C(C4=C(C5=C3[C@@H]([C@]6(CC(=O)C(=C([C@]6(C5=O)O)O)C(=O)N)O)O)O)O)OC)(C)C
• InChI: InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32,34-36,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28-,29-,30+/m0/s1
• InChI Key: FNSQKFOXORBCCC-WBWZXODPSA-N
• Popularity: 15 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₁NO₁₀
• Molecular Weight: 565.60 g/mol
• Exact Mass: 565.19479619 g/mol
• Topological Polar Surface Area (TPSA): 208.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 2

Synonyms

• 39277-41-3
• VIRIDITOXIN (FORMERLY)
• NSC 159628
• S8N62PLU21
• NSC-159628
• (3'S,4'S,6S,9'S)-3',4',8',9',12',14'-hexahydroxy-16'-methoxy-1,5,5-trimethyl-6',10'-dioxospiro[cyclohexene-6,18'-pentacyclo[11.6.1.02,11.04,9.017,20]icosa-1(20),2(11),7,12,14,16-hexaene]-7'-carboxamide
• SC 28762
• UNII-S8N62PLU21
• viridicatumtoxin A
• BRN 2934660
• CHEMBL1984811
• SCHEMBL17340089
• SCHEMBL29426345
• CHEBI:85616
• DTXSID20893991
• SID436556
• NCI60_001174
• NS00094937
• Q27158664
• Q63392839
• (1S,7'aS,11'aS,12'S)-5',6',7'a,10',11'a,12'-Hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-7',7'a,8',11',11'a,12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide
• (1S,7a'S,11a'R)-5',6',7a',10',11a'-Pentahydroxy-3'-methoxy-2,6,6-trimethyl-7',8',12'-trioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide
• (1S,7a'S,11a'S,12'S)-5',6',7a',10',11a',12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-7',7a',8',11',11a',12'-hexahydro-1'H-spiro[cyclohex-2-ene-1,2'-cyclopenta[de]tetracene]-9'-carboxamide
• (8,3-c]pyran)-3,3'-diacetic acid, 3,3',4,4'-tetrahydro-9,9',10,10'-tetrahydroxy-7,7'-dimethoxy-1,1'-dioxo-, dimethyl ester
• Spiro(2-cyclohexene-1,2'(1'H)-cyclopenta(de)naphthacene)-9'-carboxamide, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (2'alpha,7'abeta,11'abeta,12'beta)-(-)-
• Spiro[2-cyclohexene-1, 7',7'a,8',11',11'a,12'-hexahydro-5',6',7'a,10',11'a,12'-hexahydroxy-3'-methoxy-2,6,6-trimethyl-7',8'-dioxo-, (2'.alpha.,7'a.beta.,11'a.beta.,12'.beta.)-(-)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9835	98.35%
Caco-2	-	0.8072	80.72%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6627	66.27%
OATP2B1 inhibitior	-	0.5644	56.44%
OATP1B1 inhibitior	+	0.8776	87.76%
OATP1B3 inhibitior	+	0.9204	92.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8143	81.43%
BSEP inhibitior	+	0.9307	93.07%
P-glycoprotein inhibitior	-	0.4451	44.51%
P-glycoprotein substrate	+	0.6855	68.55%
CYP3A4 substrate	+	0.7104	71.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8591	85.91%
CYP3A4 inhibition	-	0.8785	87.85%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8995	89.95%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.6443	64.43%
CYP inhibitory promiscuity	-	0.8343	83.43%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6057	60.57%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.7469	74.69%
Skin corrosion	-	0.9298	92.98%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7092	70.92%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8566	85.66%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	-	0.7487	74.87%
Acute Oral Toxicity (c)	II	0.7179	71.79%
Estrogen receptor binding	+	0.7524	75.24%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	+	0.5853	58.53%
Glucocorticoid receptor binding	+	0.7063	70.63%
Aromatase binding	+	0.7666	76.66%
PPAR gamma	+	0.7304	73.04%
Honey bee toxicity	-	0.7504	75.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9931	99.31%

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	99.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.49%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.63%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.51%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	94.47%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.66%	92.94%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	93.13%	91.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.31%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.92%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.72%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.31%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.95%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.29%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.45%	97.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.43%	93.99%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	88.14%	94.42%
CHEMBL3474	P14555	Phospholipase A2 group IIA	87.69%	94.05%
CHEMBL2535	P11166	Glucose transporter	86.94%	98.75%
CHEMBL340	P08684	Cytochrome P450 3A4	84.97%	91.19%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.79%	98.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.69%	91.03%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.00%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.59%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.32%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.68%	85.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.62%	93.03%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.61%	80.00%
CHEMBL2056	P21728	Dopamine D1 receptor	81.36%	91.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.07%	93.04%
CHEMBL4208	P20618	Proteasome component C5	80.73%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.47%	100.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.26%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.17%	90.71%
CHEMBL5028	O14672	ADAM10	80.00%	97.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 54686377
• LOTUS: LTS0005976
• wikiData: Q63392839