vaticanol A

Details

• Internal ID: 33c6fd2e-caec-456c-9baa-93f8c595cb81
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (1S,2S,3S,9R,10R,17R)-3-(3,5-dihydroxyphenyl)-2,9,17-tris(4-hydroxyphenyl)-8-oxapentacyclo[8.7.2.04,18.07,19.011,16]nonadeca-4(18),5,7(19),11(16),12,14-hexaene-5,13,15-triol
• SMILES (Canonical): C1=CC(=CC=C1C2C3C(C4=C(C=C(C=C4O)O)C5C(OC6=C5C3=C(C2C7=CC(=CC(=C7)O)O)C(=C6)O)C8=CC=C(C=C8)O)C9=CC=C(C=C9)O)O
• SMILES (Isomeric): C1=CC(=CC=C1[C@H]2[C@H]3[C@@H](C4=C(C=C(C=C4O)O)[C@H]5[C@@H](OC6=C5C3=C([C@@H]2C7=CC(=CC(=C7)O)O)C(=C6)O)C8=CC=C(C=C8)O)C9=CC=C(C=C9)O)O
• InChI: InChI=1S/C42H32O9/c43-23-7-1-19(2-8-23)33-35(22-13-26(46)15-27(47)14-22)38-31(50)18-32-39-37(42(51-32)21-5-11-25(45)12-6-21)29-16-28(48)17-30(49)36(29)34(40(33)41(38)39)20-3-9-24(44)10-4-20/h1-18,33-35,37,40,42-50H/t33-,34-,35-,37-,40+,42+/m1/s1
• InChI Key: MBGBQHRAJPLAPN-WTEBWGKASA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₃₂O₉
• Molecular Weight: 680.70 g/mol
• Exact Mass: 680.20463259 g/mol
• Topological Polar Surface Area (TPSA): 171.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 7.76
• H-Bond Acceptor: 9
• H-Bond Donor: 8
• Rotatable Bonds: 4

Synonyms

• CHEMBL508745
• BDBM50362647

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	-	0.8649	86.49%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.5984	59.84%
OATP2B1 inhibitior	+	0.5774	57.74%
OATP1B1 inhibitior	+	0.7650	76.50%
OATP1B3 inhibitior	-	0.3378	33.78%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8431	84.31%
P-glycoprotein inhibitior	+	0.6364	63.64%
P-glycoprotein substrate	-	0.7958	79.58%
CYP3A4 substrate	+	0.5494	54.94%
CYP2C9 substrate	-	0.7778	77.78%
CYP2D6 substrate	+	0.4927	49.27%
CYP3A4 inhibition	+	0.5280	52.80%
CYP2C9 inhibition	+	0.8315	83.15%
CYP2C19 inhibition	+	0.8416	84.16%
CYP2D6 inhibition	-	0.8469	84.69%
CYP1A2 inhibition	+	0.8607	86.07%
CYP2C8 inhibition	+	0.7286	72.86%
CYP inhibitory promiscuity	+	0.9212	92.12%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4584	45.84%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.5891	58.91%
Skin irritation	+	0.5289	52.89%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8116	81.16%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8034	80.34%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.5563	55.63%
Acute Oral Toxicity (c)	III	0.4139	41.39%
Estrogen receptor binding	+	0.7375	73.75%
Androgen receptor binding	+	0.8126	81.26%
Thyroid receptor binding	+	0.7218	72.18%
Glucocorticoid receptor binding	+	0.6895	68.95%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7971	79.71%
Honey bee toxicity	-	0.8221	82.21%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9646	96.46%

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	97.53%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.88%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.92%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.81%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	84.51%	94.73%
CHEMBL301	P24941	Cyclin-dependent kinase 2	83.23%	91.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.22%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.85%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.97%	96.09%

Plants that contains it

• Aristeguietia glutinosa
• Cinnamosma macrocarpa
• Cotylelobium melanoxylon
• Hopea hainanensis
• Hopea reticulata
• Leptinella filicula
• Leucosceptrum canum
• Maytenus imbricata
• Packera toluccana
• Piper caninum
• Polyalthia evecta
• Sideritis chamaedryfolia
• Vatica rassak

Cross-Links

• PubChem: 44566412
• NPASS: NPC148516
• ChEMBL: CHEMBL508745
• LOTUS: LTS0176340
• wikiData: Q104400515