Vaticanol B

Details

• Internal ID: e6e7ce52-956a-4880-917f-ca8baf7c71f2
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (1R,2S,3S,9R,10R,17R)-3-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-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=C8C(C(OC8=CC(=C7)O)C9=CC=C(C=C9)O)C1=CC(=CC(=C1)O)O)C(=C6)O)C1=CC=C(C=C1)O)C1=CC=C(C=C1)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=C8[C@H]([C@@H](OC8=CC(=C7)O)C9=CC=C(C=C9)O)C1=CC(=CC(=C1)O)O)C(=C6)O)C1=CC=C(C=C1)O)C1=CC=C(C=C1)O)O
• InChI: InChI=1S/C56H42O12/c57-30-9-1-25(2-10-30)44-47-38(20-36(63)22-40(47)65)50-52-43(68-56(50)28-7-15-33(60)16-8-28)24-41(66)51-49(45(53(44)54(51)52)26-3-11-31(58)12-4-26)39-21-37(64)23-42-48(39)46(29-17-34(61)19-35(62)18-29)55(67-42)27-5-13-32(59)14-6-27/h1-24,44-46,49-50,53,55-66H/t44-,45-,46-,49-,50-,53+,55+,56+/m1/s1
• InChI Key: VOANMQWFRWOKSM-ATGKYDEGSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₆H₄₂O₁₂
• Molecular Weight: 906.90 g/mol
• Exact Mass: 906.26762677 g/mol
• Topological Polar Surface Area (TPSA): 221.00 Ų
• XlogP: 9.10
• Atomic LogP (AlogP): 10.43
• H-Bond Acceptor: 12
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 287101-83-1
• CHEMBL2368899
• (1R,2S,3S,9R,10R,17R)-3-[(2R,3R)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9795	97.95%
Caco-2	-	0.8831	88.31%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6549	65.49%
OATP2B1 inhibitior	-	0.5637	56.37%
OATP1B1 inhibitior	+	0.7698	76.98%
OATP1B3 inhibitior	-	0.2844	28.44%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8601	86.01%
P-glycoprotein inhibitior	+	0.7135	71.35%
P-glycoprotein substrate	-	0.7644	76.44%
CYP3A4 substrate	+	0.5741	57.41%
CYP2C9 substrate	-	0.7778	77.78%
CYP2D6 substrate	+	0.4927	49.27%
CYP3A4 inhibition	+	0.6046	60.46%
CYP2C9 inhibition	+	0.8654	86.54%
CYP2C19 inhibition	+	0.8323	83.23%
CYP2D6 inhibition	-	0.8061	80.61%
CYP1A2 inhibition	+	0.8273	82.73%
CYP2C8 inhibition	+	0.7517	75.17%
CYP inhibitory promiscuity	+	0.9045	90.45%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.4530	45.30%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8324	83.24%
Skin irritation	+	0.5182	51.82%
Skin corrosion	-	0.9311	93.11%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8474	84.74%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7943	79.43%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5267	52.67%
Acute Oral Toxicity (c)	III	0.4055	40.55%
Estrogen receptor binding	+	0.7667	76.67%
Androgen receptor binding	+	0.7968	79.68%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.5889	58.89%
Aromatase binding	-	0.5086	50.86%
PPAR gamma	+	0.7283	72.83%
Honey bee toxicity	-	0.8067	80.67%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9554	95.54%

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	97.82%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.17%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.20%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.46%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.25%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.79%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.17%	96.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.55%	97.33%
CHEMBL301	P24941	Cyclin-dependent kinase 2	81.48%	91.23%

Plants that contains it

• Aristeguietia glutinosa
• Cinnamosma macrocarpa
• Dipterocarpus grandiflorus
• Hopea utilis
• Leptinella filicula
• Leucosceptrum canum
• Maytenus imbricata
• Packera toluccana
• Piper caninum
• Polyalthia evecta
• Sideritis chamaedryfolia
• Upuna borneensis
• Vatica albiramis
• Vatica rassak

Cross-Links

• PubChem: 10010985
• NPASS: NPC224528
• ChEMBL: CHEMBL2368899
• LOTUS: LTS0151929
• wikiData: Q104399120