Vaginol

Details

• Internal ID: d84c4f2e-d90d-4edf-b0b7-38e0e220f80f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Angular furanocoumarins
• IUPAC Name: (8S,9S)-9-hydroxy-8-(2-hydroxypropan-2-yl)-8,9-dihydrofuro[2,3-h]chromen-2-one
• SMILES (Canonical): CC(C)(C1C(C2=C(O1)C=CC3=C2OC(=O)C=C3)O)O
• SMILES (Isomeric): CC(C)([C@@H]1[C@H](C2=C(O1)C=CC3=C2OC(=O)C=C3)O)O
• InChI: InChI=1S/C14H14O5/c1-14(2,17)13-11(16)10-8(18-13)5-3-7-4-6-9(15)19-12(7)10/h3-6,11,13,16-17H,1-2H3/t11-,13-/m0/s1
• InChI Key: DQISGWRLCDLKJI-AAEUAGOBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.26 g/mol
• Exact Mass: 262.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 26992-52-9
• (+)-Vaginol
• Vaginol, (+)-
• DB6SNE9JN2
• DTXSID301336811
• (8S,9S)-8,9-Dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo(2,3-H)-1-benzopyran-2-one
• 2H-Furo(2,3-H)-1-benzopyran-2-one, 8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-, (+)-
• 2H-Furo(2,3-H)-1-benzopyran-2-one, 8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-, (8S,9S)-
• 2H-Furo(2,3-H)-1-benzopyran-2-one, 8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-, trans-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9355	93.55%
Caco-2	-	0.6222	62.22%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7544	75.44%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9356	93.56%
OATP1B3 inhibitior	+	0.8592	85.92%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7888	78.88%
P-glycoprotein inhibitior	-	0.7794	77.94%
P-glycoprotein substrate	-	0.9215	92.15%
CYP3A4 substrate	-	0.5919	59.19%
CYP2C9 substrate	-	0.6755	67.55%
CYP2D6 substrate	-	0.8200	82.00%
CYP3A4 inhibition	+	0.5166	51.66%
CYP2C9 inhibition	+	0.5249	52.49%
CYP2C19 inhibition	-	0.6920	69.20%
CYP2D6 inhibition	-	0.8161	81.61%
CYP1A2 inhibition	-	0.5910	59.10%
CYP2C8 inhibition	-	0.9010	90.10%
CYP inhibitory promiscuity	-	0.5276	52.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4757	47.57%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.7519	75.19%
Skin irritation	-	0.6578	65.78%
Skin corrosion	-	0.9127	91.27%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6633	66.33%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.5283	52.83%
skin sensitisation	-	0.7607	76.07%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5852	58.52%
Acute Oral Toxicity (c)	III	0.6097	60.97%
Estrogen receptor binding	+	0.8422	84.22%
Androgen receptor binding	+	0.5365	53.65%
Thyroid receptor binding	-	0.5576	55.76%
Glucocorticoid receptor binding	+	0.5727	57.27%
Aromatase binding	+	0.7539	75.39%
PPAR gamma	+	0.7632	76.32%
Honey bee toxicity	-	0.9388	93.88%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9612	96.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.06%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.80%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.38%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.97%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	86.48%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.55%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.96%	85.14%

Plants that contains it

• Angelica komarovii

Cross-Links

• PubChem: 16062330
• LOTUS: LTS0246233
• wikiData: Q104986978