(-)-Variabilin

Details

• Internal ID: f05b5282-ec4e-4554-92cc-e4f97f083d7b
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (6aR,11aR)-3,9-dimethoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromen-6a-ol
• SMILES (Canonical): COC1=CC2=C(C=C1)C3C(CO2)(C4=C(O3)C=C(C=C4)OC)O
• SMILES (Isomeric): COC1=CC2=C(C=C1)[C@@H]3[C@](CO2)(C4=C(O3)C=C(C=C4)OC)O
• InChI: InChI=1S/C17H16O5/c1-19-10-3-5-12-14(7-10)21-9-17(18)13-6-4-11(20-2)8-15(13)22-16(12)17/h3-8,16,18H,9H2,1-2H3/t16-,17+/m1/s1
• InChI Key: VVPGAJNPGZZNBM-SJORKVTESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.30 g/mol
• Exact Mass: 300.09977361 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Homopisatin
• 3187-52-8
• 6a-Hydroxy-3,9-dimethoxypterocarpan
• (6aR,11aR)-3,9-dimethoxy-6,11a-dihydro-[1]benzofuro[3,2-c]chromen-6a-ol
• 370102-93-5
• CHEBI:123
• DTXSID20331964
• 6H-Benzofuro[3,2-c][1]benzopyran-6a(11aH)-ol, 3,9-dimethoxy-, (6aR-cis)-
• LMPK12070130
• Q27105251

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9853	98.53%
Caco-2	+	0.8275	82.75%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6817	68.17%
OATP2B1 inhibitior	-	0.8608	86.08%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4918	49.18%
P-glycoprotein inhibitior	-	0.6283	62.83%
P-glycoprotein substrate	-	0.7049	70.49%
CYP3A4 substrate	+	0.5433	54.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4480	44.80%
CYP3A4 inhibition	-	0.5471	54.71%
CYP2C9 inhibition	-	0.7852	78.52%
CYP2C19 inhibition	+	0.5561	55.61%
CYP2D6 inhibition	+	0.5146	51.46%
CYP1A2 inhibition	+	0.5871	58.71%
CYP2C8 inhibition	-	0.6880	68.80%
CYP inhibitory promiscuity	-	0.6471	64.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4504	45.04%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.6642	66.42%
Skin irritation	-	0.8024	80.24%
Skin corrosion	-	0.9670	96.70%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6107	61.07%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7138	71.38%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6419	64.19%
Acute Oral Toxicity (c)	III	0.6385	63.85%
Estrogen receptor binding	+	0.8249	82.49%
Androgen receptor binding	+	0.7329	73.29%
Thyroid receptor binding	+	0.7804	78.04%
Glucocorticoid receptor binding	+	0.5493	54.93%
Aromatase binding	+	0.6373	63.73%
PPAR gamma	+	0.8079	80.79%
Honey bee toxicity	-	0.9264	92.64%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.5862	58.62%

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	97.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.46%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.04%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.19%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.53%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.96%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.84%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.70%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.46%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.02%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.39%	99.15%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.33%	100.00%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	82.00%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.90%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.70%	90.24%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Trifolium pratense
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 442828
• NPASS: NPC143578
• LOTUS: LTS0115221
• wikiData: Q27105251