Isovouacapenol A

Details

• Internal ID: f42bc2c8-75e6-49c4-b107-1414909236ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(4aR,5R,6aR,11aS,11bR)-4a-hydroxy-4,4,11b-trimethyl-7-methylidene-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-5-yl] benzoate
• SMILES (Canonical): CC1(CCCC2(C1(C(CC3C2CC4=C(C3=C)C=CO4)OC(=O)C5=CC=CC=C5)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@]1([C@@H](C[C@@H]3[C@@H]2CC4=C(C3=C)C=CO4)OC(=O)C5=CC=CC=C5)O)(C)C
• InChI: InChI=1S/C27H32O4/c1-17-19-11-14-30-22(19)16-21-20(17)15-23(31-24(28)18-9-6-5-7-10-18)27(29)25(2,3)12-8-13-26(21,27)4/h5-7,9-11,14,20-21,23,29H,1,8,12-13,15-16H2,2-4H3/t20-,21-,23+,26+,27+/m0/s1
• InChI Key: CAKOAOJDETWCQH-BSMIGITPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₄
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.23005950 g/mol
• Topological Polar Surface Area (TPSA): 59.70 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 5.66
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• CHEMBL491583
• (4a ,5 ,6a ,11a ,11b )-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydro-4,4,11b-trimethyl-7-methylenephenanthro[3,2-b]furan-4a,5-diol-5-benzoate
• (4aR,5R,6aR,11aS,11bR)-4a-hydroxy-4,4,11b-trimethyl-7-methylene-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-5-yl rel-benzoate
• Benzoic acid 4a-hydroxy-4,4,11b-trimethyl-7-methylene-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydro-10-oxa-cyclopenta[b]phenanthren-5-yl ester
• InChI=1/C27H32O4/c1-17-19-11-14-30-22(19)16-21-20(17)15-23(31-24(28)18-9-6-5-7-10-18)27(29)25(2,3)12-8-13-26(21,27)4/h5-7,9-11,14,20-21,23,29H,1,8,12-13,15-16H2,2-4H3/t20-,21-,23+,26+,27+/m0/s
• phenanthro[3,2-b]furan-4a,5(2H)-diol, 1,3,4,5,6,6a,7,11,11a,11b-decahydro-4,4,11b-trimethyl-7-methylene-, 5-benzoate, (4aR,5R,6aR,11aS,11bR)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9908	99.08%
Caco-2	+	0.5712	57.12%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7910	79.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8301	83.01%
OATP1B3 inhibitior	-	0.4387	43.87%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	+	0.6042	60.42%
P-glycoprotein inhibitior	+	0.6097	60.97%
P-glycoprotein substrate	-	0.7363	73.63%
CYP3A4 substrate	+	0.6870	68.70%
CYP2C9 substrate	-	0.8102	81.02%
CYP2D6 substrate	-	0.8464	84.64%
CYP3A4 inhibition	+	0.6391	63.91%
CYP2C9 inhibition	-	0.5570	55.70%
CYP2C19 inhibition	+	0.6660	66.60%
CYP2D6 inhibition	-	0.8707	87.07%
CYP1A2 inhibition	+	0.7767	77.67%
CYP2C8 inhibition	+	0.6895	68.95%
CYP inhibitory promiscuity	-	0.6404	64.04%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6058	60.58%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.9493	94.93%
Skin irritation	-	0.6131	61.31%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.9205	92.05%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7965	79.65%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8488	84.88%
Acute Oral Toxicity (c)	III	0.5288	52.88%
Estrogen receptor binding	+	0.7193	71.93%
Androgen receptor binding	+	0.7456	74.56%
Thyroid receptor binding	+	0.6057	60.57%
Glucocorticoid receptor binding	+	0.7825	78.25%
Aromatase binding	+	0.7676	76.76%
PPAR gamma	+	0.6789	67.89%
Honey bee toxicity	-	0.7988	79.88%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.85%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.23%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	91.62%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.54%	99.23%
CHEMBL2581	P07339	Cathepsin D	90.24%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	89.64%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.18%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.42%	91.11%
CHEMBL4208	P20618	Proteasome component C5	83.89%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.66%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.14%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.50%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.37%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.29%	95.50%

Plants that contains it

• Aeschynanthus pulcher
• Betula papyrifera
• Boronia alata
• Caesalpinia pulcherrima
• Cinnamomum philippinense
• Coronilla cretica
• Cryptochilus siamensis
• Cyperus capitatus
• Delphinium tricorne
• Ephedra altissima
• Erica cinerea
• Gymnosporia emarginata
• Haemanthus albiflos
• Helleborus viridis
• Hordeum bulbosum
• Iris sibirica
• Isolona pilosa
• Jatropha gossypiifolia
• Lepidaploa aurea
• Litsea nitida
• Lobelia langeana
• Magnolia henryi
• Micromelum minutum
• Peltophorum dubium
• Prunus pseudocerasus
• Salvia miniata
• Sibiraea angustata
• Tamarix dioica
• Tripterygium wilfordii
• Valeriana officinalis
• Xanthium spinosum subsp. spinosum

Cross-Links

• PubChem: 636673
• NPASS: NPC7059
• LOTUS: LTS0022415
• wikiData: Q104951452