(+)-Isoalantolactone

Details

• Internal ID: 3eabaac4-eb29-4ee8-a8c5-4793fb5532d4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1
• InChI Key: CVUANYCQTOGILD-QVHKTLOISA-N
• Popularity: 294 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.32 g/mol
• Exact Mass: 232.146329876 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 470-17-7
• iso-alantolacton
• BYH07P620U
• CHEBI:5981
• (+)-Isoalantolactone
• NSC-241036
• Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aS,8aR,9aR)-
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo(f)(1)benzofuran-2-one
• RefChem:791523
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-bis(methylidene)decahydronaphtho(2,3-b)furan-2(3H)-one;eudesma-4(14),11(13)-dieno-12,8beta-olactone
• MFCD08689940
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one
• (+/-)-Isoalantolactone
• QTF89ZHT7V
• Isoalantolactone, (+/-)-
• (3aR,4aS,8aR,9aR)-Decahydro-8a-methyl-3,5-bis(methylene)naphtho[2,3-b]furan-2(3H)-one
• NSC241036
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f]benzofuran-2-one
• eudesma-4(14),11(13)-dieno-12,8beta-olactone
• 8beta-hydroxyeudesma-4(14),11(13)-dien-12-oic acid gamma-lactone
• (3aR,4aS,8aR,9aR)-8a-methyl-3,5-bis(methylidene)decahydronaphtho[2,3-b]furan-2(3H)-one
• Rel-(3aR,4aS,8aR,9aR)-decahydro-8a-methyl-3,5-bis(methylene)naphtho(2,3-b)furan-2(3H)-one
• Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aS,8aR,9aR)-rel-
• 4677-48-9
• (+)-Isoalantolactone;Isohelenin
• NSC 241036
• NSC 601353
• BRN 0013402
• AI3-31148
• (3AR,4AS,8AR,9AR)-DECAHYDRO-8A-METHYL-3,5-BIS(METHYLENE)NAPHTHO(2,3-B)FURAN-2(3H)-ONE
• ISOALLANTOLACTONE
• UNII-QTF89ZHT7V
• Epitope ID:119705
• Isoalantolactone (Standard)
• UNII-BYH07P620U
• Isoalantolactone (Isohelenin)
• 4-17-00-05031 (Beilstein Handbook Reference)
• SCHEMBL510111
• CHEMBL137803
• orb1304967
• ISOALANTOLACTONE, (+)-
• HY-N0780R
• (3aR,4aS,8aR,9aR)-8a-Methyl-3,5-dimethylene-decahydro-naphtho[2,3-b]furan-2-one
• HY-N0780
• BDBM50433448
• s3829
• AKOS015892694
• Eudesma-4(14),11(13)-dien-12-oic acid, 8-beta-hydroxy-, gamma-lactone
• CCG-266809
• CS-3635
• FI32778
• (3AR,4AS,8AR,9AR)-8A-METHYL-3,5-DIMETHYLIDENE-DODECAHYDRONAPHTHO[2,3-B]FURAN-2-ONE
• AS-74081
• Naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3a alpha,4a alpha,8a beta,9a alpha))-
• SY045136
• C09484
• 689I940
• Q27089356
• 5.ALPHA.H-EUDESMA-4(15),11(13)-DIEN-12,8.BETA.-OLIDE
• EUDESMA-4(14),11(13)-DIEN-12-OIC ACID, 8.BETA.-HYDROXY-, .GAMMA.-LACTONE
• Eudesma-4(14),11(13)-dien-12-oic acid, 8beta-hydroxy-, gamma-lactone, (+/-)-
• 107439-69-0
• EUDESMA-4(14),11(13)-DIEN-12-OIC ACID, 8.BETA.-HYDROXY-, .GAMMA.-LACTONE, (+/-)-
• Naphtho[2, decahydro-8a-methyl-3,5-bis(methylene)-, [3aR-(3a.alpha.,4a.alpha.,8a.beta.,9a.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7851	78.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.4086	40.86%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.8697	86.97%
OATP1B3 inhibitior	+	0.8964	89.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.9692	96.92%
P-glycoprotein inhibitior	-	0.9100	91.00%
P-glycoprotein substrate	-	0.9196	91.96%
CYP3A4 substrate	+	0.5614	56.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8497	84.97%
CYP3A4 inhibition	-	0.5304	53.04%
CYP2C9 inhibition	-	0.9519	95.19%
CYP2C19 inhibition	+	0.8862	88.62%
CYP2D6 inhibition	-	0.9529	95.29%
CYP1A2 inhibition	+	0.8835	88.35%
CYP2C8 inhibition	-	0.8182	81.82%
CYP inhibitory promiscuity	-	0.8125	81.25%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4535	45.35%
Eye corrosion	-	0.9772	97.72%
Eye irritation	-	0.5134	51.34%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6419	64.19%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.8336	83.36%
skin sensitisation	+	0.5326	53.26%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.5863	58.63%
Acute Oral Toxicity (c)	III	0.7258	72.58%
Estrogen receptor binding	+	0.6976	69.76%
Androgen receptor binding	+	0.5757	57.57%
Thyroid receptor binding	-	0.5938	59.38%
Glucocorticoid receptor binding	+	0.7132	71.32%
Aromatase binding	-	0.5637	56.37%
PPAR gamma	-	0.5846	58.46%
Honey bee toxicity	-	0.7734	77.34%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9947	99.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.17%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.76%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.25%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.70%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.35%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.76%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	87.38%	97.79%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	86.98%	96.00%
CHEMBL299	P17252	Protein kinase C alpha	86.07%	98.03%
CHEMBL259	P32245	Melanocortin receptor 4	85.50%	95.38%
CHEMBL3920	Q04759	Protein kinase C theta	84.31%	97.69%
CHEMBL221	P23219	Cyclooxygenase-1	82.74%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.59%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.48%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.19%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.76%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.22%	91.24%

Plants that contains it

• Abutilon indicum
• Ambrosia artemisioides
• Artemisia lancea
• Bidens subalternans
• Carpesium longifolium
• Carpesium macrocephalum
• Craspedia glauca
• Critonia quadrangularis
• Cronquistianthus bishopii
• Dittrichia viscosa subsp. viscosa
• Eupatorium cannabinum
• Flourensia riparia
• Inula helenium
• Inula japonica
• Inula magnifica
• Inula racemosa
• Ratibida columnifera
• Rudbeckia mollis
• Saussurea costus
• Stevia polyphylla
• Telekia speciosa
• Trilophozia quinquedentata
• Ursinia cakilefolia
• Xanthium strumarium

Cross-Links

• PubChem: 73285
• NPASS: NPC226988
• ChEMBL: CHEMBL137803
• LOTUS: LTS0028543
• wikiData: Q27089356