Ambreinolide

Details

• Internal ID: b96e30e7-2974-4868-bbe3-f7189aab9f4c
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (4aR,6aS,10aS,10bR)-4a,7,7,10a-tetramethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-3-one
• SMILES (Canonical): CC1(CCCC2(C1CCC3(C2CCC(=O)O3)C)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CCC(=O)O3)C)(C)C
• InChI: InChI=1S/C17H28O2/c1-15(2)9-5-10-16(3)12(15)8-11-17(4)13(16)6-7-14(18)19-17/h12-13H,5-11H2,1-4H3/t12-,13+,16-,17+/m0/s1
• InChI Key: OXLWUQRYCMJFSG-UWWPHRKUSA-N
• Popularity: 19 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₈O₂
• Molecular Weight: 264.40 g/mol
• Exact Mass: 264.208930132 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Ambreinolid
• (+)-Ambreinolide
• 468-84-8
• EINECS 207-413-7
• 8M8TY60818
• 3H-Naphtho(2,1-b)pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR,6aS,10aS,10bR)-
• 3H-Naphtho[2,1-b]pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR,6aS,10aS,10bR)-
• ( )-Ambreinolide
• [4aR-(4aalpha,6abeta,10aalpha,10bbeta)]-dodecahydro-4a,7,7,10a-tetramethyl-3H-naphth[2,1-b]pyran-3-one
• 3H-Naphtho(2,1-b)pyran-3-one, dodecahydro-4a,7,7,10a-tetramethyl-, (4aR-(4aalpha,6abeta,10aalpha,10bbeta))-
• (4AR-(4aalpha,6abeta,10aalpha,10bbeta))-dodecahydro-4a,7,7,10a-tetramethyl-3H-naphth(2,1-b)pyran-3-one
• AMBREINOLIDE, (+)-
• SCHEMBL5148266
• UNII-8M8TY60818
• DTXSID10883386
• Q27896558
• 14,15,16-Trinorlabdan-13-oic acid, 8-hydroxy-, .delta.-lactone
• 14,15,16-Trinorlabdan-13-oic acid, 8-hydroxy-, delta-lactone
• 1-Naphthalenepropionic acid, decahydro-2-hydroxy-2,5,5,8a-tetramethyl-,delta-lactone
• (4AR,6AS,10AS,10BR)-DODECAHYDRO-4A,7,7,10A-TETRAMETHYL-3H-NAPHTHO(2,1-B)PYRAN-3-ONE
• 1-NAPHTHALENEPROPIONIC ACID, DECAHYDRO-2-HYDROXY-2,5,5,8A-TETRAMETHYL-, .DELTA.-LACTONE
• 3H-NAPHTHO(2,1-B)PYRAN-3-ONE, DODECAHYDRO-4A,7,7,10A-TETRAMETHYL-, (4AR-(4A.ALPHA.,6A.BETA.,10A.ALPHA.,10B.BETA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.8319	83.19%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5373	53.73%
OATP2B1 inhibitior	-	0.8519	85.19%
OATP1B1 inhibitior	+	0.9026	90.26%
OATP1B3 inhibitior	+	0.9803	98.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.6994	69.94%
P-glycoprotein inhibitior	-	0.7986	79.86%
P-glycoprotein substrate	-	0.9602	96.02%
CYP3A4 substrate	+	0.5676	56.76%
CYP2C9 substrate	-	0.5878	58.78%
CYP2D6 substrate	-	0.8387	83.87%
CYP3A4 inhibition	-	0.9313	93.13%
CYP2C9 inhibition	-	0.8409	84.09%
CYP2C19 inhibition	+	0.5345	53.45%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.8530	85.30%
CYP2C8 inhibition	-	0.8386	83.86%
CYP inhibitory promiscuity	-	0.9828	98.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6630	66.30%
Eye corrosion	-	0.9363	93.63%
Eye irritation	+	0.5369	53.69%
Skin irritation	-	0.6082	60.82%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5275	52.75%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	+	0.5204	52.04%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	+	0.6173	61.73%
Acute Oral Toxicity (c)	III	0.8794	87.94%
Estrogen receptor binding	+	0.6773	67.73%
Androgen receptor binding	-	0.6043	60.43%
Thyroid receptor binding	-	0.5129	51.29%
Glucocorticoid receptor binding	-	0.4829	48.29%
Aromatase binding	-	0.5232	52.32%
PPAR gamma	-	0.7139	71.39%
Honey bee toxicity	-	0.9154	91.54%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.8882	88.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.93%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.57%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.85%	96.38%
CHEMBL2581	P07339	Cathepsin D	87.50%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.90%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.76%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.09%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.99%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.10%	82.69%
CHEMBL1871	P10275	Androgen Receptor	83.92%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.03%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.28%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	80.85%	94.75%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.65%	99.18%

Plants that contains it

• Bryum weigelii
• Cyperus erectus
• Eragrostis viscosa
• Fritillaria thunbergii
• Plantago cornuti
• Plectranthus sylvestris
• Pseudoclausena chrysogyne
• Salvia palaestina
• Salvia yosgadensis
• Tulipa sylvestris
• Vatica harmandiana

Cross-Links

• PubChem: 11807560
• NPASS: NPC221072
• LOTUS: LTS0181724
• wikiData: Q27896558