(-)-Ambroxide

Details

• Internal ID: 46371186-5388-4491-8224-c7132c331948
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran
• SMILES (Canonical): CC1(CCCC2(C1CCC3(C2CCO3)C)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CCO3)C)(C)C
• InChI: InChI=1S/C16H28O/c1-14(2)8-5-9-15(3)12(14)6-10-16(4)13(15)7-11-17-16/h12-13H,5-11H2,1-4H3/t12-,13+,15-,16+/m0/s1
• InChI Key: YPZUZOLGGMJZJO-LQKXBSAESA-N
• Popularity: 130 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₈O
• Molecular Weight: 236.39 g/mol
• Exact Mass: 236.214015512 g/mol
• Topological Polar Surface Area (TPSA): 9.20 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.41
• H-Bond Acceptor: 1
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 6790-58-5
• Ambroxide
• Ambroxan
• Ambrox
• (-)-ambrox
• FEMA No. 3471
• (+/-)-Ambrox
• Ambroxide, (+/-)-
• K60YJF1E9A
• TD34B3O8M9
• DTXSID0047113
• CHEBI:78307
• 8alpha,12-Oxido-13,14,15,16-tetranorlabdane
• (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan
• Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-
• (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran
• 1,5,5,9-Tetramethyl-13-oxatricyclo (8.3.0.0.(4.9))tridecane
• 1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(4,9))tridecane, (-)-
• Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR,5aS,9aS,9bR)-rel-
• 100679-85-4
• Ambroxide, (-)-
• UNII-TD34B3O8M9
• 1,5,5,9-Tetramethyl-13-oxatricyclo[8.3.0.04,9]tridecane
• EINECS 229-861-2
• AMBERMOX
• AMBROFIX
• ORCANOX
• AMBROXIDE [MI]
• UNII-K60YJF1E9A
• (-)-Ambroxide, 99%
• EC 229-861-2
• (-)-NORLABDANE OXIDE
• SCHEMBL114912
• (-)-Ambroxide, >=99%
• CHEMBL496447
• DTXCID8027113
• YPZUZOLGGMJZJO-LQKXBSAESA-N
• (-)-Ambroxide, analytical standard
• HY-N1384
• Tox21_302674
• MFCD00134491
• s5175
• AKOS025311143
• CCG-266845
• NCGC00256883-01
• AC-35128
• AS-56452
• Dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan, (3aR-(3aalpha,5abeta,9aalpha,9bbeta))-
• Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aR-(3aalpha,5abeta,9aalpha,9bbeta))-
• CAS-6790-58-5
• CS-0016804
• 4-Pentyloxyphenyl-4-Trans-PropylcyclohexylBenzo
• D88521
• A575915
• A-575915
• Q2793438
• F0001-1783
• 1,5,5,9-Tetramethyl-13-oxatricyclo[8.3.0.0(4,9)]tridecane
• 1,5,5,9-Tetramethyl-13-oxatricyclo(8.3.0.0(sup 4,9))tridecane
• (+/-)-(3aalpha,5abeta,9aalpha,9bbeta)-3a,6,6,9a-Tetramethyldodecahydronaphtho(2,1-b)furan
• Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aalpha,5abeta,9aalpha,9bbeta)-
• (+/-)-(3A.ALPHA.,5A.BETA.,9A.ALPHA.,9B.BETA.)-3A,6,6,9A-TETRAMETHYLDODECAHYDRONAPHTHO(2,1-B)FURAN
• (3AR-(3aalpha,5abeta,9aalpha,9bbeta))-dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan
• NAPHTHO(2,1-B)FURAN, DODECAHYDRO-3A,6,6,9A-TETRAMETHYL-, (3A.ALPHA.,5A.BETA.,9A.ALPHA.,9B.BETA.)-
• NAPHTHO(2,1-B)FURAN, DODECAHYDRO-3A,6,6,9A-TETRAMETHYL-, (3A.ALPHA.,5A.BETA.,9A.ALPHA.,9B.BETA.)-(+/-)-
• Naphtho(2,1-b)furan, dodecahydro-3a,6,6,9a-tetramethyl-, (3aalpha,5abeta,9aalpha,9bbeta)-(+/-)-
• NAPHTHO(2,1-B)FURAN, DODECAHYDRO-3A,6,6,9A-TETRAMETHYL-, (3AR-(3A.ALPHA.,5A.BETA.,9A.ALPHA.,9B.BETA.))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.8745	87.45%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Lysosomes	0.4426	44.26%
OATP2B1 inhibitior	-	0.8486	84.86%
OATP1B1 inhibitior	+	0.9278	92.78%
OATP1B3 inhibitior	+	0.9452	94.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.8258	82.58%
P-glycoprotein inhibitior	-	0.8828	88.28%
P-glycoprotein substrate	-	0.9452	94.52%
CYP3A4 substrate	+	0.5480	54.80%
CYP2C9 substrate	-	0.8017	80.17%
CYP2D6 substrate	-	0.7026	70.26%
CYP3A4 inhibition	-	0.9360	93.60%
CYP2C9 inhibition	-	0.6488	64.88%
CYP2C19 inhibition	+	0.5693	56.93%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.8075	80.75%
CYP2C8 inhibition	-	0.8203	82.03%
CYP inhibitory promiscuity	-	0.7931	79.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5560	55.60%
Eye corrosion	-	0.9102	91.02%
Eye irritation	+	0.8195	81.95%
Skin irritation	-	0.8721	87.21%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.8070	80.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5942	59.42%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.5584	55.84%
skin sensitisation	+	0.4761	47.61%
Respiratory toxicity	-	0.6889	68.89%
Reproductive toxicity	-	0.8889	88.89%
Mitochondrial toxicity	-	0.8000	80.00%
Nephrotoxicity	+	0.6541	65.41%
Acute Oral Toxicity (c)	III	0.8160	81.60%
Estrogen receptor binding	+	0.5295	52.95%
Androgen receptor binding	-	0.6061	60.61%
Thyroid receptor binding	-	0.5323	53.23%
Glucocorticoid receptor binding	-	0.6829	68.29%
Aromatase binding	-	0.6265	62.65%
PPAR gamma	-	0.7394	73.94%
Honey bee toxicity	-	0.8213	82.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8925	89.25%

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	95.81%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.43%	91.11%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.29%	96.38%
CHEMBL237	P41145	Kappa opioid receptor	88.28%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.28%	97.09%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	87.05%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.11%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.21%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.71%	93.04%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.73%	99.18%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	83.57%	95.58%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.34%	98.99%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.02%	95.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.84%	95.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.36%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.59%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.30%	82.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.20%	85.30%
CHEMBL1937	Q92769	Histone deacetylase 2	80.04%	94.75%

Plants that contains it

• Cistus × incanus
• Cistus creticus

Cross-Links

• PubChem: 10857465
• LOTUS: LTS0264157
• wikiData: Q2793438