Macrocarpal A

Details

• Internal ID: 43c89341-214a-40f7-b5a2-5f6c9fea68fd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Aromadendrane sesquiterpenoids > 5,10-cycloaromadendrane sesquiterpenoids
• IUPAC Name: 5-[(1R)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• SMILES (Canonical): CC(C)CC(C1=C(C(=C(C(=C1O)C=O)O)C=O)O)C2(CCC3C2C4C(C4(C)C)CCC3(C)O)C
• SMILES (Isomeric): CC(C)C[C@@H](C1=C(C(=C(C(=C1O)C=O)O)C=O)O)[C@]2(CC[C@@H]3[C@@H]2[C@H]4[C@H](C4(C)C)CC[C@@]3(C)O)C
• InChI: InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19+,21-,22-,27-,28-/m1/s1
• InChI Key: IBLPTYJTKWQCDX-MOTAWSDJSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₀O₆
• Molecular Weight: 472.60 g/mol
• Exact Mass: 472.28248899 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.41
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• 132951-90-7
• 5-[(1R)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• 5-((1R)-1-((11S,7R)-7-hydroxy-3,3,7,11-tetramethyltricyclo(6.3.0.0(2,4))undec-11-yl)-3-methylbutyl)-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• MacrocarpalA
• SCHEMBL96208
• CHEMBL396609
• DTXSID70157878
• HY-N3346
• AKOS032948754
• CS-0023952
• 2,4,6-Trihydroxy-5-[(1R)-1-[(1abeta,4R,4abeta,7aalpha,7bbeta)-1,1,4,7-tetramethyl-4beta-hydroxydecahydro-1H-cyclopro
• 2,4,6-Trihydroxy-5-[(1R)-1-[(1Ass,4R,4Ass,7Aa,7Bss)-1,1,4,7-Tetramethyl-4ss-Hydroxydecahydro-1H-Cyclopro
• 5-(1R)-1-(1aR,4R,4aR,7S,7aS,7bR)-ecahydro-4-ydroxy-1,1,4,7-etramethyl-1H-ycloprop[e]zulen-7-l]-3-ethylbutyl]-2,4,6-rihydroxy-1,3-enzenedicarboxaldehde; 10-pi-ucarobustol F
• 5-[(1R)-1-((11S,7R)-7-hydroxy-3,3,7,11-tetramethyltricyclo[6.3.0.0<2,4>]undec-11-yl)-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde
• 5-[(1R)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methyl-butyl]-2,4,6-trihydroxy-benzene-1,3-dicarbaldehyde

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.6451	64.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7576	75.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8128	81.28%
OATP1B3 inhibitior	+	0.9142	91.42%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6478	64.78%
P-glycoprotein inhibitior	-	0.5676	56.76%
P-glycoprotein substrate	-	0.5906	59.06%
CYP3A4 substrate	+	0.6333	63.33%
CYP2C9 substrate	+	0.6085	60.85%
CYP2D6 substrate	-	0.8201	82.01%
CYP3A4 inhibition	-	0.6565	65.65%
CYP2C9 inhibition	-	0.6294	62.94%
CYP2C19 inhibition	-	0.7900	79.00%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	+	0.5311	53.11%
CYP2C8 inhibition	-	0.6984	69.84%
CYP inhibitory promiscuity	-	0.8797	87.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.7074	70.74%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8956	89.56%
Skin irritation	-	0.5982	59.82%
Skin corrosion	-	0.9245	92.45%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7452	74.52%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5340	53.40%
skin sensitisation	-	0.7968	79.68%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.5866	58.66%
Acute Oral Toxicity (c)	III	0.3662	36.62%
Estrogen receptor binding	+	0.7583	75.83%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	+	0.5732	57.32%
Glucocorticoid receptor binding	+	0.7998	79.98%
Aromatase binding	+	0.7587	75.87%
PPAR gamma	+	0.6581	65.81%
Honey bee toxicity	-	0.8334	83.34%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	96.20%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.05%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.37%	95.56%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	92.81%	98.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.75%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.34%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	87.70%	94.75%
CHEMBL268	P43235	Cathepsin K	87.10%	96.85%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.57%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.55%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.34%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.24%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.05%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.14%	90.71%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.33%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	82.17%	90.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.52%	96.90%
CHEMBL237	P41145	Kappa opioid receptor	80.27%	98.10%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.07%	98.75%

Plants that contains it

• Eucalyptus amplifolia
• Eucalyptus globulus
• Eucalyptus macrocarpa
• Eucalyptus sideroxylon
• Lonicera japonica

Cross-Links

• PubChem: 454457
• NPASS: NPC244640
• LOTUS: LTS0091941
• wikiData: Q72487948