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Methylangolensate

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Limonoid

Canonical Smiles	COC(=O)C[C@@H]1[C@]2(C)[C@H](CC(=O)C1(C)C)O[C@]13C(=C)[C@@H]2CC[C@@]3(C)[C@@H](OC(=O)C1)c1cocc1
InChI	InChI=1S/C27H34O7/c1-15-17-7-9-25(4)23(16-8-10-32-14-16)33-22(30)13-27(15,25)34-20-12-19(28)24(2,3)18(26(17,20)5)11-21(29)31-6/h8,10,14,17-18,20,23H,1,7,9,11-13H2,2-6H3/t17-,18-,20-,23-,25-,26+,27-/m0/s1
InChIKey	YNMYHRYTRCKSMI-SQHTYAHXSA-N
Formula	C₂₇H₃₄O₇
HBA	7
HBD	0
MW	470.56
Rotatable Bonds	3
TPSA	92.04
LogP	4.56
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	470.23
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ekebergia capensis	Meliaceae	Plantae	124949

Showing of synonyms

Murata T, Miyase T, et al. (2008). Antiplasmodial triterpenoids from Ekebergia capensis.. Journal of Natural Products,2008,71(2),167-174. [View] [PubMed]

Pubchem: 21596327

Gnps: CCMSLIB00000850935

Zinc: ZINC000003978132

Nmrshiftdb2: 60114439

Chembl: CHEMBL483006

CPRiL: 245920

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)C(OC(=O)C4)c5ccoc5

Level: 1

Mol. Weight: 470.56 g/mol

SMILES: C1CC(=O)CC(O2)C1C(C3=C)CCC(C234)COC(=O)C4

Level: 0

Mol. Weight: 470.56 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 470.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.93
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.860
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.230
Plasma Protein Binding: 73.59
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.350
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.110
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.560
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.580
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -222.500
Rat (Acute): 4.100
Rat (Chronic Oral): 2.060
Fathead Minnow: 3.960
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 475.350
Hydration Free Energy: -2.970
Log(D) at pH=7.4: 3.290
Log(P): 3.48
Log S: -5.43
Log(Vapor Pressure): -9.03
Melting Point: 227.35
pKa Acid: 7.03
pKa Basic: 4.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8881
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8881
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8257
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.8257
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7824
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7824
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7816
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7816
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7648
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7648
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7507
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7507
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7442
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7442
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7416
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7416
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7372
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7372
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7337
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7337
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7274
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7274
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7271
Heat shock cognate 71 kDa protein	P11142	HSP7C_HUMAN	Homo sapiens	3	0.7271
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7269
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7269
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7238
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7238
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	2	0.7205
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	2	0.7205
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7197
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7197
Ferric enterobactin-binding periplasmic protein FepB	P0AEL6	FEPB_ECOLI	Escherichia coli	3	0.7182
Ferric enterobactin-binding periplasmic protein FepB	P0AEL6	FEPB_ECOLI	Escherichia coli	3	0.7182
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7098
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7098
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7097
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7097
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7094
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7094
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7077
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7077
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7039
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7039
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7025
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7025
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7021
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7021
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7013
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7013
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	2	0.7010
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	2	0.7010

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