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Swietenolide

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

Canonical Smiles	COC(=O)C([C@@H]1[C@@]2(C)C3CC[C@@]4(C(=C3CC(C2=O)C(C1(C)C)O)CC(=O)O[C@H]4c1cocc1)C)O
InChI	InChI=1S/C27H34O8/c1-25(2)20(19(29)24(32)33-5)27(4)16-6-8-26(3)17(14(16)10-15(21(25)30)22(27)31)11-18(28)35-23(26)13-7-9-34-12-13/h7,9,12,15-16,19-21,23,29-30H,6,8,10-11H2,1-5H3/t15?,16?,19?,20-,21?,23-,26+,27+/m0/s1
InChIKey	CWIUUACMAKLANV-RYOFWEKOSA-N
Formula	C₂₇H₃₄O₈
HBA	8
HBD	2
MW	486.56
Rotatable Bonds	3
TPSA	123.27
LogP	3.13
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	486.23
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: 44575315

Zinc: ZINC000042852756

Nmrshiftdb2: 60114481

Chembl: CHEMBL515239

No compound-protein relationship available.

SMILES: c1occc1C(OC(=O)C2)C3CCC(C4=C23)C5C(=O)C(C4)CCC5

Level: 1

Mol. Weight: 486.56 g/mol

SMILES: C1C(=O)OCC(C1=C23)CCC2C4C(=O)C(C3)CCC4

Level: 0

Mol. Weight: 486.56 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 486.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.12
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.890
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.28

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 67.38
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: Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.190
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.570
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.320
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.190
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: -363.850
Rat (Acute): 4.060
Rat (Chronic Oral): 2.510
Fathead Minnow: 4.570
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 459.830
Hydration Free Energy: -2.720
Log(D) at pH=7.4: 2.860
Log(P): 1.78
Log S: -4.48
Log(Vapor Pressure): -9.43
Melting Point: 245.82
pKa Acid: 5.63
pKa Basic: 3.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8848
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8848
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8815
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8815
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8610
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8610
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.8470
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.8470
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8461
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8461
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8448
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8448
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8395
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8395
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8270
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8270
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8088
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8088
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.8032
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.8032
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.8029
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.8029
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7875
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7875
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7874
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7874
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7840
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7840
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7816
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7816
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7790
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7790
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7722
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7722
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7698
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7698
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7697
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7697
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7674
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7674
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7629
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7629
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7621
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7621
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7537
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7537
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7512
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7512
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7465
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7465
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7463
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7463
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7461
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7461
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7457
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7457
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7415
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7415
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7399
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7399
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7388
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7388
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7383
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7383
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7382
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7382
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7354
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7354
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7342
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7342
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7334
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7334
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7322
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7322
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7295
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7295
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7289
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7289
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7280
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7280
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7262
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7262
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7259
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7259
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7247
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7247
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7239
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7239
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7231
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7231
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7229
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7229
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	2	0.7227
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	2	0.7227
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7209
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7209
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7199
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7199
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7119
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7119
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7110
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7110
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7097
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7097
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7082
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7082
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7074
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7074
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7062
Amino-acid acetyltransferase	Q5FAK7	Q5FAK7_NEIG1	Neisseria gonorrhoeae	2	0.7062
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7048
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7048
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7033
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7033
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7013
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7013

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