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Swietephragmin H

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

Canonical Smiles	COC(=O)C[C@@H]1[C@]2(C)[C@@]34C[C@@]1(C)[C@@H]([C@]4(OC(=O)C)[C@H]([C@]14[C@@]2(CC[C@@]2([C@H]4CC(=O)O[C@H]2c2ccoc2)C)O[C@](O3)(O1)CC)O)OC/C(=C/C)/C
InChI	InChI=1S/C37H48O12/c1-9-20(3)17-44-29-31(6)19-34-32(7,23(31)15-25(39)42-8)33-13-12-30(5)24(16-26(40)45-27(30)22-11-14-43-18-22)36(33,49-35(10-2,47-33)48-34)28(41)37(29,34)46-21(4)38/h9,11,14,18,23-24,27-29,41H,10,12-13,15-17,19H2,1-8H3/b20-9+/t23-,24+,27-,28-,29-,30+,31+,32-,33-,34+,35+,36+,37+/m0/s1
InChIKey	WVCIOHAUGFJOKT-CQZZKOATSA-N
Formula	C₃₇H₄₈O₁₂
HBA	12
HBD	1
MW	684.78
Rotatable Bonds	8
TPSA	149.19
LogP	4.68
Number Rings	8
Number Aromatic Rings	1
Heavy Atom Count	49
Formal Charge	0
Fraction CSP3	0.76
Exact Mass	684.31
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Swietenia mahogani	Meliaceae	Plantae	459165

Showing of synonyms

Abdelgaleil SA, Doe M, et al. (2013). Rings B,D-seco limonoid antifeedants from Swietenia mahogani. Phytochemistry,2013,96,312-317. [View] [PubMed]

Pubchem: 101471346

No compound-protein relationship available.

SMILES: c1occc1C(OC(=O)C2)C(CC3)C2C4(C356)CC7C8(OC(O6)O4)C5CC(C8)C7

Level: 1

Mol. Weight: 684.78 g/mol

SMILES: C1C(=O)OCC(CC2)C1C3(C245)CC6C7(OC(O5)O3)C4CC(C7)C6

Level: 0

Mol. Weight: 684.78 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 684.78 g/mol

Antifeedant

Absorption

Caco-2 (logPapp): -5.35
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.290
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 241.51

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.600
Plasma Protein Binding: 93.23
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: Inhibitor

Excretion

Clearance: 4.630
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.370
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.440
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 8.900
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -440548.140
Rat (Acute): 5.180
Rat (Chronic Oral): 2.540
Fathead Minnow: 566.130
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 45901.200
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.450
Log(P): 4.18
Log S: -5.9
Log(Vapor Pressure): -1487.01
Melting Point: 215.33
pKa Acid: 4.35
pKa Basic: 2.44

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	0.8009
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8009
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7838
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7838
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7602
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7602
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7409
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7409
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7340
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7340
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7321
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7321
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7317
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7317
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7248
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7248
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7206
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7206
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7179
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7179

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