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Khayanoside

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

Canonical Smiles	OC[C@H]1O[C@@H](OC[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3([C@]4([C@@]2(C)C(=O)OC)O[C@@H]4C(=O)O[C@H]3c2ccoc2)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C33H44O13/c1-29(2)19(15-43-27-23(38)22(37)21(36)17(13-34)44-27)30(3,10-8-20(29)35)18-7-11-31(4)24(16-9-12-42-14-16)45-26(39)25-33(31,46-25)32(18,5)28(40)41-6/h8-10,12,14,17-19,21-25,27,34,36-38H,7,11,13,15H2,1-6H3/t17-,18-,19+,21-,22+,23-,24+,25-,27-,30-,31+,32-,33-/m1/s1
InChIKey	OOWUHRQISTYBRO-NBPOMTDNSA-N
Formula	C₃₃H₄₄O₁₃
HBA	13
HBD	4
MW	648.7
Rotatable Bonds	7
TPSA	194.72
LogP	1.21
Number Rings	6
Number Aromatic Rings	1
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.73
Exact Mass	648.28
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Khaya senegalensis	Meliaceae	Plantae	587579

Showing of synonyms

Nakatani M, Abdelgaleil SA, et al. (2002). Three new modified limonoids from Khaya senegalensis. Journal of Natural Products,2002,65(8),1219-1221. [View] [PubMed]

Pubchem: 101094894

Nmrshiftdb2: 80003819

No compound-protein relationship available.

SMILES: O1CCCCC1OCC(C2)C(C=CC2=O)C(C3)CCC4C(OC(=O)C(C345)O5)c6ccoc6

Level: 3

Mol. Weight: 648.7 g/mol

SMILES: O1CCCCC1OCC(C2)C(C=CC2=O)C(C3)CCC4COC(=O)C(C345)O5

Level: 2

Mol. Weight: 648.7 g/mol

SMILES: c1occc1C(OC(=O)C(C234)O4)C2CCC(C3)C(CC5)C=CC5=O

Level: 2

Mol. Weight: 648.7 g/mol

SMILES: C123C(O3)C(=O)OCC1CCC(C2)C(CC4)C=CC4=O

Level: 1

Mol. Weight: 648.7 g/mol

SMILES: C1CCCC2C(OC(=O)C(C123)O3)c4ccoc4

Level: 1

Mol. Weight: 648.7 g/mol

SMILES: O=C1C=CCC(C1)COC2CCCCO2

Level: 1

Mol. Weight: 648.7 g/mol

SMILES: C123C(O3)C(=O)OCC1CCCC2

Level: 0

Mol. Weight: 648.7 g/mol

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 648.7 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 648.7 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 648.7 g/mol

Antifeedant

Absorption

Caco-2 (logPapp): -5.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.900
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 37.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.720
Plasma Protein Binding: 71.38
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: Non-Inhibitor

Excretion

Clearance: 8.030
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.500
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.180
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: -71765.160
Rat (Acute): 3.970
Rat (Chronic Oral): 3.310
Fathead Minnow: 104.060
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: 3723.760
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.910
Log(P): 0.76
Log S: -3.83
Log(Vapor Pressure): -112.76
Melting Point: 202.13
pKa Acid: 4.39
pKa Basic: 3.43

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	0.8503
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8503
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.8251
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.8251
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8246
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8246
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8170
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8170
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8108
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.8108
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8042
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8042
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7945
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7945
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7914
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7914
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7902
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7902
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7885
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7885
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7858
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7858
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7822
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7822
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7793
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7793
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7629
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7629
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7620
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7620
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7565
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7565
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7504
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7504
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7486
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	2	0.7486
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7453
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7453
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7441
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7441
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7416
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7416
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7416
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7416
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7393
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7393
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7373
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7373
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7359
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7359
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7358
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7358
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7319
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7319
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7315
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7315
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7312
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7312
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7274
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7274
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7190
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7190
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7188
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7188
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7182
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7182
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7170
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7170
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7165
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7165
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7164
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7164
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7162
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7162
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7161
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7161
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7145
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7145
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7137
Alanine racemase	Q180W0	Q180W0_CLOD6	Clostridioides difficile	2	0.7137
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7110
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7110
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7109
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7109
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7090
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7090
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7088
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	2	0.7088
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7087
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7087
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	2	0.7067
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	2	0.7067
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7039
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7039
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7034
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7034

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