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Ciwujianoside C3

Family: Plantae - Araliaceae
Kingdom: Plantae
Class: Saponin
- Subclass: Oleanane-Type Saponin

Canonical Smiles	OCC1O[C@H]([C@H](C([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI	InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14?,17-,19?,20+,21+/m1/s1
InChIKey	MYXNWGACZJSMBT-RAFLFOFHSA-N
Formula	C₂₁H₂₀O₁₀
HBA	10
HBD	7
MW	432.38
Rotatable Bonds	3
TPSA	181.05
LogP	0.09
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	432.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Oreopanax guatemalensis	Araliaceae	Plantae	2951918

Showing of synonyms

Meleka FR, Miyase T, et al. (2002). Triterpenoid saponins from Oreopanax guatemalensis. Phytochemistry,2002,60(2),185-195. [View] [PubMed]

Pubchem: 21626481

Cas: 114906-74-0

Nmrshiftdb2: 60072001

Chembl: CHEMBL1171250

Bindingdb: 50322751

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 432.38 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 432.38 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 432.38 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 432.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.66
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 74.77
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.46
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.45
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.88
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.39
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: -47.06
Rat (Acute): 2.5
Rat (Chronic Oral): 4.4
Fathead Minnow: 3.94
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 621.16
Hydration Free Energy: -6.77
Log(D) at pH=7.4: 0.55
Log(P): 1.33
Log S: -3.84
Log(Vapor Pressure): -13.44
Melting Point: 232.35
pKa Acid: 4.34
pKa Basic: 8.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9498
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9498
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9493
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9493
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9241
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9241
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9140
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9140
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8939
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8939
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8867
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8867
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8773
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8773
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8762
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8762
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8599
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8599
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8560
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8560
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8304
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8304
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8303
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8303
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8255
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8255
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8244
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8244
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8239
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8239
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8231
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8231
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8187
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8187
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8001
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8001
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7796
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7796
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7785
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7785
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7760
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7760
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7720
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7720
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7689
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7689
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7668
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7668
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7663
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7663
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7597
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7597
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7590
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7590
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7552
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7552
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7501
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7501
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7498
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7498
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7480
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7480
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7423
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7423
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7386
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7386
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7336
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7336
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7335
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7335
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7329
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7329
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7314
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7314
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7313
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7313
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7273
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7273
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7226
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7226
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7213
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7213
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7212
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7212
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7155
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7155
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7119
C-1-tetrahydrofolate synthase, cytoplasmic	P11586	C1TC_HUMAN	Homo sapiens	3	0.7119
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7062
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7062
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041

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