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Callistephin

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Anthocyanin
- Subclass: Anthocyanin Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OC2=C(Oc3c(C2)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H22O10/c22-8-16-17(26)18(27)19(28)21(31-16)30-15-7-12-13(25)5-11(24)6-14(12)29-20(15)9-1-3-10(23)4-2-9/h1-6,16-19,21-28H,7-8H2/t16-,17-,18+,19-,21-/m1/s1
InChIKey	KNBXTHCIVPQMCC-GQUPQBGVSA-N
Formula	C₂₁H₂₂O₁₀
HBA	10
HBD	7
MW	434.4
Rotatable Bonds	4
TPSA	169.3
LogP	-0.08
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	434.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rubus rigidus	Rosaceae	Plantae	59497

Showing of synonyms

Nguelefack TB, Mbakam FH, et al. (2011). A dimeric triterpenoid glycoside and flavonoid glycosides with free radical-scavenging activity isolated from Rubus rigidus var. camerunensis.. Archives of pharmacal research,2011, 34(4), 543-550. [View] [PubMed]

Pubchem: 3080714

Cas: 18466-51-8

Gnps: CCMSLIB00000215588

Chebi: 36122

CPRiL: 91618

SMILES: c1ccccc1C(Oc(c23)cccc2)=C(C3)OC4CCCCO4

Level: 2

Mol. Weight: 434.4 g/mol

SMILES: c1cccc(c12)OC=C(C2)OC3CCCCO3

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: c1ccccc1C(=CC2)Oc(c23)cccc3

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: C1C=COc(c12)cccc2

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -7.0
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.370
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: 72.01
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: 15.400
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.790
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.880
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.380
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: -48.700
Rat (Acute): 2.210
Rat (Chronic Oral): 3.940
Fathead Minnow: 3.980
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 580.300
Hydration Free Energy: -6.210
Log(D) at pH=7.4: 0.460
Log(P): -0.52
Log S: -3.58
Log(Vapor Pressure): -12.13
Melting Point: 202.33
pKa Acid: 5.9
pKa Basic: 5.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9823
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9412
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9226
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9132
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9089
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.9056
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.9028
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8999
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8866
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8733
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8698
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8689
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8669
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8659
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8610
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8506
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8433
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8356
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	4	0.8316
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.8135
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8132
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8026
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7912
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7895
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7830
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7827
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7803
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7799
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7763
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7734
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7686
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7638
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7628
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7623
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7598
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7583
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7580
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7569
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7553
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7433
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7431
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7428
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7404
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7370
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7354
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7349
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7322
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7318
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7312
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7294
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7292
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7257
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7222
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7205
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7198
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7132
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7049
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7026
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7018
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7015
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7014
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7012
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7003

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