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Spinosin
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavone Glycoside
| Canonical Smiles | COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O |
|---|---|
| InChI | InChI=1S/C28H32O15/c1-39-14-7-15-18(12(32)6-13(40-15)10-2-4-11(31)5-3-10)22(35)19(14)26-27(24(37)21(34)16(8-29)41-26)43-28-25(38)23(36)20(33)17(9-30)42-28/h2-7,16-17,20-21,23-31,33-38H,8-9H2,1H3 |
| InChIKey | VGGSULWDCMWZPO-UHFFFAOYSA-N |
| Formula | C28H32O15 |
| HBA | 15 |
| HBD | 9 |
| MW | 608.55 |
| Rotatable Bonds | 7 |
| TPSA | 249.2 |
| LogP | -1.78 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.46 |
| Exact Mass | 608.17 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ziziphus spina-christi | Rhamnaceae | Plantae | 264981 |
Showing of synonyms
Spinosin
72063-39-9
Flavoayamenin
6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
2''-O-glycosylswertisin
CHEBI:81360
DTXSID50222396
6-(2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
(1S)-1,5-anhydro-2-O-beta-D-glucopyranosyl-1-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-6-yl]-D-glucitol
4H-1-Benzopyran-4-one, 6-(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
(1S)-1,5-anhydro-2-O-beta-D-glucopyranosyl-1-(5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-6-yl)-D-glucitol
6-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxan-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one
DTXCID50144887
6-(2-O-b-D-Glucopyranosyl-b-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
6-((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
Spinocin
4H-1-Benzopyran-4-one, 6-(2-O-ss-D-glucopyranosyl-ss-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
6-(2-O-ss-D-Glucopyranosyl-ss-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Swertisin 2''-O-glucoside
MFCD09754430
Spinosin (Standard)
SCHEMBL2980651
GTPL13281
HY-N0651R
HMS3886F18
HY-N0651
S9134
AKOS015897169
CCG-270216
FS65586
AC-31296
BS-17968
DA-67722
CS-0009676
P2887
C17834
Q27155298
Pubchem:
155692
Cas:
72063-39-9
Gnps:
CCMSLIB00006427606
Zinc:
ZINC000085539971
Kegg Ligand:
C17834
Chebi:
81360
Nmrshiftdb2:
60023007
Metabolights:
MTBLC81360
Comptox:
DTXSID50222396
CPRiL:
81203
SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C(CCCO4)OC5CCCCO5
Level: 3
Mol. Weight: 608.55 g/mol
SMILES: O=c1ccoc(c12)ccc(c2)C3C(CCCO3)OC4CCCCO4
Level: 2
Mol. Weight: 608.55 g/mol
SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4
Level: 2
Mol. Weight: 608.55 g/mol
SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3
Level: 1
Mol. Weight: 608.55 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 608.55 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 608.55 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 608.55 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 608.55 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 608.55 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.63
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.270
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 11.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.860
- Plasma Protein Binding
- -20.04
- 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
- 7.930
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.940
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.790
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.620
- 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
- -17020.770
- Rat (Acute)
- 2.600
- Rat (Chronic Oral)
- 4.520
- Fathead Minnow
- 36.120
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 421.700
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.360
- Log(P)
- -0.07
- Log S
- -3.88
- Log(Vapor Pressure)
- -15.63
- Melting Point
- 198.76
- pKa Acid
- 3.8
- pKa Basic
- 6.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9524 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9494 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8981 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8783 |
| Bromodomain adjacent to zinc finger domain protein 2B | Q9UIF8 | BAZ2B_HUMAN | Homo sapiens | 3 | 0.8778 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8510 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8345 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 3 | 0.8336 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8307 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8284 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.8247 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.8194 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8105 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 4 | 0.8100 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7994 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7989 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7831 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7681 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7673 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7650 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 4 | 0.7625 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 3 | 0.7606 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.7563 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7504 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7499 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7478 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7444 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7415 |
| 4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7355 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | P0AF12 | MTNN_ECOLI | Escherichia coli | 3 | 0.7347 |
| Cytosolic purine 5'-nucleotidase | P49902 | 5NTC_HUMAN | Homo sapiens | 2 | 0.7327 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7319 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7311 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7298 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7243 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7073 |
| Phenolphthiocerol/phthiocerol polyketide synthase subunit C | P96202 | PPSC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7067 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7065 |
| 2-phospho-L-lactate transferase | Q8PVT6 | COFD_METMA | Methanosarcina mazei | 2 | 0.7062 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7046 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 3 | 0.7042 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7028 |