Natural Product: NPC195196

Natural Product IDNPC195196
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Sinapyl 9-O-[Beta-D-Apiofuranosyl(1->6)]-O-Beta-D-Glucopyranoside
IUPAC Name (2R,3S,4S,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoxy]oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL519405
PubChem CID 11386564
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0001766] Fatty acyl glycosides
          • [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey AZWYALFKHJLDEH-AFDHUBDESA-N
Standard InCHI InChI=1S/C22H32O13/c1-30-12-6-11(7-13(31-2)15(12)24)4-3-5-32-20-18(27)17(26)16(25)14(35-20)8-33-21-19(28)22(29,9-23)10-34-21/h3-4,6-7,14,16-21,23-29H,5,8-10H2,1-2H3/b4-3+/t14-,16-,17+,18-,19+,20-,21-,22-/m1/s1
SMILES OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](OC/C=C/c2cc(OC)c(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   504.18 Volume:   467.126
?
Van der Waals volume.
Dense:   1.079 LogP:   -0.074
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   0.705
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -1.842
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   10.0 Rigid Bonds:   18.0
TPSA:   196.99
?
Topological Polar Surface Area.
 H-Bond Acceptor:   13.0
H-Bond Donor:   7.0 Rings:   3.0
Heavy Atoms:   13.0

MedChem Properties

QED Drug-Likeness Score:   0.18 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.567 Fsp3:   0.636
MCE-18:   80.5
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Accepted
Pfizer Rule:   Rejected GSK Rule:   Accepted
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   1 PAINS Alert:   0
Colloidal aggregators:   0.359 Fluc inhibitor:   0.367
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.027
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.067
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.12 Promiscuous compounds:   0.152

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -6.194 MDCK Permeability:   -5.352
Pgp-inhibitor:   0.001 Pgp-substrate:   0.728
PAMPA:   0.78
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.525
20% Bioavailability (F20%):   0.277 30% Bioavailability (F30%):   0.961
50% Bioavailability (F50%):   0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.029 MRP1:   0.508
Plasma Protein Binding (PPB):   72.404% Volume Distribution (VD):   -0.518
Fu: 29.052%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   1.0
OATP1B3 inhibitor:   1.0 BCRP inhibitor:   0.523
BSEP inhibitor:   0.011

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.001 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.001 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   0.002
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.101
HLM stability:   0.067
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  2.024 Half-life (T1/2):  2.149

ADMET: Toxicity

hERG Blockers:  0.038 hERG Blockers (10um):  0.098
Human Hepatotoxicity (H-HT):  0.522 Drug-induced Liver Injury (DILI):  0.418
AMES Toxicity:  0.938 Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.057 Skin Sensitization:  0.992
Carcinogencity:  0.274 Eye Corrosion:  0.0
Eye Irritation:  0.169 Respiratory Toxicity:  0.019
Drug-induced Neurotoxicity:  0.068 Ototoxicity:  0.925
Hematotoxicity:  0.162 Drug-induced Nephrotoxicity:  0.538
Genotoxicity:  0.149 RPMI-8226 Immunitoxicity:  0.179
A549 Cytotoxicity:  0.625 Hek293 Cytotoxicity:  0.526
BCF:   0.532
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   3.055
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.811
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   3.769
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. fruit n.a. DOI[10.1007/s00217-007-0799-1]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. flower n.a. DOI[10.1016/j.foodchem.2011.01.077]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. PMID[12932140]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seeds n.a. n.a. PMID[15620261]
NPO20779 Garcinia hombroniana Species Clusiaceae Eukaryota leaves n.a. n.a. PMID[16124765]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20121251]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21438588]
NPO20146 Cladiella krempfi Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[21861494]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21899269]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22612410]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[23822585]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[26295595]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[36560643]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[36985451]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38792265]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[38794396]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[39138188]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[39527985]
NPO22052 Aspergillus candidus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[5391291]
NPO20972 Oscillatoria princeps Species Oscillatoriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19899 Crepis foetida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22121 Piper arboreum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22568 Aristolochia elegans Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21227 Aglaia elaeagnoidea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21282 Aplidium orthium Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22893 Apterostigma dentigerum Species Formicidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22052 Aspergillus candidus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28912 Astragalus gummifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2780 Brenneria rubrifaciens Species Pectobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO21096 Cardiospermum halicacabum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21859 Centaurea nigrescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20146 Cladiella krempfi Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12362 Coreopsis fasciculata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23010 Crinum defixum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22763 Cuphea carthagenensis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20332 Dioscoreophyllum cumminsii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20209 Dorstenia lindeniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21603 Eskemukerjea megacarpum n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO22381 Euphorbia segetalis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20779 Garcinia hombroniana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21991 Modiolus demissus Species Mytilidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22829 Ozoroa insignis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22250 Parastrephia lepidophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22635 Penstemon secundiflorus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6395 Phedimus kamtschaticus Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22315 Phlogacanthus thyrsiflorus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21420 Phormia regina Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21730 Pouzolzia occidentalis Species Urticaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22976 Ruta microcarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13355 Selinum carvifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22447 Sidastrum acuminatum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22509 Syncolostemon parviflorus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29466 Triglochin maritima Species Juncaginaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21473 Urtica triangularis Species Urticaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23953 Zanthoxylum monophyllum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Root Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota Twig n.a. n.a. Database[FooDB]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[FooDB]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22976 Ruta microcarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21096 Cardiospermum halicacabum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO21349 Punica granatum Species Lythraceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO6395 Phedimus kamtschaticus Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29466 Triglochin maritima Species Juncaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22976 Ruta microcarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21096 Cardiospermum halicacabum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22121 Piper arboreum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21096 Cardiospermum halicacabum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22976 Ruta microcarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28912 Astragalus gummifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22447 Sidastrum acuminatum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23953 Zanthoxylum monophyllum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21859 Centaurea nigrescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21730 Pouzolzia occidentalis Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23010 Crinum defixum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22568 Aristolochia elegans Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20652 Phytolacca acinosa Species Phytolaccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21227 Aglaia elaeagnoidea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20209 Dorstenia lindeniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20146 Cladiella krempfi Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21473 Urtica triangularis Species Urticaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20842 Beauveria felina Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16414 Thuja plicata Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22250 Parastrephia lepidophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20779 Garcinia hombroniana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6395 Phedimus kamtschaticus Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22635 Penstemon secundiflorus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21603 Eskemukerjea megacarpum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20096 Cirsium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22829 Ozoroa insignis Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21096 Cardiospermum halicacabum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20332 Dioscoreophyllum cumminsii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20972 Oscillatoria princeps Species Oscillatoriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22976 Ruta microcarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13355 Selinum carvifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22052 Aspergillus candidus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21282 Aplidium orthium Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22509 Syncolostemon parviflorus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22121 Piper arboreum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21349 Punica granatum Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22315 Phlogacanthus thyrsiflorus Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22893 Apterostigma dentigerum Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22763 Cuphea carthagenensis Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19899 Crepis foetida Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22381 Euphorbia segetalis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29466 Triglochin maritima Species Juncaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21991 Modiolus demissus Species Mytilidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28912 Astragalus gummifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21420 Phormia regina Species Calliphoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12362 Coreopsis fasciculata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2780 Brenneria rubrifaciens Species Pectobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT632 Tissue Brain Rattus norvegicus Activity = 32.1 % PMID[15620261]
NPT632 Tissue Brain Rattus norvegicus Activity = 29.8 % PMID[15620261]
NPT632 Tissue Brain Rattus norvegicus Activity = 26.5 % PMID[15620261]
NPT2535 Tissue Plasma Oryctolagus cuniculus Activity = 12.2 % PMID[15620261]
NPT2535 Tissue Plasma Oryctolagus cuniculus Activity = 14.4 % PMID[15620261]
NPT2535 Tissue Plasma Oryctolagus cuniculus Activity = 17.6 % PMID[15620261]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC195196 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.8235 Intermediate Similarity NPC252833
0.6875 Remote Similarity NPC132895
0.6053 Remote Similarity NPC470881
0.6 Remote Similarity NPC6836
0.5753 Remote Similarity NPC473867
0.5658 Remote Similarity NPC473924
0.5556 Remote Similarity NPC307110
0.5467 Remote Similarity NPC90318
0.5352 Remote Similarity NPC469527
0.5352 Remote Similarity NPC264784
0.5316 Remote Similarity NPC470510
0.5316 Remote Similarity NPC34965
0.5312 Remote Similarity NPC219040
0.525 Remote Similarity NPC602810
0.5205 Remote Similarity NPC171533
0.5195 Remote Similarity NPC289438
0.5195 Remote Similarity NPC227980
0.5128 Remote Similarity NPC25821
0.5063 Remote Similarity NPC242756
0.5059 Remote Similarity NPC472612

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC195196 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
NPD

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data