Structure

Physi-Chem Properties

Molecular Weight:  362.12
Volume:  319.036
LogP:  -1.572
LogD:  -0.636
LogS:  -1.356
# Rotatable Bonds:  4
TPSA:  161.6
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.276
Synthetic Accessibility Score:  5.091
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.085
MDCK Permeability:  0.00010553788888501003
Pgp-inhibitor:  0.002
Pgp-substrate:  0.613
Human Intestinal Absorption (HIA):  0.717
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.207
Plasma Protein Binding (PPB):  19.307941436767578%
Volume Distribution (VD):  0.357
Pgp-substrate:  58.8671989440918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.059
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.192
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.025
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.014
CYP3A4-substrate:  0.028

ADMET: Excretion

Clearance (CL):  1.268
Half-life (T1/2):  0.872

ADMET: Toxicity

hERG Blockers:  0.093
Human Hepatotoxicity (H-HT):  0.198
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.084
Rat Oral Acute Toxicity:  0.153
Maximum Recommended Daily Dose:  0.004
Skin Sensitization:  0.28
Carcinogencity:  0.848
Eye Corrosion:  0.007
Eye Irritation:  0.102
Respiratory Toxicity:  0.92

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC258501

Natural Product ID:  NPC258501
Common Name*:   Catalpol
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[[(1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:   Catalpol
Standard InCHIKey:  LHDWRKICQLTVDL-PZYDOOQISA-N
Standard InCHI:  InChI=1S/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@]2(CO)O[C@H]2[C@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL513223
PubChem CID:   91520
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(79)80020-5]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. Brazilian n.a. PMID[10328294]
NPO12175 Iostephane heterophylla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11473422]
NPO12492 Dictyophora indusiata Species Phallaceae Eukaryota n.a. n.a. n.a. PMID[12502311]
NPO13309 Buddleja cordobensis Species Scrophulariaceae Eukaryota Aerial parts Cerro de La Cruz, Departamento La Capital, San Luis, Argentina 2001-JUN PMID[15043410]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[15568764]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota pericarp n.a. n.a. PMID[16038565]
NPO12653 Diacarnus levii Species Podospongiidae Eukaryota n.a. at a depth of -10 M off the coast of Papua New Guinea 1998-JUN PMID[17253866]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[17944538]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18166016]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20232858]
NPO30110 Veronica lavaudiana Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[21568305]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[22823026]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota Roots n.a. n.a. PMID[22916954]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[2488968]
NPO14207 Euphorbia neriifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25252924]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota leaves and stems Ha Long, Quang Ninh province, Vietnam 2014-Jul PMID[25769817]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. seed n.a. PMID[2610694]
NPO20005 Penstemon barbatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO33356 vitex mollis Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO33328 cresentia alata Species n.a. n.a. n.a. n.a. n.a. PMID[26351040]
NPO33113 castilleja tenuiflora Species Orobanchaceae Eukaryota n.a. n.a. n.a. PMID[26351040]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. PMID[26562611]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. bark n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. PMID[26767291]
NPO40316 Rehmannia chingii Species Orobanchaceae Eukaryota n.a. n.a. n.a. PMID[26859776]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[29792702]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. PMID[30892891]
NPO14207 Euphorbia neriifolia Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[32822173]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. xylem n.a. Database[Article]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3599 Rheum maximowiczii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12373 Vinca minor Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10011 Myrsine capitellata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10011 Myrsine capitellata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7135 Mollugo spergula Species Molluginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3599 Rheum maximowiczii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO214 Platycodon grandiflorus Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6413 Viguiera stenoloba Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12373 Vinca minor Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO214 Platycodon grandiflorus Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2580 Globularia vulgaris Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3671 Rhodiola coccinea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO396 Ventilago goughii Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3477 Plantago asiatica Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11674 Viburnum lantanoides Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11342 Sideritis trojana Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22168 Scutellaria rivularis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1455 Aspergillus caelatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12175 Iostephane heterophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11946 Cleistanthus gracilis Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2576 Eusideroxylon zwageri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24096 Furcraea macrophylla Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12418 Myroxylon peruiferum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10011 Myrsine capitellata Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1790 Plectranthus comosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1314 Goodenia strophiolata Species Goodeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8101 Rehmannia glutinosa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14818 Neofusicoccum mangiferae Species Botryosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13466 Atroxima afzeliana Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14207 Euphorbia neriifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12598 Osteospermum fruticosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9550 Eritrichium incanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO214 Platycodon grandiflorus Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12492 Dictyophora indusiata Species Phallaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18170 Aconitum miyabei Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6413 Viguiera stenoloba Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4923 Ononis hircina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14776 Petrosia weinbergi Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17497 Bohadschia koellikeri Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1350 Danaus plexippus Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12241 Hypericum reflexum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11397 Cladophora rupestris Species Cladophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1150 Juncus effusus Species Juncaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13581 Daphnandra repandula Species Atherospermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5173 Antidesma pentandrum Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1882 Genista transcaucasica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5311 Isertia haenkeana Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12653 Diacarnus levii Species Podospongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15078 Suckleya suckleyana Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7135 Mollugo spergula Species Molluginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12047 Solanum unguiculatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5908 Dianella tasmanica Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4005 Andrachne rotundifolia Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14462 Jasonia tuberosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO34 Epidendrum mosenii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11255 Veronica thomsonii Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6864 Lactarius spinosulus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO959 Ligularia vellerea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9162 Nicotiana affinis Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8918 Plantago depressa Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12526 Veronica turrilliana Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18375 Bauhinia tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26737 Solanum mauritianum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3040 Acanthella carteri Species Melastomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13096 Lecidea kochiana Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13955 Lippia javanica Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10092 Hesperocyparis bakeri Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2471 Axinyssa variabilis Species Halichondriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3211 Liatris microcephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10003 Veronica cymbalaria Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15456 Sideritis soluta Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10553 Heterophyllaea pustulata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11625 Markhamia stipulata Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7323 Lindera pipericarpa Species Tineidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7648 Geigeria plumosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7006 Garcinia subelliptica Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3093 Phyllanthus tenellus Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9908 Adenium somalense Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20005 Penstemon barbatus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19124 Guevaria sodiroi n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2289 Vicia hirsuta Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12762 Elattostachys apetala Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5598 Caesalpinia brevifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3599 Rheum maximowiczii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5805 Chlorociboria aeruginascens Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18057 Chlorobium phaeobacteroides Species Chlorobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19265 Metarhizium viride Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10035 Ficus pantoniana Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11491 Vellozia declinans Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13309 Buddleja cordobensis Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9254 Scutellaria racemosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13327 Phomopsis leptostromiformis Species Valsaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9561 Preussia australis Species Sporormiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4691 Stereocaulon spathuliferum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16962 Dipsacus laciniatus Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10102 Pithecellobium albicans Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12373 Vinca minor Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25931 Psammogeton canescens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO944 Senecio sandersonii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14065 Artemisia koidzumii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3432 Tovomita brasiliensis Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13951 Phialophora alba Species Herpotrichiellaceae Eukaryota 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT179 Cell Line A2780 Homo sapiens GI50 > 100000.0 nM PMID[570013]
NPT1577 Cell Line SW1573 Homo sapiens GI50 > 100000.0 nM PMID[570013]
NPT1183 Cell Line WiDr Homo sapiens GI50 > 100000.0 nM PMID[570013]
NPT396 Cell Line T47D Homo sapiens GI50 > 100000.0 nM PMID[570013]
NPT4623 Individual Protein Taq polymerase 1 Thermus aquaticus IC50 = 47800.0 nM PMID[570014]
NPT179 Cell Line A2780 Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT1723 Cell Line HBL-100 Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT165 Cell Line HeLa Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT1577 Cell Line SW1573 Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT396 Cell Line T47D Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT1183 Cell Line WiDr Homo sapiens GI50 > 100000.0 nM PMID[570015]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[570017]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 54.03 % PMID[570018]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 75.78 % PMID[570018]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 11.32 % PMID[570019]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 44.2 % PMID[570020]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 47.6 % PMID[570020]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens Inhibition = 63.7 % PMID[570020]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens Inhibition <= 30.0 % PMID[570020]
NPT65 Cell Line HepG2 Homo sapiens Survival = 69.1 % PMID[570021]
NPT34 Cell Line BV-2 Mus musculus IC50 = 7300.0 nM PMID[570021]
NPT179 Cell Line A2780 Homo sapiens IC50 > 10000.0 nM PMID[570021]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 10000.0 nM PMID[570021]
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[570021]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Activity = 8.2 day PMID[570014]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Activity = 73.3 % PMID[570014]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Activity = -0.01 mg/mg/day PMID[570014]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Activity = 0.017 mg/mg/day PMID[570014]
NPT1419 Organism Tribolium castaneum Tribolium castaneum Activity = -66.1 % PMID[570014]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 24.33 % PMID[570016]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 8.53 % PMID[570016]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -5.36 % PMID[570019]
NPT27 Others Unspecified Activity = 86.1 % PMID[570021]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[570021]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC258501 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9878 High Similarity NPC148534
0.9759 High Similarity NPC22918
0.9529 High Similarity NPC276298
0.939 High Similarity NPC98276
0.939 High Similarity NPC259296
0.9167 High Similarity NPC171484
0.9167 High Similarity NPC149018
0.8851 High Similarity NPC50464
0.8652 High Similarity NPC473150
0.8652 High Similarity NPC294643
0.8652 High Similarity NPC274274
0.8427 Intermediate Similarity NPC93190
0.8387 Intermediate Similarity NPC470683
0.8387 Intermediate Similarity NPC470684
0.7865 Intermediate Similarity NPC136699
0.7865 Intermediate Similarity NPC220167
0.7708 Intermediate Similarity NPC284063
0.767 Intermediate Similarity NPC193741
0.7629 Intermediate Similarity NPC86843
0.7604 Intermediate Similarity NPC6765
0.7604 Intermediate Similarity NPC93869
0.76 Intermediate Similarity NPC329834
0.7579 Intermediate Similarity NPC280390
0.7558 Intermediate Similarity NPC279575
0.7524 Intermediate Similarity NPC475851
0.7524 Intermediate Similarity NPC475924
0.75 Intermediate Similarity NPC170595
0.75 Intermediate Similarity NPC274588
0.7474 Intermediate Similarity NPC235051
0.7451 Intermediate Similarity NPC127235
0.7412 Intermediate Similarity NPC248427
0.7412 Intermediate Similarity NPC470659
0.7412 Intermediate Similarity NPC470660
0.74 Intermediate Similarity NPC216911
0.74 Intermediate Similarity NPC476228
0.7379 Intermediate Similarity NPC197813
0.7379 Intermediate Similarity NPC80338
0.7379 Intermediate Similarity NPC148270
0.7347 Intermediate Similarity NPC170527
0.73 Intermediate Similarity NPC476320
0.73 Intermediate Similarity NPC476211
0.7292 Intermediate Similarity NPC66504
0.7282 Intermediate Similarity NPC170432
0.7263 Intermediate Similarity NPC299527
0.7255 Intermediate Similarity NPC475928
0.7255 Intermediate Similarity NPC37240
0.7228 Intermediate Similarity NPC3488
0.7228 Intermediate Similarity NPC476230
0.7228 Intermediate Similarity NPC27474
0.7228 Intermediate Similarity NPC287539
0.7172 Intermediate Similarity NPC161293
0.7157 Intermediate Similarity NPC35185
0.7157 Intermediate Similarity NPC304163
0.7157 Intermediate Similarity NPC4899
0.7157 Intermediate Similarity NPC474730
0.7157 Intermediate Similarity NPC177013
0.7143 Intermediate Similarity NPC110701
0.7143 Intermediate Similarity NPC63897
0.7129 Intermediate Similarity NPC244878
0.7115 Intermediate Similarity NPC474569
0.71 Intermediate Similarity NPC76486
0.7087 Intermediate Similarity NPC329704
0.7059 Intermediate Similarity NPC20673
0.703 Intermediate Similarity NPC151093
0.703 Intermediate Similarity NPC37866
0.7021 Intermediate Similarity NPC470658
0.7019 Intermediate Similarity NPC312774
0.6989 Remote Similarity NPC260852
0.6972 Remote Similarity NPC287075
0.6964 Remote Similarity NPC219656
0.6961 Remote Similarity NPC91497
0.6952 Remote Similarity NPC26798
0.6939 Remote Similarity NPC48463
0.6931 Remote Similarity NPC263674
0.6931 Remote Similarity NPC261372
0.6931 Remote Similarity NPC58267
0.6916 Remote Similarity NPC40440
0.6916 Remote Similarity NPC42482
0.6907 Remote Similarity NPC249408
0.6907 Remote Similarity NPC104129
0.69 Remote Similarity NPC241407
0.69 Remote Similarity NPC291709
0.6893 Remote Similarity NPC4637
0.6893 Remote Similarity NPC31346
0.6893 Remote Similarity NPC219038
0.6893 Remote Similarity NPC98859
0.6887 Remote Similarity NPC226642
0.6882 Remote Similarity NPC20072
0.6881 Remote Similarity NPC19888
0.6875 Remote Similarity NPC472080
0.6863 Remote Similarity NPC469919
0.6863 Remote Similarity NPC469918
0.6863 Remote Similarity NPC157739
0.6863 Remote Similarity NPC117066
0.6863 Remote Similarity NPC158088
0.6863 Remote Similarity NPC223700
0.6863 Remote Similarity NPC96399
0.6857 Remote Similarity NPC474464
0.6857 Remote Similarity NPC475521
0.6857 Remote Similarity NPC475365
0.6848 Remote Similarity NPC100697
0.6842 Remote Similarity NPC233500
0.6837 Remote Similarity NPC117596
0.6837 Remote Similarity NPC197107
0.6837 Remote Similarity NPC307699
0.6832 Remote Similarity NPC241911
0.6832 Remote Similarity NPC472989
0.6832 Remote Similarity NPC207617
0.6827 Remote Similarity NPC136816
0.6827 Remote Similarity NPC106668
0.6827 Remote Similarity NPC272015
0.6827 Remote Similarity NPC471599
0.6822 Remote Similarity NPC7213
0.6804 Remote Similarity NPC248312
0.6796 Remote Similarity NPC471247
0.6792 Remote Similarity NPC242748
0.6792 Remote Similarity NPC473923
0.6792 Remote Similarity NPC181845
0.6792 Remote Similarity NPC474015
0.6792 Remote Similarity NPC473476
0.6789 Remote Similarity NPC197231
0.6789 Remote Similarity NPC477032
0.6789 Remote Similarity NPC477028
0.6789 Remote Similarity NPC124677
0.6783 Remote Similarity NPC196130
0.6768 Remote Similarity NPC472126
0.6768 Remote Similarity NPC472125
0.6768 Remote Similarity NPC472124
0.6765 Remote Similarity NPC278939
0.6765 Remote Similarity NPC347923
0.6765 Remote Similarity NPC243728
0.6765 Remote Similarity NPC473555
0.6765 Remote Similarity NPC472290
0.6765 Remote Similarity NPC153559
0.6765 Remote Similarity NPC473890
0.6765 Remote Similarity NPC476057
0.6765 Remote Similarity NPC471770
0.6762 Remote Similarity NPC475701
0.6762 Remote Similarity NPC27687
0.6759 Remote Similarity NPC472901
0.6759 Remote Similarity NPC208307
0.675 Remote Similarity NPC175333
0.6737 Remote Similarity NPC116613
0.6737 Remote Similarity NPC474156
0.6733 Remote Similarity NPC240838
0.6733 Remote Similarity NPC101051
0.6731 Remote Similarity NPC47566
0.6731 Remote Similarity NPC4831
0.6731 Remote Similarity NPC160734
0.6731 Remote Similarity NPC88000
0.6731 Remote Similarity NPC309425
0.6731 Remote Similarity NPC129372
0.6731 Remote Similarity NPC472023
0.6731 Remote Similarity NPC267510
0.6731 Remote Similarity NPC470168
0.6729 Remote Similarity NPC283829
0.6729 Remote Similarity NPC113044
0.6729 Remote Similarity NPC305423
0.6729 Remote Similarity NPC161676
0.6729 Remote Similarity NPC473469
0.6729 Remote Similarity NPC94272
0.6729 Remote Similarity NPC230507
0.6729 Remote Similarity NPC14704
0.6729 Remote Similarity NPC470432
0.6729 Remote Similarity NPC33053
0.6727 Remote Similarity NPC254255
0.6727 Remote Similarity NPC216595
0.6727 Remote Similarity NPC308140
0.6727 Remote Similarity NPC473567
0.6724 Remote Similarity NPC219804
0.6703 Remote Similarity NPC188793
0.6701 Remote Similarity NPC31349
0.67 Remote Similarity NPC61201
0.67 Remote Similarity NPC470187
0.6699 Remote Similarity NPC473307
0.6699 Remote Similarity NPC124181
0.6699 Remote Similarity NPC79449
0.6699 Remote Similarity NPC312325
0.6699 Remote Similarity NPC274458
0.6699 Remote Similarity NPC90819
0.6699 Remote Similarity NPC474957
0.6698 Remote Similarity NPC470885
0.6698 Remote Similarity NPC471111
0.6698 Remote Similarity NPC187400
0.6698 Remote Similarity NPC221562
0.6667 Remote Similarity NPC235824
0.6667 Remote Similarity NPC474297
0.6667 Remote Similarity NPC476541
0.6667 Remote Similarity NPC476539
0.6667 Remote Similarity NPC476538
0.6667 Remote Similarity NPC200672
0.6667 Remote Similarity NPC154452
0.6667 Remote Similarity NPC475634
0.6667 Remote Similarity NPC472896
0.6667 Remote Similarity NPC472897
0.6667 Remote Similarity NPC13171
0.6667 Remote Similarity NPC295980
0.6667 Remote Similarity NPC195510
0.6667 Remote Similarity NPC98696
0.6667 Remote Similarity NPC476546

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC258501 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.6552 Remote Similarity NPD7503 Approved
0.6273 Remote Similarity NPD6412 Phase 2
0.6271 Remote Similarity NPD8033 Approved
0.6263 Remote Similarity NPD4249 Approved
0.62 Remote Similarity NPD4251 Approved
0.62 Remote Similarity NPD4250 Approved
0.6154 Remote Similarity NPD7328 Approved
0.6154 Remote Similarity NPD7327 Approved
0.6102 Remote Similarity NPD7516 Approved
0.6058 Remote Similarity NPD8171 Discontinued
0.605 Remote Similarity NPD8294 Approved
0.605 Remote Similarity NPD8377 Approved
0.604 Remote Similarity NPD7524 Approved
0.6 Remote Similarity NPD8296 Approved
0.6 Remote Similarity NPD8380 Approved
0.6 Remote Similarity NPD8378 Approved
0.6 Remote Similarity NPD8335 Approved
0.6 Remote Similarity NPD8379 Approved
0.5948 Remote Similarity NPD8133 Approved
0.59 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5854 Remote Similarity NPD891 Phase 3
0.5854 Remote Similarity NPD887 Approved
0.5854 Remote Similarity NPD893 Approved
0.5854 Remote Similarity NPD888 Phase 3
0.5854 Remote Similarity NPD890 Clinical (unspecified phase)
0.5854 Remote Similarity NPD889 Approved
0.5854 Remote Similarity NPD895 Approved
0.5854 Remote Similarity NPD894 Approved
0.5854 Remote Similarity NPD892 Phase 3
0.582 Remote Similarity NPD6370 Approved
0.5816 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5806 Remote Similarity NPD7507 Approved
0.5802 Remote Similarity NPD905 Approved
0.5802 Remote Similarity NPD904 Phase 3
0.58 Remote Similarity NPD6695 Phase 3
0.5789 Remote Similarity NPD6686 Approved
0.5776 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5726 Remote Similarity NPD6053 Discontinued
0.5714 Remote Similarity NPD6698 Approved
0.5714 Remote Similarity NPD3168 Discontinued
0.5714 Remote Similarity NPD7838 Discovery
0.5714 Remote Similarity NPD46 Approved
0.5684 Remote Similarity NPD1811 Approved
0.5684 Remote Similarity NPD1810 Approved
0.5669 Remote Similarity NPD7319 Approved
0.5657 Remote Similarity NPD4822 Approved
0.5657 Remote Similarity NPD4819 Approved
0.5657 Remote Similarity NPD4821 Approved
0.5657 Remote Similarity NPD4820 Approved
0.5656 Remote Similarity NPD6054 Approved
0.5636 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5612 Remote Similarity NPD4268 Approved
0.5612 Remote Similarity NPD4271 Approved
0.561 Remote Similarity NPD6015 Approved
0.561 Remote Similarity NPD8513 Phase 3
0.561 Remote Similarity NPD6016 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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