Structure

Physi-Chem Properties

Molecular Weight:  198.05
Volume:  189.069
LogP:  1.56
LogD:  0.976
LogS:  -1.408
# Rotatable Bonds:  3
TPSA:  86.99
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.487
Synthetic Accessibility Score:  2.025
Fsp3:  0.222
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.936
MDCK Permeability:  1.4024974916537758e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.794
30% Bioavailability (F30%):  0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.124
Plasma Protein Binding (PPB):  90.2824935913086%
Volume Distribution (VD):  0.392
Pgp-substrate:  7.842890739440918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.851
CYP1A2-substrate:  0.236
CYP2C19-inhibitor:  0.062
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.287
CYP2C9-substrate:  0.431
CYP2D6-inhibitor:  0.212
CYP2D6-substrate:  0.2
CYP3A4-inhibitor:  0.165
CYP3A4-substrate:  0.133

ADMET: Excretion

Clearance (CL):  17.076
Half-life (T1/2):  0.934

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.02
Drug-inuced Liver Injury (DILI):  0.425
AMES Toxicity:  0.178
Rat Oral Acute Toxicity:  0.01
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.928
Carcinogencity:  0.035
Eye Corrosion:  0.53
Eye Irritation:  0.954
Respiratory Toxicity:  0.116

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Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC1321

Natural Product ID:  NPC1321
Common Name*:   Ethylgallate
IUPAC Name:   ethyl 3,4,5-trihydroxybenzoate
Synonyms:   E313
Standard InCHIKey:  VFPFQHQNJCMNBZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H10O5/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,2H2,1H3
SMILES:  CCOC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL453196
PubChem CID:   13250
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001248] Hydroxybenzoic acid derivatives
            • [CHEMONTID:0001251] Gallic acid and derivatives
              • [CHEMONTID:0003539] Galloyl esters

*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
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2004.07.004]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.jfca.2005.08.001]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. retail stores, supermarkets and market stalls in Forssa and in the Helsinki area 2003–2005 DOI[10.1016/j.jfca.2006.05.007]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. DOI[10.1246/bcsj.30.618]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. leaf n.a. PMID[11816040]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. leaf n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. bark n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. xylem n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. root n.a. PMID[14727919]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO11357 Nephelium lappaceum Species Sapindaceae Eukaryota Seeds n.a. n.a. PMID[16180821]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[16309313]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[16792421]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[17011103]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. PMID[17125224]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. leaf n.a. PMID[17125224]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[17716892]
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[17764148]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21534540]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota whole plants Panshi, Jilin Province, China 2009-JUN PMID[21534540]
NPO5258 Fagara zanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. PMID[22472691]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota n.a. seed n.a. PMID[24533783]]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota Flowers Muyang, China n.a. PMID[24621197]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota anomalous fruits n.a. n.a. PMID[25442304]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25453801]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26702644]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota leaves n.a. n.a. PMID[27400231]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. PMID[27466882]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. PMID[2831703]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[28383891]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31117521]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. Barks Iksan, Chunbuk, Korea n.a. PMID[3127544]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31873014]
NPO40956 Woodfordia uniflora Species n.a. n.a. n.a. n.a. n.a. PMID[32639158]
NPO21322 Plinia cauliflora Species Myrtaceae Eukaryota leaves n.a. n.a. PMID[32706260]
NPO7631 Gleditsia japonica Species Fabaceae Eukaryota Fruits n.a. n.a. PMID[7494144]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota n.a. n.a. Database[FooDB]
NPO11357 Nephelium lappaceum Species Sapindaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota Roots n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO1191 Castanea mollissima Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31111 Ampelopsis brevipedunculata Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27557 Toona sinensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23516 Potentilla discolor Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30551 Acer ginnala Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24168 Rhus coriaria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7352 Acacia arabica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24775 Rhodiola sacra Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26209.1 Acer tataricum subsp. ginnala Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5271.1 Ampelopsis glandulosa var. brevipedunculata Varieties Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1191 Castanea mollissima Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27557 Toona sinensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23516 Potentilla discolor Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23984 Metagentiana rhodantha Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24775 Rhodiola sacra Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7352 Acacia arabica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3469 Pteris dactylina Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21458 Radix paeoniae rubra Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24168 Rhus coriaria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7352 Acacia arabica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30551 Acer ginnala Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1191 Castanea mollissima Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31111 Ampelopsis brevipedunculata Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24168 Rhus coriaria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24775 Rhodiola sacra Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7576.2 Brassica oleracea var. sabauda Varieties Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7631 Gleditsia japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16419 Rumex chalepensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18093 Rosa chinensis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9180 Pyrostegia venusta Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11636 Ideopsis similis Species Nymphalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3619 Ilex hainanensis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1245 Eunicella cavolinii Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28824 Forsteronia refracta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25981 Crinipellis scabella Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29127 Cystophora scalaris Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23984 Metagentiana rhodantha Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25381 Litsea rotundifolia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28784 Alseodaphne corneri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1191 Castanea mollissima Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16290 Mutisia spinosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10997 Kitasatospora mediocidica Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22543 Cleome chrysantha Species Cleomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27557 Toona sinensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26209.1 Acer tataricum subsp. ginnala Subspecies Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3744 Polycephalomyces nipponicus Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24360 Centaurea squarrosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3084 Xylopia brasiliensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28898 Grewia mollis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29510 Aulacocephalus temmincki Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27269 Annona impressivenia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4244 Doodia picta Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9157 Rubrivivax gelatinosus Species n.a. Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29400 Conocephalum japonicum Species Conocephalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17962 Tagetes erecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12510 Aronia arbutifolia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29415 Hovenia acerba Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29142 Kaunia saltensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29488 Sophora angustifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29446 Stevia polycephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13016 Viscaria viscosa Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29154 Heliotropium floridum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16419 Rumex chalepensis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29203 Gymnocarpium robertianum Species Cystopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21977 Psora corallina Species Psoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5868 Morus rubra Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29292 Teucrium depressum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5271.1 Ampelopsis glandulosa var. brevipedunculata Varieties Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25023 Lactarius camphoratus Species Russulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20026 Senecio callosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4676 Melicope sarcococca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7352 Acacia arabica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3580 Rana amurensis Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24168 Rhus coriaria Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29242 Salvia dorrii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28918 Ophiolepis superba Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6469 Clematis angustifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1933 Sideritis nutans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21322 Plinia cauliflora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20608 Gleditsia sinensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28937 Heterotheca grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29047 Disynaphia halimifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO998 Justicia hayatai Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3340 Fridericia chica Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29225 Oncoba echinata Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29068 Papilio phorcas Species Papilionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15025 Celtis reticulosa Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7631 Gleditsia japonica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11357 Nephelium lappaceum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13070 Clibadium mexiae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5258 Fagara zanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28971 Bersama yangambiensis Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4124 Dimocarpus longan Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO816 Stenomesson miniatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29363 Aconitum nevadense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12378 Streptomyces blastmyceticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29189 Castanopsis sclerophylla Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1744 Discaria serratifolia Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25658 Rumex japonicus Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28845 Eragrostis viscosa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3469 Pteris dactylina Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26192 Cordylanthus kingii Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10396 Pteris australis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13818 Narcissus concolor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22230 Rhodiola crenulata Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24775 Rhodiola sacra Species Crassulaceae 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
NPO21556 NPC1321 n.a. Sclerotia 0.155 ± 0.019 n.a. n.a. % PMID[20527951]

☑ 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
NPT326 Individual Protein Squalene monooxygenase Rattus norvegicus IC50 = 4200.0 nM PMID[463774]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 42000.0 nM PMID[463775]
NPT333 Cell Line CEM Homo sapiens CC50 = 23000.0 nM PMID[463779]
NPT327 Organism Microsporum gypseum Microsporum gypseum MIC = 100.0 ug.mL-1 PMID[463776]
NPT328 Organism Epidermophyton floccosum Epidermophyton floccosum MIC = 100.0 ug.mL-1 PMID[463776]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 100.0 ug.mL-1 PMID[463776]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 100.0 ug.mL-1 PMID[463776]
NPT20 Organism Candida albicans Candida albicans MIC > 250.0 ug.mL-1 PMID[463776]
NPT186 Organism Candida tropicalis Candida tropicalis MIC > 250.0 ug.mL-1 PMID[463776]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC > 250.0 ug.mL-1 PMID[463776]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC > 250.0 ug.mL-1 PMID[463776]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC > 250.0 ug.mL-1 PMID[463776]
NPT185 Organism Aspergillus flavus Aspergillus flavus MIC > 250.0 ug.mL-1 PMID[463776]
NPT21 Organism Aspergillus niger Aspergillus niger MIC > 250.0 ug.mL-1 PMID[463776]
NPT331 Organism Ralstonia solanacearum Ralstonia solanacearum IZ = 42.0 mm PMID[463777]
NPT331 Organism Ralstonia solanacearum Ralstonia solanacearum IZ = 18.0 mm PMID[463777]
NPT35 Others n.a. Retention_time = 20.55 min PMID[463778]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 55.7 % PMID[463778]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 > 10000.0 nM PMID[463779]
NPT332 Organism Human immunodeficiency virus type 2 (ISOLATE ROD) Human immunodeficiency virus type 2 (ISOLATE ROD) EC50 > 10000.0 nM PMID[463779]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 19000.0 nM PMID[463779]
NPT27 Others Unspecified CC50 = 45000.0 nM PMID[463779]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC90 > 45.0 uM PMID[463779]
NPT27 Others Unspecified Activity = 100.0 % PMID[463780]
NPT20950 CELL-LINE Erythrocyte n.a. IC50 = 1000000.0 nM PMID[463781]
NPT20950 CELL-LINE Erythrocyte n.a. IC50 = 1240000.0 nM PMID[463781]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 126200.0 nM PMID[463782]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 252500.0 nM PMID[463782]
NPT20 Organism Candida albicans Candida albicans MIC > 252500.0 nM PMID[463782]

☑ 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 NPC1321 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
1.0 High Similarity NPC304929
1.0 High Similarity NPC156124
0.9844 High Similarity NPC18646
0.9841 High Similarity NPC264145
0.9767 High Similarity NPC156892
0.9528 High Similarity NPC226855
0.947 High Similarity NPC239943
0.9398 High Similarity NPC105525
0.9398 High Similarity NPC12218
0.9398 High Similarity NPC75763
0.9398 High Similarity NPC225036
0.9394 High Similarity NPC25305
0.9394 High Similarity NPC110899
0.9394 High Similarity NPC125417
0.9394 High Similarity NPC112068
0.9394 High Similarity NPC95679
0.937 High Similarity NPC158654
0.9167 High Similarity NPC155098
0.9127 High Similarity NPC225710
0.9124 High Similarity NPC50221
0.9124 High Similarity NPC190587
0.9124 High Similarity NPC226738
0.9124 High Similarity NPC229036
0.9124 High Similarity NPC121573
0.9124 High Similarity NPC114242
0.9124 High Similarity NPC22176
0.9111 High Similarity NPC471819
0.9077 High Similarity NPC94810
0.9058 High Similarity NPC108455
0.8955 High Similarity NPC274613
0.8955 High Similarity NPC208760
0.8947 High Similarity NPC283823
0.8947 High Similarity NPC239855
0.8947 High Similarity NPC159418
0.8947 High Similarity NPC288743
0.8897 High Similarity NPC207516
0.8889 High Similarity NPC475111
0.8881 High Similarity NPC237330
0.8881 High Similarity NPC248150
0.8873 High Similarity NPC306343
0.8872 High Similarity NPC111888
0.8865 High Similarity NPC120621
0.8865 High Similarity NPC43123
0.8865 High Similarity NPC248257
0.8865 High Similarity NPC142528
0.8864 High Similarity NPC299010
0.8849 High Similarity NPC134975
0.8832 High Similarity NPC4796
0.8803 High Similarity NPC92117
0.8803 High Similarity NPC75945
0.8803 High Similarity NPC42464
0.8803 High Similarity NPC107636
0.8794 High Similarity NPC268366
0.875 High Similarity NPC156307
0.875 High Similarity NPC221249
0.875 High Similarity NPC75695
0.8723 High Similarity NPC262282
0.8722 High Similarity NPC285776
0.8692 High Similarity NPC145134
0.869 High Similarity NPC310661
0.869 High Similarity NPC105827
0.8681 High Similarity NPC252979
0.8681 High Similarity NPC96501
0.8681 High Similarity NPC140151
0.8667 High Similarity NPC153783
0.8661 High Similarity NPC156654
0.8643 High Similarity NPC299154
0.8636 High Similarity NPC214620
0.8633 High Similarity NPC326065
0.863 High Similarity NPC281703
0.863 High Similarity NPC125487
0.8623 High Similarity NPC112135
0.8611 High Similarity NPC473091
0.8601 High Similarity NPC476463
0.8583 High Similarity NPC27633
0.8583 High Similarity NPC94298
0.8582 High Similarity NPC469615
0.8571 High Similarity NPC156624
0.8571 High Similarity NPC145425
0.8571 High Similarity NPC172920
0.8562 High Similarity NPC61152
0.8562 High Similarity NPC205037
0.8562 High Similarity NPC16024
0.8562 High Similarity NPC161159
0.8562 High Similarity NPC3746
0.8562 High Similarity NPC44260
0.8561 High Similarity NPC474875
0.8561 High Similarity NPC295492
0.8561 High Similarity NPC26241
0.8561 High Similarity NPC274891
0.8561 High Similarity NPC476819
0.8561 High Similarity NPC476820
0.8561 High Similarity NPC205751
0.8561 High Similarity NPC95309
0.8561 High Similarity NPC303683
0.8529 High Similarity NPC157478
0.8529 High Similarity NPC200422
0.8529 High Similarity NPC289572
0.8529 High Similarity NPC295406
0.8521 High Similarity NPC469683
0.8521 High Similarity NPC257025
0.8519 High Similarity NPC219892
0.8519 High Similarity NPC189823
0.8519 High Similarity NPC318799
0.8511 High Similarity NPC312256
0.8503 High Similarity NPC238672
0.8503 High Similarity NPC144801
0.8503 High Similarity NPC281477
0.8503 High Similarity NPC197188
0.8503 High Similarity NPC43872
0.8503 High Similarity NPC291510
0.8503 High Similarity NPC116850
0.85 High Similarity NPC187690
0.85 High Similarity NPC158472
0.85 High Similarity NPC50823
0.8496 Intermediate Similarity NPC107672
0.8493 Intermediate Similarity NPC204350
0.8493 Intermediate Similarity NPC92747
0.8493 Intermediate Similarity NPC265862
0.8489 Intermediate Similarity NPC302857
0.8489 Intermediate Similarity NPC142703
0.8489 Intermediate Similarity NPC219428
0.8489 Intermediate Similarity NPC278068
0.8489 Intermediate Similarity NPC37250
0.8489 Intermediate Similarity NPC152942
0.8478 Intermediate Similarity NPC326847
0.8478 Intermediate Similarity NPC235115
0.8472 Intermediate Similarity NPC472969
0.8467 Intermediate Similarity NPC106406
0.8462 Intermediate Similarity NPC83272
0.8462 Intermediate Similarity NPC473867
0.8456 Intermediate Similarity NPC1913
0.8456 Intermediate Similarity NPC104275
0.8456 Intermediate Similarity NPC472860
0.8456 Intermediate Similarity NPC4747
0.8451 Intermediate Similarity NPC287722
0.8446 Intermediate Similarity NPC203757
0.8446 Intermediate Similarity NPC199926
0.8446 Intermediate Similarity NPC79998
0.8446 Intermediate Similarity NPC82592
0.8446 Intermediate Similarity NPC16082
0.844 Intermediate Similarity NPC90411
0.844 Intermediate Similarity NPC110419
0.8433 Intermediate Similarity NPC79332
0.8433 Intermediate Similarity NPC304747
0.8433 Intermediate Similarity NPC109275
0.8429 Intermediate Similarity NPC52358
0.8429 Intermediate Similarity NPC203351
0.8429 Intermediate Similarity NPC247409
0.8429 Intermediate Similarity NPC275356
0.8425 Intermediate Similarity NPC131192
0.8421 Intermediate Similarity NPC154275
0.8417 Intermediate Similarity NPC70380
0.8417 Intermediate Similarity NPC135837
0.8414 Intermediate Similarity NPC476394
0.8414 Intermediate Similarity NPC98809
0.8406 Intermediate Similarity NPC176102
0.8406 Intermediate Similarity NPC29317
0.8406 Intermediate Similarity NPC267539
0.8406 Intermediate Similarity NPC204257
0.8406 Intermediate Similarity NPC139519
0.8406 Intermediate Similarity NPC254832
0.8406 Intermediate Similarity NPC229638
0.8406 Intermediate Similarity NPC71108
0.8403 Intermediate Similarity NPC138978
0.8403 Intermediate Similarity NPC143903
0.8403 Intermediate Similarity NPC165389
0.8403 Intermediate Similarity NPC229264
0.8403 Intermediate Similarity NPC226987
0.84 Intermediate Similarity NPC289811
0.84 Intermediate Similarity NPC160780
0.84 Intermediate Similarity NPC87317
0.8392 Intermediate Similarity NPC207732
0.8392 Intermediate Similarity NPC105213
0.8392 Intermediate Similarity NPC113397
0.8389 Intermediate Similarity NPC239019
0.8389 Intermediate Similarity NPC250436
0.8389 Intermediate Similarity NPC150227
0.8389 Intermediate Similarity NPC300845
0.8389 Intermediate Similarity NPC134925
0.8389 Intermediate Similarity NPC318432
0.8389 Intermediate Similarity NPC104983
0.8389 Intermediate Similarity NPC88803
0.8389 Intermediate Similarity NPC247629
0.8389 Intermediate Similarity NPC291948
0.838 Intermediate Similarity NPC43158
0.838 Intermediate Similarity NPC472016
0.838 Intermediate Similarity NPC258469
0.838 Intermediate Similarity NPC277315
0.838 Intermediate Similarity NPC192831
0.838 Intermediate Similarity NPC284556
0.838 Intermediate Similarity NPC301178
0.837 Intermediate Similarity NPC48315
0.8369 Intermediate Similarity NPC290664
0.8369 Intermediate Similarity NPC327187
0.8367 Intermediate Similarity NPC93498
0.8367 Intermediate Similarity NPC163883
0.8358 Intermediate Similarity NPC281020
0.8357 Intermediate Similarity NPC94248
0.8357 Intermediate Similarity NPC478200

  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 NPC1321 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
1.0 High Similarity NPD230 Phase 1
0.9127 High Similarity NPD9269 Phase 2
0.881 High Similarity NPD9268 Approved
0.8583 High Similarity NPD9545 Approved
0.8389 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD6190 Approved
0.8222 Intermediate Similarity NPD9494 Approved
0.8188 Intermediate Similarity NPD943 Approved
0.8169 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8138 Intermediate Similarity NPD1511 Approved
0.8085 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD1934 Approved
0.8027 Intermediate Similarity NPD1512 Approved
0.8026 Intermediate Similarity NPD3882 Suspended
0.8013 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD1465 Phase 2
0.8013 Intermediate Similarity NPD2801 Approved
0.7872 Intermediate Similarity NPD447 Suspended
0.7843 Intermediate Similarity NPD3817 Phase 2
0.7838 Intermediate Similarity NPD2532 Approved
0.7838 Intermediate Similarity NPD2534 Approved
0.7838 Intermediate Similarity NPD2533 Approved
0.7764 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD9493 Approved
0.7727 Intermediate Similarity NPD5353 Approved
0.7717 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD1510 Phase 2
0.7688 Intermediate Similarity NPD3818 Discontinued
0.7676 Intermediate Similarity NPD1240 Approved
0.7658 Intermediate Similarity NPD6232 Discontinued
0.7655 Intermediate Similarity NPD1551 Phase 2
0.7651 Intermediate Similarity NPD6799 Approved
0.7616 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD1607 Approved
0.7568 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD4628 Phase 3
0.7562 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6166 Phase 2
0.7561 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1549 Phase 2
0.7535 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD3764 Approved
0.7531 Intermediate Similarity NPD5844 Phase 1
0.7531 Intermediate Similarity NPD7054 Approved
0.7516 Intermediate Similarity NPD7473 Discontinued
0.7516 Intermediate Similarity NPD7075 Discontinued
0.7485 Intermediate Similarity NPD7074 Phase 3
0.7485 Intermediate Similarity NPD7472 Approved
0.7483 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD7266 Discontinued
0.7468 Intermediate Similarity NPD6234 Discontinued
0.7468 Intermediate Similarity NPD4380 Phase 2
0.7465 Intermediate Similarity NPD3027 Phase 3
0.7451 Intermediate Similarity NPD1653 Approved
0.745 Intermediate Similarity NPD3750 Approved
0.7439 Intermediate Similarity NPD6797 Phase 2
0.7436 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7819 Suspended
0.7417 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD2935 Discontinued
0.7403 Intermediate Similarity NPD3455 Phase 2
0.7394 Intermediate Similarity NPD7685 Pre-registration
0.7394 Intermediate Similarity NPD7251 Discontinued
0.7391 Intermediate Similarity NPD5242 Approved
0.7368 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD919 Approved
0.7355 Intermediate Similarity NPD6599 Discontinued
0.7347 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD9717 Approved
0.7333 Intermediate Similarity NPD8166 Discontinued
0.7324 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD1613 Approved
0.7308 Intermediate Similarity NPD7411 Suspended
0.7308 Intermediate Similarity NPD6385 Approved
0.7308 Intermediate Similarity NPD6386 Approved
0.7296 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD5402 Approved
0.7273 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD920 Approved
0.7267 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD422 Phase 1
0.7261 Intermediate Similarity NPD6801 Discontinued
0.7261 Intermediate Similarity NPD37 Approved
0.7246 Intermediate Similarity NPD7808 Phase 3
0.7233 Intermediate Similarity NPD4967 Phase 2
0.7233 Intermediate Similarity NPD4966 Approved
0.7233 Intermediate Similarity NPD4965 Approved
0.7219 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7214 Intermediate Similarity NPD1608 Approved
0.7205 Intermediate Similarity NPD5494 Approved
0.7192 Intermediate Similarity NPD826 Approved
0.7192 Intermediate Similarity NPD825 Approved
0.7183 Intermediate Similarity NPD1203 Approved
0.7181 Intermediate Similarity NPD2796 Approved
0.7172 Intermediate Similarity NPD411 Approved
0.716 Intermediate Similarity NPD1247 Approved
0.7152 Intermediate Similarity NPD7228 Approved
0.7152 Intermediate Similarity NPD2800 Approved
0.7152 Intermediate Similarity NPD1243 Approved
0.7143 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD555 Phase 2
0.7125 Intermediate Similarity NPD7768 Phase 2
0.7121 Intermediate Similarity NPD9266 Approved
0.7121 Intermediate Similarity NPD74 Approved
0.7118 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD5710 Approved
0.7117 Intermediate Similarity NPD5711 Approved
0.7114 Intermediate Similarity NPD3748 Approved
0.709 Intermediate Similarity NPD228 Approved
0.7081 Intermediate Similarity NPD3749 Approved
0.7067 Intermediate Similarity NPD9570 Approved
0.7055 Intermediate Similarity NPD7199 Phase 2
0.7051 Intermediate Similarity NPD5403 Approved
0.7045 Intermediate Similarity NPD9263 Approved
0.7045 Intermediate Similarity NPD9267 Approved
0.7045 Intermediate Similarity NPD9264 Approved
0.7032 Intermediate Similarity NPD5401 Approved
0.7032 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD258 Approved
0.7014 Intermediate Similarity NPD257 Approved
0.7014 Intermediate Similarity NPD1019 Discontinued
0.7013 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD259 Phase 1
0.7 Intermediate Similarity NPD17 Approved
0.7 Intermediate Similarity NPD1778 Approved
0.6982 Remote Similarity NPD6559 Discontinued
0.697 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4357 Discontinued
0.6962 Remote Similarity NPD824 Approved
0.6957 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6951 Remote Similarity NPD6959 Discontinued
0.6923 Remote Similarity NPD5953 Discontinued
0.6923 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6917 Remote Similarity NPD1358 Approved
0.6913 Remote Similarity NPD1933 Approved
0.6905 Remote Similarity NPD7286 Phase 2
0.6905 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6897 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6894 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6651 Approved
0.6867 Remote Similarity NPD3926 Phase 2
0.6866 Remote Similarity NPD2182 Approved
0.6861 Remote Similarity NPD1241 Discontinued
0.6859 Remote Similarity NPD7390 Discontinued
0.6855 Remote Similarity NPD3226 Approved
0.6853 Remote Similarity NPD1481 Phase 2
0.6849 Remote Similarity NPD9569 Approved
0.6846 Remote Similarity NPD1242 Phase 1
0.6842 Remote Similarity NPD6100 Approved
0.6842 Remote Similarity NPD6099 Approved
0.6828 Remote Similarity NPD1164 Approved
0.6824 Remote Similarity NPD1296 Phase 2
0.6818 Remote Similarity NPD164 Approved
0.6818 Remote Similarity NPD1652 Phase 2
0.6815 Remote Similarity NPD3146 Approved
0.6815 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6812 Remote Similarity NPD9281 Approved
0.6803 Remote Similarity NPD6832 Phase 2
0.6786 Remote Similarity NPD5536 Phase 2
0.6783 Remote Similarity NPD1535 Discovery
0.6782 Remote Similarity NPD8150 Discontinued
0.6779 Remote Similarity NPD6233 Phase 2
0.6779 Remote Similarity NPD520 Approved
0.6776 Remote Similarity NPD2799 Discontinued
0.6776 Remote Similarity NPD4308 Phase 3
0.6772 Remote Similarity NPD9509 Clinical (unspecified phase)
0.6769 Remote Similarity NPD1238 Approved
0.6768 Remote Similarity NPD6971 Discontinued
0.6763 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6759 Remote Similarity NPD3225 Approved
0.6759 Remote Similarity NPD1283 Approved
0.6757 Remote Similarity NPD9537 Phase 1
0.6757 Remote Similarity NPD9536 Phase 1
0.6746 Remote Similarity NPD3751 Discontinued
0.6742 Remote Similarity NPD9261 Approved
0.6738 Remote Similarity NPD1548 Phase 1
0.6732 Remote Similarity NPD5405 Approved
0.6732 Remote Similarity NPD5406 Approved
0.6732 Remote Similarity NPD5408 Approved
0.6732 Remote Similarity NPD5404 Approved
0.6731 Remote Similarity NPD2354 Approved
0.6723 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6716 Remote Similarity NPD3134 Approved
0.6714 Remote Similarity NPD405 Clinical (unspecified phase)
0.6713 Remote Similarity NPD3496 Discontinued
0.6712 Remote Similarity NPD1470 Approved
0.6711 Remote Similarity NPD2313 Discontinued
0.671 Remote Similarity NPD2654 Approved
0.6709 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6707 Remote Similarity NPD7229 Phase 3
0.6691 Remote Similarity NPD3022 Approved
0.6691 Remote Similarity NPD3021 Approved
0.6691 Remote Similarity NPD690 Clinical (unspecified phase)
0.669 Remote Similarity NPD4196 Clinical (unspecified phase)

  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