Structure

Physi-Chem Properties

Molecular Weight:  360.19
Volume:  382.792
LogP:  3.151
LogD:  2.816
LogS:  -3.648
# Rotatable Bonds:  3
TPSA:  69.67
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.7
Synthetic Accessibility Score:  5.057
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.71
MDCK Permeability:  2.3409718778566457e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.99
30% Bioavailability (F30%):  0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.161
Plasma Protein Binding (PPB):  92.85262298583984%
Volume Distribution (VD):  1.374
Pgp-substrate:  6.957096099853516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.611
CYP1A2-substrate:  0.787
CYP2C19-inhibitor:  0.829
CYP2C19-substrate:  0.872
CYP2C9-inhibitor:  0.895
CYP2C9-substrate:  0.208
CYP2D6-inhibitor:  0.732
CYP2D6-substrate:  0.118
CYP3A4-inhibitor:  0.891
CYP3A4-substrate:  0.71

ADMET: Excretion

Clearance (CL):  2.952
Half-life (T1/2):  0.843

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.275
Drug-inuced Liver Injury (DILI):  0.257
AMES Toxicity:  0.363
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.951
Carcinogencity:  0.385
Eye Corrosion:  0.271
Eye Irritation:  0.288
Respiratory Toxicity:  0.367

Download Data

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC221231

Natural Product ID:  NPC221231
Common Name*:   Sarcrassin E
IUPAC Name:   methyl (4E,6E,11S)-11-methyl-10,15-dioxo-4-propan-2-yl-16-oxabicyclo[9.3.2]hexadeca-1(14),4,6-triene-7-carboxylate
Synonyms:   Sarcrassin E
Standard InCHIKey:  SSRWHVBVQPAITB-WYLCAHHTSA-N
Standard InCHI:  InChI=1S/C21H28O5/c1-14(2)15-7-9-16-6-5-13-21(3,26-20(16)24)18(22)12-11-17(10-8-15)19(23)25-4/h6,8,10,14H,5,7,9,11-13H2,1-4H3/b15-8+,17-10+/t21-/m0/s1
SMILES:  COC(=O)/C/1=C/C=C(CCC2=CCC[C@](C(=O)CC1)(C)OC2=O)/C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470654
PubChem CID:   16091635
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[10556916]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10757709]
NPO20809 Sarcophyton trocheliophorum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[10923847]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. formosan soft coral n.a. PMID[11141104]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. Thai n.a. PMID[12088444]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. PMID[14640532]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[16872152]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17067165]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[17125220]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. leaf n.a. PMID[17685627]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19406895]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[19917748]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[20932054]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. Formosan soft coral n.a. PMID[22014827]
NPO25715 Senna siamea Species Fabaceae Eukaryota Stems n.a. n.a. PMID[23078294]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23513740]
NPO20809 Sarcophyton trocheliophorum Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[23859780]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25043228]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[25960261]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. PMID[31994397]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. PMID[32603106]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. Antarctic n.a. PMID[8882433]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2584 Monostroma fuscum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13264 Alstonia lanceolifera Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5127 Cladocroce incurvata Species Chalinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7023 Tetracera rosiflora Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16206 Umbilicaria indica Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13036 Culicinomyces clavisporus Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20404.1 Eruca vesicaria subsp. sativa Subspecies Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14107 Teucrium montanum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16453 Lycium cestroides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15037 Echinops spinosissimus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14909 Artemisia caerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6809 Cailliea cinerea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO26988 Acinos thymoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21926 Pseudomonas aeruginosa Species Pseudomonadaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10443 Sloanea zuliaensis Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16534 Pterocaulon alopecuroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15983 Udotea cyathiformis Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12764 Tillandsia fragrans Species Bromeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15879 Euphorbia nivulia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO639 Formica polyctena Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20809 Sarcophyton trocheliophorum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16774 Hermidium alipes n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 13.0 ug.mL-1 PMID[477017]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 6330.0 nM PMID[477018]

☑ 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 NPC221231 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 NPC471326
0.9342 High Similarity NPC180290
0.8353 Intermediate Similarity NPC38576
0.8353 Intermediate Similarity NPC279859
0.8235 Intermediate Similarity NPC99395
0.8235 Intermediate Similarity NPC197903
0.8095 Intermediate Similarity NPC173609
0.8022 Intermediate Similarity NPC474490
0.8 Intermediate Similarity NPC170377
0.7978 Intermediate Similarity NPC471818
0.7955 Intermediate Similarity NPC469653
0.7955 Intermediate Similarity NPC469628
0.7955 Intermediate Similarity NPC475906
0.7955 Intermediate Similarity NPC469631
0.7955 Intermediate Similarity NPC471047
0.7931 Intermediate Similarity NPC234038
0.7907 Intermediate Similarity NPC149869
0.7901 Intermediate Similarity NPC244166
0.7889 Intermediate Similarity NPC45579
0.7857 Intermediate Similarity NPC474510
0.7831 Intermediate Similarity NPC128276
0.7791 Intermediate Similarity NPC474703
0.7778 Intermediate Similarity NPC469718
0.7778 Intermediate Similarity NPC329857
0.7765 Intermediate Similarity NPC42470
0.7753 Intermediate Similarity NPC475902
0.7738 Intermediate Similarity NPC472965
0.7738 Intermediate Similarity NPC63649
0.7738 Intermediate Similarity NPC264227
0.7727 Intermediate Similarity NPC122502
0.7711 Intermediate Similarity NPC316324
0.7711 Intermediate Similarity NPC57744
0.7701 Intermediate Similarity NPC196487
0.7701 Intermediate Similarity NPC14575
0.7701 Intermediate Similarity NPC474359
0.7692 Intermediate Similarity NPC166110
0.7674 Intermediate Similarity NPC474291
0.7674 Intermediate Similarity NPC85772
0.7634 Intermediate Similarity NPC474947
0.7619 Intermediate Similarity NPC471220
0.7609 Intermediate Similarity NPC165383
0.7609 Intermediate Similarity NPC248193
0.7586 Intermediate Similarity NPC53867
0.7579 Intermediate Similarity NPC54843
0.7561 Intermediate Similarity NPC476355
0.7558 Intermediate Similarity NPC301477
0.7558 Intermediate Similarity NPC471325
0.7558 Intermediate Similarity NPC25684
0.7558 Intermediate Similarity NPC281949
0.7558 Intermediate Similarity NPC286229
0.7553 Intermediate Similarity NPC301596
0.7553 Intermediate Similarity NPC476275
0.7553 Intermediate Similarity NPC299396
0.7553 Intermediate Similarity NPC172998
0.7529 Intermediate Similarity NPC471740
0.7529 Intermediate Similarity NPC178277
0.7528 Intermediate Similarity NPC261721
0.7528 Intermediate Similarity NPC164393
0.7527 Intermediate Similarity NPC469632
0.75 Intermediate Similarity NPC193396
0.75 Intermediate Similarity NPC265574
0.75 Intermediate Similarity NPC476794
0.75 Intermediate Similarity NPC219874
0.75 Intermediate Similarity NPC238197
0.75 Intermediate Similarity NPC20713
0.75 Intermediate Similarity NPC470240
0.75 Intermediate Similarity NPC232812
0.75 Intermediate Similarity NPC32944
0.75 Intermediate Similarity NPC65603
0.7473 Intermediate Similarity NPC115179
0.7473 Intermediate Similarity NPC212598
0.7473 Intermediate Similarity NPC106040
0.7473 Intermediate Similarity NPC95364
0.7473 Intermediate Similarity NPC142159
0.747 Intermediate Similarity NPC193351
0.747 Intermediate Similarity NPC138408
0.747 Intermediate Similarity NPC226669
0.7449 Intermediate Similarity NPC25666
0.7449 Intermediate Similarity NPC271059
0.7447 Intermediate Similarity NPC234339
0.7447 Intermediate Similarity NPC273197
0.7444 Intermediate Similarity NPC478145
0.7419 Intermediate Similarity NPC475302
0.7416 Intermediate Similarity NPC474547
0.7416 Intermediate Similarity NPC470177
0.7416 Intermediate Similarity NPC261380
0.7412 Intermediate Similarity NPC299235
0.7407 Intermediate Similarity NPC67183
0.7407 Intermediate Similarity NPC64234
0.7407 Intermediate Similarity NPC37929
0.7403 Intermediate Similarity NPC155849
0.7391 Intermediate Similarity NPC476369
0.7391 Intermediate Similarity NPC476437
0.7386 Intermediate Similarity NPC475989
0.7386 Intermediate Similarity NPC318468
0.7386 Intermediate Similarity NPC222358
0.7381 Intermediate Similarity NPC266159
0.7381 Intermediate Similarity NPC40353
0.7381 Intermediate Similarity NPC473223
0.7381 Intermediate Similarity NPC123360
0.7381 Intermediate Similarity NPC472967
0.7356 Intermediate Similarity NPC141810
0.7349 Intermediate Similarity NPC294434
0.7349 Intermediate Similarity NPC140287
0.7349 Intermediate Similarity NPC259599
0.7349 Intermediate Similarity NPC474758
0.7349 Intermediate Similarity NPC15499
0.7349 Intermediate Similarity NPC117746
0.734 Intermediate Similarity NPC148463
0.7333 Intermediate Similarity NPC107787
0.7326 Intermediate Similarity NPC469690
0.7326 Intermediate Similarity NPC469620
0.7326 Intermediate Similarity NPC469617
0.7326 Intermediate Similarity NPC270126
0.7317 Intermediate Similarity NPC163003
0.7317 Intermediate Similarity NPC288667
0.7312 Intermediate Similarity NPC472705
0.7303 Intermediate Similarity NPC70424
0.7303 Intermediate Similarity NPC243618
0.7303 Intermediate Similarity NPC115786
0.7294 Intermediate Similarity NPC471225
0.7294 Intermediate Similarity NPC41780
0.7294 Intermediate Similarity NPC187568
0.7284 Intermediate Similarity NPC470693
0.7283 Intermediate Similarity NPC284561
0.7263 Intermediate Similarity NPC470978
0.7263 Intermediate Similarity NPC470974
0.7263 Intermediate Similarity NPC31021
0.7262 Intermediate Similarity NPC155587
0.7253 Intermediate Similarity NPC475703
0.7253 Intermediate Similarity NPC471738
0.7253 Intermediate Similarity NPC478144
0.7245 Intermediate Similarity NPC476270
0.7245 Intermediate Similarity NPC469851
0.7241 Intermediate Similarity NPC47747
0.7241 Intermediate Similarity NPC304795
0.7241 Intermediate Similarity NPC302426
0.7241 Intermediate Similarity NPC233377
0.7241 Intermediate Similarity NPC223904
0.7234 Intermediate Similarity NPC476049
0.7229 Intermediate Similarity NPC135703
0.7229 Intermediate Similarity NPC287878
0.7222 Intermediate Similarity NPC96621
0.7222 Intermediate Similarity NPC474369
0.7222 Intermediate Similarity NPC78089
0.7222 Intermediate Similarity NPC189311
0.7215 Intermediate Similarity NPC470688
0.7209 Intermediate Similarity NPC108816
0.7209 Intermediate Similarity NPC474341
0.7209 Intermediate Similarity NPC472960
0.7209 Intermediate Similarity NPC93763
0.7204 Intermediate Similarity NPC49342
0.7204 Intermediate Similarity NPC77337
0.7204 Intermediate Similarity NPC62815
0.7204 Intermediate Similarity NPC316228
0.7204 Intermediate Similarity NPC251385
0.7195 Intermediate Similarity NPC475310
0.7195 Intermediate Similarity NPC469660
0.7191 Intermediate Similarity NPC39588
0.7191 Intermediate Similarity NPC16488
0.7191 Intermediate Similarity NPC475947
0.7191 Intermediate Similarity NPC288281
0.7188 Intermediate Similarity NPC473291
0.7176 Intermediate Similarity NPC235906
0.7176 Intermediate Similarity NPC27205
0.7174 Intermediate Similarity NPC473658
0.7174 Intermediate Similarity NPC474471
0.7174 Intermediate Similarity NPC227379
0.7174 Intermediate Similarity NPC153805
0.7172 Intermediate Similarity NPC140591
0.7172 Intermediate Similarity NPC303653
0.7172 Intermediate Similarity NPC291500
0.7172 Intermediate Similarity NPC197835
0.7172 Intermediate Similarity NPC189609
0.716 Intermediate Similarity NPC218477
0.716 Intermediate Similarity NPC134385
0.7159 Intermediate Similarity NPC325031
0.7159 Intermediate Similarity NPC112868
0.7159 Intermediate Similarity NPC10276
0.7159 Intermediate Similarity NPC35089
0.7158 Intermediate Similarity NPC121825
0.7158 Intermediate Similarity NPC476596
0.7143 Intermediate Similarity NPC469551
0.7143 Intermediate Similarity NPC261253
0.7143 Intermediate Similarity NPC472863
0.7143 Intermediate Similarity NPC284902
0.7143 Intermediate Similarity NPC316426
0.7143 Intermediate Similarity NPC198314
0.7143 Intermediate Similarity NPC220478
0.7143 Intermediate Similarity NPC116575
0.7143 Intermediate Similarity NPC315395
0.7143 Intermediate Similarity NPC474045
0.7128 Intermediate Similarity NPC284185
0.7126 Intermediate Similarity NPC276647
0.7126 Intermediate Similarity NPC617
0.7126 Intermediate Similarity NPC622
0.7125 Intermediate Similarity NPC142423
0.7125 Intermediate Similarity NPC308294
0.7113 Intermediate Similarity NPC47834
0.7111 Intermediate Similarity NPC72464

  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 NPC221231 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
0.7294 Intermediate Similarity NPD4756 Discovery
0.7079 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5209 Approved
0.7059 Intermediate Similarity NPD8039 Approved
0.7 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5693 Phase 1
0.6842 Remote Similarity NPD5692 Phase 3
0.6771 Remote Similarity NPD6050 Approved
0.6771 Remote Similarity NPD5694 Approved
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5737 Approved
0.6632 Remote Similarity NPD6672 Approved
0.6566 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6562 Remote Similarity NPD6673 Approved
0.6562 Remote Similarity NPD6904 Approved
0.6562 Remote Similarity NPD6080 Approved
0.6535 Remote Similarity NPD5696 Approved
0.6506 Remote Similarity NPD7331 Phase 2
0.6506 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5785 Approved
0.6495 Remote Similarity NPD46 Approved
0.6495 Remote Similarity NPD6698 Approved
0.6415 Remote Similarity NPD7899 Clinical (unspecified phase)
0.64 Remote Similarity NPD5695 Phase 3
0.64 Remote Similarity NPD5654 Approved
0.6392 Remote Similarity NPD1695 Approved
0.6354 Remote Similarity NPD3573 Approved
0.6327 Remote Similarity NPD7838 Discovery
0.6316 Remote Similarity NPD5363 Approved
0.6277 Remote Similarity NPD7154 Phase 3
0.6275 Remote Similarity NPD6083 Phase 2
0.6275 Remote Similarity NPD6084 Phase 2
0.6275 Remote Similarity NPD5959 Approved
0.6263 Remote Similarity NPD7983 Approved
0.625 Remote Similarity NPD6098 Approved
0.6214 Remote Similarity NPD8029 Clinical (unspecified phase)
0.62 Remote Similarity NPD5778 Approved
0.62 Remote Similarity NPD5779 Approved
0.619 Remote Similarity NPD7341 Phase 2
0.617 Remote Similarity NPD6435 Approved
0.6162 Remote Similarity NPD5207 Approved
0.6145 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6129 Remote Similarity NPD4695 Discontinued
0.6111 Remote Similarity NPD6614 Approved
0.6111 Remote Similarity NPD5697 Approved
0.6105 Remote Similarity NPD5362 Discontinued
0.6091 Remote Similarity NPD2067 Discontinued
0.6091 Remote Similarity NPD6371 Approved
0.6087 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6082 Remote Similarity NPD7521 Approved
0.6082 Remote Similarity NPD5786 Approved
0.6082 Remote Similarity NPD7334 Approved
0.6082 Remote Similarity NPD6409 Approved
0.6082 Remote Similarity NPD5330 Approved
0.6082 Remote Similarity NPD7146 Approved
0.6082 Remote Similarity NPD6684 Approved
0.6071 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6064 Remote Similarity NPD5369 Approved
0.6061 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6061 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6101 Approved
0.6055 Remote Similarity NPD6881 Approved
0.6055 Remote Similarity NPD6899 Approved
0.6055 Remote Similarity NPD6011 Approved
0.6019 Remote Similarity NPD5739 Approved
0.6019 Remote Similarity NPD7732 Phase 3
0.6019 Remote Similarity NPD6402 Approved
0.6019 Remote Similarity NPD6675 Approved
0.6019 Remote Similarity NPD7839 Suspended
0.6019 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD4269 Approved
0.6 Remote Similarity NPD6014 Approved
0.6 Remote Similarity NPD4270 Approved
0.6 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6 Remote Similarity NPD6013 Approved
0.6 Remote Similarity NPD6012 Approved
0.5979 Remote Similarity NPD1696 Phase 3
0.5979 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5963 Remote Similarity NPD5701 Approved
0.596 Remote Similarity NPD5208 Approved
0.596 Remote Similarity NPD6903 Approved
0.596 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5957 Remote Similarity NPD5368 Approved
0.5946 Remote Similarity NPD7102 Approved
0.5946 Remote Similarity NPD7290 Approved
0.5946 Remote Similarity NPD6883 Approved
0.5941 Remote Similarity NPD6411 Approved
0.5941 Remote Similarity NPD5284 Approved
0.5941 Remote Similarity NPD5281 Approved
0.593 Remote Similarity NPD3704 Approved
0.5922 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4629 Approved
0.5922 Remote Similarity NPD5210 Approved
0.5918 Remote Similarity NPD4694 Approved
0.5918 Remote Similarity NPD5279 Phase 3
0.5918 Remote Similarity NPD5280 Approved
0.5909 Remote Similarity NPD7320 Approved
0.5893 Remote Similarity NPD6847 Approved
0.5893 Remote Similarity NPD8130 Phase 1
0.5893 Remote Similarity NPD6869 Approved
0.5893 Remote Similarity NPD6649 Approved
0.5893 Remote Similarity NPD6617 Approved
0.5893 Remote Similarity NPD6650 Approved
0.5856 Remote Similarity NPD6372 Approved
0.5856 Remote Similarity NPD6373 Approved
0.5849 Remote Similarity NPD6648 Approved
0.5841 Remote Similarity NPD6882 Approved
0.5841 Remote Similarity NPD8297 Approved
0.5841 Remote Similarity NPD6053 Discontinued
0.5826 Remote Similarity NPD690 Clinical (unspecified phase)
0.5825 Remote Similarity NPD7900 Approved
0.5825 Remote Similarity NPD5282 Discontinued
0.5825 Remote Similarity NPD7748 Approved
0.5825 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5806 Remote Similarity NPD7260 Phase 2
0.5789 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4819 Approved
0.5789 Remote Similarity NPD4252 Approved
0.5789 Remote Similarity NPD4821 Approved
0.5789 Remote Similarity NPD4822 Approved
0.5789 Remote Similarity NPD4820 Approved
0.5789 Remote Similarity NPD8259 Clinical (unspecified phase)
0.578 Remote Similarity NPD5909 Discontinued
0.5773 Remote Similarity NPD6110 Phase 1
0.5769 Remote Similarity NPD29 Approved
0.5769 Remote Similarity NPD28 Approved
0.5769 Remote Similarity NPD6927 Phase 3
0.5766 Remote Similarity NPD6686 Approved
0.5758 Remote Similarity NPD6422 Discontinued
0.5758 Remote Similarity NPD5690 Phase 2
0.5755 Remote Similarity NPD7638 Approved
0.5755 Remote Similarity NPD4225 Approved
0.5752 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5743 Remote Similarity NPD4753 Phase 2
0.5714 Remote Similarity NPD4197 Approved
0.5714 Remote Similarity NPD7614 Phase 1
0.5701 Remote Similarity NPD7639 Approved
0.5701 Remote Similarity NPD7640 Approved
0.5698 Remote Similarity NPD3197 Phase 1
0.569 Remote Similarity NPD6274 Approved
0.5688 Remote Similarity NPD6647 Phase 2
0.5673 Remote Similarity NPD5122 Clinical (unspecified phase)
0.5673 Remote Similarity NPD6001 Approved
0.566 Remote Similarity NPD7902 Approved
0.5657 Remote Similarity NPD5329 Approved
0.5656 Remote Similarity NPD6637 Approved
0.5652 Remote Similarity NPD4058 Approved
0.5647 Remote Similarity NPD4194 Approved
0.5647 Remote Similarity NPD4191 Approved
0.5647 Remote Similarity NPD4193 Approved
0.5647 Remote Similarity NPD4192 Approved
0.5641 Remote Similarity NPD7115 Discovery
0.5641 Remote Similarity NPD6317 Approved
0.5631 Remote Similarity NPD7515 Phase 2
0.563 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5625 Remote Similarity NPD3172 Approved
0.5614 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5614 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5614 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5612 Remote Similarity NPD5332 Approved
0.5612 Remote Similarity NPD5331 Approved
0.5604 Remote Similarity NPD5276 Approved
0.56 Remote Similarity NPD4519 Discontinued
0.56 Remote Similarity NPD4623 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