Structure

Physi-Chem Properties

Molecular Weight:  316.2
Volume:  344.632
LogP:  4.508
LogD:  3.855
LogS:  -4.562
# Rotatable Bonds:  0
TPSA:  38.83
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.286
Synthetic Accessibility Score:  4.825
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.618
MDCK Permeability:  3.173829463776201e-05
Pgp-inhibitor:  0.035
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.899
30% Bioavailability (F30%):  0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.194
Plasma Protein Binding (PPB):  94.79181671142578%
Volume Distribution (VD):  0.627
Pgp-substrate:  1.587590217590332%

ADMET: Metabolism

CYP1A2-inhibitor:  0.128
CYP1A2-substrate:  0.111
CYP2C19-inhibitor:  0.36
CYP2C19-substrate:  0.283
CYP2C9-inhibitor:  0.506
CYP2C9-substrate:  0.087
CYP2D6-inhibitor:  0.081
CYP2D6-substrate:  0.094
CYP3A4-inhibitor:  0.749
CYP3A4-substrate:  0.23

ADMET: Excretion

Clearance (CL):  7.688
Half-life (T1/2):  0.163

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.206
Drug-inuced Liver Injury (DILI):  0.518
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.094
Maximum Recommended Daily Dose:  0.955
Skin Sensitization:  0.971
Carcinogencity:  0.392
Eye Corrosion:  0.684
Eye Irritation:  0.801
Respiratory Toxicity:  0.98

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  Natural Product: NPC272814

Natural Product ID:  NPC272814
Common Name*:   Sarcocrassolide
IUPAC Name:   n.a.
Synonyms:   Sarcocrassolide
Standard InCHIKey:  DFVBARBOGQRBPH-PWRSXACBSA-N
Standard InCHI:  InChI=1S/C20H28O3/c1-13-7-5-8-14(2)11-17-16(15(3)19(21)22-17)12-18-20(4,23-18)10-6-9-13/h8-9,16-18H,3,5-7,10-12H2,1-2,4H3/b13-9+,14-8+/t16-,17+,18-,20-/m0/s1
SMILES:  C/C/1=CCC/C(=C/CC[C@]2([C@H](C[C@@H]3[C@@H](C1)OC(=O)C3=C)O2)C)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL519251
PubChem CID:   643719
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000147] Macrolides and analogues

*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]
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]
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]
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]
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]
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]
NPO1655 Corydendrium parasiticum Species Oceaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25715 Senna siamea Species Fabaceae 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]
NPO15674 Acanthosyris spinescens Species Cervantesiaceae 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]
NPO13577 Pieris formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9314 Gouania ulmifolia Species Gobiesocidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16206 Umbilicaria indica Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15773 Ecteinascidia thurstoni Species Perophoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14107 Teucrium montanum Species Lamiaceae 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]
NPO14909 Artemisia caerulescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae 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]
NPO15294 Magnolia salicifolia Species Magnoliaceae 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]
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]
NPO16534 Pterocaulon alopecuroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9909 Sarcophyton crassocaule Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15428 Cheilanthes tenuifolia Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15983 Udotea cyathiformis Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO639 Formica polyctena Species Formicidae 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]
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]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO73 Pseudanabaena persicina Species Pseudanabaenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12451 Dermocybe cinnabarina Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12217 Buccinum undatum Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria 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]
NPO14434 Alluaudia humbertii Species Didiereaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16560 Palhinhaea cernua Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14591 Rhabdodendron amazonicum Species Rhabdodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16301 Ilex macropoda Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16740 Helipterum venustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2584 Monostroma fuscum Species Monostromataceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 8.31 ug ml-1 PMID[545556]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 7.55 ug ml-1 PMID[545556]
NPT91 Cell Line KB Homo sapiens ED50 = 9.15 ug ml-1 PMID[545556]
NPT168 Cell Line P388 Mus musculus ED50 = 0.16 ug ml-1 PMID[545556]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 1.1 % PMID[545557]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 3.9 % PMID[545557]

☑ 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 NPC272814 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
0.9506 High Similarity NPC231889
0.9277 High Similarity NPC166919
0.9277 High Similarity NPC151770
0.9268 High Similarity NPC475703
0.9231 High Similarity NPC617
0.9167 High Similarity NPC475748
0.9167 High Similarity NPC329857
0.9167 High Similarity NPC469718
0.9146 High Similarity NPC50637
0.9059 High Similarity NPC20713
0.9024 High Similarity NPC50362
0.9024 High Similarity NPC319795
0.9024 High Similarity NPC38468
0.9 High Similarity NPC141810
0.8953 High Similarity NPC212486
0.8941 High Similarity NPC62815
0.8929 High Similarity NPC202672
0.8851 High Similarity NPC473316
0.8851 High Similarity NPC473330
0.8851 High Similarity NPC140543
0.8851 High Similarity NPC474035
0.8851 High Similarity NPC81386
0.8824 High Similarity NPC307411
0.8795 High Similarity NPC474547
0.875 High Similarity NPC14961
0.875 High Similarity NPC270013
0.875 High Similarity NPC474947
0.8721 High Similarity NPC312042
0.8721 High Similarity NPC51004
0.869 High Similarity NPC284902
0.8675 High Similarity NPC470238
0.8675 High Similarity NPC138647
0.8652 High Similarity NPC476275
0.8652 High Similarity NPC476315
0.8636 High Similarity NPC471147
0.8636 High Similarity NPC476267
0.8621 High Similarity NPC12172
0.8621 High Similarity NPC208886
0.8621 High Similarity NPC30515
0.8621 High Similarity NPC184463
0.8605 High Similarity NPC4986
0.8588 High Similarity NPC5130
0.8554 High Similarity NPC474472
0.8554 High Similarity NPC250315
0.8554 High Similarity NPC257358
0.8554 High Similarity NPC170377
0.8539 High Similarity NPC475659
0.8523 High Similarity NPC475838
0.8523 High Similarity NPC179746
0.8523 High Similarity NPC476300
0.8523 High Similarity NPC228451
0.8523 High Similarity NPC475912
0.8523 High Similarity NPC125674
0.8523 High Similarity NPC81419
0.8506 High Similarity NPC49342
0.8506 High Similarity NPC251385
0.85 High Similarity NPC476794
0.85 High Similarity NPC470240
0.8488 Intermediate Similarity NPC224652
0.8471 Intermediate Similarity NPC470242
0.8462 Intermediate Similarity NPC279561
0.8444 Intermediate Similarity NPC473859
0.8427 Intermediate Similarity NPC474247
0.8427 Intermediate Similarity NPC303942
0.8427 Intermediate Similarity NPC57405
0.8415 Intermediate Similarity NPC474510
0.8391 Intermediate Similarity NPC295312
0.8375 Intermediate Similarity NPC235906
0.8372 Intermediate Similarity NPC270270
0.837 Intermediate Similarity NPC288876
0.8353 Intermediate Similarity NPC304509
0.8353 Intermediate Similarity NPC215364
0.8353 Intermediate Similarity NPC47958
0.8353 Intermediate Similarity NPC235792
0.8353 Intermediate Similarity NPC149725
0.8333 Intermediate Similarity NPC163003
0.8333 Intermediate Similarity NPC36954
0.8333 Intermediate Similarity NPC170286
0.8333 Intermediate Similarity NPC318468
0.8313 Intermediate Similarity NPC281949
0.8313 Intermediate Similarity NPC25684
0.8313 Intermediate Similarity NPC301477
0.8313 Intermediate Similarity NPC207188
0.8295 Intermediate Similarity NPC474761
0.8295 Intermediate Similarity NPC476004
0.828 Intermediate Similarity NPC476270
0.828 Intermediate Similarity NPC264477
0.828 Intermediate Similarity NPC477511
0.8276 Intermediate Similarity NPC281516
0.8272 Intermediate Similarity NPC65603
0.8261 Intermediate Similarity NPC473326
0.8261 Intermediate Similarity NPC208233
0.8256 Intermediate Similarity NPC122502
0.8256 Intermediate Similarity NPC469676
0.825 Intermediate Similarity NPC138408
0.825 Intermediate Similarity NPC193351
0.825 Intermediate Similarity NPC155587
0.825 Intermediate Similarity NPC226669
0.8242 Intermediate Similarity NPC279621
0.8242 Intermediate Similarity NPC35498
0.8242 Intermediate Similarity NPC230800
0.8242 Intermediate Similarity NPC17585
0.8202 Intermediate Similarity NPC133698
0.8193 Intermediate Similarity NPC474981
0.8182 Intermediate Similarity NPC474032
0.8171 Intermediate Similarity NPC472960
0.8161 Intermediate Similarity NPC186148
0.8161 Intermediate Similarity NPC160138
0.8152 Intermediate Similarity NPC471140
0.8132 Intermediate Similarity NPC471141
0.8125 Intermediate Similarity NPC476355
0.8125 Intermediate Similarity NPC140287
0.8118 Intermediate Similarity NPC39588
0.8118 Intermediate Similarity NPC475842
0.8118 Intermediate Similarity NPC128429
0.8118 Intermediate Similarity NPC11620
0.8118 Intermediate Similarity NPC53867
0.8111 Intermediate Similarity NPC135776
0.8095 Intermediate Similarity NPC10276
0.8095 Intermediate Similarity NPC35089
0.809 Intermediate Similarity NPC144133
0.809 Intermediate Similarity NPC179394
0.809 Intermediate Similarity NPC475855
0.809 Intermediate Similarity NPC80875
0.8072 Intermediate Similarity NPC470239
0.8072 Intermediate Similarity NPC470244
0.8072 Intermediate Similarity NPC182550
0.8068 Intermediate Similarity NPC475902
0.8068 Intermediate Similarity NPC58219
0.8068 Intermediate Similarity NPC91248
0.8068 Intermediate Similarity NPC177629
0.8065 Intermediate Similarity NPC474213
0.8049 Intermediate Similarity NPC141789
0.8049 Intermediate Similarity NPC41780
0.8049 Intermediate Similarity NPC187568
0.8049 Intermediate Similarity NPC476028
0.8049 Intermediate Similarity NPC171204
0.8049 Intermediate Similarity NPC97516
0.8046 Intermediate Similarity NPC67493
0.8046 Intermediate Similarity NPC474045
0.8046 Intermediate Similarity NPC261253
0.8046 Intermediate Similarity NPC64153
0.8023 Intermediate Similarity NPC72464
0.8023 Intermediate Similarity NPC115786
0.8022 Intermediate Similarity NPC474338
0.8022 Intermediate Similarity NPC198853
0.8022 Intermediate Similarity NPC477131
0.8021 Intermediate Similarity NPC474741
0.8021 Intermediate Similarity NPC477510
0.8021 Intermediate Similarity NPC471143
0.8 Intermediate Similarity NPC221282
0.8 Intermediate Similarity NPC269206
0.8 Intermediate Similarity NPC131209
0.8 Intermediate Similarity NPC58956
0.8 Intermediate Similarity NPC246076
0.8 Intermediate Similarity NPC470379
0.8 Intermediate Similarity NPC70251
0.8 Intermediate Similarity NPC295633
0.8 Intermediate Similarity NPC475881
0.8 Intermediate Similarity NPC173609
0.8 Intermediate Similarity NPC470373
0.7979 Intermediate Similarity NPC477512
0.7978 Intermediate Similarity NPC92974
0.7978 Intermediate Similarity NPC472872
0.7978 Intermediate Similarity NPC78008
0.7976 Intermediate Similarity NPC276356
0.7976 Intermediate Similarity NPC223904
0.7976 Intermediate Similarity NPC302426
0.7955 Intermediate Similarity NPC248602
0.7955 Intermediate Similarity NPC118601
0.7952 Intermediate Similarity NPC474341
0.7952 Intermediate Similarity NPC267231
0.7938 Intermediate Similarity NPC243998
0.7938 Intermediate Similarity NPC223450
0.7935 Intermediate Similarity NPC476053
0.7935 Intermediate Similarity NPC273197
0.7935 Intermediate Similarity NPC234339
0.7935 Intermediate Similarity NPC107476
0.7935 Intermediate Similarity NPC304886
0.7935 Intermediate Similarity NPC67584
0.7931 Intermediate Similarity NPC197903
0.7931 Intermediate Similarity NPC21469
0.7931 Intermediate Similarity NPC161957
0.7931 Intermediate Similarity NPC137033
0.7931 Intermediate Similarity NPC255307
0.7931 Intermediate Similarity NPC99395
0.7931 Intermediate Similarity NPC110405
0.7927 Intermediate Similarity NPC123360
0.7895 Intermediate Similarity NPC201718
0.7895 Intermediate Similarity NPC474339
0.7895 Intermediate Similarity NPC164598
0.7895 Intermediate Similarity NPC473332
0.7895 Intermediate Similarity NPC47880
0.7889 Intermediate Similarity NPC37607
0.7889 Intermediate Similarity NPC301969
0.7889 Intermediate Similarity NPC473619
0.7882 Intermediate Similarity NPC47635
0.7875 Intermediate Similarity NPC477084
0.7872 Intermediate Similarity NPC221615
0.7865 Intermediate Similarity NPC474471

  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 NPC272814 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
0.9024 High Similarity NPD1733 Clinical (unspecified phase)
0.8605 High Similarity NPD1695 Approved
0.75 Intermediate Similarity NPD46 Approved
0.75 Intermediate Similarity NPD6698 Approved
0.7368 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6008 Approved
0.7157 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1694 Approved
0.7128 Intermediate Similarity NPD7838 Discovery
0.7 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6371 Approved
0.6875 Remote Similarity NPD7983 Approved
0.6735 Remote Similarity NPD5282 Discontinued
0.6667 Remote Similarity NPD6053 Discontinued
0.6634 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6633 Remote Similarity NPD5779 Approved
0.6633 Remote Similarity NPD5778 Approved
0.663 Remote Similarity NPD5209 Approved
0.663 Remote Similarity NPD6435 Approved
0.6598 Remote Similarity NPD5785 Approved
0.6591 Remote Similarity NPD8039 Approved
0.6574 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6569 Remote Similarity NPD6648 Approved
0.6559 Remote Similarity NPD7154 Phase 3
0.6526 Remote Similarity NPD5786 Approved
0.6526 Remote Similarity NPD4249 Approved
0.6522 Remote Similarity NPD5369 Approved
0.6509 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5344 Discontinued
0.6458 Remote Similarity NPD4251 Approved
0.6458 Remote Similarity NPD4250 Approved
0.6449 Remote Similarity NPD6686 Approved
0.6421 Remote Similarity NPD5363 Approved
0.6421 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6413 Remote Similarity NPD5368 Approved
0.6383 Remote Similarity NPD5362 Discontinued
0.6354 Remote Similarity NPD7334 Approved
0.6354 Remote Similarity NPD6409 Approved
0.6354 Remote Similarity NPD5330 Approved
0.6354 Remote Similarity NPD7146 Approved
0.6354 Remote Similarity NPD6684 Approved
0.6354 Remote Similarity NPD7521 Approved
0.633 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6327 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6327 Remote Similarity NPD6101 Approved
0.6311 Remote Similarity NPD4225 Approved
0.6311 Remote Similarity NPD7638 Approved
0.63 Remote Similarity NPD6399 Phase 3
0.6289 Remote Similarity NPD3573 Approved
0.6277 Remote Similarity NPD4270 Approved
0.6277 Remote Similarity NPD4269 Approved
0.6275 Remote Similarity NPD7839 Suspended
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD7639 Approved
0.6239 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6237 Remote Similarity NPD4821 Approved
0.6237 Remote Similarity NPD4819 Approved
0.6237 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6237 Remote Similarity NPD4822 Approved
0.6237 Remote Similarity NPD4820 Approved
0.6235 Remote Similarity NPD7331 Phase 2
0.6224 Remote Similarity NPD6903 Approved
0.6224 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8517 Approved
0.6207 Remote Similarity NPD8516 Approved
0.6207 Remote Similarity NPD8515 Approved
0.6207 Remote Similarity NPD8513 Phase 3
0.62 Remote Similarity NPD5693 Phase 1
0.62 Remote Similarity NPD6411 Approved
0.6186 Remote Similarity NPD6422 Discontinued
0.6176 Remote Similarity NPD6356 Clinical (unspecified phase)
0.614 Remote Similarity NPD7115 Discovery
0.6118 Remote Similarity NPD7341 Phase 2
0.6102 Remote Similarity NPD7642 Approved
0.61 Remote Similarity NPD5207 Approved
0.6078 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6078 Remote Similarity NPD6001 Approved
0.6078 Remote Similarity NPD7900 Approved
0.6064 Remote Similarity NPD4252 Approved
0.6061 Remote Similarity NPD6672 Approved
0.6061 Remote Similarity NPD5737 Approved
0.6055 Remote Similarity NPD5697 Approved
0.6022 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6022 Remote Similarity NPD4268 Approved
0.6022 Remote Similarity NPD4271 Approved
0.6018 Remote Similarity NPD4632 Approved
0.6 Remote Similarity NPD6881 Approved
0.6 Remote Similarity NPD6011 Approved
0.6 Remote Similarity NPD6899 Approved
0.5982 Remote Similarity NPD6650 Approved
0.5982 Remote Similarity NPD6649 Approved
0.5966 Remote Similarity NPD7830 Approved
0.5966 Remote Similarity NPD7829 Approved
0.5963 Remote Similarity NPD7128 Approved
0.5963 Remote Similarity NPD6402 Approved
0.5963 Remote Similarity NPD6675 Approved
0.5963 Remote Similarity NPD5739 Approved
0.595 Remote Similarity NPD8074 Phase 3
0.5946 Remote Similarity NPD6012 Approved
0.5946 Remote Similarity NPD6013 Approved
0.5946 Remote Similarity NPD6373 Approved
0.5946 Remote Similarity NPD6014 Approved
0.5946 Remote Similarity NPD6372 Approved
0.5909 Remote Similarity NPD5701 Approved
0.5905 Remote Similarity NPD7902 Approved
0.59 Remote Similarity NPD5208 Approved
0.5893 Remote Similarity NPD7102 Approved
0.5893 Remote Similarity NPD7290 Approved
0.5893 Remote Similarity NPD6883 Approved
0.5887 Remote Similarity NPD7260 Phase 2
0.5876 Remote Similarity NPD5331 Approved
0.5876 Remote Similarity NPD5332 Approved
0.5868 Remote Similarity NPD7507 Approved
0.5865 Remote Similarity NPD5695 Phase 3
0.5862 Remote Similarity NPD6009 Approved
0.5859 Remote Similarity NPD6098 Approved
0.5856 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5856 Remote Similarity NPD7320 Approved
0.5849 Remote Similarity NPD5696 Approved
0.5847 Remote Similarity NPD6319 Approved
0.5842 Remote Similarity NPD6080 Approved
0.5842 Remote Similarity NPD6673 Approved
0.5842 Remote Similarity NPD6051 Approved
0.5842 Remote Similarity NPD6904 Approved
0.5841 Remote Similarity NPD6847 Approved
0.5841 Remote Similarity NPD6617 Approved
0.5841 Remote Similarity NPD6869 Approved
0.5841 Remote Similarity NPD8130 Phase 1
0.5841 Remote Similarity NPD2181 Clinical (unspecified phase)
0.5833 Remote Similarity NPD4790 Discontinued
0.5833 Remote Similarity NPD7604 Phase 2
0.5812 Remote Similarity NPD7641 Discontinued
0.581 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5798 Remote Similarity NPD5983 Phase 2
0.5795 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6882 Approved
0.5789 Remote Similarity NPD8297 Approved
0.5785 Remote Similarity NPD7492 Approved
0.5784 Remote Similarity NPD5692 Phase 3
0.5781 Remote Similarity NPD7966 Clinical (unspecified phase)
0.5773 Remote Similarity NPD3667 Approved
0.5769 Remote Similarity NPD7748 Approved
0.5755 Remote Similarity NPD6084 Phase 2
0.5755 Remote Similarity NPD6083 Phase 2
0.5752 Remote Similarity NPD2067 Discontinued
0.5745 Remote Similarity NPD4756 Discovery
0.5738 Remote Similarity NPD6616 Approved
0.5738 Remote Similarity NPD8451 Approved
0.5738 Remote Similarity NPD8273 Phase 1
0.5728 Remote Similarity NPD5281 Approved
0.5728 Remote Similarity NPD6079 Approved
0.5728 Remote Similarity NPD7637 Suspended
0.5728 Remote Similarity NPD5284 Approved
0.5728 Remote Similarity NPD5694 Approved
0.5728 Remote Similarity NPD6050 Approved
0.5726 Remote Similarity NPD7319 Approved
0.5714 Remote Similarity NPD6845 Suspended
0.5714 Remote Similarity NPD6054 Approved
0.5702 Remote Similarity NPD6401 Clinical (unspecified phase)
0.57 Remote Similarity NPD3618 Phase 1
0.5696 Remote Similarity NPD29 Approved
0.5696 Remote Similarity NPD6927 Phase 3
0.5696 Remote Similarity NPD28 Approved
0.5691 Remote Similarity NPD8448 Approved
0.5691 Remote Similarity NPD7078 Approved
0.5688 Remote Similarity NPD5211 Phase 2
0.5688 Remote Similarity NPD7632 Discontinued
0.5686 Remote Similarity NPD5370 Suspended
0.5686 Remote Similarity NPD5328 Approved
0.5682 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5667 Remote Similarity NPD6016 Approved
0.5667 Remote Similarity NPD6015 Approved
0.5667 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5657 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5657 Remote Similarity NPD3665 Phase 1
0.5657 Remote Similarity NPD3668 Phase 3
0.5657 Remote Similarity NPD3133 Approved
0.5657 Remote Similarity NPD4786 Approved
0.5657 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5657 Remote Similarity NPD3666 Approved
0.5648 Remote Similarity NPD5286 Approved
0.5648 Remote Similarity NPD5285 Approved
0.5648 Remote Similarity NPD4696 Approved
0.5645 Remote Similarity NPD7736 Approved
0.5641 Remote Similarity NPD6274 Approved
0.5632 Remote Similarity NPD3197 Phase 1
0.5632 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5631 Remote Similarity NPD3168 Discontinued
0.5625 Remote Similarity NPD6412 Phase 2
0.562 Remote Similarity NPD5988 Approved
0.562 Remote Similarity NPD6370 Approved
0.5612 Remote Similarity NPD4800 Clinical (unspecified phase)
0.561 Remote Similarity NPD6336 Discontinued
0.5607 Remote Similarity NPD4755 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