Structure

Physi-Chem Properties

Molecular Weight:  334.21
Volume:  361.978
LogP:  3.404
LogD:  3.287
LogS:  -4.397
# Rotatable Bonds:  0
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.404
Synthetic Accessibility Score:  4.833
Fsp3:  0.65
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.634
MDCK Permeability:  3.323465716675855e-05
Pgp-inhibitor:  0.056
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.93
20% Bioavailability (F20%):  0.866
30% Bioavailability (F30%):  0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.535
Plasma Protein Binding (PPB):  93.5382308959961%
Volume Distribution (VD):  0.377
Pgp-substrate:  2.5019943714141846%

ADMET: Metabolism

CYP1A2-inhibitor:  0.047
CYP1A2-substrate:  0.075
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.142
CYP2C9-inhibitor:  0.151
CYP2C9-substrate:  0.25
CYP2D6-inhibitor:  0.058
CYP2D6-substrate:  0.107
CYP3A4-inhibitor:  0.238
CYP3A4-substrate:  0.237

ADMET: Excretion

Clearance (CL):  8.147
Half-life (T1/2):  0.599

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.22
Drug-inuced Liver Injury (DILI):  0.193
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.202
Maximum Recommended Daily Dose:  0.945
Skin Sensitization:  0.959
Carcinogencity:  0.106
Eye Corrosion:  0.305
Eye Irritation:  0.675
Respiratory Toxicity:  0.96

Download Data

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

  Natural Product: NPC202672

Natural Product ID:  NPC202672
Common Name*:   Crassocolide D
IUPAC Name:   (3aR,5S,6R,9E,13E,15aS)-5,6-dihydroxy-6,10,14-trimethyl-3-methylidene-4,5,7,8,11,12,15,15a-octahydro-3aH-cyclotetradeca[b]furan-2-one
Synonyms:   Crassocolide D
Standard InCHIKey:  HZAPTPBMBOIGCM-SFQXUBQZSA-N
Standard InCHI:  InChI=1S/C20H30O4/c1-13-7-5-8-14(2)11-17-16(15(3)19(22)24-17)12-18(21)20(4,23)10-6-9-13/h8-9,16-18,21,23H,3,5-7,10-12H2,1-2,4H3/b13-9+,14-8+/t16-,17+,18+,20-/m1/s1
SMILES:  C/C/1=CCC[C@](C)([C@H](C[C@@H]2C(=C)C(=O)O[C@H]2C/C(=C/CC1)/C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL516995
PubChem CID:   11995281
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones
            • [CHEMONTID:0002502] Cembranolides

*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]
NPO16101 Gleditsia triacanthos Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
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]
NPO15294 Magnolia salicifolia Species Magnoliaceae 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]
NPO16560 Palhinhaea cernua Species Lycopodiaceae 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[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14909 Artemisia caerulescens Species Asteraceae 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]
NPO11762 Agrimonia eupatoria Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13733 Saccharopolyspora erythraea Species Pseudonocardiaceae Bacteria 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]
NPO26508 Uvariopsis tripetala Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5719 Hedyotis lawsoniae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13417 Campanula medium Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13931 Selaginella uncinata Species Selaginellaceae 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]
NPO11365 Lecidea lithophila Species Lecideaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16617 Paepalanthus hilairei Species Eriocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12764 Tillandsia fragrans Species Bromeliaceae 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]
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]
NPO13577 Pieris formosa Species Ericaceae 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]
NPO2584 Monostroma fuscum Species Monostromataceae 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]
NPO25278 Cystofilobasidium infirmominiatum Species Cystofilobasidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10877 Humboldtia laurifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1655 Corydendrium parasiticum Species Oceaniidae 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]
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]
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]
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]
NPO639 Formica polyctena Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14107 Teucrium montanum Species Lamiaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 15.3 ug.mL-1 PMID[515217]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 30.0 ug.mL-1 PMID[515217]
NPT81 Cell Line A549 Homo sapiens IC50 = 12.5 ug.mL-1 PMID[515217]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 30.0 ug.mL-1 PMID[515217]

☑ 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 NPC202672 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
0.9647 High Similarity NPC208886
0.9647 High Similarity NPC12172
0.9647 High Similarity NPC184463
0.9647 High Similarity NPC30515
0.9643 High Similarity NPC307411
0.9535 High Similarity NPC81419
0.9535 High Similarity NPC475912
0.9535 High Similarity NPC212486
0.9535 High Similarity NPC179746
0.9529 High Similarity NPC51004
0.9425 High Similarity NPC81386
0.9425 High Similarity NPC474035
0.9318 High Similarity NPC270013
0.9318 High Similarity NPC14961
0.9318 High Similarity NPC36954
0.931 High Similarity NPC476300
0.9302 High Similarity NPC474761
0.9302 High Similarity NPC476004
0.9176 High Similarity NPC186148
0.9157 High Similarity NPC11620
0.907 High Similarity NPC177629
0.907 High Similarity NPC58219
0.9 High Similarity NPC476315
0.8966 High Similarity NPC92974
0.8966 High Similarity NPC474032
0.8966 High Similarity NPC295312
0.8953 High Similarity NPC231889
0.8953 High Similarity NPC248602
0.8941 High Similarity NPC21469
0.8941 High Similarity NPC137033
0.8929 High Similarity NPC272814
0.8864 High Similarity NPC473619
0.8851 High Similarity NPC281516
0.8851 High Similarity NPC473715
0.8851 High Similarity NPC153805
0.8837 High Similarity NPC474949
0.8837 High Similarity NPC475019
0.8824 High Similarity NPC474780
0.8817 High Similarity NPC476270
0.8804 High Similarity NPC473326
0.8791 High Similarity NPC473859
0.8778 High Similarity NPC303942
0.8778 High Similarity NPC57405
0.8778 High Similarity NPC71589
0.8764 High Similarity NPC473321
0.875 High Similarity NPC151770
0.8723 High Similarity NPC474747
0.8721 High Similarity NPC149725
0.8721 High Similarity NPC47958
0.8721 High Similarity NPC329749
0.8721 High Similarity NPC304509
0.871 High Similarity NPC288876
0.8706 High Similarity NPC250315
0.8681 High Similarity NPC475659
0.8667 High Similarity NPC228451
0.8667 High Similarity NPC125674
0.8667 High Similarity NPC162205
0.8667 High Similarity NPC273579
0.8667 High Similarity NPC475838
0.8667 High Similarity NPC288240
0.8667 High Similarity NPC295204
0.8652 High Similarity NPC475748
0.8652 High Similarity NPC475855
0.8636 High Similarity NPC474471
0.8636 High Similarity NPC227379
0.8632 High Similarity NPC475871
0.8632 High Similarity NPC475945
0.8621 High Similarity NPC470242
0.8621 High Similarity NPC164393
0.8621 High Similarity NPC476015
0.8621 High Similarity NPC474762
0.8621 High Similarity NPC284902
0.8617 High Similarity NPC47880
0.8605 High Similarity NPC475963
0.8605 High Similarity NPC9868
0.8605 High Similarity NPC3464
0.8605 High Similarity NPC151176
0.8602 High Similarity NPC187268
0.8602 High Similarity NPC474213
0.8602 High Similarity NPC471144
0.8587 High Similarity NPC279621
0.8571 High Similarity NPC474247
0.8571 High Similarity NPC190294
0.8556 High Similarity NPC70251
0.8556 High Similarity NPC133698
0.8556 High Similarity NPC475881
0.8556 High Similarity NPC470373
0.8556 High Similarity NPC131209
0.8556 High Similarity NPC470379
0.8542 High Similarity NPC100487
0.8539 High Similarity NPC173926
0.8539 High Similarity NPC166919
0.8526 High Similarity NPC149371
0.8523 High Similarity NPC475703
0.8523 High Similarity NPC160138
0.8506 High Similarity NPC255307
0.8478 Intermediate Similarity NPC471141
0.8478 Intermediate Similarity NPC471142
0.8478 Intermediate Similarity NPC107476
0.8478 Intermediate Similarity NPC304886
0.8462 Intermediate Similarity NPC135776
0.8454 Intermediate Similarity NPC243998
0.8452 Intermediate Similarity NPC470239
0.8452 Intermediate Similarity NPC470244
0.8444 Intermediate Similarity NPC469718
0.8444 Intermediate Similarity NPC206614
0.8444 Intermediate Similarity NPC473448
0.8444 Intermediate Similarity NPC144133
0.8444 Intermediate Similarity NPC179394
0.8444 Intermediate Similarity NPC474323
0.8444 Intermediate Similarity NPC329857
0.8421 Intermediate Similarity NPC150923
0.8421 Intermediate Similarity NPC473332
0.8421 Intermediate Similarity NPC474742
0.8409 Intermediate Similarity NPC112685
0.8409 Intermediate Similarity NPC50637
0.8409 Intermediate Similarity NPC305475
0.8409 Intermediate Similarity NPC150755
0.8409 Intermediate Similarity NPC475461
0.8391 Intermediate Similarity NPC114979
0.8391 Intermediate Similarity NPC70424
0.8391 Intermediate Similarity NPC243618
0.8391 Intermediate Similarity NPC474776
0.8391 Intermediate Similarity NPC191476
0.8391 Intermediate Similarity NPC72464
0.8387 Intermediate Similarity NPC470883
0.8387 Intermediate Similarity NPC230800
0.8387 Intermediate Similarity NPC158416
0.8387 Intermediate Similarity NPC39859
0.8387 Intermediate Similarity NPC477921
0.8387 Intermediate Similarity NPC76862
0.8387 Intermediate Similarity NPC476009
0.837 Intermediate Similarity NPC473330
0.837 Intermediate Similarity NPC477131
0.837 Intermediate Similarity NPC473316
0.837 Intermediate Similarity NPC474338
0.837 Intermediate Similarity NPC198853
0.8367 Intermediate Similarity NPC477513
0.8353 Intermediate Similarity NPC233377
0.8352 Intermediate Similarity NPC20713
0.8351 Intermediate Similarity NPC474741
0.8351 Intermediate Similarity NPC203659
0.8333 Intermediate Similarity NPC86077
0.8333 Intermediate Similarity NPC474951
0.8333 Intermediate Similarity NPC473564
0.8333 Intermediate Similarity NPC324017
0.8333 Intermediate Similarity NPC225353
0.8333 Intermediate Similarity NPC477011
0.8333 Intermediate Similarity NPC471148
0.8333 Intermediate Similarity NPC320019
0.8316 Intermediate Similarity NPC475949
0.8315 Intermediate Similarity NPC5130
0.8315 Intermediate Similarity NPC179659
0.8315 Intermediate Similarity NPC118601
0.8315 Intermediate Similarity NPC190753
0.8315 Intermediate Similarity NPC474765
0.8298 Intermediate Similarity NPC323421
0.8298 Intermediate Similarity NPC328562
0.8298 Intermediate Similarity NPC161493
0.8298 Intermediate Similarity NPC471150
0.8298 Intermediate Similarity NPC40812
0.8295 Intermediate Similarity NPC319795
0.8295 Intermediate Similarity NPC215364
0.8295 Intermediate Similarity NPC165162
0.8295 Intermediate Similarity NPC38468
0.8295 Intermediate Similarity NPC50362
0.828 Intermediate Similarity NPC272050
0.828 Intermediate Similarity NPC477922
0.828 Intermediate Similarity NPC475900
0.828 Intermediate Similarity NPC474947
0.828 Intermediate Similarity NPC213698
0.828 Intermediate Similarity NPC52044
0.828 Intermediate Similarity NPC67584
0.8276 Intermediate Similarity NPC131669
0.8276 Intermediate Similarity NPC473390
0.8276 Intermediate Similarity NPC170286
0.8265 Intermediate Similarity NPC223450
0.8256 Intermediate Similarity NPC141810
0.8247 Intermediate Similarity NPC110989
0.8247 Intermediate Similarity NPC475873
0.8247 Intermediate Similarity NPC472755
0.8247 Intermediate Similarity NPC474775
0.8242 Intermediate Similarity NPC106510
0.8242 Intermediate Similarity NPC62815
0.8242 Intermediate Similarity NPC71533
0.8235 Intermediate Similarity NPC617
0.8229 Intermediate Similarity NPC474339
0.8229 Intermediate Similarity NPC46998
0.8229 Intermediate Similarity NPC128733
0.8229 Intermediate Similarity NPC110443
0.8229 Intermediate Similarity NPC185141
0.8229 Intermediate Similarity NPC133907
0.8229 Intermediate Similarity NPC472753
0.8229 Intermediate Similarity NPC164598
0.8229 Intermediate Similarity NPC15993
0.8229 Intermediate Similarity NPC201718
0.8222 Intermediate Similarity NPC178875
0.8222 Intermediate Similarity NPC91248
0.8222 Intermediate Similarity NPC476803
0.8214 Intermediate Similarity NPC116177

  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 NPC202672 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
0.8295 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD6698 Approved
0.8043 Intermediate Similarity NPD46 Approved
0.7895 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7822 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD7983 Approved
0.7742 Intermediate Similarity NPD1695 Approved
0.766 Intermediate Similarity NPD7838 Discovery
0.7596 Intermediate Similarity NPD6371 Approved
0.7358 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD6686 Approved
0.7174 Intermediate Similarity NPD6435 Approved
0.7143 Intermediate Similarity NPD5778 Approved
0.7143 Intermediate Similarity NPD5779 Approved
0.713 Intermediate Similarity NPD6053 Discontinued
0.7129 Intermediate Similarity NPD4225 Approved
0.7113 Intermediate Similarity NPD5785 Approved
0.7097 Intermediate Similarity NPD7154 Phase 3
0.7071 Intermediate Similarity NPD5282 Discontinued
0.7065 Intermediate Similarity NPD5369 Approved
0.7053 Intermediate Similarity NPD4249 Approved
0.7053 Intermediate Similarity NPD5786 Approved
0.699 Remote Similarity NPD5344 Discontinued
0.6979 Remote Similarity NPD4250 Approved
0.6979 Remote Similarity NPD4251 Approved
0.6957 Remote Similarity NPD5368 Approved
0.6947 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5363 Approved
0.693 Remote Similarity NPD8516 Approved
0.693 Remote Similarity NPD8513 Phase 3
0.693 Remote Similarity NPD8515 Approved
0.693 Remote Similarity NPD8517 Approved
0.6915 Remote Similarity NPD5362 Discontinued
0.6837 Remote Similarity NPD6101 Approved
0.6837 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4269 Approved
0.6809 Remote Similarity NPD4270 Approved
0.6796 Remote Similarity NPD7638 Approved
0.6774 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4821 Approved
0.6774 Remote Similarity NPD4820 Approved
0.6774 Remote Similarity NPD4822 Approved
0.6774 Remote Similarity NPD4819 Approved
0.6771 Remote Similarity NPD1694 Approved
0.6765 Remote Similarity NPD7839 Suspended
0.6757 Remote Similarity NPD4632 Approved
0.6731 Remote Similarity NPD7639 Approved
0.6731 Remote Similarity NPD7640 Approved
0.6729 Remote Similarity NPD6008 Approved
0.67 Remote Similarity NPD6411 Approved
0.6697 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6639 Remote Similarity NPD8074 Phase 3
0.6634 Remote Similarity NPD6399 Phase 3
0.6606 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4252 Approved
0.6579 Remote Similarity NPD7115 Discovery
0.6571 Remote Similarity NPD6648 Approved
0.6559 Remote Similarity NPD4271 Approved
0.6559 Remote Similarity NPD4268 Approved
0.6559 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7507 Approved
0.6552 Remote Similarity NPD6319 Approved
0.6525 Remote Similarity NPD7642 Approved
0.6522 Remote Similarity NPD7641 Discontinued
0.6514 Remote Similarity NPD5697 Approved
0.6512 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6899 Approved
0.6455 Remote Similarity NPD6881 Approved
0.6455 Remote Similarity NPD6011 Approved
0.6437 Remote Similarity NPD7331 Phase 2
0.6435 Remote Similarity NPD6009 Approved
0.6429 Remote Similarity NPD6650 Approved
0.6429 Remote Similarity NPD6649 Approved
0.6429 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6422 Remote Similarity NPD6675 Approved
0.6422 Remote Similarity NPD6402 Approved
0.6422 Remote Similarity NPD5739 Approved
0.6422 Remote Similarity NPD7128 Approved
0.6417 Remote Similarity NPD8451 Approved
0.6396 Remote Similarity NPD6014 Approved
0.6396 Remote Similarity NPD6373 Approved
0.6396 Remote Similarity NPD6012 Approved
0.6396 Remote Similarity NPD6372 Approved
0.6396 Remote Similarity NPD6013 Approved
0.6395 Remote Similarity NPD3197 Phase 1
0.6393 Remote Similarity NPD7319 Approved
0.6392 Remote Similarity NPD5332 Approved
0.6392 Remote Similarity NPD5331 Approved
0.6392 Remote Similarity NPD6110 Phase 1
0.6387 Remote Similarity NPD7829 Approved
0.6387 Remote Similarity NPD7830 Approved
0.6372 Remote Similarity NPD8297 Approved
0.6364 Remote Similarity NPD6422 Discontinued
0.6364 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6412 Phase 2
0.6364 Remote Similarity NPD8448 Approved
0.6364 Remote Similarity NPD5701 Approved
0.6356 Remote Similarity NPD5983 Phase 2
0.6354 Remote Similarity NPD4790 Discontinued
0.6339 Remote Similarity NPD7290 Approved
0.6339 Remote Similarity NPD6883 Approved
0.6339 Remote Similarity NPD7102 Approved
0.6333 Remote Similarity NPD7492 Approved
0.6322 Remote Similarity NPD7341 Phase 2
0.6306 Remote Similarity NPD7320 Approved
0.629 Remote Similarity NPD7260 Phase 2
0.6289 Remote Similarity NPD5209 Approved
0.6289 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6847 Approved
0.6283 Remote Similarity NPD6869 Approved
0.6283 Remote Similarity NPD6617 Approved
0.6283 Remote Similarity NPD8130 Phase 1
0.6281 Remote Similarity NPD6616 Approved
0.6271 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD7604 Phase 2
0.6237 Remote Similarity NPD8039 Approved
0.623 Remote Similarity NPD7078 Approved
0.6228 Remote Similarity NPD6882 Approved
0.6226 Remote Similarity NPD7902 Approved
0.6226 Remote Similarity NPD6083 Phase 2
0.6226 Remote Similarity NPD6084 Phase 2
0.6218 Remote Similarity NPD8444 Approved
0.6218 Remote Similarity NPD6015 Approved
0.6218 Remote Similarity NPD6016 Approved
0.6216 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7637 Suspended
0.621 Remote Similarity NPD8390 Approved
0.621 Remote Similarity NPD8392 Approved
0.621 Remote Similarity NPD8391 Approved
0.6207 Remote Similarity NPD7909 Approved
0.6198 Remote Similarity NPD8341 Approved
0.6198 Remote Similarity NPD8340 Approved
0.6198 Remote Similarity NPD8299 Approved
0.6198 Remote Similarity NPD8342 Approved
0.6195 Remote Similarity NPD4634 Approved
0.619 Remote Similarity NPD5695 Phase 3
0.6179 Remote Similarity NPD7736 Approved
0.6176 Remote Similarity NPD5370 Suspended
0.6174 Remote Similarity NPD8133 Approved
0.6168 Remote Similarity NPD5696 Approved
0.6167 Remote Similarity NPD5988 Approved
0.6167 Remote Similarity NPD6370 Approved
0.6162 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6162 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6148 Remote Similarity NPD8273 Phase 1
0.6148 Remote Similarity NPD6336 Discontinued
0.6147 Remote Similarity NPD7632 Discontinued
0.6147 Remote Similarity NPD5211 Phase 2
0.614 Remote Similarity NPD2204 Approved
0.614 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6139 Remote Similarity NPD7524 Approved
0.6134 Remote Similarity NPD6059 Approved
0.6122 Remote Similarity NPD3667 Approved
0.6116 Remote Similarity NPD8328 Phase 3
0.6111 Remote Similarity NPD5286 Approved
0.6111 Remote Similarity NPD6845 Suspended
0.6111 Remote Similarity NPD4696 Approved
0.6111 Remote Similarity NPD5285 Approved
0.6105 Remote Similarity NPD4756 Discovery
0.6098 Remote Similarity NPD8293 Discontinued
0.6095 Remote Similarity NPD7748 Approved
0.6083 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6075 Remote Similarity NPD4755 Approved
0.6068 Remote Similarity NPD6274 Approved
0.6061 Remote Similarity NPD6695 Phase 3
0.6058 Remote Similarity NPD6079 Approved
0.6058 Remote Similarity NPD7515 Phase 2
0.6058 Remote Similarity NPD5281 Approved
0.6058 Remote Similarity NPD5284 Approved
0.6058 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6058 Remote Similarity NPD5693 Phase 1
0.6055 Remote Similarity NPD5223 Approved
0.604 Remote Similarity NPD5330 Approved
0.604 Remote Similarity NPD7334 Approved
0.604 Remote Similarity NPD6409 Approved
0.604 Remote Similarity NPD7521 Approved
0.604 Remote Similarity NPD7146 Approved
0.604 Remote Similarity NPD6684 Approved
0.604 Remote Similarity NPD3618 Phase 1
0.6036 Remote Similarity NPD5141 Approved
0.6033 Remote Similarity NPD8080 Discontinued
0.6019 Remote Similarity NPD5328 Approved
0.6017 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6017 Remote Similarity NPD6317 Approved
0.6 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD3665 Phase 1
0.6 Remote Similarity NPD4633 Approved
0.6 Remote Similarity NPD5225 Approved
0.6 Remote Similarity NPD4786 Approved
0.6 Remote Similarity NPD3666 Approved
0.6 Remote Similarity NPD3133 Approved
0.6 Remote Similarity NPD5224 Approved
0.5981 Remote Similarity NPD5221 Approved
0.5981 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5981 Remote Similarity NPD4697 Phase 3
0.5981 Remote Similarity NPD5222 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