Structure

Physi-Chem Properties

Molecular Weight:  392.22
Volume:  411.514
LogP:  2.606
LogD:  2.476
LogS:  -4.086
# Rotatable Bonds:  2
TPSA:  93.06
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.405
Synthetic Accessibility Score:  5.013
Fsp3:  0.636
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.73
MDCK Permeability:  4.045238165417686e-05
Pgp-inhibitor:  0.112
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.985
20% Bioavailability (F20%):  0.195
30% Bioavailability (F30%):  0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.508
Plasma Protein Binding (PPB):  90.25662994384766%
Volume Distribution (VD):  0.888
Pgp-substrate:  10.355870246887207%

ADMET: Metabolism

CYP1A2-inhibitor:  0.077
CYP1A2-substrate:  0.08
CYP2C19-inhibitor:  0.062
CYP2C19-substrate:  0.126
CYP2C9-inhibitor:  0.222
CYP2C9-substrate:  0.18
CYP2D6-inhibitor:  0.053
CYP2D6-substrate:  0.074
CYP3A4-inhibitor:  0.254
CYP3A4-substrate:  0.209

ADMET: Excretion

Clearance (CL):  6.489
Half-life (T1/2):  0.557

ADMET: Toxicity

hERG Blockers:  0.039
Human Hepatotoxicity (H-HT):  0.953
Drug-inuced Liver Injury (DILI):  0.316
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.339
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.928
Carcinogencity:  0.048
Eye Corrosion:  0.241
Eye Irritation:  0.056
Respiratory Toxicity:  0.958

Download Data

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

  Natural Product: NPC30515

Natural Product ID:  NPC30515
Common Name*:   Crassolide A
IUPAC Name:   [(3aR,5S,6R,9E,13E,15S,15aR)-5,6-dihydroxy-6,10,14-trimethyl-3-methylidene-2-oxo-4,5,7,8,11,12,15,15a-octahydro-3aH-cyclotetradeca[b]furan-15-yl] acetate
Synonyms:  
Standard InCHIKey:  LOBTUTHTMBAWQV-RCJCYISHSA-N
Standard InCHI:  InChI=1S/C22H32O6/c1-13-8-6-10-14(2)19(27-16(4)23)20-17(15(3)21(25)28-20)12-18(24)22(5,26)11-7-9-13/h9-10,17-20,24,26H,3,6-8,11-12H2,1-2,4-5H3/b13-9+,14-10+/t17-,18+,19+,20-,22-/m1/s1
SMILES:  C/C/1=CCC[C@](C)([C@H](C[C@@H]2C(=C)C(=O)O[C@H]2[C@H](/C(=C/CC1)/C)OC(=O)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462803
PubChem CID:   11995173
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 = 8.9 ug.mL-1 PMID[457256]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 8.6 ug.mL-1 PMID[457256]
NPT81 Cell Line A549 Homo sapiens IC50 = 11.9 ug.mL-1 PMID[457256]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 3.1 ug.mL-1 PMID[457256]

☑ 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 NPC30515 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
0.9882 High Similarity NPC51004
0.9767 High Similarity NPC184463
0.9765 High Similarity NPC307411
0.9659 High Similarity NPC36954
0.9655 High Similarity NPC81419
0.9655 High Similarity NPC179746
0.9655 High Similarity NPC476300
0.9655 High Similarity NPC475912
0.9651 High Similarity NPC474761
0.9651 High Similarity NPC476004
0.9647 High Similarity NPC202672
0.9545 High Similarity NPC81386
0.9545 High Similarity NPC474035
0.954 High Similarity NPC12172
0.954 High Similarity NPC208886
0.9438 High Similarity NPC14961
0.9438 High Similarity NPC270013
0.9432 High Similarity NPC212486
0.9333 High Similarity NPC476315
0.9195 High Similarity NPC58219
0.9195 High Similarity NPC177629
0.9091 High Similarity NPC92974
0.9091 High Similarity NPC474032
0.908 High Similarity NPC231889
0.908 High Similarity NPC186148
0.908 High Similarity NPC248602
0.907 High Similarity NPC137033
0.907 High Similarity NPC21469
0.9059 High Similarity NPC11620
0.8989 High Similarity NPC475748
0.8989 High Similarity NPC473619
0.8977 High Similarity NPC153805
0.8977 High Similarity NPC474471
0.8977 High Similarity NPC227379
0.8966 High Similarity NPC474949
0.8966 High Similarity NPC475019
0.8953 High Similarity NPC474780
0.8925 High Similarity NPC473326
0.8913 High Similarity NPC473859
0.8901 High Similarity NPC303942
0.8901 High Similarity NPC57405
0.8889 High Similarity NPC473321
0.8876 High Similarity NPC295312
0.8851 High Similarity NPC304509
0.8851 High Similarity NPC47958
0.8851 High Similarity NPC149725
0.8851 High Similarity NPC329749
0.883 High Similarity NPC288876
0.8804 High Similarity NPC475659
0.8791 High Similarity NPC273579
0.8791 High Similarity NPC288240
0.8791 High Similarity NPC295204
0.8791 High Similarity NPC162205
0.8764 High Similarity NPC281516
0.8764 High Similarity NPC473715
0.875 High Similarity NPC112685
0.875 High Similarity NPC475945
0.875 High Similarity NPC476015
0.875 High Similarity NPC475871
0.875 High Similarity NPC164393
0.875 High Similarity NPC474762
0.8737 High Similarity NPC476270
0.8736 High Similarity NPC9868
0.8736 High Similarity NPC3464
0.8736 High Similarity NPC475963
0.8736 High Similarity NPC151176
0.8723 High Similarity NPC471144
0.8723 High Similarity NPC187268
0.8723 High Similarity NPC474213
0.871 High Similarity NPC279621
0.8696 High Similarity NPC71589
0.8667 High Similarity NPC477011
0.8667 High Similarity NPC151770
0.866 High Similarity NPC100487
0.8652 High Similarity NPC179659
0.8646 High Similarity NPC320019
0.8646 High Similarity NPC324017
0.8646 High Similarity NPC149371
0.8646 High Similarity NPC474747
0.8621 High Similarity NPC250315
0.8621 High Similarity NPC272814
0.8617 High Similarity NPC40812
0.8602 High Similarity NPC107476
0.8602 High Similarity NPC471142
0.8587 High Similarity NPC125674
0.8587 High Similarity NPC228451
0.8587 High Similarity NPC475838
0.8571 High Similarity NPC475855
0.8571 High Similarity NPC473448
0.8571 High Similarity NPC243998
0.8557 High Similarity NPC472755
0.8542 High Similarity NPC473332
0.8542 High Similarity NPC472753
0.8542 High Similarity NPC15993
0.8542 High Similarity NPC474742
0.8542 High Similarity NPC47880
0.8539 High Similarity NPC232555
0.8539 High Similarity NPC142117
0.8539 High Similarity NPC62118
0.8539 High Similarity NPC231096
0.8539 High Similarity NPC114694
0.8539 High Similarity NPC475581
0.8539 High Similarity NPC284902
0.8539 High Similarity NPC240695
0.8539 High Similarity NPC107717
0.8539 High Similarity NPC171174
0.8526 High Similarity NPC83895
0.8526 High Similarity NPC187761
0.8523 High Similarity NPC70424
0.8523 High Similarity NPC474776
0.8523 High Similarity NPC243618
0.8511 High Similarity NPC158416
0.8511 High Similarity NPC477921
0.8511 High Similarity NPC39859
0.8511 High Similarity NPC76862
0.8511 High Similarity NPC470883
0.8495 Intermediate Similarity NPC473316
0.8495 Intermediate Similarity NPC473330
0.8495 Intermediate Similarity NPC474247
0.8495 Intermediate Similarity NPC190294
0.8485 Intermediate Similarity NPC477513
0.8478 Intermediate Similarity NPC470379
0.8478 Intermediate Similarity NPC475881
0.8478 Intermediate Similarity NPC470373
0.8478 Intermediate Similarity NPC70251
0.8469 Intermediate Similarity NPC203659
0.8469 Intermediate Similarity NPC474741
0.8462 Intermediate Similarity NPC474951
0.8462 Intermediate Similarity NPC473564
0.8462 Intermediate Similarity NPC166919
0.8462 Intermediate Similarity NPC173926
0.8454 Intermediate Similarity NPC472754
0.8454 Intermediate Similarity NPC86077
0.8454 Intermediate Similarity NPC471148
0.8444 Intermediate Similarity NPC475703
0.8444 Intermediate Similarity NPC474765
0.8444 Intermediate Similarity NPC160138
0.8438 Intermediate Similarity NPC475949
0.8427 Intermediate Similarity NPC100921
0.8427 Intermediate Similarity NPC473478
0.8427 Intermediate Similarity NPC66346
0.8427 Intermediate Similarity NPC286338
0.8427 Intermediate Similarity NPC473669
0.8427 Intermediate Similarity NPC283085
0.8427 Intermediate Similarity NPC1083
0.8427 Intermediate Similarity NPC110710
0.8427 Intermediate Similarity NPC477018
0.8427 Intermediate Similarity NPC82795
0.8427 Intermediate Similarity NPC255307
0.8427 Intermediate Similarity NPC107986
0.8427 Intermediate Similarity NPC132496
0.8427 Intermediate Similarity NPC473651
0.8427 Intermediate Similarity NPC223871
0.8427 Intermediate Similarity NPC103284
0.8427 Intermediate Similarity NPC231009
0.8421 Intermediate Similarity NPC323421
0.8421 Intermediate Similarity NPC328562
0.8409 Intermediate Similarity NPC170286
0.8404 Intermediate Similarity NPC475900
0.8404 Intermediate Similarity NPC477922
0.8404 Intermediate Similarity NPC304886
0.8404 Intermediate Similarity NPC471141
0.8387 Intermediate Similarity NPC135776
0.8384 Intermediate Similarity NPC223450
0.837 Intermediate Similarity NPC206614
0.837 Intermediate Similarity NPC474323
0.837 Intermediate Similarity NPC144133
0.837 Intermediate Similarity NPC179394
0.8367 Intermediate Similarity NPC472747
0.8367 Intermediate Similarity NPC472750
0.8367 Intermediate Similarity NPC474775
0.8367 Intermediate Similarity NPC110989
0.8352 Intermediate Similarity NPC191929
0.8352 Intermediate Similarity NPC20339
0.8352 Intermediate Similarity NPC133730
0.8352 Intermediate Similarity NPC261952
0.8352 Intermediate Similarity NPC61257
0.8352 Intermediate Similarity NPC287164
0.8352 Intermediate Similarity NPC40376
0.8352 Intermediate Similarity NPC100454
0.8352 Intermediate Similarity NPC171135
0.8352 Intermediate Similarity NPC169511
0.8352 Intermediate Similarity NPC39754
0.8352 Intermediate Similarity NPC48338
0.8352 Intermediate Similarity NPC242364
0.8352 Intermediate Similarity NPC172821
0.8352 Intermediate Similarity NPC320569
0.8352 Intermediate Similarity NPC89001
0.8352 Intermediate Similarity NPC151403
0.8352 Intermediate Similarity NPC21208
0.8352 Intermediate Similarity NPC233551
0.8352 Intermediate Similarity NPC81045
0.8352 Intermediate Similarity NPC280621
0.8352 Intermediate Similarity NPC234077
0.8352 Intermediate Similarity NPC274446
0.8351 Intermediate Similarity NPC133907
0.8351 Intermediate Similarity NPC164598
0.8351 Intermediate Similarity NPC474339
0.8351 Intermediate Similarity NPC46998
0.8351 Intermediate Similarity NPC201718

  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 NPC30515 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
0.837 Intermediate Similarity NPD46 Approved
0.837 Intermediate Similarity NPD6698 Approved
0.8222 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.8119 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.8085 Intermediate Similarity NPD7983 Approved
0.7979 Intermediate Similarity NPD7838 Discovery
0.7885 Intermediate Similarity NPD6371 Approved
0.7653 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7642 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD6686 Approved
0.75 Intermediate Similarity NPD1695 Approved
0.7282 Intermediate Similarity NPD5344 Discontinued
0.7273 Intermediate Similarity NPD5778 Approved
0.7273 Intermediate Similarity NPD5779 Approved
0.7255 Intermediate Similarity NPD4225 Approved
0.7248 Intermediate Similarity NPD6053 Discontinued
0.7245 Intermediate Similarity NPD5785 Approved
0.7234 Intermediate Similarity NPD7154 Phase 3
0.7193 Intermediate Similarity NPD8513 Phase 3
0.7193 Intermediate Similarity NPD8516 Approved
0.7193 Intermediate Similarity NPD8515 Approved
0.7193 Intermediate Similarity NPD8517 Approved
0.7188 Intermediate Similarity NPD5786 Approved
0.7128 Intermediate Similarity NPD6435 Approved
0.7113 Intermediate Similarity NPD4251 Approved
0.7113 Intermediate Similarity NPD4250 Approved
0.7083 Intermediate Similarity NPD6082 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5363 Approved
0.7053 Intermediate Similarity NPD5362 Discontinued
0.7021 Intermediate Similarity NPD5369 Approved
0.701 Intermediate Similarity NPD4249 Approved
0.6947 Remote Similarity NPD4270 Approved
0.6947 Remote Similarity NPD4269 Approved
0.6923 Remote Similarity NPD7638 Approved
0.6915 Remote Similarity NPD4820 Approved
0.6915 Remote Similarity NPD4822 Approved
0.6915 Remote Similarity NPD4819 Approved
0.6915 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5368 Approved
0.6915 Remote Similarity NPD4821 Approved
0.6893 Remote Similarity NPD7839 Suspended
0.6891 Remote Similarity NPD8074 Phase 3
0.6863 Remote Similarity NPD5282 Discontinued
0.6857 Remote Similarity NPD7639 Approved
0.6857 Remote Similarity NPD6648 Approved
0.6857 Remote Similarity NPD7640 Approved
0.6842 Remote Similarity NPD7115 Discovery
0.6818 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6807 Remote Similarity NPD7507 Approved
0.68 Remote Similarity NPD5764 Clinical (unspecified phase)
0.68 Remote Similarity NPD6101 Approved
0.678 Remote Similarity NPD7642 Approved
0.6771 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6737 Remote Similarity NPD4252 Approved
0.6735 Remote Similarity NPD1694 Approved
0.6727 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6726 Remote Similarity NPD4632 Approved
0.6702 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4268 Approved
0.6702 Remote Similarity NPD4271 Approved
0.6701 Remote Similarity NPD6110 Phase 1
0.6667 Remote Similarity NPD8451 Approved
0.6667 Remote Similarity NPD6411 Approved
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6639 Remote Similarity NPD7829 Approved
0.6639 Remote Similarity NPD7319 Approved
0.6639 Remote Similarity NPD7830 Approved
0.6638 Remote Similarity NPD7641 Discontinued
0.6612 Remote Similarity NPD8448 Approved
0.6607 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6602 Remote Similarity NPD6399 Phase 3
0.6545 Remote Similarity NPD6008 Approved
0.6532 Remote Similarity NPD7260 Phase 2
0.6531 Remote Similarity NPD5331 Approved
0.6531 Remote Similarity NPD5332 Approved
0.6525 Remote Similarity NPD6319 Approved
0.6517 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6495 Remote Similarity NPD4790 Discontinued
0.6491 Remote Similarity NPD8297 Approved
0.6486 Remote Similarity NPD6412 Phase 2
0.6477 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8444 Approved
0.6452 Remote Similarity NPD8392 Approved
0.6452 Remote Similarity NPD8391 Approved
0.6452 Remote Similarity NPD8390 Approved
0.6446 Remote Similarity NPD7492 Approved
0.6446 Remote Similarity NPD8299 Approved
0.6446 Remote Similarity NPD8341 Approved
0.6446 Remote Similarity NPD8340 Approved
0.6446 Remote Similarity NPD8342 Approved
0.6429 Remote Similarity NPD6881 Approved
0.6429 Remote Similarity NPD6899 Approved
0.6429 Remote Similarity NPD4800 Clinical (unspecified phase)
0.641 Remote Similarity NPD6009 Approved
0.6404 Remote Similarity NPD7331 Phase 2
0.6404 Remote Similarity NPD6649 Approved
0.6404 Remote Similarity NPD6650 Approved
0.6396 Remote Similarity NPD7128 Approved
0.6396 Remote Similarity NPD6402 Approved
0.6396 Remote Similarity NPD6675 Approved
0.6396 Remote Similarity NPD5739 Approved
0.6393 Remote Similarity NPD8273 Phase 1
0.6393 Remote Similarity NPD6616 Approved
0.6387 Remote Similarity NPD6054 Approved
0.6383 Remote Similarity NPD8039 Approved
0.6372 Remote Similarity NPD6373 Approved
0.6372 Remote Similarity NPD6372 Approved
0.6364 Remote Similarity NPD3197 Phase 1
0.6364 Remote Similarity NPD7604 Phase 2
0.6349 Remote Similarity NPD6845 Suspended
0.6346 Remote Similarity NPD7637 Suspended
0.6341 Remote Similarity NPD7078 Approved
0.6339 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6339 Remote Similarity NPD5697 Approved
0.6337 Remote Similarity NPD6422 Discontinued
0.6333 Remote Similarity NPD5983 Phase 2
0.6316 Remote Similarity NPD7102 Approved
0.6316 Remote Similarity NPD7290 Approved
0.6316 Remote Similarity NPD6883 Approved
0.6311 Remote Similarity NPD5370 Suspended
0.63 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6293 Remote Similarity NPD8133 Approved
0.6292 Remote Similarity NPD7341 Phase 2
0.629 Remote Similarity NPD7736 Approved
0.6283 Remote Similarity NPD7320 Approved
0.6283 Remote Similarity NPD6011 Approved
0.6281 Remote Similarity NPD6370 Approved
0.6275 Remote Similarity NPD7524 Approved
0.6273 Remote Similarity NPD7632 Discontinued
0.6271 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5209 Approved
0.6261 Remote Similarity NPD8130 Phase 1
0.6261 Remote Similarity NPD6847 Approved
0.6261 Remote Similarity NPD6869 Approved
0.6261 Remote Similarity NPD6617 Approved
0.6261 Remote Similarity NPD2204 Approved
0.626 Remote Similarity NPD6336 Discontinued
0.625 Remote Similarity NPD6059 Approved
0.623 Remote Similarity NPD8328 Phase 3
0.6228 Remote Similarity NPD6013 Approved
0.6228 Remote Similarity NPD6014 Approved
0.6228 Remote Similarity NPD6012 Approved
0.6218 Remote Similarity NPD7328 Approved
0.6218 Remote Similarity NPD7327 Approved
0.621 Remote Similarity NPD8293 Discontinued
0.6207 Remote Similarity NPD6882 Approved
0.6204 Remote Similarity NPD6083 Phase 2
0.6204 Remote Similarity NPD7902 Approved
0.6204 Remote Similarity NPD6084 Phase 2
0.6198 Remote Similarity NPD6015 Approved
0.6198 Remote Similarity NPD7503 Approved
0.6198 Remote Similarity NPD6016 Approved
0.6198 Remote Similarity NPD8033 Approved
0.6195 Remote Similarity NPD5701 Approved
0.619 Remote Similarity NPD4810 Clinical (unspecified phase)
0.618 Remote Similarity NPD7909 Approved
0.6174 Remote Similarity NPD6421 Discontinued
0.6167 Remote Similarity NPD7516 Approved
0.6148 Remote Similarity NPD5988 Approved
0.6148 Remote Similarity NPD8080 Discontinued
0.6139 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6134 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6134 Remote Similarity NPD7500 Approved
0.6121 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6121 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6116 Remote Similarity NPD8377 Approved
0.6116 Remote Similarity NPD8294 Approved
0.6111 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6082 Remote Similarity NPD4756 Discovery
0.6075 Remote Similarity NPD7748 Approved
0.6066 Remote Similarity NPD8378 Approved
0.6066 Remote Similarity NPD8267 Approved
0.6066 Remote Similarity NPD8296 Approved
0.6066 Remote Similarity NPD8380 Approved
0.6066 Remote Similarity NPD8379 Approved
0.6066 Remote Similarity NPD8266 Approved
0.6066 Remote Similarity NPD8269 Approved
0.6066 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6066 Remote Similarity NPD8335 Approved
0.6066 Remote Similarity NPD8268 Approved
0.6066 Remote Similarity NPD6921 Approved
0.604 Remote Similarity NPD6695 Phase 3
0.6038 Remote Similarity NPD6079 Approved
0.6038 Remote Similarity NPD7515 Phase 2
0.6034 Remote Similarity NPD4634 Approved
0.6019 Remote Similarity NPD6409 Approved
0.6019 Remote Similarity NPD5695 Phase 3
0.6019 Remote Similarity NPD7521 Approved
0.6019 Remote Similarity NPD7334 Approved
0.6019 Remote Similarity NPD6684 Approved
0.6019 Remote Similarity NPD7146 Approved
0.6019 Remote Similarity NPD5330 Approved
0.6 Remote Similarity NPD5696 Approved
0.6 Remote Similarity NPD5328 Approved
0.5982 Remote Similarity NPD5211 Phase 2
0.598 Remote Similarity NPD4786 Approved
0.5954 Remote Similarity NPD8387 Clinical (unspecified phase)
0.595 Remote Similarity NPD6335 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