Structure

Physi-Chem Properties

Molecular Weight:  444.32
Volume:  485.87
LogP:  4.193
LogD:  3.905
LogS:  -4.745
# Rotatable Bonds:  4
TPSA:  77.76
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.535
Synthetic Accessibility Score:  5.261
Fsp3:  0.821
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.926
MDCK Permeability:  2.935595330200158e-05
Pgp-inhibitor:  0.034
Pgp-substrate:  0.53
Human Intestinal Absorption (HIA):  0.033
20% Bioavailability (F20%):  0.974
30% Bioavailability (F30%):  0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.399
Plasma Protein Binding (PPB):  84.55328369140625%
Volume Distribution (VD):  1.106
Pgp-substrate:  2.2668447494506836%

ADMET: Metabolism

CYP1A2-inhibitor:  0.024
CYP1A2-substrate:  0.811
CYP2C19-inhibitor:  0.191
CYP2C19-substrate:  0.935
CYP2C9-inhibitor:  0.28
CYP2C9-substrate:  0.09
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.068
CYP3A4-inhibitor:  0.878
CYP3A4-substrate:  0.953

ADMET: Excretion

Clearance (CL):  3.685
Half-life (T1/2):  0.254

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.208
Drug-inuced Liver Injury (DILI):  0.077
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.83
Maximum Recommended Daily Dose:  0.91
Skin Sensitization:  0.724
Carcinogencity:  0.021
Eye Corrosion:  0.006
Eye Irritation:  0.125
Respiratory Toxicity:  0.807

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

  Natural Product: NPC247957

Natural Product ID:  NPC247957
Common Name*:   Ergosta-7,22-Dien-3Beta,5Alpha,9Alpha-Trihydroxy-6-One
IUPAC Name:   (3S,5R,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3,5,9-trihydroxy-10,13-dimethyl-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
Synonyms:  
Standard InCHIKey:  GUERPVMWCQXYEU-IHEPTZRRSA-N
Standard InCHI:  InChI=1S/C28H44O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28(32)16-20(29)11-12-26(28,6)27(23,31)14-13-25(21,22)5/h7-8,15,17-22,29,31-32H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,21+,22-,25+,26+,27+,28-/m0/s1
SMILES:  O[C@H]1CC[C@]2([C@@](C1)(O)C(=O)C=C1[C@]2(O)CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2012312
PubChem CID:   21772319
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003567] Ergostane steroids
          • [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(02)00378-3]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[11170686]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16156520]
NPO16239 Rhodiola rosea Species Crassulaceae Eukaryota roots n.a. n.a. PMID[19729316]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. mycelium n.a. PMID[21043476]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21275386]
NPO20231 Sarcodon scabrosus Species Thelephoraceae Eukaryota n.a. n.a. n.a. PMID[22401866]
NPO33483 Diaporthe sp. Species Diaporthaceae Eukaryota n.a. n.a. n.a. PMID[23006147]
NPO33483 Diaporthe sp. Species Diaporthaceae Eukaryota n.a. Mangrove-Derived Endophytic Fungus Diaporthe sp. n.a. PMID[23006147]
NPO33483 Diaporthe sp. Species Diaporthaceae Eukaryota n.a. n.a. n.a. PMID[26186257]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. seed n.a. PMID[5348524]
NPO20231 Sarcodon scabrosus Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16239 Rhodiola rosea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4483 Ganonema farinosum Species Liagoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8684 Nymphaea ampla Species Nymphaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17677 Eremophila latrobei Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16239 Rhodiola rosea Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO370 Rhizophora apiculata Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24388 Pinus pinaster Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6631 Elaeagnus glabra Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19426 Diospyros ferrea Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9378 Halocynthia aurantium Species Pyuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8301 Erythrina suberosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14503 Glycosmis craibii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1779 Sargassum kjellmanianum Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20231 Sarcodon scabrosus Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11051 Nicotiana cavicola Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17323 Murex brandaris Species Muricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO155 Artemisia lanata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5443 Coltricia cinnamomea Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5288 Stomatanthes corumbensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14094 Aspergillus ochraceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3499 Macaranga conifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2271 Cassia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28832 Baccharoides adoensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28869 Neonectria obtusispora Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12752 Yucca baccata Species Asparagaceae 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 10.0 ug.mL-1 PMID[489851]
NPT19 Organism Escherichia coli Escherichia coli MIC > 10.0 ug.mL-1 PMID[489851]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 5.0 ug.mL-1 PMID[489851]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 10.0 ug.mL-1 PMID[489851]
NPT1228 Organism Streptococcus pyogenes Streptococcus pyogenes MIC > 10.0 ug.mL-1 PMID[489851]

☑ 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 NPC247957 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC249187
0.9794 High Similarity NPC257353
0.9691 High Similarity NPC72255
0.9263 High Similarity NPC271195
0.9158 High Similarity NPC245972
0.9158 High Similarity NPC196485
0.9082 High Similarity NPC154072
0.901 High Similarity NPC166607
0.9 High Similarity NPC311612
0.898 High Similarity NPC191565
0.898 High Similarity NPC103051
0.8958 High Similarity NPC8993
0.8952 High Similarity NPC108721
0.8952 High Similarity NPC73300
0.8947 High Similarity NPC475806
0.8932 High Similarity NPC214644
0.8922 High Similarity NPC185
0.8922 High Similarity NPC477916
0.8911 High Similarity NPC160843
0.89 High Similarity NPC87351
0.8889 High Similarity NPC327431
0.8866 High Similarity NPC272617
0.8866 High Similarity NPC476245
0.8842 High Similarity NPC48010
0.8824 High Similarity NPC149047
0.8776 High Similarity NPC249954
0.8763 High Similarity NPC292793
0.8763 High Similarity NPC474690
0.875 High Similarity NPC473998
0.875 High Similarity NPC233116
0.8738 High Similarity NPC220229
0.8738 High Similarity NPC475060
0.8738 High Similarity NPC83744
0.8737 High Similarity NPC473999
0.8737 High Similarity NPC31985
0.8737 High Similarity NPC309603
0.8737 High Similarity NPC474245
0.8737 High Similarity NPC1015
0.8725 High Similarity NPC204833
0.8725 High Similarity NPC209502
0.8713 High Similarity NPC477054
0.8687 High Similarity NPC474785
0.8687 High Similarity NPC320306
0.8687 High Similarity NPC108078
0.8687 High Similarity NPC474938
0.8673 High Similarity NPC259286
0.8673 High Similarity NPC180950
0.8654 High Similarity NPC217201
0.8654 High Similarity NPC329417
0.8654 High Similarity NPC65941
0.8646 High Similarity NPC46758
0.8641 High Similarity NPC476027
0.8641 High Similarity NPC85829
0.8641 High Similarity NPC97202
0.8641 High Similarity NPC214264
0.8641 High Similarity NPC319077
0.8641 High Similarity NPC260268
0.8641 High Similarity NPC49958
0.8641 High Similarity NPC302607
0.8641 High Similarity NPC296945
0.8641 High Similarity NPC48733
0.8641 High Similarity NPC50692
0.8641 High Similarity NPC171137
0.8641 High Similarity NPC150531
0.8641 High Similarity NPC152695
0.8641 High Similarity NPC202167
0.8627 High Similarity NPC191892
0.8627 High Similarity NPC111323
0.8614 High Similarity NPC477053
0.8614 High Similarity NPC477052
0.8614 High Similarity NPC477051
0.8586 High Similarity NPC49371
0.8571 High Similarity NPC11710
0.8571 High Similarity NPC209662
0.8571 High Similarity NPC299100
0.8571 High Similarity NPC111015
0.8558 High Similarity NPC472925
0.8557 High Similarity NPC185936
0.8557 High Similarity NPC168027
0.8557 High Similarity NPC131872
0.8542 High Similarity NPC186688
0.8529 High Similarity NPC293753
0.8529 High Similarity NPC234892
0.8529 High Similarity NPC477915
0.8526 High Similarity NPC475740
0.8526 High Similarity NPC58063
0.8515 High Similarity NPC144956
0.85 High Similarity NPC126815
0.85 High Similarity NPC18509
0.8485 Intermediate Similarity NPC297199
0.8476 Intermediate Similarity NPC472219
0.8476 Intermediate Similarity NPC472218
0.8476 Intermediate Similarity NPC472217
0.8469 Intermediate Similarity NPC69454
0.8469 Intermediate Similarity NPC12722
0.8469 Intermediate Similarity NPC472930
0.8469 Intermediate Similarity NPC474736
0.8447 Intermediate Similarity NPC251017
0.844 Intermediate Similarity NPC148458
0.8438 Intermediate Similarity NPC193360
0.8438 Intermediate Similarity NPC471722
0.8431 Intermediate Similarity NPC163372
0.8431 Intermediate Similarity NPC302537
0.8421 Intermediate Similarity NPC472986
0.8421 Intermediate Similarity NPC261266
0.8421 Intermediate Similarity NPC472985
0.8421 Intermediate Similarity NPC51014
0.8421 Intermediate Similarity NPC31564
0.8421 Intermediate Similarity NPC474732
0.8421 Intermediate Similarity NPC474778
0.8421 Intermediate Similarity NPC145879
0.8421 Intermediate Similarity NPC474733
0.8421 Intermediate Similarity NPC94666
0.8421 Intermediate Similarity NPC6391
0.8416 Intermediate Similarity NPC114274
0.8411 Intermediate Similarity NPC472928
0.84 Intermediate Similarity NPC192428
0.84 Intermediate Similarity NPC117133
0.8396 Intermediate Similarity NPC87335
0.8384 Intermediate Similarity NPC119562
0.8384 Intermediate Similarity NPC279410
0.8381 Intermediate Similarity NPC165873
0.8381 Intermediate Similarity NPC64844
0.8381 Intermediate Similarity NPC42847
0.8367 Intermediate Similarity NPC472978
0.8367 Intermediate Similarity NPC97404
0.8367 Intermediate Similarity NPC63748
0.8367 Intermediate Similarity NPC116726
0.8367 Intermediate Similarity NPC41554
0.8367 Intermediate Similarity NPC272746
0.8364 Intermediate Similarity NPC471854
0.8351 Intermediate Similarity NPC2983
0.8351 Intermediate Similarity NPC119416
0.8351 Intermediate Similarity NPC76879
0.8351 Intermediate Similarity NPC310010
0.8351 Intermediate Similarity NPC32830
0.8351 Intermediate Similarity NPC326627
0.835 Intermediate Similarity NPC119601
0.835 Intermediate Similarity NPC308726
0.835 Intermediate Similarity NPC473424
0.8333 Intermediate Similarity NPC207251
0.8333 Intermediate Similarity NPC474720
0.8333 Intermediate Similarity NPC15390
0.8319 Intermediate Similarity NPC222688
0.8318 Intermediate Similarity NPC76084
0.8317 Intermediate Similarity NPC122294
0.8317 Intermediate Similarity NPC291634
0.8317 Intermediate Similarity NPC99726
0.8316 Intermediate Similarity NPC470360
0.8316 Intermediate Similarity NPC471224
0.8316 Intermediate Similarity NPC470574
0.8302 Intermediate Similarity NPC295244
0.83 Intermediate Similarity NPC473170
0.83 Intermediate Similarity NPC472932
0.83 Intermediate Similarity NPC472485
0.8288 Intermediate Similarity NPC146786
0.8286 Intermediate Similarity NPC51452
0.8286 Intermediate Similarity NPC323834
0.8283 Intermediate Similarity NPC109305
0.8283 Intermediate Similarity NPC233118
0.8283 Intermediate Similarity NPC475255
0.8269 Intermediate Similarity NPC478057
0.8269 Intermediate Similarity NPC475050
0.8269 Intermediate Similarity NPC222153
0.8265 Intermediate Similarity NPC320026
0.8265 Intermediate Similarity NPC291484
0.8265 Intermediate Similarity NPC80561
0.8265 Intermediate Similarity NPC11216
0.8265 Intermediate Similarity NPC204188
0.8265 Intermediate Similarity NPC473099
0.8265 Intermediate Similarity NPC3345
0.8265 Intermediate Similarity NPC329596
0.8257 Intermediate Similarity NPC317210
0.8257 Intermediate Similarity NPC122056
0.8252 Intermediate Similarity NPC282524
0.8252 Intermediate Similarity NPC118964
0.8252 Intermediate Similarity NPC115899
0.8252 Intermediate Similarity NPC476897
0.8247 Intermediate Similarity NPC328539
0.8247 Intermediate Similarity NPC310752
0.8247 Intermediate Similarity NPC292491
0.8235 Intermediate Similarity NPC16021
0.8229 Intermediate Similarity NPC299068
0.8229 Intermediate Similarity NPC222613
0.8229 Intermediate Similarity NPC118648
0.8229 Intermediate Similarity NPC475022
0.8229 Intermediate Similarity NPC72133
0.8224 Intermediate Similarity NPC284828
0.8224 Intermediate Similarity NPC472216
0.8224 Intermediate Similarity NPC173905
0.8224 Intermediate Similarity NPC5475
0.8218 Intermediate Similarity NPC305483
0.8218 Intermediate Similarity NPC250757
0.8218 Intermediate Similarity NPC301534
0.8218 Intermediate Similarity NPC96859
0.8218 Intermediate Similarity NPC471463
0.8218 Intermediate Similarity NPC328162
0.8218 Intermediate Similarity NPC7124
0.8214 Intermediate Similarity NPC472933
0.8211 Intermediate Similarity NPC205845

  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 NPC247957 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
0.8713 High Similarity NPD5211 Phase 2
0.8544 High Similarity NPD5141 Approved
0.8515 High Similarity NPD5286 Approved
0.8515 High Similarity NPD5285 Approved
0.8515 High Similarity NPD4696 Approved
0.85 High Similarity NPD4755 Approved
0.8421 Intermediate Similarity NPD3618 Phase 1
0.84 Intermediate Similarity NPD5222 Approved
0.84 Intermediate Similarity NPD5221 Approved
0.84 Intermediate Similarity NPD4697 Phase 3
0.84 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD6079 Approved
0.8351 Intermediate Similarity NPD5328 Approved
0.8351 Intermediate Similarity NPD4753 Phase 2
0.835 Intermediate Similarity NPD5226 Approved
0.835 Intermediate Similarity NPD4633 Approved
0.835 Intermediate Similarity NPD5225 Approved
0.835 Intermediate Similarity NPD5224 Approved
0.8333 Intermediate Similarity NPD4700 Approved
0.8317 Intermediate Similarity NPD5173 Approved
0.83 Intermediate Similarity NPD5210 Approved
0.83 Intermediate Similarity NPD4629 Approved
0.8269 Intermediate Similarity NPD5174 Approved
0.8269 Intermediate Similarity NPD5175 Approved
0.8252 Intermediate Similarity NPD5223 Approved
0.8211 Intermediate Similarity NPD4786 Approved
0.8148 Intermediate Similarity NPD4634 Approved
0.8131 Intermediate Similarity NPD6899 Approved
0.8131 Intermediate Similarity NPD6881 Approved
0.8113 Intermediate Similarity NPD6675 Approved
0.8113 Intermediate Similarity NPD6402 Approved
0.8113 Intermediate Similarity NPD5739 Approved
0.8113 Intermediate Similarity NPD7128 Approved
0.81 Intermediate Similarity NPD4202 Approved
0.8073 Intermediate Similarity NPD6650 Approved
0.8073 Intermediate Similarity NPD6649 Approved
0.8056 Intermediate Similarity NPD6372 Approved
0.8056 Intermediate Similarity NPD6373 Approved
0.8037 Intermediate Similarity NPD5697 Approved
0.8036 Intermediate Similarity NPD7115 Discovery
0.8 Intermediate Similarity NPD3667 Approved
0.7982 Intermediate Similarity NPD7102 Approved
0.7982 Intermediate Similarity NPD7290 Approved
0.7982 Intermediate Similarity NPD6883 Approved
0.7963 Intermediate Similarity NPD4730 Approved
0.7963 Intermediate Similarity NPD7320 Approved
0.7963 Intermediate Similarity NPD4729 Approved
0.7961 Intermediate Similarity NPD6083 Phase 2
0.7961 Intermediate Similarity NPD6084 Phase 2
0.7944 Intermediate Similarity NPD4768 Approved
0.7944 Intermediate Similarity NPD4767 Approved
0.7938 Intermediate Similarity NPD5329 Approved
0.7925 Intermediate Similarity NPD4754 Approved
0.7909 Intermediate Similarity NPD6617 Approved
0.7909 Intermediate Similarity NPD6869 Approved
0.7909 Intermediate Similarity NPD6847 Approved
0.7909 Intermediate Similarity NPD8130 Phase 1
0.789 Intermediate Similarity NPD6013 Approved
0.789 Intermediate Similarity NPD6012 Approved
0.789 Intermediate Similarity NPD6014 Approved
0.787 Intermediate Similarity NPD5701 Approved
0.7857 Intermediate Similarity NPD5279 Phase 3
0.7838 Intermediate Similarity NPD8297 Approved
0.7838 Intermediate Similarity NPD6882 Approved
0.7835 Intermediate Similarity NPD3666 Approved
0.7835 Intermediate Similarity NPD3133 Approved
0.7835 Intermediate Similarity NPD3665 Phase 1
0.7835 Intermediate Similarity NPD4197 Approved
0.7818 Intermediate Similarity NPD5247 Approved
0.7818 Intermediate Similarity NPD5248 Approved
0.7818 Intermediate Similarity NPD5249 Phase 3
0.7818 Intermediate Similarity NPD5250 Approved
0.7818 Intermediate Similarity NPD5251 Approved
0.781 Intermediate Similarity NPD7639 Approved
0.781 Intermediate Similarity NPD7640 Approved
0.7798 Intermediate Similarity NPD5128 Approved
0.7798 Intermediate Similarity NPD6011 Approved
0.7768 Intermediate Similarity NPD4632 Approved
0.7748 Intermediate Similarity NPD5216 Approved
0.7748 Intermediate Similarity NPD5215 Approved
0.7748 Intermediate Similarity NPD5217 Approved
0.7745 Intermediate Similarity NPD6399 Phase 3
0.7714 Intermediate Similarity NPD5696 Approved
0.7714 Intermediate Similarity NPD7638 Approved
0.7677 Intermediate Similarity NPD5690 Phase 2
0.7677 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD6054 Approved
0.7658 Intermediate Similarity NPD5135 Approved
0.7658 Intermediate Similarity NPD5169 Approved
0.7658 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD7515 Phase 2
0.7636 Intermediate Similarity NPD5168 Approved
0.7629 Intermediate Similarity NPD4221 Approved
0.7629 Intermediate Similarity NPD4223 Phase 3
0.7596 Intermediate Similarity NPD5695 Phase 3
0.7589 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD5127 Approved
0.7565 Intermediate Similarity NPD6009 Approved
0.7542 Intermediate Similarity NPD6370 Approved
0.7525 Intermediate Similarity NPD6672 Approved
0.7525 Intermediate Similarity NPD5737 Approved
0.7521 Intermediate Similarity NPD6319 Approved
0.7521 Intermediate Similarity NPD6059 Approved
0.75 Intermediate Similarity NPD4623 Approved
0.75 Intermediate Similarity NPD4519 Discontinued
0.75 Intermediate Similarity NPD5280 Approved
0.75 Intermediate Similarity NPD4694 Approved
0.7475 Intermediate Similarity NPD3668 Phase 3
0.7458 Intermediate Similarity NPD6016 Approved
0.7458 Intermediate Similarity NPD6015 Approved
0.7455 Intermediate Similarity NPD6008 Approved
0.7436 Intermediate Similarity NPD7100 Approved
0.7436 Intermediate Similarity NPD7101 Approved
0.7426 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD6930 Phase 2
0.7423 Intermediate Similarity NPD7514 Phase 3
0.7423 Intermediate Similarity NPD7525 Registered
0.7423 Intermediate Similarity NPD4695 Discontinued
0.7423 Intermediate Similarity NPD6931 Approved
0.7417 Intermediate Similarity NPD7492 Approved
0.7396 Intermediate Similarity NPD3617 Approved
0.7395 Intermediate Similarity NPD5988 Approved
0.7391 Intermediate Similarity NPD5167 Approved
0.7374 Intermediate Similarity NPD6695 Phase 3
0.7355 Intermediate Similarity NPD6616 Approved
0.735 Intermediate Similarity NPD6335 Approved
0.7333 Intermediate Similarity NPD7748 Approved
0.7333 Intermediate Similarity NPD7604 Phase 2
0.7328 Intermediate Similarity NPD6274 Approved
0.7328 Intermediate Similarity NPD6868 Approved
0.7327 Intermediate Similarity NPD4688 Approved
0.7327 Intermediate Similarity NPD4690 Approved
0.7327 Intermediate Similarity NPD4693 Phase 3
0.7327 Intermediate Similarity NPD4689 Approved
0.7327 Intermediate Similarity NPD4138 Approved
0.7327 Intermediate Similarity NPD5205 Approved
0.732 Intermediate Similarity NPD6929 Approved
0.7311 Intermediate Similarity NPD5983 Phase 2
0.7308 Intermediate Similarity NPD5281 Approved
0.7308 Intermediate Similarity NPD7637 Suspended
0.7308 Intermediate Similarity NPD5284 Approved
0.73 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD7078 Approved
0.729 Intermediate Similarity NPD7902 Approved
0.7282 Intermediate Similarity NPD6904 Approved
0.7282 Intermediate Similarity NPD6080 Approved
0.7282 Intermediate Similarity NPD6673 Approved
0.7265 Intermediate Similarity NPD6317 Approved
0.7264 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7339 Approved
0.7263 Intermediate Similarity NPD6942 Approved
0.7245 Intermediate Similarity NPD7332 Phase 2
0.7236 Intermediate Similarity NPD7736 Approved
0.7232 Intermediate Similarity NPD6412 Phase 2
0.7228 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7145 Approved
0.7213 Intermediate Similarity NPD6336 Discontinued
0.7203 Intermediate Similarity NPD6313 Approved
0.7203 Intermediate Similarity NPD6314 Approved
0.72 Intermediate Similarity NPD4788 Approved
0.7182 Intermediate Similarity NPD5091 Approved
0.7182 Intermediate Similarity NPD7632 Discontinued
0.7172 Intermediate Similarity NPD6902 Approved
0.7167 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6908 Approved
0.7167 Intermediate Similarity NPD6909 Approved
0.7157 Intermediate Similarity NPD7146 Approved
0.7157 Intermediate Similarity NPD7521 Approved
0.7157 Intermediate Similarity NPD7334 Approved
0.7157 Intermediate Similarity NPD6409 Approved
0.7157 Intermediate Similarity NPD6684 Approved
0.7157 Intermediate Similarity NPD5330 Approved
0.7154 Intermediate Similarity NPD8293 Discontinued
0.7143 Intermediate Similarity NPD4522 Approved
0.7143 Intermediate Similarity NPD4195 Approved
0.7143 Intermediate Similarity NPD5693 Phase 1
0.7113 Intermediate Similarity NPD6932 Approved
0.7113 Intermediate Similarity NPD6925 Approved
0.7113 Intermediate Similarity NPD5776 Phase 2
0.7105 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7524 Approved
0.7087 Intermediate Similarity NPD7750 Discontinued
0.7071 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD4225 Approved
0.7059 Intermediate Similarity NPD1696 Phase 3
0.7059 Intermediate Similarity NPD6893 Approved
0.7043 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6903 Approved
0.7018 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD7900 Approved
0.7009 Intermediate Similarity NPD5282 Discontinued
0.699 Remote Similarity NPD6098 Approved
0.6981 Remote Similarity NPD6050 Approved
0.6981 Remote Similarity NPD5694 Approved
0.6981 Remote Similarity NPD8035 Phase 2
0.6981 Remote Similarity NPD8034 Phase 2

  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