Structure

Physi-Chem Properties

Molecular Weight:  558.39
Volume:  598.67
LogP:  5.098
LogD:  4.652
LogS:  -5.012
# Rotatable Bonds:  7
TPSA:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.323
Synthetic Accessibility Score:  5.161
Fsp3:  0.824
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.964
MDCK Permeability:  2.6783123757923022e-05
Pgp-inhibitor:  0.991
Pgp-substrate:  0.974
Human Intestinal Absorption (HIA):  0.734
20% Bioavailability (F20%):  0.826
30% Bioavailability (F30%):  0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  90.10315704345703%
Volume Distribution (VD):  1.5
Pgp-substrate:  1.8070193529129028%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.323
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.914
CYP2C9-inhibitor:  0.081
CYP2C9-substrate:  0.024
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.075
CYP3A4-inhibitor:  0.126
CYP3A4-substrate:  0.841

ADMET: Excretion

Clearance (CL):  0.4
Half-life (T1/2):  0.292

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.195
Drug-inuced Liver Injury (DILI):  0.023
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.915
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.786
Carcinogencity:  0.013
Eye Corrosion:  0.003
Eye Irritation:  0.016
Respiratory Toxicity:  0.97

Download Data

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

  Natural Product: NPC267510

Natural Product ID:  NPC267510
Common Name*:   Ergosteryl-3-O-Beta-D-Glucopyranoside
IUPAC Name:   (2R,3R,4S,5S,6R)-2-[[(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  MKZPNGBJJJZJMI-GBLVNJONSA-N
Standard InCHI:  InChI=1S/C34H54O6/c1-19(2)20(3)7-8-21(4)25-11-12-26-24-10-9-22-17-23(13-15-33(22,5)27(24)14-16-34(25,26)6)39-32-31(38)30(37)29(36)28(18-35)40-32/h7-10,19-21,23,25-32,35-38H,11-18H2,1-6H3/b8-7+/t20-,21+,23-,25+,26-,27-,28+,29+,30-,31+,32+,33-,34+/m0/s1
SMILES:  CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1822159
PubChem CID:   44176397
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0003-9861(62)90112-1]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[10423860]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[11035032]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[12902239]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[13835567]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14389294]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[1449509]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14607989]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15375647]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15744050]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[15863936]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[16850348]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[17439666]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21848266]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[21848266]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[22031445]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2405251]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24305546]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24678285]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24733517]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24831709]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24981409]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2687322]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[3289762]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4266242]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4616942]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[5764336]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[6306574]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[767332]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[7929110]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8017107]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8798704]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8852895]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8971708]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[9748245]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5.62 ug.mL-1 PMID[490544]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5.42 ug.mL-1 PMID[490544]

☑ 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 NPC267510 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
0.9785 High Similarity NPC158088
0.9677 High Similarity NPC473890
0.9677 High Similarity NPC243728
0.957 High Similarity NPC207617
0.9479 High Similarity NPC272015
0.9474 High Similarity NPC282669
0.9375 High Similarity NPC470434
0.9278 High Similarity NPC154452
0.9271 High Similarity NPC469942
0.9175 High Similarity NPC21568
0.9175 High Similarity NPC121072
0.9175 High Similarity NPC21064
0.9175 High Similarity NPC285231
0.9167 High Similarity NPC234287
0.9167 High Similarity NPC280825
0.91 High Similarity NPC33053
0.9091 High Similarity NPC187400
0.9091 High Similarity NPC470885
0.9091 High Similarity NPC75608
0.9091 High Similarity NPC221562
0.9091 High Similarity NPC93352
0.9082 High Similarity NPC136816
0.9072 High Similarity NPC7341
0.9072 High Similarity NPC473200
0.9 High Similarity NPC242748
0.9 High Similarity NPC309448
0.9 High Similarity NPC181845
0.9 High Similarity NPC473476
0.9 High Similarity NPC474569
0.9 High Similarity NPC473923
0.899 High Similarity NPC473129
0.899 High Similarity NPC473198
0.899 High Similarity NPC99627
0.898 High Similarity NPC47566
0.898 High Similarity NPC472023
0.898 High Similarity NPC309425
0.898 High Similarity NPC160734
0.898 High Similarity NPC4831
0.898 High Similarity NPC88000
0.898 High Similarity NPC129372
0.8947 High Similarity NPC305160
0.8932 High Similarity NPC208189
0.8932 High Similarity NPC65034
0.8911 High Similarity NPC190395
0.8911 High Similarity NPC226642
0.8911 High Similarity NPC305423
0.8911 High Similarity NPC283829
0.8911 High Similarity NPC470432
0.8911 High Similarity NPC94272
0.8911 High Similarity NPC14704
0.8911 High Similarity NPC230507
0.8911 High Similarity NPC113044
0.8911 High Similarity NPC161676
0.89 High Similarity NPC109792
0.89 High Similarity NPC57065
0.89 High Similarity NPC54521
0.8889 High Similarity NPC288694
0.8889 High Similarity NPC312553
0.8889 High Similarity NPC159036
0.8846 High Similarity NPC231797
0.883 High Similarity NPC159876
0.8824 High Similarity NPC476538
0.8824 High Similarity NPC476541
0.8824 High Similarity NPC476540
0.8824 High Similarity NPC98696
0.8824 High Similarity NPC295980
0.8824 High Similarity NPC476539
0.8824 High Similarity NPC295389
0.8812 High Similarity NPC472898
0.8812 High Similarity NPC26798
0.8812 High Similarity NPC472900
0.8812 High Similarity NPC472899
0.88 High Similarity NPC8039
0.88 High Similarity NPC157659
0.88 High Similarity NPC120123
0.88 High Similarity NPC31907
0.88 High Similarity NPC245280
0.88 High Similarity NPC189852
0.88 High Similarity NPC16573
0.88 High Similarity NPC155010
0.88 High Similarity NPC213190
0.88 High Similarity NPC211879
0.88 High Similarity NPC473020
0.88 High Similarity NPC286969
0.88 High Similarity NPC472252
0.88 High Similarity NPC114874
0.88 High Similarity NPC131479
0.88 High Similarity NPC16520
0.8776 High Similarity NPC5358
0.8776 High Similarity NPC216260
0.875 High Similarity NPC72817
0.875 High Similarity NPC477927
0.8738 High Similarity NPC249265
0.8738 High Similarity NPC248746
0.8738 High Similarity NPC150372
0.8738 High Similarity NPC475670
0.8738 High Similarity NPC309278
0.8738 High Similarity NPC46190
0.8738 High Similarity NPC232054
0.8738 High Similarity NPC470433
0.8738 High Similarity NPC477026
0.8738 High Similarity NPC475333
0.8738 High Similarity NPC244086
0.8738 High Similarity NPC6806
0.8738 High Similarity NPC95051
0.8738 High Similarity NPC302057
0.8738 High Similarity NPC42482
0.8738 High Similarity NPC475550
0.8738 High Similarity NPC22779
0.8738 High Similarity NPC73243
0.8738 High Similarity NPC306131
0.8738 High Similarity NPC224098
0.8738 High Similarity NPC70204
0.8738 High Similarity NPC477809
0.8738 High Similarity NPC477027
0.8738 High Similarity NPC300557
0.8738 High Similarity NPC40440
0.8738 High Similarity NPC171073
0.8738 High Similarity NPC208383
0.8738 High Similarity NPC84956
0.8738 High Similarity NPC102016
0.8738 High Similarity NPC194207
0.8738 High Similarity NPC218571
0.8737 High Similarity NPC48463
0.8725 High Similarity NPC257964
0.8725 High Similarity NPC473469
0.8723 High Similarity NPC473058
0.8713 High Similarity NPC165033
0.8713 High Similarity NPC475365
0.8713 High Similarity NPC312774
0.8713 High Similarity NPC273879
0.8654 High Similarity NPC87998
0.8654 High Similarity NPC269297
0.8654 High Similarity NPC103627
0.8654 High Similarity NPC247037
0.8654 High Similarity NPC477811
0.8654 High Similarity NPC141433
0.8654 High Similarity NPC222202
0.8654 High Similarity NPC154856
0.8654 High Similarity NPC23808
0.8654 High Similarity NPC191439
0.8654 High Similarity NPC170974
0.8654 High Similarity NPC224314
0.8654 High Similarity NPC52241
0.8654 High Similarity NPC475317
0.8641 High Similarity NPC472896
0.8641 High Similarity NPC7213
0.8641 High Similarity NPC472897
0.8641 High Similarity NPC126147
0.8627 High Similarity NPC269627
0.8627 High Similarity NPC160816
0.8627 High Similarity NPC127801
0.8627 High Similarity NPC208477
0.8627 High Similarity NPC208594
0.8627 High Similarity NPC194842
0.8627 High Similarity NPC152584
0.8627 High Similarity NPC69737
0.8627 High Similarity NPC473199
0.8614 High Similarity NPC475701
0.8585 High Similarity NPC307642
0.8571 High Similarity NPC13190
0.8571 High Similarity NPC114188
0.8571 High Similarity NPC472989
0.8571 High Similarity NPC470748
0.8571 High Similarity NPC477032
0.8571 High Similarity NPC475247
0.8571 High Similarity NPC13193
0.8571 High Similarity NPC477028
0.8571 High Similarity NPC294129
0.8571 High Similarity NPC476547
0.8571 High Similarity NPC124677
0.8571 High Similarity NPC197231
0.8558 High Similarity NPC473328
0.8558 High Similarity NPC250089
0.8558 High Similarity NPC157530
0.8558 High Similarity NPC28844
0.8558 High Similarity NPC246205
0.8558 High Similarity NPC472901
0.8558 High Similarity NPC14630
0.8558 High Similarity NPC473318
0.8544 High Similarity NPC234160
0.8544 High Similarity NPC63368
0.8544 High Similarity NPC231340
0.8544 High Similarity NPC208650
0.8544 High Similarity NPC181467
0.8544 High Similarity NPC14946
0.8529 High Similarity NPC31430
0.8529 High Similarity NPC230948
0.8529 High Similarity NPC473734
0.8529 High Similarity NPC85593
0.8529 High Similarity NPC474464
0.8515 High Similarity NPC22634
0.85 High Similarity NPC473790
0.85 High Similarity NPC64348
0.85 High Similarity NPC324598
0.8491 Intermediate Similarity NPC112274
0.8491 Intermediate Similarity NPC130427
0.8491 Intermediate Similarity NPC32361
0.8491 Intermediate Similarity NPC31896
0.8491 Intermediate Similarity NPC474265

  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 NPC267510 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
0.819 Intermediate Similarity NPD6412 Phase 2
0.7895 Intermediate Similarity NPD7503 Approved
0.7755 Intermediate Similarity NPD7524 Approved
0.7739 Intermediate Similarity NPD8033 Approved
0.7652 Intermediate Similarity NPD8294 Approved
0.7652 Intermediate Similarity NPD8377 Approved
0.7632 Intermediate Similarity NPD7328 Approved
0.7632 Intermediate Similarity NPD7327 Approved
0.7629 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD8380 Approved
0.7586 Intermediate Similarity NPD8296 Approved
0.7586 Intermediate Similarity NPD8378 Approved
0.7586 Intermediate Similarity NPD8379 Approved
0.7586 Intermediate Similarity NPD8335 Approved
0.7565 Intermediate Similarity NPD7516 Approved
0.7526 Intermediate Similarity NPD6695 Phase 3
0.7419 Intermediate Similarity NPD6942 Approved
0.7419 Intermediate Similarity NPD7339 Approved
0.74 Intermediate Similarity NPD7750 Discontinued
0.7387 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD8171 Discontinued
0.734 Intermediate Similarity NPD6933 Approved
0.7297 Intermediate Similarity NPD6686 Approved
0.7292 Intermediate Similarity NPD6929 Approved
0.7281 Intermediate Similarity NPD8133 Approved
0.7263 Intermediate Similarity NPD6932 Approved
0.7258 Intermediate Similarity NPD8449 Approved
0.7227 Intermediate Similarity NPD6370 Approved
0.7216 Intermediate Similarity NPD6931 Approved
0.7216 Intermediate Similarity NPD6930 Phase 2
0.7216 Intermediate Similarity NPD7525 Registered
0.7213 Intermediate Similarity NPD7736 Approved
0.72 Intermediate Similarity NPD8450 Suspended
0.719 Intermediate Similarity NPD7507 Approved
0.7188 Intermediate Similarity NPD7145 Approved
0.7158 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6926 Approved
0.7128 Intermediate Similarity NPD6924 Approved
0.7097 Intermediate Similarity NPD7152 Approved
0.7097 Intermediate Similarity NPD7151 Approved
0.7097 Intermediate Similarity NPD7150 Approved
0.7094 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5776 Phase 2
0.7083 Intermediate Similarity NPD6925 Approved
0.7059 Intermediate Similarity NPD6054 Approved
0.7048 Intermediate Similarity NPD6399 Phase 3
0.7041 Intermediate Similarity NPD7514 Phase 3
0.7025 Intermediate Similarity NPD8328 Phase 3
0.7016 Intermediate Similarity NPD7319 Approved
0.6992 Remote Similarity NPD8293 Discontinued
0.6989 Remote Similarity NPD7144 Approved
0.6989 Remote Similarity NPD7143 Approved
0.697 Remote Similarity NPD6902 Approved
0.6952 Remote Similarity NPD7087 Discontinued
0.6952 Remote Similarity NPD7637 Suspended
0.6939 Remote Similarity NPD7645 Phase 2
0.6939 Remote Similarity NPD6683 Phase 2
0.6931 Remote Similarity NPD4786 Approved
0.6917 Remote Similarity NPD6059 Approved
0.6893 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6923 Approved
0.6882 Remote Similarity NPD6922 Approved
0.6869 Remote Similarity NPD7332 Phase 2
0.6869 Remote Similarity NPD6928 Phase 2
0.6863 Remote Similarity NPD6893 Approved
0.686 Remote Similarity NPD8517 Approved
0.686 Remote Similarity NPD8516 Approved
0.686 Remote Similarity NPD8515 Approved
0.686 Remote Similarity NPD6016 Approved
0.686 Remote Similarity NPD6015 Approved
0.686 Remote Similarity NPD8513 Phase 3
0.6829 Remote Similarity NPD7492 Approved
0.6807 Remote Similarity NPD6009 Approved
0.6803 Remote Similarity NPD5988 Approved
0.6774 Remote Similarity NPD6616 Approved
0.6771 Remote Similarity NPD4785 Approved
0.6771 Remote Similarity NPD4784 Approved
0.6752 Remote Similarity NPD6882 Approved
0.6752 Remote Similarity NPD8297 Approved
0.6748 Remote Similarity NPD6067 Discontinued
0.6733 Remote Similarity NPD3667 Approved
0.6727 Remote Similarity NPD7638 Approved
0.6726 Remote Similarity NPD8170 Clinical (unspecified phase)
0.672 Remote Similarity NPD7078 Approved
0.67 Remote Similarity NPD7509 Discontinued
0.6695 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD7640 Approved
0.6667 Remote Similarity NPD7115 Discovery
0.6667 Remote Similarity NPD7639 Approved
0.6639 Remote Similarity NPD6319 Approved
0.6634 Remote Similarity NPD6898 Phase 1
0.6562 Remote Similarity NPD4243 Approved
0.6552 Remote Similarity NPD6899 Approved
0.6552 Remote Similarity NPD6881 Approved
0.6531 Remote Similarity NPD8264 Approved
0.6525 Remote Similarity NPD8130 Phase 1
0.6522 Remote Similarity NPD6402 Approved
0.6522 Remote Similarity NPD7128 Approved
0.6522 Remote Similarity NPD5739 Approved
0.6522 Remote Similarity NPD6675 Approved
0.65 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6084 Phase 2
0.6486 Remote Similarity NPD6083 Phase 2
0.6481 Remote Similarity NPD8035 Phase 2
0.6481 Remote Similarity NPD8034 Phase 2
0.6481 Remote Similarity NPD6079 Approved
0.6481 Remote Similarity NPD6411 Approved
0.6466 Remote Similarity NPD5697 Approved
0.6449 Remote Similarity NPD5328 Approved
0.6441 Remote Similarity NPD6883 Approved
0.6441 Remote Similarity NPD7290 Approved
0.6441 Remote Similarity NPD4634 Approved
0.6441 Remote Similarity NPD7102 Approved
0.6429 Remote Similarity NPD8029 Clinical (unspecified phase)
0.641 Remote Similarity NPD7320 Approved
0.6406 Remote Similarity NPD6033 Approved
0.64 Remote Similarity NPD5126 Approved
0.64 Remote Similarity NPD5125 Phase 3
0.6389 Remote Similarity NPD7136 Phase 2
0.6389 Remote Similarity NPD7838 Discovery
0.6387 Remote Similarity NPD6847 Approved
0.6387 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6869 Approved
0.6387 Remote Similarity NPD6650 Approved
0.6387 Remote Similarity NPD6617 Approved
0.6387 Remote Similarity NPD6649 Approved
0.6379 Remote Similarity NPD6640 Phase 3
0.6373 Remote Similarity NPD4748 Discontinued
0.6372 Remote Similarity NPD5286 Approved
0.6372 Remote Similarity NPD5285 Approved
0.6372 Remote Similarity NPD4696 Approved
0.6364 Remote Similarity NPD7748 Approved
0.6356 Remote Similarity NPD6372 Approved
0.6356 Remote Similarity NPD6013 Approved
0.6356 Remote Similarity NPD6014 Approved
0.6356 Remote Similarity NPD6373 Approved
0.6356 Remote Similarity NPD6012 Approved
0.6349 Remote Similarity NPD7604 Phase 2
0.6339 Remote Similarity NPD7902 Approved
0.6339 Remote Similarity NPD4755 Approved
0.6325 Remote Similarity NPD5701 Approved
0.6321 Remote Similarity NPD3618 Phase 1
0.6321 Remote Similarity NPD5279 Phase 3
0.632 Remote Similarity NPD5983 Phase 2
0.6308 Remote Similarity NPD5956 Approved
0.6296 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4753 Phase 2
0.6296 Remote Similarity NPD6051 Approved
0.6296 Remote Similarity NPD6101 Approved
0.6286 Remote Similarity NPD3665 Phase 1
0.6286 Remote Similarity NPD3133 Approved
0.6286 Remote Similarity NPD3666 Approved
0.6286 Remote Similarity NPD3668 Phase 3
0.6283 Remote Similarity NPD4225 Approved
0.6275 Remote Similarity NPD4195 Approved
0.6273 Remote Similarity NPD4202 Approved
0.6271 Remote Similarity NPD6011 Approved
0.6261 Remote Similarity NPD4633 Approved
0.6261 Remote Similarity NPD5226 Approved
0.6261 Remote Similarity NPD5225 Approved
0.6261 Remote Similarity NPD5224 Approved
0.6261 Remote Similarity NPD5211 Phase 2
0.625 Remote Similarity NPD5221 Approved
0.625 Remote Similarity NPD5220 Clinical (unspecified phase)
0.625 Remote Similarity NPD6336 Discontinued
0.625 Remote Similarity NPD5222 Approved
0.624 Remote Similarity NPD7741 Discontinued
0.6239 Remote Similarity NPD3168 Discontinued
0.6239 Remote Similarity NPD6008 Approved
0.6228 Remote Similarity NPD4700 Approved
0.6226 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6218 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5174 Approved
0.6207 Remote Similarity NPD5175 Approved
0.6204 Remote Similarity NPD6672 Approved
0.6204 Remote Similarity NPD5737 Approved
0.6204 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6202 Remote Similarity NPD8074 Phase 3
0.62 Remote Similarity NPD4190 Phase 3
0.62 Remote Similarity NPD5275 Approved
0.6195 Remote Similarity NPD5173 Approved
0.6186 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5281 Approved
0.6182 Remote Similarity NPD7515 Phase 2
0.6182 Remote Similarity NPD7983 Approved
0.6182 Remote Similarity NPD5284 Approved
0.6174 Remote Similarity NPD5344 Discontinued
0.6174 Remote Similarity NPD5223 Approved
0.6174 Remote Similarity NPD4159 Approved
0.6168 Remote Similarity NPD7521 Approved
0.6168 Remote Similarity NPD7334 Approved
0.6168 Remote Similarity NPD7146 Approved
0.6168 Remote Similarity NPD5330 Approved
0.6168 Remote Similarity NPD6409 Approved
0.6168 Remote Similarity NPD6684 Approved
0.6161 Remote Similarity NPD5210 Approved
0.6161 Remote Similarity NPD4629 Approved
0.6161 Remote Similarity NPD7991 Discontinued
0.6161 Remote Similarity NPD5695 Phase 3
0.6154 Remote Similarity NPD5141 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