Structure

Physi-Chem Properties

Molecular Weight:  428.22
Volume:  425.893
LogP:  4.238
LogD:  3.637
LogS:  -5.304
# Rotatable Bonds:  3
TPSA:  77.66
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  7
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.389
Synthetic Accessibility Score:  5.87
Fsp3:  0.84
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.04
MDCK Permeability:  5.369581049308181e-05
Pgp-inhibitor:  0.293
Pgp-substrate:  0.055
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.27
30% Bioavailability (F30%):  0.271

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.822
Plasma Protein Binding (PPB):  68.12775421142578%
Volume Distribution (VD):  1.903
Pgp-substrate:  14.060011863708496%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.144
CYP2C19-inhibitor:  0.196
CYP2C19-substrate:  0.283
CYP2C9-inhibitor:  0.23
CYP2C9-substrate:  0.012
CYP2D6-inhibitor:  0.049
CYP2D6-substrate:  0.132
CYP3A4-inhibitor:  0.82
CYP3A4-substrate:  0.335

ADMET: Excretion

Clearance (CL):  3.747
Half-life (T1/2):  0.378

ADMET: Toxicity

hERG Blockers:  0.797
Human Hepatotoxicity (H-HT):  0.991
Drug-inuced Liver Injury (DILI):  0.69
AMES Toxicity:  0.969
Rat Oral Acute Toxicity:  0.947
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.954
Carcinogencity:  0.938
Eye Corrosion:  0.043
Eye Irritation:  0.145
Respiratory Toxicity:  0.973

Download Data

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

  Natural Product: NPC150228

Natural Product ID:  NPC150228
Common Name*:   CMYYMVGNLZUIOQ-PKLRSUGZSA-N
IUPAC Name:   n.a.
Synonyms:   20S,21-Epoxy-Resibufogenin Formate
Standard InCHIKey:  CMYYMVGNLZUIOQ-PKLRSUGZSA-N
Standard InCHI:  InChI=1S/C25H32O6/c1-22-8-5-15(28-13-26)11-14(22)3-4-17-16(22)6-9-23(2)18(12-19-25(17,23)30-19)24-10-7-20(27)29-21(24)31-24/h7,10,13-19,21H,3-6,8-9,11-12H2,1-2H3/t14-,15+,16+,17-,18+,19-,21+,22+,23-,24-,25-/m1/s1
SMILES:  C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](C[C@@H]3[C@]12O3)[C@]12C=CC(=O)O[C@H]1O2)OC=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL455361
PubChem CID:   11026341
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001557] Bufanolides 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
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)99818-1]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota roots n.a. n.a. PMID[10346940]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[11421725]
NPO33241 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[11575946]
NPO33241 Bufo gargarizans Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[12141860]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. PMID[15165135]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[15635246]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[15730237]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[17504571]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. PMID[21185919]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. leaf n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. twig n.a. PMID[21954912]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[22708620]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. PMID[26722868]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[32223924]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9398 Cortinarius rubellus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2498 Kochia trichophylla Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11515 Streptomyces plumbeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26231 Vicia villosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6887 Lytanthus salicinus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12735 Halimeda macroloba Species Halimedaceae 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
NPT91 Cell Line KB Homo sapiens IC50 > 25.0 ug.mL-1 PMID[512828]
NPT1366 Cell Line MH60 Mus musculus IC50 > 25.0 ug.mL-1 PMID[512828]
NPT1366 Cell Line MH60 Mus musculus IC50 = 8900.0 nM PMID[512829]
NPT1366 Cell Line MH60 Mus musculus IC50 > 58400.0 nM PMID[512829]

☑ 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 NPC150228 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 NPC214005
0.9533 High Similarity NPC113425
0.9533 High Similarity NPC232564
0.9174 High Similarity NPC268213
0.8534 High Similarity NPC115349
0.8421 Intermediate Similarity NPC290693
0.8257 Intermediate Similarity NPC165969
0.8246 Intermediate Similarity NPC69576
0.8246 Intermediate Similarity NPC471633
0.8246 Intermediate Similarity NPC31354
0.8246 Intermediate Similarity NPC84949
0.819 Intermediate Similarity NPC16701
0.8174 Intermediate Similarity NPC193382
0.8174 Intermediate Similarity NPC99620
0.8174 Intermediate Similarity NPC5311
0.8174 Intermediate Similarity NPC310341
0.8174 Intermediate Similarity NPC199428
0.812 Intermediate Similarity NPC29639
0.812 Intermediate Similarity NPC35171
0.812 Intermediate Similarity NPC44899
0.812 Intermediate Similarity NPC304260
0.812 Intermediate Similarity NPC278681
0.812 Intermediate Similarity NPC213761
0.812 Intermediate Similarity NPC5883
0.812 Intermediate Similarity NPC268326
0.812 Intermediate Similarity NPC153085
0.8103 Intermediate Similarity NPC93883
0.8103 Intermediate Similarity NPC471354
0.8103 Intermediate Similarity NPC471353
0.8103 Intermediate Similarity NPC474418
0.8103 Intermediate Similarity NPC142066
0.8103 Intermediate Similarity NPC309034
0.8103 Intermediate Similarity NPC157380
0.8103 Intermediate Similarity NPC157376
0.8103 Intermediate Similarity NPC158344
0.8103 Intermediate Similarity NPC471355
0.8103 Intermediate Similarity NPC473852
0.8103 Intermediate Similarity NPC471351
0.8103 Intermediate Similarity NPC243196
0.8103 Intermediate Similarity NPC203862
0.8103 Intermediate Similarity NPC196429
0.8103 Intermediate Similarity NPC77319
0.8103 Intermediate Similarity NPC84987
0.8103 Intermediate Similarity NPC27507
0.8103 Intermediate Similarity NPC152615
0.8103 Intermediate Similarity NPC244402
0.8103 Intermediate Similarity NPC99728
0.8103 Intermediate Similarity NPC50305
0.8103 Intermediate Similarity NPC34390
0.8103 Intermediate Similarity NPC87250
0.8053 Intermediate Similarity NPC103491
0.8051 Intermediate Similarity NPC112936
0.8034 Intermediate Similarity NPC218093
0.8034 Intermediate Similarity NPC83287
0.8 Intermediate Similarity NPC165608
0.8 Intermediate Similarity NPC171126
0.7983 Intermediate Similarity NPC475219
0.7983 Intermediate Similarity NPC231518
0.7966 Intermediate Similarity NPC30483
0.7966 Intermediate Similarity NPC470897
0.7966 Intermediate Similarity NPC469756
0.7966 Intermediate Similarity NPC291820
0.7966 Intermediate Similarity NPC55532
0.7966 Intermediate Similarity NPC32177
0.7966 Intermediate Similarity NPC329905
0.7966 Intermediate Similarity NPC236973
0.7966 Intermediate Similarity NPC292467
0.7966 Intermediate Similarity NPC81222
0.7949 Intermediate Similarity NPC185287
0.7944 Intermediate Similarity NPC8954
0.7944 Intermediate Similarity NPC94905
0.7917 Intermediate Similarity NPC193893
0.7899 Intermediate Similarity NPC475136
0.7899 Intermediate Similarity NPC475629
0.7899 Intermediate Similarity NPC107607
0.7899 Intermediate Similarity NPC474466
0.7899 Intermediate Similarity NPC475556
0.7899 Intermediate Similarity NPC135369
0.7899 Intermediate Similarity NPC257610
0.7899 Intermediate Similarity NPC72260
0.7881 Intermediate Similarity NPC472080
0.7857 Intermediate Similarity NPC477090
0.7833 Intermediate Similarity NPC173555
0.7833 Intermediate Similarity NPC474908
0.7833 Intermediate Similarity NPC314535
0.7833 Intermediate Similarity NPC475419
0.7833 Intermediate Similarity NPC475590
0.7833 Intermediate Similarity NPC40749
0.7833 Intermediate Similarity NPC312481
0.7833 Intermediate Similarity NPC120390
0.7833 Intermediate Similarity NPC204731
0.7826 Intermediate Similarity NPC470076
0.7823 Intermediate Similarity NPC473593
0.781 Intermediate Similarity NPC302280
0.7807 Intermediate Similarity NPC475030
0.7807 Intermediate Similarity NPC472901
0.7788 Intermediate Similarity NPC43063
0.7788 Intermediate Similarity NPC79298
0.7788 Intermediate Similarity NPC471601
0.7787 Intermediate Similarity NPC8374
0.7769 Intermediate Similarity NPC264336
0.7769 Intermediate Similarity NPC74259
0.7769 Intermediate Similarity NPC474423
0.7759 Intermediate Similarity NPC222834
0.7759 Intermediate Similarity NPC44537
0.7724 Intermediate Similarity NPC469750
0.7724 Intermediate Similarity NPC179261
0.7724 Intermediate Similarity NPC250556
0.7712 Intermediate Similarity NPC207637
0.7705 Intermediate Similarity NPC27363
0.7705 Intermediate Similarity NPC117445
0.7705 Intermediate Similarity NPC208193
0.7705 Intermediate Similarity NPC6193
0.7705 Intermediate Similarity NPC308262
0.7699 Intermediate Similarity NPC119855
0.7699 Intermediate Similarity NPC220217
0.7698 Intermediate Similarity NPC231240
0.7686 Intermediate Similarity NPC233500
0.7685 Intermediate Similarity NPC281134
0.768 Intermediate Similarity NPC471407
0.7679 Intermediate Similarity NPC472821
0.7679 Intermediate Similarity NPC160583
0.7672 Intermediate Similarity NPC472987
0.7672 Intermediate Similarity NPC473021
0.7667 Intermediate Similarity NPC219656
0.7661 Intermediate Similarity NPC287423
0.7661 Intermediate Similarity NPC471356
0.7661 Intermediate Similarity NPC179412
0.7658 Intermediate Similarity NPC247701
0.7658 Intermediate Similarity NPC295110
0.7658 Intermediate Similarity NPC222875
0.7658 Intermediate Similarity NPC25177
0.7658 Intermediate Similarity NPC268829
0.7652 Intermediate Similarity NPC75389
0.7652 Intermediate Similarity NPC112457
0.7642 Intermediate Similarity NPC241456
0.7642 Intermediate Similarity NPC32868
0.7638 Intermediate Similarity NPC316915
0.7627 Intermediate Similarity NPC43213
0.7627 Intermediate Similarity NPC216665
0.7623 Intermediate Similarity NPC153700
0.7623 Intermediate Similarity NPC88326
0.7623 Intermediate Similarity NPC471082
0.7623 Intermediate Similarity NPC196130
0.7615 Intermediate Similarity NPC475178
0.7615 Intermediate Similarity NPC75616
0.7607 Intermediate Similarity NPC475354
0.7603 Intermediate Similarity NPC470312
0.7603 Intermediate Similarity NPC170814
0.76 Intermediate Similarity NPC473620
0.7597 Intermediate Similarity NPC62172
0.7597 Intermediate Similarity NPC289700
0.7593 Intermediate Similarity NPC128488
0.7593 Intermediate Similarity NPC304968
0.7593 Intermediate Similarity NPC477722
0.7586 Intermediate Similarity NPC12795
0.7568 Intermediate Similarity NPC477971
0.7568 Intermediate Similarity NPC228251
0.7568 Intermediate Similarity NPC477972
0.7568 Intermediate Similarity NPC219285
0.7568 Intermediate Similarity NPC161527
0.7568 Intermediate Similarity NPC477968
0.7568 Intermediate Similarity NPC20113
0.7565 Intermediate Similarity NPC61411
0.7565 Intermediate Similarity NPC137462
0.7565 Intermediate Similarity NPC275060
0.7565 Intermediate Similarity NPC304276
0.7563 Intermediate Similarity NPC470075
0.7563 Intermediate Similarity NPC190286
0.7563 Intermediate Similarity NPC243981
0.7563 Intermediate Similarity NPC212660
0.7561 Intermediate Similarity NPC219804
0.7561 Intermediate Similarity NPC204812
0.7559 Intermediate Similarity NPC155529
0.7559 Intermediate Similarity NPC471855
0.7544 Intermediate Similarity NPC295843
0.7544 Intermediate Similarity NPC473199
0.7544 Intermediate Similarity NPC51719
0.7544 Intermediate Similarity NPC186668
0.7541 Intermediate Similarity NPC470878
0.7541 Intermediate Similarity NPC67569
0.7541 Intermediate Similarity NPC473256
0.754 Intermediate Similarity NPC284406
0.754 Intermediate Similarity NPC125077
0.754 Intermediate Similarity NPC276838
0.754 Intermediate Similarity NPC471360
0.754 Intermediate Similarity NPC471359
0.754 Intermediate Similarity NPC9499
0.754 Intermediate Similarity NPC70542
0.754 Intermediate Similarity NPC188234
0.754 Intermediate Similarity NPC469753
0.754 Intermediate Similarity NPC469751
0.754 Intermediate Similarity NPC471352
0.754 Intermediate Similarity NPC471358
0.754 Intermediate Similarity NPC219085
0.754 Intermediate Similarity NPC469752
0.754 Intermediate Similarity NPC91
0.754 Intermediate Similarity NPC140092
0.754 Intermediate Similarity NPC180079
0.754 Intermediate Similarity NPC197707

  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 NPC150228 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
0.8034 Intermediate Similarity NPD7327 Approved
0.8034 Intermediate Similarity NPD7328 Approved
0.7983 Intermediate Similarity NPD7503 Approved
0.7983 Intermediate Similarity NPD8033 Approved
0.7966 Intermediate Similarity NPD7516 Approved
0.7899 Intermediate Similarity NPD8377 Approved
0.7899 Intermediate Similarity NPD8294 Approved
0.7833 Intermediate Similarity NPD8378 Approved
0.7833 Intermediate Similarity NPD8296 Approved
0.7833 Intermediate Similarity NPD8335 Approved
0.7833 Intermediate Similarity NPD8379 Approved
0.7833 Intermediate Similarity NPD8380 Approved
0.7724 Intermediate Similarity NPD7507 Approved
0.754 Intermediate Similarity NPD7319 Approved
0.7321 Intermediate Similarity NPD7638 Approved
0.7257 Intermediate Similarity NPD7640 Approved
0.7257 Intermediate Similarity NPD7639 Approved
0.7213 Intermediate Similarity NPD7115 Discovery
0.7188 Intermediate Similarity NPD7736 Approved
0.7105 Intermediate Similarity NPD6648 Approved
0.7094 Intermediate Similarity NPD6008 Approved
0.7043 Intermediate Similarity NPD5344 Discontinued
0.7034 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.6975 Remote Similarity NPD6686 Approved
0.6935 Remote Similarity NPD6009 Approved
0.6929 Remote Similarity NPD6370 Approved
0.6917 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6051 Approved
0.6891 Remote Similarity NPD6412 Phase 2
0.686 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7632 Discontinued
0.6829 Remote Similarity NPD8133 Approved
0.6822 Remote Similarity NPD7492 Approved
0.6772 Remote Similarity NPD6054 Approved
0.6769 Remote Similarity NPD6616 Approved
0.6748 Remote Similarity NPD6882 Approved
0.6718 Remote Similarity NPD7078 Approved
0.6718 Remote Similarity NPD8293 Discontinued
0.6694 Remote Similarity NPD4632 Approved
0.6615 Remote Similarity NPD7604 Phase 2
0.6613 Remote Similarity NPD8297 Approved
0.6589 Remote Similarity NPD6015 Approved
0.6589 Remote Similarity NPD6016 Approved
0.6573 Remote Similarity NPD7625 Phase 1
0.6557 Remote Similarity NPD6881 Approved
0.6557 Remote Similarity NPD6899 Approved
0.6538 Remote Similarity NPD5988 Approved
0.6518 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6512 Remote Similarity NPD6319 Approved
0.6512 Remote Similarity NPD6059 Approved
0.6475 Remote Similarity NPD5697 Approved
0.6466 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6462 Remote Similarity NPD5983 Phase 2
0.6452 Remote Similarity NPD7290 Approved
0.6452 Remote Similarity NPD6883 Approved
0.6452 Remote Similarity NPD7102 Approved
0.6441 Remote Similarity NPD4225 Approved
0.6423 Remote Similarity NPD6011 Approved
0.64 Remote Similarity NPD6869 Approved
0.64 Remote Similarity NPD6649 Approved
0.64 Remote Similarity NPD6847 Approved
0.64 Remote Similarity NPD8130 Phase 1
0.64 Remote Similarity NPD6617 Approved
0.64 Remote Similarity NPD6650 Approved
0.6393 Remote Similarity NPD5739 Approved
0.6393 Remote Similarity NPD6402 Approved
0.6393 Remote Similarity NPD6675 Approved
0.6393 Remote Similarity NPD7128 Approved
0.6391 Remote Similarity NPD6336 Discontinued
0.6371 Remote Similarity NPD6014 Approved
0.6371 Remote Similarity NPD6012 Approved
0.6371 Remote Similarity NPD6013 Approved
0.6364 Remote Similarity NPD6067 Discontinued
0.6349 Remote Similarity NPD6053 Discontinued
0.6348 Remote Similarity NPD5693 Phase 1
0.6339 Remote Similarity NPD7521 Approved
0.6339 Remote Similarity NPD6684 Approved
0.6339 Remote Similarity NPD5330 Approved
0.6339 Remote Similarity NPD7334 Approved
0.6339 Remote Similarity NPD6409 Approved
0.6339 Remote Similarity NPD7146 Approved
0.629 Remote Similarity NPD7320 Approved
0.6241 Remote Similarity NPD8328 Phase 3
0.624 Remote Similarity NPD8132 Clinical (unspecified phase)
0.624 Remote Similarity NPD6373 Approved
0.624 Remote Similarity NPD6372 Approved
0.6239 Remote Similarity NPD7525 Registered
0.6239 Remote Similarity NPD7900 Approved
0.6239 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6001 Approved
0.6228 Remote Similarity NPD6903 Approved
0.6212 Remote Similarity NPD8513 Phase 3
0.621 Remote Similarity NPD5701 Approved
0.6176 Remote Similarity NPD6033 Approved
0.6174 Remote Similarity NPD6080 Approved
0.6174 Remote Similarity NPD6904 Approved
0.6174 Remote Similarity NPD6673 Approved
0.6167 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6399 Phase 3
0.6154 Remote Similarity NPD8171 Discontinued
0.6154 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6148 Remote Similarity NPD5211 Phase 2
0.6142 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6126 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6121 Remote Similarity NPD7838 Discovery
0.6116 Remote Similarity NPD5286 Approved
0.6116 Remote Similarity NPD4696 Approved
0.6116 Remote Similarity NPD5285 Approved
0.6107 Remote Similarity NPD6335 Approved
0.6106 Remote Similarity NPD1694 Approved
0.6102 Remote Similarity NPD7748 Approved
0.6091 Remote Similarity NPD6928 Phase 2
0.609 Remote Similarity NPD8516 Approved
0.609 Remote Similarity NPD8515 Approved
0.609 Remote Similarity NPD8517 Approved
0.6087 Remote Similarity NPD5737 Approved
0.6087 Remote Similarity NPD6672 Approved
0.6083 Remote Similarity NPD6084 Phase 2
0.6083 Remote Similarity NPD6083 Phase 2
0.6083 Remote Similarity NPD7902 Approved
0.6068 Remote Similarity NPD8034 Phase 2
0.6068 Remote Similarity NPD8035 Phase 2
0.6066 Remote Similarity NPD4159 Approved
0.6066 Remote Similarity NPD5223 Approved
0.6063 Remote Similarity NPD4634 Approved
0.6063 Remote Similarity NPD6371 Approved
0.6061 Remote Similarity NPD7100 Approved
0.6061 Remote Similarity NPD7101 Approved
0.6048 Remote Similarity NPD5141 Approved
0.6032 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6031 Remote Similarity NPD6317 Approved
0.6018 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6017 Remote Similarity NPD4202 Approved
0.6016 Remote Similarity NPD5225 Approved
0.6016 Remote Similarity NPD5226 Approved
0.6016 Remote Similarity NPD4633 Approved
0.6016 Remote Similarity NPD5224 Approved
0.6 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6 Remote Similarity NPD4195 Approved
0.6 Remote Similarity NPD3573 Approved
0.5985 Remote Similarity NPD6314 Approved
0.5985 Remote Similarity NPD6313 Approved
0.5983 Remote Similarity NPD3168 Discontinued
0.5968 Remote Similarity NPD5175 Approved
0.5968 Remote Similarity NPD5174 Approved
0.5954 Remote Similarity NPD6274 Approved
0.5951 Remote Similarity NPD7799 Discontinued
0.595 Remote Similarity NPD4755 Approved
0.5948 Remote Similarity NPD5208 Approved
0.5932 Remote Similarity NPD7637 Suspended
0.5932 Remote Similarity NPD7515 Phase 2
0.5932 Remote Similarity NPD5694 Approved
0.5932 Remote Similarity NPD6050 Approved
0.5932 Remote Similarity NPD6079 Approved
0.592 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5917 Remote Similarity NPD5695 Phase 3
0.5913 Remote Similarity NPD6098 Approved
0.5902 Remote Similarity NPD5696 Approved
0.5897 Remote Similarity NPD1695 Approved
0.5891 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5877 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5862 Remote Similarity NPD7524 Approved
0.5857 Remote Similarity NPD5956 Approved
0.5854 Remote Similarity NPD4700 Approved
0.5852 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5847 Remote Similarity NPD6698 Approved
0.5847 Remote Similarity NPD5207 Approved
0.5847 Remote Similarity NPD5692 Phase 3
0.5847 Remote Similarity NPD5785 Approved
0.5847 Remote Similarity NPD46 Approved
0.5827 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5826 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5816 Remote Similarity NPD7260 Phase 2
0.5798 Remote Similarity NPD5284 Approved
0.5798 Remote Similarity NPD5281 Approved
0.5789 Remote Similarity NPD6695 Phase 3
0.5781 Remote Similarity NPD4730 Approved
0.5781 Remote Similarity NPD4729 Approved
0.5775 Remote Similarity NPD8338 Approved
0.5763 Remote Similarity NPD5328 Approved
0.5738 Remote Similarity NPD5221 Approved
0.5738 Remote Similarity NPD5222 Approved
0.5738 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5735 Remote Similarity NPD6909 Approved
0.5735 Remote Similarity NPD6908 Approved
0.5727 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5724 Remote Similarity NPD7236 Approved
0.5714 Remote Similarity NPD6868 Approved
0.5714 Remote Similarity NPD4754 Approved
0.5714 Remote Similarity NPD8336 Approved
0.5714 Remote Similarity NPD8337 Approved
0.5703 Remote Similarity NPD6614 Approved
0.5692 Remote Similarity NPD5247 Approved
0.5692 Remote Similarity NPD5251 Approved
0.5692 Remote Similarity NPD5169 Approved
0.5692 Remote Similarity NPD5135 Approved
0.5692 Remote Similarity NPD5248 Approved
0.5692 Remote Similarity NPD5250 Approved
0.5692 Remote Similarity NPD5249 Phase 3
0.5692 Remote Similarity NPD5134 Clinical (unspecified phase)

  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