Structure

Physi-Chem Properties

Molecular Weight:  542.32
Volume:  567.595
LogP:  5.364
LogD:  3.758
LogS:  -4.758
# Rotatable Bonds:  10
TPSA:  114.04
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.281
Synthetic Accessibility Score:  4.484
Fsp3:  0.781
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:  -5.092
MDCK Permeability:  4.900134081253782e-05
Pgp-inhibitor:  0.979
Pgp-substrate:  0.496
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.993
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.156
Plasma Protein Binding (PPB):  90.36617279052734%
Volume Distribution (VD):  0.898
Pgp-substrate:  2.736273765563965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.14
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.075
CYP2C9-inhibitor:  0.297
CYP2C9-substrate:  0.976
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.21
CYP3A4-inhibitor:  0.42
CYP3A4-substrate:  0.141

ADMET: Excretion

Clearance (CL):  10.042
Half-life (T1/2):  0.517

ADMET: Toxicity

hERG Blockers:  0.344
Human Hepatotoxicity (H-HT):  0.536
Drug-inuced Liver Injury (DILI):  0.066
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.799
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.922
Carcinogencity:  0.373
Eye Corrosion:  0.005
Eye Irritation:  0.014
Respiratory Toxicity:  0.962

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

  Natural Product: NPC16270

Natural Product ID:  NPC16270
Common Name*:   Bufalin-3-Hemisuberate
IUPAC Name:   8-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(6-oxopyran-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-8-oxooctanoic acid
Synonyms:  
Standard InCHIKey:  RMMRFKRTCRMYRY-IHSZOXLFSA-N
Standard InCHI:  InChI=1S/C32H46O7/c1-30-16-13-23(39-29(36)8-6-4-3-5-7-27(33)34)19-22(30)10-11-26-25(30)14-17-31(2)24(15-18-32(26,31)37)21-9-12-28(35)38-20-21/h9,12,20,22-26,37H,3-8,10-11,13-19H2,1-2H3,(H,33,34)/t22-,23+,24-,25+,26-,30+,31-,32+/m1/s1
SMILES:  C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](CC[C@]12O)c1ccc(=O)oc1)OC(=O)CCCCCCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2069056
PubChem CID:   67050194
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]
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 twigs and leaves Yunnan Province, China 2008-OCT PMID[21954912]
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]
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]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO10672 Vitex megapotamica Species Lamiaceae 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]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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]
NPO10672 Vitex megapotamica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12952 Cabucala madagascariensis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO223 Rhaponticum carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10043 Phebalium ozothamnoides Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5177 Lecanora conizaeoides Species Lecanoraceae 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]
NPO9576 Bufo bufo Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9398 Cortinarius rubellus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2498 Kochia trichophylla Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19205 Buxus sempervirens Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6011 Pleurotus citrinopileatus Species Pleurotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21463 Aruncus dioicus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11885 Dysoxylum lenticellatum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7884 Centaurea amara Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO664 Potentilla multifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11515 Streptomyces plumbeus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2917 Artemisia oranensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26231 Vicia villosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12250 Strychnos fendleri Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7543 Haplopappus venetus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4797 Gavia immer Species Gaviidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3983 Piper futokadsura Species Piperaceae 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
NPT1317 Cell Line CCRF S-180 Mus musculus IC50 > 50000.0 nM PMID[509464]
NPT1357 Cell Line H22 Mus musculus IC50 > 50000.0 nM PMID[509464]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 100000.0 nM PMID[509464]
NPT2 Others Unspecified IC50 = 0.00075 ug.mL-1 PMID[509463]
NPT2 Others Unspecified IC50 = 0.0036 ug.mL-1 PMID[509463]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 7375.0 nM PMID[509464]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4990.0 nM PMID[509464]

☑ 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 NPC16270 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
0.934 High Similarity NPC73050
0.9223 High Similarity NPC189863
0.9216 High Similarity NPC171014
0.9182 High Similarity NPC145074
0.9182 High Similarity NPC114939
0.9182 High Similarity NPC41123
0.9135 High Similarity NPC79298
0.9135 High Similarity NPC43063
0.9038 High Similarity NPC266570
0.9038 High Similarity NPC295843
0.902 High Similarity NPC168319
0.902 High Similarity NPC194028
0.9 High Similarity NPC146786
0.8962 High Similarity NPC75389
0.8938 High Similarity NPC6193
0.8879 High Similarity NPC103491
0.8868 High Similarity NPC275060
0.8868 High Similarity NPC304276
0.8868 High Similarity NPC137462
0.8846 High Similarity NPC180204
0.8839 High Similarity NPC184555
0.8772 High Similarity NPC55602
0.8762 High Similarity NPC165969
0.8716 High Similarity NPC44537
0.8704 High Similarity NPC12795
0.8667 High Similarity NPC112009
0.8641 High Similarity NPC108368
0.8641 High Similarity NPC57079
0.8636 High Similarity NPC171126
0.8624 High Similarity NPC183603
0.8571 High Similarity NPC155332
0.8571 High Similarity NPC114540
0.8571 High Similarity NPC32577
0.8558 High Similarity NPC201406
0.8545 High Similarity NPC247760
0.8534 High Similarity NPC233041
0.8491 Intermediate Similarity NPC475526
0.8491 Intermediate Similarity NPC72151
0.8491 Intermediate Similarity NPC473283
0.8491 Intermediate Similarity NPC329345
0.8468 Intermediate Similarity NPC154815
0.8468 Intermediate Similarity NPC241977
0.8462 Intermediate Similarity NPC98868
0.8462 Intermediate Similarity NPC159499
0.8455 Intermediate Similarity NPC474315
0.8435 Intermediate Similarity NPC312481
0.8407 Intermediate Similarity NPC185287
0.8407 Intermediate Similarity NPC157380
0.8403 Intermediate Similarity NPC221414
0.8396 Intermediate Similarity NPC320447
0.8381 Intermediate Similarity NPC266955
0.8365 Intermediate Similarity NPC110937
0.8349 Intermediate Similarity NPC473482
0.8349 Intermediate Similarity NPC318363
0.8349 Intermediate Similarity NPC475418
0.8333 Intermediate Similarity NPC16701
0.8304 Intermediate Similarity NPC122056
0.8302 Intermediate Similarity NPC99411
0.8302 Intermediate Similarity NPC115899
0.8273 Intermediate Similarity NPC475065
0.8269 Intermediate Similarity NPC250757
0.8269 Intermediate Similarity NPC301534
0.8261 Intermediate Similarity NPC264954
0.8261 Intermediate Similarity NPC35171
0.8261 Intermediate Similarity NPC278681
0.8261 Intermediate Similarity NPC213761
0.8257 Intermediate Similarity NPC475294
0.8241 Intermediate Similarity NPC472868
0.823 Intermediate Similarity NPC147912
0.823 Intermediate Similarity NPC67259
0.8214 Intermediate Similarity NPC100267
0.8214 Intermediate Similarity NPC475524
0.8208 Intermediate Similarity NPC251680
0.819 Intermediate Similarity NPC112936
0.819 Intermediate Similarity NPC474370
0.819 Intermediate Similarity NPC2049
0.819 Intermediate Similarity NPC202705
0.819 Intermediate Similarity NPC257610
0.819 Intermediate Similarity NPC253826
0.8182 Intermediate Similarity NPC472825
0.8174 Intermediate Similarity NPC311554
0.8174 Intermediate Similarity NPC257457
0.8173 Intermediate Similarity NPC171395
0.8173 Intermediate Similarity NPC84383
0.8173 Intermediate Similarity NPC33473
0.8173 Intermediate Similarity NPC293052
0.8173 Intermediate Similarity NPC279974
0.8165 Intermediate Similarity NPC478052
0.8165 Intermediate Similarity NPC34768
0.8158 Intermediate Similarity NPC190286
0.8155 Intermediate Similarity NPC472871
0.8155 Intermediate Similarity NPC38232
0.8148 Intermediate Similarity NPC297617
0.8137 Intermediate Similarity NPC475965
0.8137 Intermediate Similarity NPC471896
0.8137 Intermediate Similarity NPC474842
0.8131 Intermediate Similarity NPC25177
0.8131 Intermediate Similarity NPC268829
0.8131 Intermediate Similarity NPC282524
0.8131 Intermediate Similarity NPC222875
0.8131 Intermediate Similarity NPC247701
0.8131 Intermediate Similarity NPC295110
0.8131 Intermediate Similarity NPC118174
0.813 Intermediate Similarity NPC248703
0.8113 Intermediate Similarity NPC92275
0.8113 Intermediate Similarity NPC477813
0.8108 Intermediate Similarity NPC170221
0.8108 Intermediate Similarity NPC10064
0.8108 Intermediate Similarity NPC137911
0.8108 Intermediate Similarity NPC228477
0.8103 Intermediate Similarity NPC305260
0.8103 Intermediate Similarity NPC270850
0.8095 Intermediate Similarity NPC16967
0.8091 Intermediate Similarity NPC329048
0.8091 Intermediate Similarity NPC330011
0.8091 Intermediate Similarity NPC302788
0.8091 Intermediate Similarity NPC473284
0.8091 Intermediate Similarity NPC179380
0.8087 Intermediate Similarity NPC140055
0.8087 Intermediate Similarity NPC167606
0.8087 Intermediate Similarity NPC470492
0.8087 Intermediate Similarity NPC286528
0.8087 Intermediate Similarity NPC20302
0.8077 Intermediate Similarity NPC201725
0.8077 Intermediate Similarity NPC299100
0.8073 Intermediate Similarity NPC473175
0.8073 Intermediate Similarity NPC272632
0.8058 Intermediate Similarity NPC474018
0.8058 Intermediate Similarity NPC473986
0.8056 Intermediate Similarity NPC22388
0.8056 Intermediate Similarity NPC40918
0.8056 Intermediate Similarity NPC475320
0.8053 Intermediate Similarity NPC191620
0.8053 Intermediate Similarity NPC475970
0.8053 Intermediate Similarity NPC476163
0.8053 Intermediate Similarity NPC264634
0.8053 Intermediate Similarity NPC470063
0.8053 Intermediate Similarity NPC147180
0.8053 Intermediate Similarity NPC221144
0.8051 Intermediate Similarity NPC88326
0.8051 Intermediate Similarity NPC153700
0.8037 Intermediate Similarity NPC471413
0.8037 Intermediate Similarity NPC35751
0.8037 Intermediate Similarity NPC476303
0.8036 Intermediate Similarity NPC6206
0.8036 Intermediate Similarity NPC197428
0.8036 Intermediate Similarity NPC238850
0.8036 Intermediate Similarity NPC473627
0.8036 Intermediate Similarity NPC179642
0.8034 Intermediate Similarity NPC476962
0.8019 Intermediate Similarity NPC141401
0.8019 Intermediate Similarity NPC231751
0.8018 Intermediate Similarity NPC220155
0.8018 Intermediate Similarity NPC177064
0.8017 Intermediate Similarity NPC153440
0.8017 Intermediate Similarity NPC50774
0.8017 Intermediate Similarity NPC709
0.8 Intermediate Similarity NPC60681
0.8 Intermediate Similarity NPC180950
0.8 Intermediate Similarity NPC469794
0.8 Intermediate Similarity NPC72772
0.8 Intermediate Similarity NPC62172
0.8 Intermediate Similarity NPC474909
0.8 Intermediate Similarity NPC289700
0.8 Intermediate Similarity NPC196931
0.8 Intermediate Similarity NPC148458
0.7983 Intermediate Similarity NPC204812
0.7982 Intermediate Similarity NPC189588
0.7982 Intermediate Similarity NPC85742
0.7982 Intermediate Similarity NPC160583
0.7982 Intermediate Similarity NPC476237
0.7982 Intermediate Similarity NPC10232
0.7982 Intermediate Similarity NPC187302
0.7982 Intermediate Similarity NPC222153
0.7982 Intermediate Similarity NPC476889
0.7982 Intermediate Similarity NPC176883
0.7982 Intermediate Similarity NPC196471
0.7982 Intermediate Similarity NPC97487
0.7981 Intermediate Similarity NPC139692
0.7967 Intermediate Similarity NPC155529
0.7965 Intermediate Similarity NPC255401
0.7965 Intermediate Similarity NPC471484
0.7965 Intermediate Similarity NPC262083
0.7965 Intermediate Similarity NPC284162
0.7963 Intermediate Similarity NPC471412
0.7963 Intermediate Similarity NPC93744
0.7963 Intermediate Similarity NPC310981
0.7963 Intermediate Similarity NPC235142
0.7963 Intermediate Similarity NPC476888
0.7961 Intermediate Similarity NPC148414
0.7961 Intermediate Similarity NPC175628
0.7961 Intermediate Similarity NPC111585
0.7961 Intermediate Similarity NPC302280
0.7949 Intermediate Similarity NPC5292
0.7949 Intermediate Similarity NPC475041
0.7949 Intermediate Similarity NPC473270
0.7946 Intermediate Similarity NPC472216
0.7946 Intermediate Similarity NPC5475
0.7946 Intermediate Similarity NPC284828
0.7946 Intermediate Similarity NPC173905

  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 NPC16270 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
0.8286 Intermediate Similarity NPD7638 Approved
0.8208 Intermediate Similarity NPD7640 Approved
0.8208 Intermediate Similarity NPD7639 Approved
0.8087 Intermediate Similarity NPD7115 Discovery
0.8018 Intermediate Similarity NPD6881 Approved
0.8018 Intermediate Similarity NPD6899 Approved
0.7965 Intermediate Similarity NPD8130 Phase 1
0.7928 Intermediate Similarity NPD5697 Approved
0.7905 Intermediate Similarity NPD7748 Approved
0.7895 Intermediate Similarity NPD8297 Approved
0.7876 Intermediate Similarity NPD6883 Approved
0.7876 Intermediate Similarity NPD7102 Approved
0.7876 Intermediate Similarity NPD7290 Approved
0.7857 Intermediate Similarity NPD6011 Approved
0.7838 Intermediate Similarity NPD5739 Approved
0.7838 Intermediate Similarity NPD6675 Approved
0.7838 Intermediate Similarity NPD6402 Approved
0.7838 Intermediate Similarity NPD7128 Approved
0.7815 Intermediate Similarity NPD7503 Approved
0.7807 Intermediate Similarity NPD6847 Approved
0.7807 Intermediate Similarity NPD6869 Approved
0.7807 Intermediate Similarity NPD6650 Approved
0.7807 Intermediate Similarity NPD6617 Approved
0.7807 Intermediate Similarity NPD6649 Approved
0.7788 Intermediate Similarity NPD6013 Approved
0.7788 Intermediate Similarity NPD6014 Approved
0.7788 Intermediate Similarity NPD6012 Approved
0.7767 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD6882 Approved
0.7714 Intermediate Similarity NPD8034 Phase 2
0.7714 Intermediate Similarity NPD8035 Phase 2
0.7699 Intermediate Similarity NPD7320 Approved
0.7685 Intermediate Similarity NPD6084 Phase 2
0.7685 Intermediate Similarity NPD6083 Phase 2
0.7685 Intermediate Similarity NPD7902 Approved
0.7632 Intermediate Similarity NPD6373 Approved
0.7632 Intermediate Similarity NPD6372 Approved
0.7611 Intermediate Similarity NPD5701 Approved
0.7573 Intermediate Similarity NPD7146 Approved
0.7573 Intermediate Similarity NPD7334 Approved
0.7573 Intermediate Similarity NPD5330 Approved
0.7573 Intermediate Similarity NPD6409 Approved
0.7573 Intermediate Similarity NPD7521 Approved
0.7573 Intermediate Similarity NPD6684 Approved
0.7568 Intermediate Similarity NPD5211 Phase 2
0.7568 Intermediate Similarity NPD7632 Discontinued
0.7561 Intermediate Similarity NPD7507 Approved
0.7547 Intermediate Similarity NPD7515 Phase 2
0.7547 Intermediate Similarity NPD5284 Approved
0.7547 Intermediate Similarity NPD6079 Approved
0.7547 Intermediate Similarity NPD5693 Phase 1
0.7547 Intermediate Similarity NPD5281 Approved
0.7545 Intermediate Similarity NPD4696 Approved
0.7545 Intermediate Similarity NPD5285 Approved
0.7545 Intermediate Similarity NPD5286 Approved
0.75 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5695 Phase 3
0.7477 Intermediate Similarity NPD6399 Phase 3
0.7477 Intermediate Similarity NPD4202 Approved
0.7477 Intermediate Similarity NPD5223 Approved
0.7476 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD5696 Approved
0.7436 Intermediate Similarity NPD6053 Discontinued
0.7434 Intermediate Similarity NPD5141 Approved
0.7429 Intermediate Similarity NPD6903 Approved
0.7417 Intermediate Similarity NPD6335 Approved
0.7411 Intermediate Similarity NPD4633 Approved
0.7411 Intermediate Similarity NPD5225 Approved
0.7411 Intermediate Similarity NPD5226 Approved
0.7411 Intermediate Similarity NPD5224 Approved
0.7407 Intermediate Similarity NPD7900 Approved
0.7407 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD5694 Approved
0.7383 Intermediate Similarity NPD6050 Approved
0.7381 Intermediate Similarity NPD7319 Approved
0.7373 Intermediate Similarity NPD4632 Approved
0.7364 Intermediate Similarity NPD4755 Approved
0.7358 Intermediate Similarity NPD6673 Approved
0.7358 Intermediate Similarity NPD6080 Approved
0.7358 Intermediate Similarity NPD6051 Approved
0.7358 Intermediate Similarity NPD6904 Approved
0.7358 Intermediate Similarity NPD5328 Approved
0.7355 Intermediate Similarity NPD7101 Approved
0.7355 Intermediate Similarity NPD7100 Approved
0.7353 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD5175 Approved
0.7345 Intermediate Similarity NPD5174 Approved
0.7333 Intermediate Similarity NPD6317 Approved
0.7302 Intermediate Similarity NPD7736 Approved
0.7295 Intermediate Similarity NPD8294 Approved
0.7295 Intermediate Similarity NPD8377 Approved
0.729 Intermediate Similarity NPD5207 Approved
0.729 Intermediate Similarity NPD5692 Phase 3
0.7282 Intermediate Similarity NPD4788 Approved
0.7273 Intermediate Similarity NPD7328 Approved
0.7273 Intermediate Similarity NPD5221 Approved
0.7273 Intermediate Similarity NPD5222 Approved
0.7273 Intermediate Similarity NPD6314 Approved
0.7273 Intermediate Similarity NPD6313 Approved
0.7273 Intermediate Similarity NPD7327 Approved
0.7273 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7264 Intermediate Similarity NPD5737 Approved
0.7264 Intermediate Similarity NPD6672 Approved
0.725 Intermediate Similarity NPD6274 Approved
0.7238 Intermediate Similarity NPD3618 Phase 1
0.7236 Intermediate Similarity NPD8378 Approved
0.7236 Intermediate Similarity NPD8380 Approved
0.7236 Intermediate Similarity NPD8335 Approved
0.7236 Intermediate Similarity NPD8033 Approved
0.7236 Intermediate Similarity NPD8379 Approved
0.7236 Intermediate Similarity NPD8296 Approved
0.7232 Intermediate Similarity NPD4700 Approved
0.7217 Intermediate Similarity NPD6008 Approved
0.7213 Intermediate Similarity NPD7516 Approved
0.7212 Intermediate Similarity NPD3665 Phase 1
0.7212 Intermediate Similarity NPD3133 Approved
0.7212 Intermediate Similarity NPD3666 Approved
0.7207 Intermediate Similarity NPD5173 Approved
0.7196 Intermediate Similarity NPD4753 Phase 2
0.719 Intermediate Similarity NPD6009 Approved
0.7184 Intermediate Similarity NPD4223 Phase 3
0.7184 Intermediate Similarity NPD4221 Approved
0.7182 Intermediate Similarity NPD5210 Approved
0.7182 Intermediate Similarity NPD4629 Approved
0.717 Intermediate Similarity NPD3573 Approved
0.7154 Intermediate Similarity NPD6319 Approved
0.7143 Intermediate Similarity NPD4225 Approved
0.7143 Intermediate Similarity NPD5329 Approved
0.7143 Intermediate Similarity NPD1694 Approved
0.713 Intermediate Similarity NPD5785 Approved
0.712 Intermediate Similarity NPD7604 Phase 2
0.7107 Intermediate Similarity NPD6868 Approved
0.7103 Intermediate Similarity NPD5208 Approved
0.7097 Intermediate Similarity NPD5983 Phase 2
0.7097 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD4729 Approved
0.7094 Intermediate Similarity NPD4730 Approved
0.7091 Intermediate Similarity NPD6001 Approved
0.7075 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD4694 Approved
0.7075 Intermediate Similarity NPD6098 Approved
0.7075 Intermediate Similarity NPD5690 Phase 2
0.7075 Intermediate Similarity NPD5280 Approved
0.7063 Intermediate Similarity NPD7492 Approved
0.7048 Intermediate Similarity NPD4786 Approved
0.7048 Intermediate Similarity NPD4197 Approved
0.7043 Intermediate Similarity NPD4754 Approved
0.7037 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6054 Approved
0.7008 Intermediate Similarity NPD6336 Discontinued
0.7008 Intermediate Similarity NPD6616 Approved
0.699 Remote Similarity NPD7525 Registered
0.6975 Remote Similarity NPD5250 Approved
0.6975 Remote Similarity NPD5169 Approved
0.6975 Remote Similarity NPD5249 Phase 3
0.6975 Remote Similarity NPD4634 Approved
0.6975 Remote Similarity NPD5247 Approved
0.6975 Remote Similarity NPD5248 Approved
0.6975 Remote Similarity NPD5135 Approved
0.6975 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5251 Approved
0.6964 Remote Similarity NPD4697 Phase 3
0.696 Remote Similarity NPD6909 Approved
0.696 Remote Similarity NPD6908 Approved
0.6953 Remote Similarity NPD7078 Approved
0.6949 Remote Similarity NPD5128 Approved
0.6949 Remote Similarity NPD6686 Approved
0.6942 Remote Similarity NPD8133 Approved
0.6929 Remote Similarity NPD7236 Approved
0.6923 Remote Similarity NPD4768 Approved
0.6923 Remote Similarity NPD4767 Approved
0.6917 Remote Similarity NPD5127 Approved
0.6917 Remote Similarity NPD5215 Approved
0.6917 Remote Similarity NPD5216 Approved
0.6917 Remote Similarity NPD5217 Approved
0.6916 Remote Similarity NPD4690 Approved
0.6916 Remote Similarity NPD4693 Phase 3
0.6916 Remote Similarity NPD4138 Approved
0.6916 Remote Similarity NPD5279 Phase 3
0.6916 Remote Similarity NPD5205 Approved
0.6916 Remote Similarity NPD4689 Approved
0.6916 Remote Similarity NPD4688 Approved
0.6909 Remote Similarity NPD7637 Suspended
0.6905 Remote Similarity NPD6370 Approved
0.6893 Remote Similarity NPD4195 Approved
0.6891 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5654 Approved
0.6864 Remote Similarity NPD6412 Phase 2
0.6857 Remote Similarity NPD3667 Approved
0.6833 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6016 Approved
0.6825 Remote Similarity NPD6015 Approved
0.6822 Remote Similarity NPD8293 Discontinued
0.6803 Remote Similarity NPD6858 Approved
0.6803 Remote Similarity NPD7094 Approved
0.6792 Remote Similarity NPD5362 Discontinued
0.6783 Remote Similarity NPD6404 Discontinued
0.6772 Remote Similarity NPD5988 Approved
0.6765 Remote Similarity NPD6117 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