Structure

Physi-Chem Properties

Molecular Weight:  542.25
Volume:  539.391
LogP:  3.407
LogD:  2.763
LogS:  -4.27
# Rotatable Bonds:  8
TPSA:  132.64
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.414
Synthetic Accessibility Score:  5.286
Fsp3:  0.733
Lipinski Rule-of-5:  Accepted
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:  -5.359
MDCK Permeability:  6.999500328674912e-05
Pgp-inhibitor:  0.697
Pgp-substrate:  0.09
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.04
30% Bioavailability (F30%):  0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.164
Plasma Protein Binding (PPB):  88.33281707763672%
Volume Distribution (VD):  0.497
Pgp-substrate:  6.82456111907959%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.074
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.077
CYP2C9-substrate:  0.098
CYP2D6-inhibitor:  0.052
CYP2D6-substrate:  0.139
CYP3A4-inhibitor:  0.241
CYP3A4-substrate:  0.207

ADMET: Excretion

Clearance (CL):  6.275
Half-life (T1/2):  0.857

ADMET: Toxicity

hERG Blockers:  0.309
Human Hepatotoxicity (H-HT):  0.935
Drug-inuced Liver Injury (DILI):  0.931
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.9
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.451
Carcinogencity:  0.32
Eye Corrosion:  0.006
Eye Irritation:  0.014
Respiratory Toxicity:  0.967

Download Data

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

  Natural Product: NPC312481

Natural Product ID:  NPC312481
Common Name*:   GFKJGXMLXPRSOS-PZEZGBRNSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  GFKJGXMLXPRSOS-PZEZGBRNSA-N
Standard InCHI:  InChI=1S/C30H38O9/c1-16(31)37-26-25(17-4-8-23(34)36-15-17)29(3)13-11-20-21(30(29)27(26)39-30)6-5-18-14-19(10-12-28(18,20)2)38-24(35)9-7-22(32)33/h4,8,15,18-21,25-27H,5-7,9-14H2,1-3H3,(H,32,33)/t18-,19+,20+,21-,25+,26-,27-,28+,29-,30-/m1/s1
SMILES:  O=C(O[C@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]31O[C@@H]3[C@@H]([C@@H]2c1ccc(=O)oc1)OC(=O)C)C)C)CCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2069015
PubChem CID:   11969464
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]
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]
NPO18636 Cupressus macrocarpa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12012 Saururus cernuus Species Saururaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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[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]
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]
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]
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]

☑ 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
NPT2 Others Unspecified IC50 = 0.85 ug.mL-1 PMID[525592]
NPT2 Others Unspecified IC50 = 0.96 ug.mL-1 PMID[525592]

☑ 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 NPC312481 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
0.9478 High Similarity NPC6193
0.9464 High Similarity NPC157380
0.9381 High Similarity NPC16701
0.9298 High Similarity NPC35171
0.9298 High Similarity NPC278681
0.9298 High Similarity NPC213761
0.9292 High Similarity NPC185287
0.9217 High Similarity NPC112936
0.886 High Similarity NPC171126
0.8839 High Similarity NPC75389
0.8833 High Similarity NPC159499
0.8772 High Similarity NPC44537
0.8761 High Similarity NPC103491
0.875 High Similarity NPC275060
0.8661 High Similarity NPC43063
0.8661 High Similarity NPC79298
0.8571 High Similarity NPC114939
0.8571 High Similarity NPC145074
0.8571 High Similarity NPC41123
0.8534 High Similarity NPC241977
0.8468 Intermediate Similarity NPC221414
0.8435 Intermediate Similarity NPC12795
0.8435 Intermediate Similarity NPC16270
0.8421 Intermediate Similarity NPC137462
0.8421 Intermediate Similarity NPC304276
0.8407 Intermediate Similarity NPC295843
0.8393 Intermediate Similarity NPC171014
0.8319 Intermediate Similarity NPC165969
0.8291 Intermediate Similarity NPC247760
0.8279 Intermediate Similarity NPC470265
0.8279 Intermediate Similarity NPC23786
0.8264 Intermediate Similarity NPC257610
0.8264 Intermediate Similarity NPC474370
0.825 Intermediate Similarity NPC146786
0.8235 Intermediate Similarity NPC298278
0.822 Intermediate Similarity NPC154815
0.8211 Intermediate Similarity NPC55602
0.8205 Intermediate Similarity NPC470076
0.8205 Intermediate Similarity NPC183603
0.8197 Intermediate Similarity NPC67569
0.8182 Intermediate Similarity NPC264954
0.8182 Intermediate Similarity NPC305260
0.8182 Intermediate Similarity NPC270850
0.8182 Intermediate Similarity NPC5292
0.8151 Intermediate Similarity NPC305044
0.8151 Intermediate Similarity NPC43213
0.8151 Intermediate Similarity NPC216665
0.8151 Intermediate Similarity NPC265290
0.8145 Intermediate Similarity NPC8374
0.813 Intermediate Similarity NPC88326
0.813 Intermediate Similarity NPC153700
0.8115 Intermediate Similarity NPC79579
0.8099 Intermediate Similarity NPC153440
0.8099 Intermediate Similarity NPC50774
0.8099 Intermediate Similarity NPC709
0.8092 Intermediate Similarity NPC75616
0.8087 Intermediate Similarity NPC220217
0.8087 Intermediate Similarity NPC119855
0.8087 Intermediate Similarity NPC470980
0.8083 Intermediate Similarity NPC232564
0.8083 Intermediate Similarity NPC470075
0.8083 Intermediate Similarity NPC113425
0.808 Intermediate Similarity NPC473635
0.8067 Intermediate Similarity NPC73050
0.8065 Intermediate Similarity NPC469789
0.8049 Intermediate Similarity NPC233500
0.8033 Intermediate Similarity NPC472667
0.8033 Intermediate Similarity NPC219656
0.8017 Intermediate Similarity NPC286528
0.8017 Intermediate Similarity NPC20302
0.8017 Intermediate Similarity NPC167606
0.8017 Intermediate Similarity NPC470492
0.8017 Intermediate Similarity NPC140055
0.8016 Intermediate Similarity NPC287423
0.8 Intermediate Similarity NPC158350
0.7984 Intermediate Similarity NPC196130
0.7984 Intermediate Similarity NPC115349
0.7984 Intermediate Similarity NPC170538
0.7983 Intermediate Similarity NPC241477
0.7967 Intermediate Similarity NPC184555
0.7967 Intermediate Similarity NPC474585
0.7966 Intermediate Similarity NPC15551
0.7966 Intermediate Similarity NPC238850
0.7939 Intermediate Similarity NPC62172
0.7939 Intermediate Similarity NPC289700
0.7937 Intermediate Similarity NPC293112
0.7937 Intermediate Similarity NPC179261
0.7934 Intermediate Similarity NPC190286
0.7931 Intermediate Similarity NPC265502
0.7931 Intermediate Similarity NPC189863
0.7931 Intermediate Similarity NPC29389
0.7931 Intermediate Similarity NPC469960
0.7931 Intermediate Similarity NPC266570
0.7931 Intermediate Similarity NPC93026
0.7923 Intermediate Similarity NPC248703
0.792 Intermediate Similarity NPC219804
0.792 Intermediate Similarity NPC11895
0.792 Intermediate Similarity NPC204812
0.7917 Intermediate Similarity NPC101400
0.7917 Intermediate Similarity NPC101965
0.7917 Intermediate Similarity NPC122056
0.7913 Intermediate Similarity NPC297617
0.7907 Intermediate Similarity NPC155529
0.7903 Intermediate Similarity NPC310511
0.7899 Intermediate Similarity NPC262083
0.7899 Intermediate Similarity NPC71680
0.7899 Intermediate Similarity NPC471484
0.7891 Intermediate Similarity NPC231529
0.7886 Intermediate Similarity NPC268326
0.7886 Intermediate Similarity NPC304260
0.7886 Intermediate Similarity NPC29639
0.7886 Intermediate Similarity NPC44899
0.7886 Intermediate Similarity NPC475520
0.7886 Intermediate Similarity NPC473203
0.7886 Intermediate Similarity NPC5883
0.7886 Intermediate Similarity NPC153085
0.7886 Intermediate Similarity NPC475041
0.7869 Intermediate Similarity NPC470493
0.7869 Intermediate Similarity NPC290693
0.7869 Intermediate Similarity NPC312824
0.7869 Intermediate Similarity NPC183580
0.7863 Intermediate Similarity NPC108682
0.7863 Intermediate Similarity NPC472263
0.7863 Intermediate Similarity NPC469957
0.7863 Intermediate Similarity NPC469959
0.7857 Intermediate Similarity NPC299654
0.7857 Intermediate Similarity NPC32868
0.7857 Intermediate Similarity NPC469790
0.7857 Intermediate Similarity NPC241456
0.7857 Intermediate Similarity NPC233041
0.7857 Intermediate Similarity NPC172154
0.7857 Intermediate Similarity NPC81736
0.7857 Intermediate Similarity NPC8369
0.784 Intermediate Similarity NPC269642
0.784 Intermediate Similarity NPC107493
0.784 Intermediate Similarity NPC471082
0.7833 Intermediate Similarity NPC214005
0.7833 Intermediate Similarity NPC313921
0.7833 Intermediate Similarity NPC476163
0.7833 Intermediate Similarity NPC150228
0.7833 Intermediate Similarity NPC98038
0.7826 Intermediate Similarity NPC470972
0.7823 Intermediate Similarity NPC143755
0.7823 Intermediate Similarity NPC251226
0.7807 Intermediate Similarity NPC13743
0.7807 Intermediate Similarity NPC98813
0.7805 Intermediate Similarity NPC186525
0.7805 Intermediate Similarity NPC475372
0.7797 Intermediate Similarity NPC88701
0.7797 Intermediate Similarity NPC50124
0.7787 Intermediate Similarity NPC199428
0.7787 Intermediate Similarity NPC99620
0.7787 Intermediate Similarity NPC5311
0.7787 Intermediate Similarity NPC193382
0.7787 Intermediate Similarity NPC470793
0.7787 Intermediate Similarity NPC310341
0.7778 Intermediate Similarity NPC186668
0.7778 Intermediate Similarity NPC475290
0.7778 Intermediate Similarity NPC471206
0.7769 Intermediate Similarity NPC231240
0.776 Intermediate Similarity NPC159456
0.776 Intermediate Similarity NPC475219
0.776 Intermediate Similarity NPC473256
0.776 Intermediate Similarity NPC231518
0.776 Intermediate Similarity NPC46570
0.776 Intermediate Similarity NPC4021
0.776 Intermediate Similarity NPC470878
0.7759 Intermediate Similarity NPC187302
0.7759 Intermediate Similarity NPC85742
0.7759 Intermediate Similarity NPC472821
0.7759 Intermediate Similarity NPC189588
0.7759 Intermediate Similarity NPC10232
0.7759 Intermediate Similarity NPC97487
0.7759 Intermediate Similarity NPC160583
0.7759 Intermediate Similarity NPC196471
0.7752 Intermediate Similarity NPC470880
0.7752 Intermediate Similarity NPC473593
0.7752 Intermediate Similarity NPC471407
0.775 Intermediate Similarity NPC255401
0.775 Intermediate Similarity NPC284162
0.775 Intermediate Similarity NPC474315
0.7742 Intermediate Similarity NPC291820
0.7742 Intermediate Similarity NPC312536
0.7742 Intermediate Similarity NPC61520
0.7742 Intermediate Similarity NPC81222
0.7739 Intermediate Similarity NPC295110
0.7739 Intermediate Similarity NPC222875
0.7739 Intermediate Similarity NPC25177
0.7739 Intermediate Similarity NPC268829
0.7739 Intermediate Similarity NPC247701
0.7724 Intermediate Similarity NPC243196
0.7724 Intermediate Similarity NPC471351
0.7724 Intermediate Similarity NPC157376
0.7724 Intermediate Similarity NPC34390
0.7724 Intermediate Similarity NPC196429
0.7724 Intermediate Similarity NPC77319
0.7724 Intermediate Similarity NPC99728
0.7724 Intermediate Similarity NPC152615
0.7724 Intermediate Similarity NPC243065
0.7724 Intermediate Similarity NPC50305

  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 NPC312481 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
0.8197 Intermediate Similarity NPD7503 Approved
0.8017 Intermediate Similarity NPD7115 Discovery
0.776 Intermediate Similarity NPD8033 Approved
0.7719 Intermediate Similarity NPD7638 Approved
0.7661 Intermediate Similarity NPD7327 Approved
0.7661 Intermediate Similarity NPD7328 Approved
0.7652 Intermediate Similarity NPD7640 Approved
0.7652 Intermediate Similarity NPD7639 Approved
0.76 Intermediate Similarity NPD7516 Approved
0.754 Intermediate Similarity NPD8377 Approved
0.754 Intermediate Similarity NPD8294 Approved
0.7519 Intermediate Similarity NPD7507 Approved
0.748 Intermediate Similarity NPD8378 Approved
0.748 Intermediate Similarity NPD8379 Approved
0.748 Intermediate Similarity NPD8380 Approved
0.748 Intermediate Similarity NPD8335 Approved
0.748 Intermediate Similarity NPD8296 Approved
0.7459 Intermediate Similarity NPD6650 Approved
0.7459 Intermediate Similarity NPD6649 Approved
0.7398 Intermediate Similarity NPD8297 Approved
0.7377 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD7319 Approved
0.7295 Intermediate Similarity NPD6372 Approved
0.7295 Intermediate Similarity NPD6373 Approved
0.7266 Intermediate Similarity NPD6319 Approved
0.7265 Intermediate Similarity NPD4225 Approved
0.7258 Intermediate Similarity NPD6053 Discontinued
0.7213 Intermediate Similarity NPD6899 Approved
0.7213 Intermediate Similarity NPD6881 Approved
0.7203 Intermediate Similarity NPD6648 Approved
0.719 Intermediate Similarity NPD6008 Approved
0.7143 Intermediate Similarity NPD7736 Approved
0.7131 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7131 Intermediate Similarity NPD5697 Approved
0.712 Intermediate Similarity NPD6882 Approved
0.7097 Intermediate Similarity NPD6883 Approved
0.7097 Intermediate Similarity NPD7102 Approved
0.7097 Intermediate Similarity NPD7290 Approved
0.7083 Intermediate Similarity NPD7632 Discontinued
0.7063 Intermediate Similarity NPD4632 Approved
0.7049 Intermediate Similarity NPD6675 Approved
0.7049 Intermediate Similarity NPD6402 Approved
0.7049 Intermediate Similarity NPD7128 Approved
0.7049 Intermediate Similarity NPD5739 Approved
0.7045 Intermediate Similarity NPD7492 Approved
0.704 Intermediate Similarity NPD6617 Approved
0.704 Intermediate Similarity NPD8130 Phase 1
0.704 Intermediate Similarity NPD6847 Approved
0.704 Intermediate Similarity NPD6869 Approved
0.7016 Intermediate Similarity NPD6012 Approved
0.7016 Intermediate Similarity NPD6014 Approved
0.7016 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6013 Approved
0.7 Intermediate Similarity NPD5344 Discontinued
0.7 Intermediate Similarity NPD6054 Approved
0.6992 Remote Similarity NPD6616 Approved
0.6983 Remote Similarity NPD6399 Phase 3
0.697 Remote Similarity NPD7604 Phase 2
0.6957 Remote Similarity NPD7838 Discovery
0.694 Remote Similarity NPD7078 Approved
0.6935 Remote Similarity NPD6686 Approved
0.6935 Remote Similarity NPD6011 Approved
0.6935 Remote Similarity NPD7320 Approved
0.6899 Remote Similarity NPD6009 Approved
0.6897 Remote Similarity NPD8034 Phase 2
0.6897 Remote Similarity NPD8035 Phase 2
0.6894 Remote Similarity NPD6370 Approved
0.6891 Remote Similarity NPD7902 Approved
0.6855 Remote Similarity NPD5701 Approved
0.6833 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6016 Approved
0.6818 Remote Similarity NPD5983 Phase 2
0.6818 Remote Similarity NPD6015 Approved
0.6803 Remote Similarity NPD5211 Phase 2
0.6797 Remote Similarity NPD8133 Approved
0.6777 Remote Similarity NPD5285 Approved
0.6777 Remote Similarity NPD5286 Approved
0.6777 Remote Similarity NPD4696 Approved
0.6767 Remote Similarity NPD5988 Approved
0.6752 Remote Similarity NPD5281 Approved
0.6752 Remote Similarity NPD5284 Approved
0.6752 Remote Similarity NPD7637 Suspended
0.675 Remote Similarity NPD6084 Phase 2
0.675 Remote Similarity NPD6083 Phase 2
0.6742 Remote Similarity NPD6059 Approved
0.6741 Remote Similarity NPD6336 Discontinued
0.6739 Remote Similarity NPD7260 Phase 2
0.6724 Remote Similarity NPD6051 Approved
0.6723 Remote Similarity NPD6356 Clinical (unspecified phase)
0.672 Remote Similarity NPD6412 Phase 2
0.6694 Remote Similarity NPD5696 Approved
0.6694 Remote Similarity NPD5141 Approved
0.6693 Remote Similarity NPD4634 Approved
0.6693 Remote Similarity NPD6371 Approved
0.6691 Remote Similarity NPD8293 Discontinued
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD5225 Approved
0.6667 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD4633 Approved
0.6667 Remote Similarity NPD5226 Approved
0.6667 Remote Similarity NPD7101 Approved
0.6641 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6639 Remote Similarity NPD7748 Approved
0.6639 Remote Similarity NPD7900 Approved
0.6639 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6638 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5174 Approved
0.6613 Remote Similarity NPD5175 Approved
0.6612 Remote Similarity NPD4755 Approved
0.6591 Remote Similarity NPD6335 Approved
0.6587 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5223 Approved
0.6583 Remote Similarity NPD5695 Phase 3
0.6567 Remote Similarity NPD8513 Phase 3
0.6565 Remote Similarity NPD6274 Approved
0.6555 Remote Similarity NPD4202 Approved
0.6535 Remote Similarity NPD4729 Approved
0.6535 Remote Similarity NPD4730 Approved
0.6525 Remote Similarity NPD46 Approved
0.6525 Remote Similarity NPD6698 Approved
0.6518 Remote Similarity NPD7525 Registered
0.6515 Remote Similarity NPD6317 Approved
0.6504 Remote Similarity NPD4700 Approved
0.6471 Remote Similarity NPD5693 Phase 1
0.6471 Remote Similarity NPD6079 Approved
0.6471 Remote Similarity NPD7515 Phase 2
0.6467 Remote Similarity NPD7236 Approved
0.6466 Remote Similarity NPD7146 Approved
0.6466 Remote Similarity NPD7521 Approved
0.6466 Remote Similarity NPD6684 Approved
0.6466 Remote Similarity NPD7334 Approved
0.6466 Remote Similarity NPD6313 Approved
0.6466 Remote Similarity NPD5330 Approved
0.6466 Remote Similarity NPD6314 Approved
0.6466 Remote Similarity NPD6409 Approved
0.6452 Remote Similarity NPD4159 Approved
0.6446 Remote Similarity NPD4629 Approved
0.6446 Remote Similarity NPD5210 Approved
0.6444 Remote Similarity NPD8515 Approved
0.6444 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8517 Approved
0.6444 Remote Similarity NPD8516 Approved
0.6435 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6434 Remote Similarity NPD5248 Approved
0.6434 Remote Similarity NPD5251 Approved
0.6434 Remote Similarity NPD5247 Approved
0.6434 Remote Similarity NPD5250 Approved
0.6434 Remote Similarity NPD5249 Phase 3
0.641 Remote Similarity NPD4250 Approved
0.641 Remote Similarity NPD4251 Approved
0.641 Remote Similarity NPD7524 Approved
0.6406 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5785 Approved
0.6387 Remote Similarity NPD5207 Approved
0.6379 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6378 Remote Similarity NPD4767 Approved
0.6378 Remote Similarity NPD4768 Approved
0.6364 Remote Similarity NPD6001 Approved
0.6364 Remote Similarity NPD7239 Suspended
0.6357 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6903 Approved
0.635 Remote Similarity NPD8328 Phase 3
0.6348 Remote Similarity NPD6695 Phase 3
0.6338 Remote Similarity NPD6845 Suspended
0.6333 Remote Similarity NPD5694 Approved
0.6333 Remote Similarity NPD6050 Approved
0.6325 Remote Similarity NPD4249 Approved
0.6325 Remote Similarity NPD3618 Phase 1
0.6324 Remote Similarity NPD6909 Approved
0.6324 Remote Similarity NPD6908 Approved
0.6303 Remote Similarity NPD6904 Approved
0.6303 Remote Similarity NPD6673 Approved
0.6303 Remote Similarity NPD5328 Approved
0.6303 Remote Similarity NPD6080 Approved
0.6303 Remote Similarity NPD4753 Phase 2
0.6286 Remote Similarity NPD6033 Approved
0.6283 Remote Similarity NPD4195 Approved
0.6279 Remote Similarity NPD5128 Approved
0.6261 Remote Similarity NPD4752 Clinical (unspecified phase)
0.626 Remote Similarity NPD8413 Clinical (unspecified phase)
0.626 Remote Similarity NPD5216 Approved
0.626 Remote Similarity NPD4697 Phase 3
0.626 Remote Similarity NPD5220 Clinical (unspecified phase)
0.626 Remote Similarity NPD5217 Approved
0.626 Remote Similarity NPD5215 Approved
0.626 Remote Similarity NPD5222 Approved
0.626 Remote Similarity NPD5221 Approved
0.625 Remote Similarity NPD5692 Phase 3
0.6242 Remote Similarity NPD7799 Discontinued
0.6239 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6239 Remote Similarity NPD1694 Approved
0.6232 Remote Similarity NPD6067 Discontinued
0.6228 Remote Similarity NPD4820 Approved
0.6228 Remote Similarity NPD4821 Approved
0.6228 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6228 Remote Similarity NPD4819 Approved
0.6228 Remote Similarity NPD4822 Approved
0.6225 Remote Similarity NPD7625 Phase 1
0.622 Remote Similarity NPD4754 Approved
0.6218 Remote Similarity NPD5737 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