Structure

Physi-Chem Properties

Molecular Weight:  548.3
Volume:  547.3
LogP:  2.624
LogD:  2.59
LogS:  -3.732
# Rotatable Bonds:  5
TPSA:  138.82
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.322
Synthetic Accessibility Score:  5.426
Fsp3:  0.833
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.396
MDCK Permeability:  2.0480983948800713e-05
Pgp-inhibitor:  0.277
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.859
20% Bioavailability (F20%):  0.714
30% Bioavailability (F30%):  0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.59
Plasma Protein Binding (PPB):  73.09872436523438%
Volume Distribution (VD):  1.563
Pgp-substrate:  16.212949752807617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.773
CYP2C19-inhibitor:  0.006
CYP2C19-substrate:  0.304
CYP2C9-inhibitor:  0.026
CYP2C9-substrate:  0.062
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.126
CYP3A4-inhibitor:  0.68
CYP3A4-substrate:  0.177

ADMET: Excretion

Clearance (CL):  7.274
Half-life (T1/2):  0.405

ADMET: Toxicity

hERG Blockers:  0.411
Human Hepatotoxicity (H-HT):  0.345
Drug-inuced Liver Injury (DILI):  0.054
AMES Toxicity:  0.079
Rat Oral Acute Toxicity:  0.493
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.784
Carcinogencity:  0.23
Eye Corrosion:  0.004
Eye Irritation:  0.017
Respiratory Toxicity:  0.968

Download Data

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

  Natural Product: NPC250556

Natural Product ID:  NPC250556
Common Name*:   Peruvoside
IUPAC Name:   (3S,5R,8R,9S,10R,13R,14S,17R)-3-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms:   Peruvoside
Standard InCHIKey:  PMTSPAGBAFCORP-HBUONDEYSA-N
Standard InCHI:  InChI=1S/C30H44O9/c1-16-24(33)26(36-3)25(34)27(38-16)39-19-6-10-29(15-31)18(13-19)4-5-22-21(29)7-9-28(2)20(8-11-30(22,28)35)17-12-23(32)37-14-17/h12,15-16,18-22,24-27,33-35H,4-11,13-14H2,1-3H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28+,29+,30-/m0/s1
SMILES:  C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)O[C@H]1CC[C@@]2(C=O)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)O)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1075790
PubChem CID:   12314120
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001125] Steroid lactones
          • [CHEMONTID:0001555] Cardenolides and derivatives
            • [CHEMONTID:0001559] Cardenolide glycosides 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
NPO8402 Thevetia peruviana Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26714048]
NPO17609 Thevetia neriifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17609 Thevetia neriifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8402 Thevetia peruviana Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17609 Thevetia neriifolia Species Apocynaceae 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
NPT393 Cell Line HCT-116 Homo sapiens Survival = 3.0 % PMID[484979]
NPT139 Cell Line HT-29 Homo sapiens Survival = 24.0 % PMID[484979]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 23.1 nM PMID[484980]
NPT271 Individual Protein Delta opioid receptor Homo sapiens EC50 > 92466.0 nM PMID[484980]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 < 50.0 nM PMID[484980]
NPT1784 Individual Protein Serotonin 5a (5-HT5a) receptor Homo sapiens EC50 > 92466.0 nM PMID[484980]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 < 50.0 nM PMID[484980]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 354.8 nM PMID[484980]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 103.2 nM PMID[484980]
NPT145 Individual Protein Mu opioid receptor Homo sapiens EC50 > 92466.0 nM PMID[484980]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2310.9 nM PMID[484980]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 28.2 nM PMID[484980]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 4.45 % PMID[484981]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 206.0 nM PMID[484980]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 11.6 nM PMID[484980]
NPT1312 Cell Line SW1990 Homo sapiens IC50 = 20.0 nM PMID[484983]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Survival = 2.0 % PMID[484979]
NPT2 Others Unspecified Potency n.a. 92.0 nM PMID[484980]
NPT1258 Others Opioid receptors; mu & delta Homo sapiens EC50 > 126.78 nM PMID[484980]
NPT2 Others Unspecified Potency n.a. 6309.6 nM PMID[484980]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -1.96 % PMID[484981]
NPT2 Others Unspecified Potency n.a. 18.4 nM PMID[484980]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 206.0 nM PMID[484980]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 112.65 % PMID[484982]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 62.43 % PMID[484982]
NPT2 Others Unspecified Potency n.a. 281.8 nM PMID[484980]
NPT2 Others Unspecified Potency n.a. 20.6 nM PMID[484980]
NPT2 Others Unspecified Potency n.a. 100.0 nM PMID[484980]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[484980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 30.0 nM PMID[484983]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 20.0 nM PMID[484983]
NPT27 Others Unspecified IC50 > 10000.0 nM PMID[484983]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[484984]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[484984]

☑ 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 NPC250556 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 NPC469750
0.9914 High Similarity NPC471356
0.9914 High Similarity NPC179412
0.9826 High Similarity NPC27363
0.9746 High Similarity NPC70542
0.9746 High Similarity NPC10823
0.9746 High Similarity NPC180079
0.9746 High Similarity NPC329986
0.9746 High Similarity NPC188234
0.9746 High Similarity NPC469751
0.9746 High Similarity NPC284406
0.9746 High Similarity NPC125077
0.9746 High Similarity NPC251866
0.9746 High Similarity NPC469753
0.9746 High Similarity NPC89514
0.9746 High Similarity NPC276838
0.9746 High Similarity NPC232785
0.9746 High Similarity NPC6108
0.9746 High Similarity NPC86159
0.9746 High Similarity NPC140092
0.9746 High Similarity NPC471360
0.9746 High Similarity NPC197707
0.9746 High Similarity NPC469754
0.9746 High Similarity NPC471358
0.9746 High Similarity NPC469755
0.9746 High Similarity NPC219085
0.9746 High Similarity NPC469752
0.9746 High Similarity NPC471361
0.9746 High Similarity NPC471352
0.9746 High Similarity NPC471359
0.9746 High Similarity NPC17896
0.9746 High Similarity NPC9499
0.9664 High Similarity NPC159338
0.9664 High Similarity NPC253456
0.9664 High Similarity NPC16569
0.9583 High Similarity NPC93416
0.9583 High Similarity NPC42670
0.9583 High Similarity NPC19124
0.958 High Similarity NPC91
0.9576 High Similarity NPC329784
0.9576 High Similarity NPC146456
0.9576 High Similarity NPC469757
0.9576 High Similarity NPC240070
0.9576 High Similarity NPC117702
0.9576 High Similarity NPC471357
0.9504 High Similarity NPC32793
0.9504 High Similarity NPC298783
0.9504 High Similarity NPC104585
0.9504 High Similarity NPC247190
0.9504 High Similarity NPC477709
0.9504 High Similarity NPC225385
0.9504 High Similarity NPC476221
0.9504 High Similarity NPC157817
0.9504 High Similarity NPC146857
0.9504 High Similarity NPC469749
0.9504 High Similarity NPC116075
0.9426 High Similarity NPC329636
0.935 High Similarity NPC194716
0.9344 High Similarity NPC142756
0.9333 High Similarity NPC311534
0.9274 High Similarity NPC59288
0.9274 High Similarity NPC329675
0.9231 High Similarity NPC470312
0.9217 High Similarity NPC99620
0.9217 High Similarity NPC5311
0.9217 High Similarity NPC199428
0.9217 High Similarity NPC310341
0.9217 High Similarity NPC193382
0.9187 High Similarity NPC88668
0.9138 High Similarity NPC27507
0.9138 High Similarity NPC99728
0.9138 High Similarity NPC50305
0.9138 High Similarity NPC473852
0.9138 High Similarity NPC87250
0.9138 High Similarity NPC243196
0.9138 High Similarity NPC93883
0.9138 High Similarity NPC471353
0.9138 High Similarity NPC158344
0.9138 High Similarity NPC309034
0.9138 High Similarity NPC34390
0.9138 High Similarity NPC142066
0.9138 High Similarity NPC471355
0.9138 High Similarity NPC152615
0.9138 High Similarity NPC244402
0.9138 High Similarity NPC196429
0.9138 High Similarity NPC77319
0.9138 High Similarity NPC471351
0.9138 High Similarity NPC84987
0.9138 High Similarity NPC474418
0.9138 High Similarity NPC471354
0.9138 High Similarity NPC157376
0.913 High Similarity NPC84949
0.913 High Similarity NPC471633
0.913 High Similarity NPC31354
0.913 High Similarity NPC69576
0.906 High Similarity NPC83287
0.904 High Similarity NPC171619
0.8983 High Similarity NPC44899
0.8983 High Similarity NPC470897
0.8983 High Similarity NPC292467
0.8983 High Similarity NPC304260
0.8983 High Similarity NPC30483
0.8983 High Similarity NPC469756
0.8983 High Similarity NPC329905
0.8983 High Similarity NPC55532
0.8983 High Similarity NPC236973
0.8983 High Similarity NPC5883
0.8983 High Similarity NPC29639
0.8983 High Similarity NPC32177
0.8974 High Similarity NPC203862
0.8974 High Similarity NPC290693
0.8968 High Similarity NPC62172
0.8968 High Similarity NPC289700
0.8952 High Similarity NPC155529
0.8908 High Similarity NPC475629
0.8908 High Similarity NPC474466
0.8908 High Similarity NPC475556
0.8908 High Similarity NPC475136
0.8908 High Similarity NPC72260
0.8889 High Similarity NPC196931
0.8871 High Similarity NPC173347
0.8833 High Similarity NPC173555
0.8833 High Similarity NPC40749
0.8833 High Similarity NPC474908
0.8833 High Similarity NPC475590
0.8833 High Similarity NPC475219
0.8833 High Similarity NPC231518
0.8833 High Similarity NPC120390
0.8833 High Similarity NPC314535
0.8833 High Similarity NPC475419
0.8828 High Similarity NPC75616
0.8803 High Similarity NPC477580
0.88 High Similarity NPC471855
0.876 High Similarity NPC193893
0.876 High Similarity NPC474423
0.876 High Similarity NPC28532
0.876 High Similarity NPC115349
0.876 High Similarity NPC264336
0.876 High Similarity NPC74259
0.874 High Similarity NPC158350
0.8739 High Similarity NPC218093
0.8729 High Similarity NPC138372
0.8729 High Similarity NPC469794
0.8729 High Similarity NPC72772
0.8729 High Similarity NPC106228
0.8689 High Similarity NPC117445
0.8689 High Similarity NPC308262
0.8689 High Similarity NPC208193
0.8672 High Similarity NPC127656
0.8667 High Similarity NPC81222
0.8667 High Similarity NPC19028
0.8667 High Similarity NPC291820
0.8667 High Similarity NPC9674
0.8667 High Similarity NPC477071
0.8655 High Similarity NPC474483
0.8644 High Similarity NPC472274
0.8644 High Similarity NPC178289
0.864 High Similarity NPC471407
0.8595 High Similarity NPC281840
0.8595 High Similarity NPC107607
0.8583 High Similarity NPC45475
0.8571 High Similarity NPC471816
0.8559 High Similarity NPC260665
0.8548 High Similarity NPC174367
0.8548 High Similarity NPC47113
0.8537 High Similarity NPC41129
0.8534 High Similarity NPC475030
0.8525 High Similarity NPC202051
0.8512 High Similarity NPC153085
0.8512 High Similarity NPC268326
0.8492 Intermediate Similarity NPC231529
0.848 Intermediate Similarity NPC42399
0.848 Intermediate Similarity NPC287423
0.848 Intermediate Similarity NPC298841
0.8468 Intermediate Similarity NPC318135
0.8448 Intermediate Similarity NPC177524
0.8448 Intermediate Similarity NPC392
0.8448 Intermediate Similarity NPC219900
0.8448 Intermediate Similarity NPC230888
0.8443 Intermediate Similarity NPC472004
0.8443 Intermediate Similarity NPC476150
0.8443 Intermediate Similarity NPC476127
0.843 Intermediate Similarity NPC473617
0.843 Intermediate Similarity NPC239293
0.843 Intermediate Similarity NPC473828
0.8413 Intermediate Similarity NPC473620
0.8413 Intermediate Similarity NPC477490
0.8413 Intermediate Similarity NPC473888
0.8413 Intermediate Similarity NPC114306
0.8413 Intermediate Similarity NPC245094
0.8403 Intermediate Similarity NPC178981
0.8403 Intermediate Similarity NPC102619
0.8403 Intermediate Similarity NPC477944
0.8397 Intermediate Similarity NPC79250
0.8397 Intermediate Similarity NPC290746
0.839 Intermediate Similarity NPC263827
0.839 Intermediate Similarity NPC250481
0.839 Intermediate Similarity NPC285410
0.8387 Intermediate Similarity NPC473979
0.8376 Intermediate Similarity NPC476759

  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 NPC250556 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
1.0 High Similarity NPD7507 Approved
0.9746 High Similarity NPD7319 Approved
0.906 High Similarity NPD7328 Approved
0.906 High Similarity NPD7327 Approved
0.8983 High Similarity NPD7516 Approved
0.8908 High Similarity NPD8294 Approved
0.8908 High Similarity NPD8377 Approved
0.8833 High Similarity NPD8033 Approved
0.8833 High Similarity NPD8379 Approved
0.8833 High Similarity NPD8335 Approved
0.8833 High Similarity NPD8378 Approved
0.8833 High Similarity NPD8380 Approved
0.8833 High Similarity NPD8296 Approved
0.8448 Intermediate Similarity NPD6686 Approved
0.8268 Intermediate Similarity NPD7736 Approved
0.825 Intermediate Similarity NPD8133 Approved
0.8226 Intermediate Similarity NPD7503 Approved
0.8205 Intermediate Similarity NPD6412 Phase 2
0.8047 Intermediate Similarity NPD8293 Discontinued
0.8016 Intermediate Similarity NPD6370 Approved
0.7913 Intermediate Similarity NPD7638 Approved
0.7891 Intermediate Similarity NPD7492 Approved
0.7869 Intermediate Similarity NPD6882 Approved
0.7857 Intermediate Similarity NPD6059 Approved
0.7857 Intermediate Similarity NPD6054 Approved
0.7845 Intermediate Similarity NPD7640 Approved
0.7845 Intermediate Similarity NPD7639 Approved
0.7829 Intermediate Similarity NPD6616 Approved
0.7812 Intermediate Similarity NPD8328 Phase 3
0.7769 Intermediate Similarity NPD7078 Approved
0.776 Intermediate Similarity NPD6009 Approved
0.7724 Intermediate Similarity NPD8297 Approved
0.7717 Intermediate Similarity NPD6319 Approved
0.7686 Intermediate Similarity NPD7320 Approved
0.7667 Intermediate Similarity NPD6402 Approved
0.7667 Intermediate Similarity NPD7128 Approved
0.7667 Intermediate Similarity NPD6675 Approved
0.7667 Intermediate Similarity NPD5739 Approved
0.7661 Intermediate Similarity NPD4632 Approved
0.7656 Intermediate Similarity NPD6016 Approved
0.7656 Intermediate Similarity NPD6015 Approved
0.7623 Intermediate Similarity NPD6372 Approved
0.7623 Intermediate Similarity NPD6373 Approved
0.7597 Intermediate Similarity NPD5988 Approved
0.7541 Intermediate Similarity NPD6899 Approved
0.7541 Intermediate Similarity NPD6881 Approved
0.75 Intermediate Similarity NPD6649 Approved
0.75 Intermediate Similarity NPD6650 Approved
0.748 Intermediate Similarity NPD7115 Discovery
0.748 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD5697 Approved
0.7459 Intermediate Similarity NPD5701 Approved
0.744 Intermediate Similarity NPD6053 Discontinued
0.7438 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD7102 Approved
0.7419 Intermediate Similarity NPD6883 Approved
0.7419 Intermediate Similarity NPD7290 Approved
0.7385 Intermediate Similarity NPD8513 Phase 3
0.7385 Intermediate Similarity NPD8517 Approved
0.7385 Intermediate Similarity NPD8515 Approved
0.7385 Intermediate Similarity NPD8516 Approved
0.7377 Intermediate Similarity NPD6008 Approved
0.736 Intermediate Similarity NPD8130 Phase 1
0.736 Intermediate Similarity NPD6617 Approved
0.736 Intermediate Similarity NPD6847 Approved
0.736 Intermediate Similarity NPD6869 Approved
0.7339 Intermediate Similarity NPD6014 Approved
0.7339 Intermediate Similarity NPD6013 Approved
0.7339 Intermediate Similarity NPD6012 Approved
0.7313 Intermediate Similarity NPD6033 Approved
0.7292 Intermediate Similarity NPD7625 Phase 1
0.728 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7632 Discontinued
0.7273 Intermediate Similarity NPD6067 Discontinued
0.7273 Intermediate Similarity NPD7604 Phase 2
0.7258 Intermediate Similarity NPD6011 Approved
0.7252 Intermediate Similarity NPD5983 Phase 2
0.7227 Intermediate Similarity NPD4755 Approved
0.7222 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD6336 Discontinued
0.7143 Intermediate Similarity NPD4634 Approved
0.7131 Intermediate Similarity NPD5211 Phase 2
0.712 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5285 Approved
0.7107 Intermediate Similarity NPD4700 Approved
0.7107 Intermediate Similarity NPD5286 Approved
0.7107 Intermediate Similarity NPD4696 Approved
0.7083 Intermediate Similarity NPD6084 Phase 2
0.7083 Intermediate Similarity NPD6083 Phase 2
0.704 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD5141 Approved
0.7 Intermediate Similarity NPD6274 Approved
0.6992 Remote Similarity NPD4633 Approved
0.6992 Remote Similarity NPD5224 Approved
0.6992 Remote Similarity NPD5225 Approved
0.6992 Remote Similarity NPD5226 Approved
0.697 Remote Similarity NPD7101 Approved
0.697 Remote Similarity NPD7100 Approved
0.696 Remote Similarity NPD4768 Approved
0.696 Remote Similarity NPD4767 Approved
0.6935 Remote Similarity NPD5174 Approved
0.6935 Remote Similarity NPD5175 Approved
0.6923 Remote Similarity NPD5328 Approved
0.6911 Remote Similarity NPD5223 Approved
0.6894 Remote Similarity NPD6335 Approved
0.6891 Remote Similarity NPD4202 Approved
0.6885 Remote Similarity NPD4225 Approved
0.6866 Remote Similarity NPD6909 Approved
0.6866 Remote Similarity NPD6908 Approved
0.6864 Remote Similarity NPD46 Approved
0.6864 Remote Similarity NPD6698 Approved
0.686 Remote Similarity NPD4697 Phase 3
0.685 Remote Similarity NPD4730 Approved
0.685 Remote Similarity NPD4729 Approved
0.6838 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6833 Remote Similarity NPD7748 Approved
0.6822 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6317 Approved
0.6807 Remote Similarity NPD8034 Phase 2
0.6807 Remote Similarity NPD8035 Phase 2
0.6807 Remote Similarity NPD6079 Approved
0.6807 Remote Similarity NPD7515 Phase 2
0.6803 Remote Similarity NPD7902 Approved
0.68 Remote Similarity NPD4754 Approved
0.679 Remote Similarity NPD7799 Discontinued
0.6777 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6777 Remote Similarity NPD5695 Phase 3
0.6772 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6767 Remote Similarity NPD6313 Approved
0.6767 Remote Similarity NPD6314 Approved
0.675 Remote Similarity NPD8171 Discontinued
0.675 Remote Similarity NPD6399 Phase 3
0.6748 Remote Similarity NPD5696 Approved
0.6744 Remote Similarity NPD5248 Approved
0.6744 Remote Similarity NPD5250 Approved
0.6744 Remote Similarity NPD6371 Approved
0.6744 Remote Similarity NPD5249 Phase 3
0.6744 Remote Similarity NPD5247 Approved
0.6744 Remote Similarity NPD5251 Approved
0.6741 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6739 Remote Similarity NPD8074 Phase 3
0.6724 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6719 Remote Similarity NPD5128 Approved
0.6695 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD6684 Approved
0.6667 Remote Similarity NPD5693 Phase 1
0.6667 Remote Similarity NPD6409 Approved
0.6639 Remote Similarity NPD4753 Phase 2
0.6618 Remote Similarity NPD6921 Approved
0.6596 Remote Similarity NPD5956 Approved
0.6585 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6585 Remote Similarity NPD5221 Approved
0.6585 Remote Similarity NPD5222 Approved
0.6565 Remote Similarity NPD5217 Approved
0.6565 Remote Similarity NPD5216 Approved
0.6565 Remote Similarity NPD5215 Approved
0.6557 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6557 Remote Similarity NPD7900 Approved
0.6549 Remote Similarity NPD7260 Phase 2
0.6532 Remote Similarity NPD5173 Approved
0.6525 Remote Similarity NPD3618 Phase 1
0.6508 Remote Similarity NPD5344 Discontinued
0.65 Remote Similarity NPD6051 Approved
0.65 Remote Similarity NPD6080 Approved
0.65 Remote Similarity NPD6673 Approved
0.65 Remote Similarity NPD6904 Approved
0.6496 Remote Similarity NPD3666 Approved
0.6496 Remote Similarity NPD3665 Phase 1
0.6496 Remote Similarity NPD3133 Approved
0.6493 Remote Similarity NPD6868 Approved
0.6489 Remote Similarity NPD5169 Approved
0.6489 Remote Similarity NPD5135 Approved
0.6489 Remote Similarity NPD5134 Clinical (unspecified phase)
0.648 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6471 Remote Similarity NPD3573 Approved
0.6466 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6454 Remote Similarity NPD8336 Approved
0.6454 Remote Similarity NPD8337 Approved
0.6439 Remote Similarity NPD5127 Approved
0.6435 Remote Similarity NPD7525 Registered
0.6429 Remote Similarity NPD8451 Approved
0.6423 Remote Similarity NPD6001 Approved
0.6417 Remote Similarity NPD5737 Approved
0.6417 Remote Similarity NPD6672 Approved
0.6405 Remote Similarity NPD7236 Approved
0.6403 Remote Similarity NPD7642 Approved
0.6395 Remote Similarity NPD6334 Approved
0.6395 Remote Similarity NPD6333 Approved
0.6393 Remote Similarity NPD5281 Approved
0.6393 Remote Similarity NPD5284 Approved
0.6389 Remote Similarity NPD6845 Suspended
0.6389 Remote Similarity NPD8338 Approved
0.6383 Remote Similarity NPD8448 Approved
0.6371 Remote Similarity NPD5210 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