Structure

Physi-Chem Properties

Molecular Weight:  301.13
Volume:  313.178
LogP:  1.427
LogD:  2.117
LogS:  -2.555
# Rotatable Bonds:  7
TPSA:  89.79
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.615
Synthetic Accessibility Score:  1.909
Fsp3:  0.235
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.898
MDCK Permeability:  1.1983066542597953e-05
Pgp-inhibitor:  0.065
Pgp-substrate:  0.434
Human Intestinal Absorption (HIA):  0.635
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.049
Plasma Protein Binding (PPB):  92.42247009277344%
Volume Distribution (VD):  0.696
Pgp-substrate:  8.911904335021973%

ADMET: Metabolism

CYP1A2-inhibitor:  0.685
CYP1A2-substrate:  0.286
CYP2C19-inhibitor:  0.743
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.774
CYP2C9-substrate:  0.909
CYP2D6-inhibitor:  0.878
CYP2D6-substrate:  0.864
CYP3A4-inhibitor:  0.672
CYP3A4-substrate:  0.188

ADMET: Excretion

Clearance (CL):  19.167
Half-life (T1/2):  0.94

ADMET: Toxicity

hERG Blockers:  0.07
Human Hepatotoxicity (H-HT):  0.228
Drug-inuced Liver Injury (DILI):  0.03
AMES Toxicity:  0.638
Rat Oral Acute Toxicity:  0.084
Maximum Recommended Daily Dose:  0.27
Skin Sensitization:  0.942
Carcinogencity:  0.16
Eye Corrosion:  0.003
Eye Irritation:  0.056
Respiratory Toxicity:  0.031

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

  Natural Product: NPC268572

Natural Product ID:  NPC268572
Common Name*:   Dihydro-N-Caffeoyltyramine
IUPAC Name:   3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]propanamide
Synonyms:   Dihydro-N-Caffeoyltyramine
Standard InCHIKey:  RIYORZPRGANLCW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C17H19NO4/c19-14-5-1-12(2-6-14)9-10-18-17(22)8-4-13-3-7-15(20)16(21)11-13/h1-3,5-7,11,19-21H,4,8-10H2,(H,18,22)
SMILES:  Oc1ccc(cc1)CCN=C(CCc1ccc(c(c1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL208465
PubChem CID:   16119668
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001286] Benzenediols
          • [CHEMONTID:0000135] Catechols

*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
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[12467621]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. root n.a. PMID[16212233]
NPO17823 Lycium chinense Species Solanaceae Eukaryota root bark n.a. n.a. PMID[23282106]
NPO17823 Lycium chinense Species Solanaceae Eukaryota Root Bark n.a. n.a. PMID[26982999]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[31397570]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[9090870]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8251 Cortex lycii radicis n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23429 Lycium barbarum Species Solanaceae 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
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition = 94.0 % PMID[448171]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 30200.0 nM PMID[448172]
NPT1 Others Radical scavenging activity IC50 = 61200.0 nM PMID[448172]

☑ 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 NPC268572 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
0.9732 High Similarity NPC122009
0.9643 High Similarity NPC283468
0.931 High Similarity NPC284078
0.9204 High Similarity NPC142599
0.9024 High Similarity NPC114102
0.8934 High Similarity NPC251571
0.8862 High Similarity NPC271808
0.8839 High Similarity NPC96224
0.8839 High Similarity NPC24101
0.88 High Similarity NPC214869
0.879 High Similarity NPC35961
0.879 High Similarity NPC195749
0.879 High Similarity NPC52029
0.871 High Similarity NPC155838
0.8673 High Similarity NPC153690
0.8661 High Similarity NPC231705
0.8644 High Similarity NPC38458
0.8644 High Similarity NPC311737
0.8596 High Similarity NPC258056
0.8594 High Similarity NPC6913
0.8559 High Similarity NPC82963
0.8534 High Similarity NPC146422
0.8522 High Similarity NPC474149
0.8482 Intermediate Similarity NPC471511
0.848 Intermediate Similarity NPC153990
0.848 Intermediate Similarity NPC477839
0.848 Intermediate Similarity NPC186898
0.8462 Intermediate Similarity NPC160607
0.8462 Intermediate Similarity NPC204848
0.8462 Intermediate Similarity NPC14600
0.8462 Intermediate Similarity NPC312770
0.8462 Intermediate Similarity NPC41473
0.8435 Intermediate Similarity NPC254833
0.8435 Intermediate Similarity NPC228343
0.843 Intermediate Similarity NPC252817
0.8421 Intermediate Similarity NPC142297
0.84 Intermediate Similarity NPC301713
0.8397 Intermediate Similarity NPC299583
0.8393 Intermediate Similarity NPC178902
0.8378 Intermediate Similarity NPC223393
0.8362 Intermediate Similarity NPC226401
0.8362 Intermediate Similarity NPC147634
0.8362 Intermediate Similarity NPC79793
0.8362 Intermediate Similarity NPC174096
0.8362 Intermediate Similarity NPC120982
0.8359 Intermediate Similarity NPC130595
0.8359 Intermediate Similarity NPC93882
0.8319 Intermediate Similarity NPC317254
0.8295 Intermediate Similarity NPC285078
0.8295 Intermediate Similarity NPC6854
0.8295 Intermediate Similarity NPC313737
0.8291 Intermediate Similarity NPC179002
0.8291 Intermediate Similarity NPC297657
0.8291 Intermediate Similarity NPC187583
0.8291 Intermediate Similarity NPC257430
0.8276 Intermediate Similarity NPC55617
0.8276 Intermediate Similarity NPC62258
0.8264 Intermediate Similarity NPC85276
0.8258 Intermediate Similarity NPC296898
0.8246 Intermediate Similarity NPC239291
0.8235 Intermediate Similarity NPC118202
0.8231 Intermediate Similarity NPC218530
0.823 Intermediate Similarity NPC196479
0.8198 Intermediate Similarity NPC109955
0.8175 Intermediate Similarity NPC318965
0.8162 Intermediate Similarity NPC5462
0.814 Intermediate Similarity NPC255550
0.814 Intermediate Similarity NPC308885
0.8083 Intermediate Similarity NPC120280
0.8074 Intermediate Similarity NPC100478
0.8074 Intermediate Similarity NPC222039
0.8049 Intermediate Similarity NPC43275
0.8049 Intermediate Similarity NPC283760
0.8034 Intermediate Similarity NPC233835
0.8017 Intermediate Similarity NPC477814
0.8017 Intermediate Similarity NPC37302
0.8 Intermediate Similarity NPC473724
0.7984 Intermediate Similarity NPC115627
0.7984 Intermediate Similarity NPC118522
0.7984 Intermediate Similarity NPC169207
0.7983 Intermediate Similarity NPC268032
0.7982 Intermediate Similarity NPC110764
0.7966 Intermediate Similarity NPC71266
0.7951 Intermediate Similarity NPC277394
0.7951 Intermediate Similarity NPC299252
0.7951 Intermediate Similarity NPC61062
0.7937 Intermediate Similarity NPC471314
0.7937 Intermediate Similarity NPC471315
0.7917 Intermediate Similarity NPC51698
0.7914 Intermediate Similarity NPC115144
0.7914 Intermediate Similarity NPC277857
0.7886 Intermediate Similarity NPC175799
0.7886 Intermediate Similarity NPC145023
0.7886 Intermediate Similarity NPC610
0.7886 Intermediate Similarity NPC200988
0.7881 Intermediate Similarity NPC105727
0.7881 Intermediate Similarity NPC114392
0.7881 Intermediate Similarity NPC58427
0.7881 Intermediate Similarity NPC34864
0.7876 Intermediate Similarity NPC107619
0.7857 Intermediate Similarity NPC470935
0.7857 Intermediate Similarity NPC471032
0.7857 Intermediate Similarity NPC107522
0.7857 Intermediate Similarity NPC274678
0.7851 Intermediate Similarity NPC471485
0.7846 Intermediate Similarity NPC325651
0.7845 Intermediate Similarity NPC12278
0.7845 Intermediate Similarity NPC120719
0.7836 Intermediate Similarity NPC126637
0.7833 Intermediate Similarity NPC280382
0.7823 Intermediate Similarity NPC470626
0.7823 Intermediate Similarity NPC144343
0.7823 Intermediate Similarity NPC86198
0.7817 Intermediate Similarity NPC127402
0.7807 Intermediate Similarity NPC131587
0.7803 Intermediate Similarity NPC244866
0.7797 Intermediate Similarity NPC176527
0.7794 Intermediate Similarity NPC323123
0.7794 Intermediate Similarity NPC477838
0.7794 Intermediate Similarity NPC477837
0.7786 Intermediate Similarity NPC474091
0.7778 Intermediate Similarity NPC254610
0.7768 Intermediate Similarity NPC76938
0.7768 Intermediate Similarity NPC151715
0.7762 Intermediate Similarity NPC275027
0.776 Intermediate Similarity NPC141791
0.776 Intermediate Similarity NPC470214
0.776 Intermediate Similarity NPC217174
0.776 Intermediate Similarity NPC109371
0.776 Intermediate Similarity NPC263386
0.776 Intermediate Similarity NPC470215
0.776 Intermediate Similarity NPC70084
0.7759 Intermediate Similarity NPC68055
0.7742 Intermediate Similarity NPC277588
0.7742 Intermediate Similarity NPC278652
0.7742 Intermediate Similarity NPC293619
0.7742 Intermediate Similarity NPC86947
0.7739 Intermediate Similarity NPC155847
0.7739 Intermediate Similarity NPC289381
0.7734 Intermediate Similarity NPC140359
0.7734 Intermediate Similarity NPC13020
0.773 Intermediate Similarity NPC153644
0.7727 Intermediate Similarity NPC45191
0.7727 Intermediate Similarity NPC326966
0.7721 Intermediate Similarity NPC211468
0.7721 Intermediate Similarity NPC219233
0.7721 Intermediate Similarity NPC170170
0.7717 Intermediate Similarity NPC474862
0.7699 Intermediate Similarity NPC32714
0.7699 Intermediate Similarity NPC26244
0.7698 Intermediate Similarity NPC53596
0.7698 Intermediate Similarity NPC227217
0.7698 Intermediate Similarity NPC475245
0.7698 Intermediate Similarity NPC289330
0.7698 Intermediate Similarity NPC17388
0.7698 Intermediate Similarity NPC471308
0.7698 Intermediate Similarity NPC117780
0.7698 Intermediate Similarity NPC95614
0.7698 Intermediate Similarity NPC165133
0.7698 Intermediate Similarity NPC160120
0.7698 Intermediate Similarity NPC265454
0.7698 Intermediate Similarity NPC56214
0.7698 Intermediate Similarity NPC34634
0.7698 Intermediate Similarity NPC242885
0.7698 Intermediate Similarity NPC232316
0.7698 Intermediate Similarity NPC263835
0.7692 Intermediate Similarity NPC52087
0.7692 Intermediate Similarity NPC236347
0.7692 Intermediate Similarity NPC52475
0.7692 Intermediate Similarity NPC323775
0.7686 Intermediate Similarity NPC163674
0.7674 Intermediate Similarity NPC62101
0.7674 Intermediate Similarity NPC95733
0.7655 Intermediate Similarity NPC107602
0.7652 Intermediate Similarity NPC470706
0.7652 Intermediate Similarity NPC125732
0.7647 Intermediate Similarity NPC471283
0.7639 Intermediate Similarity NPC18614
0.7638 Intermediate Similarity NPC207613
0.7638 Intermediate Similarity NPC24125
0.7638 Intermediate Similarity NPC83279
0.7638 Intermediate Similarity NPC470848
0.7638 Intermediate Similarity NPC98305
0.7638 Intermediate Similarity NPC470849
0.7634 Intermediate Similarity NPC161593
0.7634 Intermediate Similarity NPC145888
0.7634 Intermediate Similarity NPC16031
0.7634 Intermediate Similarity NPC191302
0.7632 Intermediate Similarity NPC216520
0.7632 Intermediate Similarity NPC82664
0.7632 Intermediate Similarity NPC292730
0.7632 Intermediate Similarity NPC33168
0.7632 Intermediate Similarity NPC473388
0.7632 Intermediate Similarity NPC132271
0.7619 Intermediate Similarity NPC281298
0.7619 Intermediate Similarity NPC310338
0.7619 Intermediate Similarity NPC319950
0.7619 Intermediate Similarity NPC191866
0.7615 Intermediate Similarity NPC29477
0.7612 Intermediate Similarity NPC267237

  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 NPC268572 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
0.8833 High Similarity NPD2337 Clinical (unspecified phase)
0.8537 High Similarity NPD5310 Approved
0.8537 High Similarity NPD5311 Approved
0.8534 High Similarity NPD9379 Approved
0.8534 High Similarity NPD9377 Approved
0.8468 Intermediate Similarity NPD3055 Approved
0.8468 Intermediate Similarity NPD3053 Approved
0.8435 Intermediate Similarity NPD3021 Approved
0.8435 Intermediate Similarity NPD3022 Approved
0.8359 Intermediate Similarity NPD2674 Phase 3
0.8154 Intermediate Similarity NPD3059 Approved
0.8154 Intermediate Similarity NPD3061 Approved
0.8154 Intermediate Similarity NPD3062 Approved
0.814 Intermediate Similarity NPD3145 Approved
0.814 Intermediate Similarity NPD3144 Approved
0.814 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.8051 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.803 Intermediate Similarity NPD5314 Approved
0.8 Intermediate Similarity NPD2229 Approved
0.8 Intermediate Similarity NPD2234 Approved
0.8 Intermediate Similarity NPD2228 Approved
0.7984 Intermediate Similarity NPD9384 Approved
0.7984 Intermediate Similarity NPD9381 Approved
0.7969 Intermediate Similarity NPD7451 Discontinued
0.7953 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD4093 Discontinued
0.7815 Intermediate Similarity NPD1792 Phase 2
0.7768 Intermediate Similarity NPD2934 Approved
0.7768 Intermediate Similarity NPD2933 Approved
0.7734 Intermediate Similarity NPD1669 Approved
0.7734 Intermediate Similarity NPD9622 Approved
0.7712 Intermediate Similarity NPD1445 Approved
0.7712 Intermediate Similarity NPD1444 Approved
0.7699 Intermediate Similarity NPD2859 Approved
0.7699 Intermediate Similarity NPD2860 Approved
0.7692 Intermediate Similarity NPD9620 Approved
0.7692 Intermediate Similarity NPD9621 Approved
0.7692 Intermediate Similarity NPD9619 Approved
0.7652 Intermediate Similarity NPD3020 Approved
0.7634 Intermediate Similarity NPD9569 Approved
0.7626 Intermediate Similarity NPD6331 Phase 2
0.7612 Intermediate Similarity NPD6346 Approved
0.7597 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD598 Approved
0.7594 Intermediate Similarity NPD601 Approved
0.7594 Intermediate Similarity NPD597 Approved
0.7591 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD9608 Approved
0.7542 Intermediate Similarity NPD9610 Approved
0.754 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD1132 Approved
0.7537 Intermediate Similarity NPD1136 Approved
0.7537 Intermediate Similarity NPD1130 Approved
0.7536 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD823 Approved
0.75 Intermediate Similarity NPD817 Approved
0.75 Intermediate Similarity NPD3421 Phase 3
0.7464 Intermediate Similarity NPD2161 Phase 2
0.7429 Intermediate Similarity NPD3060 Approved
0.7424 Intermediate Similarity NPD257 Approved
0.7424 Intermediate Similarity NPD258 Approved
0.7422 Intermediate Similarity NPD1751 Approved
0.7422 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD4123 Phase 3
0.7407 Intermediate Similarity NPD259 Phase 1
0.7405 Intermediate Similarity NPD2922 Phase 1
0.7402 Intermediate Similarity NPD5304 Approved
0.7402 Intermediate Similarity NPD1759 Phase 1
0.7402 Intermediate Similarity NPD5303 Approved
0.7398 Intermediate Similarity NPD228 Approved
0.7394 Intermediate Similarity NPD3845 Phase 1
0.7394 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD9536 Phase 1
0.7388 Intermediate Similarity NPD9537 Phase 1
0.7388 Intermediate Similarity NPD3136 Phase 2
0.7385 Intermediate Similarity NPD2561 Approved
0.7385 Intermediate Similarity NPD2562 Approved
0.7377 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD1983 Approved
0.7364 Intermediate Similarity NPD1981 Approved
0.7364 Intermediate Similarity NPD1980 Approved
0.736 Intermediate Similarity NPD1793 Approved
0.736 Intermediate Similarity NPD1791 Approved
0.7357 Intermediate Similarity NPD7153 Discontinued
0.7353 Intermediate Similarity NPD1558 Phase 1
0.7343 Intermediate Similarity NPD2421 Approved
0.7343 Intermediate Similarity NPD2420 Approved
0.7338 Intermediate Similarity NPD7450 Phase 2
0.7328 Intermediate Similarity NPD4659 Approved
0.7323 Intermediate Similarity NPD1758 Phase 1
0.7313 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD555 Phase 2
0.7288 Intermediate Similarity NPD1242 Phase 1
0.7287 Intermediate Similarity NPD2668 Approved
0.7287 Intermediate Similarity NPD2667 Approved
0.7279 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD5156 Approved
0.7259 Intermediate Similarity NPD5155 Approved
0.7246 Intermediate Similarity NPD2568 Approved
0.7241 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD3637 Approved
0.7239 Intermediate Similarity NPD3635 Approved
0.7239 Intermediate Similarity NPD3636 Approved
0.7226 Intermediate Similarity NPD825 Approved
0.7226 Intermediate Similarity NPD826 Approved
0.7222 Intermediate Similarity NPD9618 Approved
0.7222 Intermediate Similarity NPD9614 Approved
0.7218 Intermediate Similarity NPD4103 Phase 2
0.7218 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD5718 Phase 2
0.7203 Intermediate Similarity NPD302 Approved
0.7197 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD856 Approved
0.7188 Intermediate Similarity NPD9615 Approved
0.7188 Intermediate Similarity NPD9613 Approved
0.7188 Intermediate Similarity NPD9616 Approved
0.7188 Intermediate Similarity NPD16 Approved
0.7185 Intermediate Similarity NPD2606 Approved
0.7185 Intermediate Similarity NPD2605 Approved
0.7185 Intermediate Similarity NPD3594 Approved
0.7185 Intermediate Similarity NPD3595 Approved
0.7183 Intermediate Similarity NPD4162 Approved
0.7172 Intermediate Similarity NPD4739 Approved
0.7164 Intermediate Similarity NPD2195 Approved
0.7164 Intermediate Similarity NPD6584 Phase 3
0.7164 Intermediate Similarity NPD2194 Approved
0.7163 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4675 Approved
0.7162 Intermediate Similarity NPD4678 Approved
0.7155 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD6405 Approved
0.7153 Intermediate Similarity NPD6407 Approved
0.7143 Intermediate Similarity NPD1973 Approved
0.7143 Intermediate Similarity NPD1972 Approved
0.7143 Intermediate Similarity NPD5283 Phase 1
0.7143 Intermediate Similarity NPD1969 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD316 Approved
0.7132 Intermediate Similarity NPD2372 Approved
0.7132 Intermediate Similarity NPD3027 Phase 3
0.7121 Intermediate Similarity NPD2232 Approved
0.7121 Intermediate Similarity NPD2230 Approved
0.7121 Intermediate Similarity NPD2233 Approved
0.7109 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD3455 Phase 2
0.7095 Intermediate Similarity NPD4005 Discontinued
0.7094 Intermediate Similarity NPD844 Approved
0.7092 Intermediate Similarity NPD9570 Approved
0.7083 Intermediate Similarity NPD5241 Discontinued
0.708 Intermediate Similarity NPD5109 Approved
0.708 Intermediate Similarity NPD5111 Phase 2
0.708 Intermediate Similarity NPD5110 Phase 2
0.7071 Intermediate Similarity NPD3555 Approved
0.7071 Intermediate Similarity NPD3552 Approved
0.7071 Intermediate Similarity NPD6895 Approved
0.7071 Intermediate Similarity NPD6896 Approved
0.7071 Intermediate Similarity NPD3553 Approved
0.7071 Intermediate Similarity NPD3554 Approved
0.7055 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD317 Approved
0.7054 Intermediate Similarity NPD318 Approved
0.705 Intermediate Similarity NPD275 Approved
0.705 Intermediate Similarity NPD274 Approved
0.7029 Intermediate Similarity NPD840 Approved
0.7029 Intermediate Similarity NPD7477 Discontinued
0.7029 Intermediate Similarity NPD839 Approved
0.7023 Intermediate Similarity NPD2286 Discontinued
0.7021 Intermediate Similarity NPD4108 Discontinued
0.702 Intermediate Similarity NPD5773 Approved
0.702 Intermediate Similarity NPD2977 Approved
0.702 Intermediate Similarity NPD5772 Approved
0.702 Intermediate Similarity NPD2978 Approved
0.7014 Intermediate Similarity NPD7066 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD52 Approved
0.7007 Intermediate Similarity NPD1024 Discontinued
0.7007 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD7526 Approved
0.7 Intermediate Similarity NPD2157 Approved
0.7 Intermediate Similarity NPD3028 Approved
0.6993 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6993 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6992 Remote Similarity NPD2231 Phase 2
0.6992 Remote Similarity NPD2235 Phase 2
0.6985 Remote Similarity NPD1712 Approved
0.6978 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6977 Remote Similarity NPD9568 Approved
0.6975 Remote Similarity NPD9273 Approved
0.697 Remote Similarity NPD3143 Discontinued
0.6964 Remote Similarity NPD111 Approved
0.6954 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6953 Remote Similarity NPD475 Phase 2
0.6944 Remote Similarity NPD5177 Phase 3
0.6944 Remote Similarity NPD4236 Phase 3
0.6944 Remote Similarity NPD4237 Approved
0.694 Remote Similarity NPD6583 Phase 3
0.694 Remote Similarity NPD1755 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