Structure

Physi-Chem Properties

Molecular Weight:  255.11
Volume:  246.034
LogP:  -0.715
LogD:  0.137
LogS:  -0.121
# Rotatable Bonds:  3
TPSA:  102.18
# H-Bond Aceptor:  6
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.481
Synthetic Accessibility Score:  3.645
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.354
MDCK Permeability:  0.00012239853094797581
Pgp-inhibitor:  0.0
Pgp-substrate:  0.431
Human Intestinal Absorption (HIA):  0.88
20% Bioavailability (F20%):  0.018
30% Bioavailability (F30%):  0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.347
Plasma Protein Binding (PPB):  32.8955078125%
Volume Distribution (VD):  1.242
Pgp-substrate:  60.528926849365234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.207
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.329
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.364
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.34
CYP3A4-inhibitor:  0.016
CYP3A4-substrate:  0.103

ADMET: Excretion

Clearance (CL):  11.549
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.8
Drug-inuced Liver Injury (DILI):  0.195
AMES Toxicity:  0.352
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.297
Carcinogencity:  0.464
Eye Corrosion:  0.032
Eye Irritation:  0.073
Respiratory Toxicity:  0.838

Download Data

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

  Natural Product: NPC160931

Natural Product ID:  NPC160931
Common Name*:   L-Radicamine A
IUPAC Name:   (2S,3S,4S,5S)-2-(3-hydroxy-4-methoxyphenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
Synonyms:  
Standard InCHIKey:  NEAQPVOYHYPSER-BVALORAHSA-N
Standard InCHI:  InChI=1S/C12H17NO5/c1-18-9-3-2-6(4-8(9)15)10-12(17)11(16)7(5-14)13-10/h2-4,7,10-17H,5H2,1H3/t7-,10-,11-,12-/m0/s1
SMILES:  OC[C@@H]1N[C@H]([C@@H]([C@H]1O)O)c1ccc(c(c1)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL454551
PubChem CID:   10083681
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000218] Pyrrolidines
        • [CHEMONTID:0002336] Phenylpyrrolidines

*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
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22540 Aquilegia vulgaris Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6890 Euphorbia jolkinii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15952 Adansonia digitata Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6890 Euphorbia jolkinii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2723 Artemisia carvifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18018 Aster multiradiatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22540 Aquilegia vulgaris Species Ranunculaceae 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
NPT497 Individual Protein Maltase-glucoamylase Homo sapiens IC50 = 6700.0 nM PMID[533851]
NPT496 Individual Protein Alpha-L-fucosidase 1 Bos taurus IC50 = 41000.0 nM PMID[533851]
NPT2 Others Unspecified IC50 > 200000.0 nM PMID[533850]
NPT2 Others Unspecified IC50 = 113000.0 nM PMID[533850]
NPT2 Others Unspecified IC50 = 25210.0 nM PMID[533851]
NPT24816 SINGLE PROTEIN Alpha-mannosidase Canavalia ensiformis IC50 = 28000.0 nM PMID[533851]

☑ 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 NPC160931 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 NPC37205
0.8553 High Similarity NPC205167
0.8493 Intermediate Similarity NPC208757
0.8487 Intermediate Similarity NPC294249
0.8481 Intermediate Similarity NPC147091
0.8462 Intermediate Similarity NPC76213
0.8462 Intermediate Similarity NPC277669
0.8438 Intermediate Similarity NPC249274
0.8425 Intermediate Similarity NPC329595
0.8425 Intermediate Similarity NPC326599
0.8375 Intermediate Similarity NPC59028
0.8375 Intermediate Similarity NPC92191
0.8354 Intermediate Similarity NPC2295
0.8354 Intermediate Similarity NPC477564
0.8333 Intermediate Similarity NPC207824
0.8333 Intermediate Similarity NPC60538
0.8253 Intermediate Similarity NPC477640
0.8253 Intermediate Similarity NPC225597
0.8253 Intermediate Similarity NPC470739
0.8221 Intermediate Similarity NPC293871
0.8221 Intermediate Similarity NPC124433
0.8193 Intermediate Similarity NPC474475
0.8182 Intermediate Similarity NPC210140
0.8176 Intermediate Similarity NPC133011
0.8176 Intermediate Similarity NPC82285
0.817 Intermediate Similarity NPC204546
0.8153 Intermediate Similarity NPC147390
0.8153 Intermediate Similarity NPC246587
0.8153 Intermediate Similarity NPC24233
0.8153 Intermediate Similarity NPC135538
0.8153 Intermediate Similarity NPC428
0.8153 Intermediate Similarity NPC476571
0.8151 Intermediate Similarity NPC323775
0.8151 Intermediate Similarity NPC236347
0.8133 Intermediate Similarity NPC58766
0.8133 Intermediate Similarity NPC475686
0.8133 Intermediate Similarity NPC266176
0.8133 Intermediate Similarity NPC290759
0.8133 Intermediate Similarity NPC82533
0.8133 Intermediate Similarity NPC158148
0.8098 Intermediate Similarity NPC18402
0.8095 Intermediate Similarity NPC66341
0.8095 Intermediate Similarity NPC477020
0.8095 Intermediate Similarity NPC2314
0.8095 Intermediate Similarity NPC192135
0.8092 Intermediate Similarity NPC253429
0.8089 Intermediate Similarity NPC321505
0.8089 Intermediate Similarity NPC179825
0.8089 Intermediate Similarity NPC191376
0.8084 Intermediate Similarity NPC109925
0.8072 Intermediate Similarity NPC150879
0.8072 Intermediate Similarity NPC100566
0.8061 Intermediate Similarity NPC134858
0.805 Intermediate Similarity NPC274026
0.8047 Intermediate Similarity NPC329969
0.8012 Intermediate Similarity NPC476002
0.8 Intermediate Similarity NPC233650
0.7987 Intermediate Similarity NPC103379
0.7987 Intermediate Similarity NPC477565
0.7977 Intermediate Similarity NPC135772
0.7976 Intermediate Similarity NPC69712
0.7976 Intermediate Similarity NPC477562
0.7976 Intermediate Similarity NPC26240
0.7964 Intermediate Similarity NPC190332
0.7964 Intermediate Similarity NPC181653
0.7963 Intermediate Similarity NPC5238
0.7963 Intermediate Similarity NPC469817
0.7963 Intermediate Similarity NPC39701
0.7963 Intermediate Similarity NPC172765
0.7963 Intermediate Similarity NPC295691
0.7963 Intermediate Similarity NPC184026
0.7963 Intermediate Similarity NPC110416
0.7963 Intermediate Similarity NPC278799
0.7963 Intermediate Similarity NPC193949
0.7963 Intermediate Similarity NPC2413
0.7963 Intermediate Similarity NPC127674
0.7963 Intermediate Similarity NPC276588
0.7963 Intermediate Similarity NPC207757
0.7963 Intermediate Similarity NPC54379
0.7963 Intermediate Similarity NPC204828
0.7963 Intermediate Similarity NPC249797
0.7963 Intermediate Similarity NPC189266
0.7962 Intermediate Similarity NPC185838
0.7952 Intermediate Similarity NPC4138
0.7952 Intermediate Similarity NPC284183
0.7952 Intermediate Similarity NPC121275
0.7945 Intermediate Similarity NPC13020
0.7945 Intermediate Similarity NPC140359
0.7937 Intermediate Similarity NPC151895
0.7937 Intermediate Similarity NPC192768
0.7937 Intermediate Similarity NPC97221
0.7937 Intermediate Similarity NPC88249
0.7937 Intermediate Similarity NPC220858
0.7917 Intermediate Similarity NPC164429
0.7908 Intermediate Similarity NPC131204
0.7908 Intermediate Similarity NPC301050
0.7907 Intermediate Similarity NPC474507
0.7907 Intermediate Similarity NPC244554
0.7904 Intermediate Similarity NPC264850
0.7904 Intermediate Similarity NPC81247
0.7904 Intermediate Similarity NPC13916
0.7904 Intermediate Similarity NPC35627
0.7904 Intermediate Similarity NPC476573
0.7895 Intermediate Similarity NPC474470
0.7879 Intermediate Similarity NPC215829
0.7879 Intermediate Similarity NPC97072
0.7879 Intermediate Similarity NPC4304
0.7877 Intermediate Similarity NPC298486
0.7866 Intermediate Similarity NPC40389
0.7866 Intermediate Similarity NPC148014
0.7866 Intermediate Similarity NPC315707
0.7866 Intermediate Similarity NPC78359
0.7866 Intermediate Similarity NPC65490
0.7866 Intermediate Similarity NPC475326
0.7862 Intermediate Similarity NPC476151
0.7861 Intermediate Similarity NPC476574
0.7861 Intermediate Similarity NPC312918
0.7861 Intermediate Similarity NPC155442
0.7861 Intermediate Similarity NPC477561
0.7857 Intermediate Similarity NPC252960
0.7857 Intermediate Similarity NPC193528
0.7844 Intermediate Similarity NPC276944
0.7844 Intermediate Similarity NPC238530
0.7844 Intermediate Similarity NPC232514
0.7844 Intermediate Similarity NPC24465
0.7836 Intermediate Similarity NPC187678
0.7829 Intermediate Similarity NPC160692
0.7824 Intermediate Similarity NPC108434
0.7824 Intermediate Similarity NPC475215
0.7818 Intermediate Similarity NPC111485
0.7816 Intermediate Similarity NPC476575
0.7816 Intermediate Similarity NPC275132
0.7811 Intermediate Similarity NPC83198
0.7811 Intermediate Similarity NPC160570
0.7811 Intermediate Similarity NPC204908
0.7809 Intermediate Similarity NPC117717
0.7798 Intermediate Similarity NPC195392
0.7791 Intermediate Similarity NPC237044
0.7791 Intermediate Similarity NPC476577
0.7791 Intermediate Similarity NPC148709
0.7791 Intermediate Similarity NPC173416
0.7784 Intermediate Similarity NPC320104
0.7784 Intermediate Similarity NPC218614
0.7778 Intermediate Similarity NPC190783
0.7778 Intermediate Similarity NPC152680
0.7778 Intermediate Similarity NPC232386
0.7778 Intermediate Similarity NPC218530
0.7765 Intermediate Similarity NPC311991
0.7763 Intermediate Similarity NPC302171
0.7763 Intermediate Similarity NPC33338
0.7763 Intermediate Similarity NPC93882
0.7763 Intermediate Similarity NPC300020
0.7763 Intermediate Similarity NPC130595
0.7758 Intermediate Similarity NPC129603
0.7756 Intermediate Similarity NPC323123
0.7751 Intermediate Similarity NPC81218
0.7751 Intermediate Similarity NPC306555
0.7751 Intermediate Similarity NPC158376
0.7751 Intermediate Similarity NPC474931
0.7751 Intermediate Similarity NPC12053
0.7751 Intermediate Similarity NPC205421
0.7751 Intermediate Similarity NPC145832
0.7751 Intermediate Similarity NPC117188
0.7748 Intermediate Similarity NPC262641
0.7746 Intermediate Similarity NPC474325
0.7742 Intermediate Similarity NPC14600
0.7742 Intermediate Similarity NPC312770
0.7742 Intermediate Similarity NPC41473
0.7742 Intermediate Similarity NPC204848
0.7742 Intermediate Similarity NPC160607
0.774 Intermediate Similarity NPC186546
0.774 Intermediate Similarity NPC476576
0.7738 Intermediate Similarity NPC76116
0.7736 Intermediate Similarity NPC130926
0.7733 Intermediate Similarity NPC304675
0.7733 Intermediate Similarity NPC49353
0.7727 Intermediate Similarity NPC11147
0.7718 Intermediate Similarity NPC320242
0.7718 Intermediate Similarity NPC318965
0.7714 Intermediate Similarity NPC248642
0.7712 Intermediate Similarity NPC6854
0.7712 Intermediate Similarity NPC313737
0.7712 Intermediate Similarity NPC285078
0.7707 Intermediate Similarity NPC328750
0.7707 Intermediate Similarity NPC66518
0.7707 Intermediate Similarity NPC213206
0.7707 Intermediate Similarity NPC474915
0.7707 Intermediate Similarity NPC188163
0.7701 Intermediate Similarity NPC474745
0.7701 Intermediate Similarity NPC99179
0.7697 Intermediate Similarity NPC186063
0.7697 Intermediate Similarity NPC175890
0.7697 Intermediate Similarity NPC82457
0.7697 Intermediate Similarity NPC48490
0.7697 Intermediate Similarity NPC274661
0.7697 Intermediate Similarity NPC11296
0.7692 Intermediate Similarity NPC124657
0.7692 Intermediate Similarity NPC219233
0.7692 Intermediate Similarity NPC170170
0.7692 Intermediate Similarity NPC211468

  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 NPC160931 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
0.8839 High Similarity NPD2977 Approved
0.8839 High Similarity NPD2978 Approved
0.86 High Similarity NPD3060 Approved
0.8493 Intermediate Similarity NPD1132 Approved
0.8493 Intermediate Similarity NPD1136 Approved
0.8493 Intermediate Similarity NPD1130 Approved
0.8425 Intermediate Similarity NPD597 Approved
0.8425 Intermediate Similarity NPD598 Approved
0.8425 Intermediate Similarity NPD601 Approved
0.8322 Intermediate Similarity NPD823 Approved
0.8322 Intermediate Similarity NPD817 Approved
0.8235 Intermediate Similarity NPD4162 Approved
0.8151 Intermediate Similarity NPD9621 Approved
0.8151 Intermediate Similarity NPD9620 Approved
0.8151 Intermediate Similarity NPD9619 Approved
0.8117 Intermediate Similarity NPD4236 Phase 3
0.8117 Intermediate Similarity NPD4237 Approved
0.8067 Intermediate Similarity NPD3062 Approved
0.8067 Intermediate Similarity NPD3059 Approved
0.8067 Intermediate Similarity NPD3061 Approved
0.805 Intermediate Similarity NPD3687 Approved
0.805 Intermediate Similarity NPD3686 Approved
0.8025 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD5314 Approved
0.7945 Intermediate Similarity NPD9622 Approved
0.7914 Intermediate Similarity NPD5772 Approved
0.7914 Intermediate Similarity NPD5773 Approved
0.7881 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD2563 Approved
0.7866 Intermediate Similarity NPD2560 Approved
0.7812 Intermediate Similarity NPD52 Approved
0.7812 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7526 Approved
0.7799 Intermediate Similarity NPD1774 Approved
0.7785 Intermediate Similarity NPD5241 Discontinued
0.7763 Intermediate Similarity NPD2674 Phase 3
0.775 Intermediate Similarity NPD1424 Approved
0.775 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD3180 Approved
0.7748 Intermediate Similarity NPD3179 Approved
0.7727 Intermediate Similarity NPD3052 Approved
0.7727 Intermediate Similarity NPD2568 Approved
0.7727 Intermediate Similarity NPD3054 Approved
0.7718 Intermediate Similarity NPD1818 Approved
0.7718 Intermediate Similarity NPD1820 Approved
0.7718 Intermediate Similarity NPD1817 Approved
0.7718 Intermediate Similarity NPD1819 Approved
0.7707 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD4773 Phase 2
0.7683 Intermediate Similarity NPD4772 Phase 2
0.7682 Intermediate Similarity NPD600 Approved
0.7682 Intermediate Similarity NPD596 Approved
0.7673 Intermediate Similarity NPD2677 Approved
0.7671 Intermediate Similarity NPD9384 Approved
0.7671 Intermediate Similarity NPD9381 Approved
0.7667 Intermediate Similarity NPD602 Approved
0.7667 Intermediate Similarity NPD599 Approved
0.7654 Intermediate Similarity NPD6031 Approved
0.7654 Intermediate Similarity NPD5976 Discontinued
0.7654 Intermediate Similarity NPD6030 Approved
0.764 Intermediate Similarity NPD2874 Phase 2
0.764 Intermediate Similarity NPD3536 Discontinued
0.7605 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD2489 Approved
0.7602 Intermediate Similarity NPD27 Approved
0.76 Intermediate Similarity NPD3055 Approved
0.76 Intermediate Similarity NPD3053 Approved
0.7595 Intermediate Similarity NPD7153 Discontinued
0.7595 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD6071 Discontinued
0.7584 Intermediate Similarity NPD7906 Approved
0.7582 Intermediate Similarity NPD3145 Approved
0.7582 Intermediate Similarity NPD3144 Approved
0.7562 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD859 Approved
0.755 Intermediate Similarity NPD858 Approved
0.7534 Intermediate Similarity NPD316 Approved
0.7532 Intermediate Similarity NPD1423 Approved
0.7531 Intermediate Similarity NPD3157 Approved
0.7531 Intermediate Similarity NPD4584 Approved
0.7531 Intermediate Similarity NPD3158 Phase 1
0.7531 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD7298 Approved
0.7529 Intermediate Similarity NPD6107 Approved
0.7528 Intermediate Similarity NPD4663 Approved
0.7516 Intermediate Similarity NPD3165 Approved
0.7516 Intermediate Similarity NPD3167 Approved
0.7516 Intermediate Similarity NPD3164 Approved
0.7516 Intermediate Similarity NPD3166 Approved
0.75 Intermediate Similarity NPD4210 Discontinued
0.7483 Intermediate Similarity NPD1794 Approved
0.7471 Intermediate Similarity NPD4666 Phase 3
0.7468 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD9613 Approved
0.7466 Intermediate Similarity NPD318 Approved
0.7466 Intermediate Similarity NPD16 Approved
0.7466 Intermediate Similarity NPD9616 Approved
0.7466 Intermediate Similarity NPD9615 Approved
0.7466 Intermediate Similarity NPD317 Approved
0.7466 Intermediate Similarity NPD856 Approved
0.7458 Intermediate Similarity NPD4578 Approved
0.7458 Intermediate Similarity NPD4577 Approved
0.7442 Intermediate Similarity NPD2969 Approved
0.7442 Intermediate Similarity NPD5137 Approved
0.7442 Intermediate Similarity NPD4083 Discontinued
0.7442 Intermediate Similarity NPD2970 Approved
0.7434 Intermediate Similarity NPD558 Phase 2
0.743 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD4123 Phase 3
0.7416 Intermediate Similarity NPD8053 Approved
0.7416 Intermediate Similarity NPD8054 Approved
0.7412 Intermediate Similarity NPD5709 Phase 3
0.7407 Intermediate Similarity NPD3845 Phase 1
0.7403 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD2562 Approved
0.74 Intermediate Similarity NPD2561 Approved
0.7399 Intermediate Similarity NPD2898 Approved
0.7386 Intermediate Similarity NPD6297 Approved
0.7384 Intermediate Similarity NPD3051 Approved
0.7384 Intermediate Similarity NPD4010 Discontinued
0.7372 Intermediate Similarity NPD2238 Phase 2
0.7368 Intermediate Similarity NPD1133 Approved
0.7368 Intermediate Similarity NPD1131 Approved
0.7368 Intermediate Similarity NPD1129 Approved
0.7368 Intermediate Similarity NPD1135 Approved
0.7368 Intermediate Similarity NPD1134 Approved
0.736 Intermediate Similarity NPD7310 Approved
0.736 Intermediate Similarity NPD7312 Approved
0.736 Intermediate Similarity NPD7311 Approved
0.736 Intermediate Similarity NPD7313 Approved
0.7358 Intermediate Similarity NPD9570 Approved
0.7358 Intermediate Similarity NPD3175 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD5160 Discontinued
0.7345 Intermediate Similarity NPD7038 Approved
0.7345 Intermediate Similarity NPD7039 Approved
0.7337 Intermediate Similarity NPD3558 Approved
0.7337 Intermediate Similarity NPD3556 Approved
0.7337 Intermediate Similarity NPD3559 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD3560 Approved
0.7337 Intermediate Similarity NPD3557 Approved
0.7329 Intermediate Similarity NPD5177 Phase 3
0.7329 Intermediate Similarity NPD2460 Phase 3
0.7329 Intermediate Similarity NPD2459 Approved
0.7329 Intermediate Similarity NPD2458 Approved
0.7318 Intermediate Similarity NPD6853 Approved
0.7318 Intermediate Similarity NPD6851 Approved
0.7318 Intermediate Similarity NPD7309 Approved
0.7312 Intermediate Similarity NPD1375 Discontinued
0.7312 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD3163 Approved
0.7308 Intermediate Similarity NPD839 Approved
0.7308 Intermediate Similarity NPD840 Approved
0.7308 Intermediate Similarity NPD3162 Approved
0.7305 Intermediate Similarity NPD4678 Approved
0.7305 Intermediate Similarity NPD4675 Approved
0.7303 Intermediate Similarity NPD9634 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD5310 Approved
0.7303 Intermediate Similarity NPD5311 Approved
0.7301 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3122 Phase 3
0.7296 Intermediate Similarity NPD2154 Approved
0.7296 Intermediate Similarity NPD2155 Approved
0.7296 Intermediate Similarity NPD2156 Approved
0.729 Intermediate Similarity NPD3027 Phase 3
0.7283 Intermediate Similarity NPD4166 Phase 2
0.7278 Intermediate Similarity NPD2653 Approved
0.7273 Intermediate Similarity NPD42 Phase 2
0.7273 Intermediate Similarity NPD6042 Phase 2
0.7273 Intermediate Similarity NPD4873 Discontinued
0.7267 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD9618 Approved
0.726 Intermediate Similarity NPD9614 Approved
0.7251 Intermediate Similarity NPD7831 Phase 2
0.7251 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7833 Phase 2
0.725 Intermediate Similarity NPD2240 Approved
0.725 Intermediate Similarity NPD2239 Approved
0.7248 Intermediate Similarity NPD1798 Approved
0.7248 Intermediate Similarity NPD1797 Approved
0.7246 Intermediate Similarity NPD824 Approved
0.7239 Intermediate Similarity NPD302 Approved
0.7226 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4227 Discontinued
0.7212 Intermediate Similarity NPD3645 Discontinued
0.7204 Intermediate Similarity NPD4604 Approved
0.7204 Intermediate Similarity NPD4605 Approved
0.7197 Intermediate Similarity NPD3532 Approved
0.7197 Intermediate Similarity NPD6405 Approved
0.7197 Intermediate Similarity NPD3531 Approved
0.7197 Intermediate Similarity NPD6407 Approved
0.7197 Intermediate Similarity NPD3530 Approved
0.7195 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6788 Approved
0.7176 Intermediate Similarity NPD4585 Approved
0.7168 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD5895 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD2845 Phase 2

  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