Structure

Physi-Chem Properties

Molecular Weight:  297.14
Volume:  301.287
LogP:  2.804
LogD:  2.191
LogS:  -3.492
# Rotatable Bonds:  1
TPSA:  30.93
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.796
Synthetic Accessibility Score:  4.573
Fsp3:  0.444
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.883
MDCK Permeability:  2.9638818887178786e-05
Pgp-inhibitor:  0.385
Pgp-substrate:  0.597
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.935
30% Bioavailability (F30%):  0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.997
Plasma Protein Binding (PPB):  80.19405364990234%
Volume Distribution (VD):  2.671
Pgp-substrate:  12.871342658996582%

ADMET: Metabolism

CYP1A2-inhibitor:  0.342
CYP1A2-substrate:  0.568
CYP2C19-inhibitor:  0.359
CYP2C19-substrate:  0.911
CYP2C9-inhibitor:  0.5
CYP2C9-substrate:  0.601
CYP2D6-inhibitor:  0.931
CYP2D6-substrate:  0.42
CYP3A4-inhibitor:  0.949
CYP3A4-substrate:  0.934

ADMET: Excretion

Clearance (CL):  17.464
Half-life (T1/2):  0.452

ADMET: Toxicity

hERG Blockers:  0.436
Human Hepatotoxicity (H-HT):  0.843
Drug-inuced Liver Injury (DILI):  0.235
AMES Toxicity:  0.914
Rat Oral Acute Toxicity:  0.224
Maximum Recommended Daily Dose:  0.962
Skin Sensitization:  0.841
Carcinogencity:  0.883
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.877

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

  Natural Product: NPC148898

Natural Product ID:  NPC148898
Common Name*:   Erythraline
IUPAC Name:   n.a.
Synonyms:   Erythraline
Standard InCHIKey:  TVOFUERNMZTYRM-KSSFIOAISA-N
Standard InCHI:  InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3/t14-,18-/m0/s1
SMILES:  CO[C@H]1C=CC2=CCN3CCc4cc5c(cc4[C@]23C1)OCO5
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518262
PubChem CID:   5317205
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001782] Erythrina alkaloids
        • [CHEMONTID:0002780] Erythrinanes

*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
NPO20031 Erythrina velutina Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[19026536]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. bark n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5703 Isotoma longiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14905.1 Erythrina variegata var. orientalis Varieties Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20031 Erythrina velutina Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7483 Doona congestiflora Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1498 Helichrysum thapsus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7297 Erythrina vespertilio Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5703 Isotoma longiflora Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9901 Aspergillus avenaceus Species Aspergillaceae 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
NPT15 Cell Line Jurkat Homo sapiens IC50 = 23.0 ug.mL-1 PMID[470308]
NPT15 Cell Line Jurkat Homo sapiens IC50 = 5.0 ug.mL-1 PMID[470308]

☑ 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 NPC148898 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
0.951 High Similarity NPC130926
0.9459 High Similarity NPC78733
0.9408 High Similarity NPC231198
0.9189 High Similarity NPC274026
0.9184 High Similarity NPC475959
0.9085 High Similarity NPC215829
0.9085 High Similarity NPC97072
0.9067 High Similarity NPC82285
0.9067 High Similarity NPC133011
0.8951 High Similarity NPC7018
0.8947 High Similarity NPC138487
0.8947 High Similarity NPC216459
0.8947 High Similarity NPC41178
0.894 High Similarity NPC210148
0.894 High Similarity NPC233029
0.8933 High Similarity NPC223125
0.8889 High Similarity NPC31311
0.8889 High Similarity NPC234392
0.8889 High Similarity NPC146288
0.8861 High Similarity NPC266176
0.8861 High Similarity NPC290759
0.8861 High Similarity NPC158148
0.8861 High Similarity NPC82533
0.8846 High Similarity NPC320104
0.8816 High Similarity NPC223124
0.8805 High Similarity NPC75958
0.8797 High Similarity NPC474324
0.8797 High Similarity NPC100566
0.8797 High Similarity NPC57812
0.879 High Similarity NPC247972
0.8774 High Similarity NPC477080
0.8774 High Similarity NPC59028
0.8774 High Similarity NPC92191
0.8767 High Similarity NPC314682
0.8758 High Similarity NPC49353
0.875 High Similarity NPC470739
0.875 High Similarity NPC477640
0.875 High Similarity NPC225597
0.8742 High Similarity NPC58766
0.8742 High Similarity NPC475686
0.8742 High Similarity NPC475845
0.8707 High Similarity NPC474915
0.8707 High Similarity NPC213206
0.8707 High Similarity NPC328750
0.8707 High Similarity NPC188163
0.8701 High Similarity NPC93593
0.8688 High Similarity NPC474475
0.8688 High Similarity NPC474708
0.8679 High Similarity NPC181653
0.8679 High Similarity NPC190332
0.8654 High Similarity NPC106786
0.8645 High Similarity NPC147091
0.8642 High Similarity NPC187678
0.8616 High Similarity NPC476002
0.8608 High Similarity NPC59567
0.8599 High Similarity NPC477559
0.8599 High Similarity NPC160298
0.8599 High Similarity NPC232924
0.8599 High Similarity NPC306902
0.8599 High Similarity NPC266753
0.859 High Similarity NPC475326
0.8589 High Similarity NPC474470
0.8553 High Similarity NPC238530
0.8553 High Similarity NPC232514
0.8553 High Similarity NPC276944
0.8535 High Similarity NPC111485
0.8531 High Similarity NPC160193
0.8528 High Similarity NPC304675
0.8519 High Similarity NPC65403
0.8487 Intermediate Similarity NPC106295
0.8487 Intermediate Similarity NPC476144
0.8487 Intermediate Similarity NPC16107
0.8487 Intermediate Similarity NPC210437
0.8487 Intermediate Similarity NPC51957
0.8485 Intermediate Similarity NPC244554
0.8477 Intermediate Similarity NPC185838
0.8476 Intermediate Similarity NPC237044
0.8467 Intermediate Similarity NPC128019
0.8467 Intermediate Similarity NPC136860
0.8467 Intermediate Similarity NPC476567
0.8466 Intermediate Similarity NPC2314
0.8462 Intermediate Similarity NPC76079
0.8457 Intermediate Similarity NPC311991
0.8438 Intermediate Similarity NPC225774
0.8431 Intermediate Similarity NPC37144
0.8431 Intermediate Similarity NPC59907
0.8431 Intermediate Similarity NPC7467
0.8424 Intermediate Similarity NPC118633
0.8424 Intermediate Similarity NPC148693
0.8424 Intermediate Similarity NPC294790
0.8424 Intermediate Similarity NPC474325
0.8385 Intermediate Similarity NPC24264
0.8385 Intermediate Similarity NPC476432
0.8385 Intermediate Similarity NPC219341
0.8383 Intermediate Similarity NPC102760
0.8375 Intermediate Similarity NPC218614
0.8373 Intermediate Similarity NPC474745
0.8366 Intermediate Similarity NPC179825
0.8366 Intermediate Similarity NPC476151
0.8366 Intermediate Similarity NPC191376
0.8366 Intermediate Similarity NPC321505
0.8365 Intermediate Similarity NPC205167
0.8365 Intermediate Similarity NPC249274
0.8333 Intermediate Similarity NPC210918
0.8333 Intermediate Similarity NPC247389
0.8333 Intermediate Similarity NPC298979
0.8323 Intermediate Similarity NPC302527
0.8323 Intermediate Similarity NPC16805
0.8323 Intermediate Similarity NPC167546
0.8313 Intermediate Similarity NPC24954
0.8312 Intermediate Similarity NPC246587
0.8312 Intermediate Similarity NPC428
0.8312 Intermediate Similarity NPC147390
0.8312 Intermediate Similarity NPC135538
0.8312 Intermediate Similarity NPC476571
0.8312 Intermediate Similarity NPC24233
0.8311 Intermediate Similarity NPC416184
0.8282 Intermediate Similarity NPC241055
0.8272 Intermediate Similarity NPC304659
0.8272 Intermediate Similarity NPC86144
0.8269 Intermediate Similarity NPC476579
0.8258 Intermediate Similarity NPC103379
0.8258 Intermediate Similarity NPC219162
0.8258 Intermediate Similarity NPC477565
0.8255 Intermediate Similarity NPC253429
0.825 Intermediate Similarity NPC4304
0.825 Intermediate Similarity NPC165797
0.8225 Intermediate Similarity NPC475981
0.8225 Intermediate Similarity NPC474746
0.8221 Intermediate Similarity NPC252960
0.821 Intermediate Similarity NPC168409
0.821 Intermediate Similarity NPC180306
0.8204 Intermediate Similarity NPC15919
0.8176 Intermediate Similarity NPC180756
0.8176 Intermediate Similarity NPC323443
0.8155 Intermediate Similarity NPC126284
0.8153 Intermediate Similarity NPC326316
0.8153 Intermediate Similarity NPC81733
0.8148 Intermediate Similarity NPC189470
0.8144 Intermediate Similarity NPC283999
0.8141 Intermediate Similarity NPC60538
0.8141 Intermediate Similarity NPC207824
0.8138 Intermediate Similarity NPC172403
0.8129 Intermediate Similarity NPC95075
0.8129 Intermediate Similarity NPC90844
0.8129 Intermediate Similarity NPC230098
0.8129 Intermediate Similarity NPC253883
0.8117 Intermediate Similarity NPC145304
0.8113 Intermediate Similarity NPC193949
0.8113 Intermediate Similarity NPC184026
0.8113 Intermediate Similarity NPC5238
0.8113 Intermediate Similarity NPC249797
0.8113 Intermediate Similarity NPC204828
0.8113 Intermediate Similarity NPC54379
0.8113 Intermediate Similarity NPC469817
0.8113 Intermediate Similarity NPC172765
0.8113 Intermediate Similarity NPC276588
0.8113 Intermediate Similarity NPC110416
0.8113 Intermediate Similarity NPC295691
0.8113 Intermediate Similarity NPC207757
0.8113 Intermediate Similarity NPC278799
0.8113 Intermediate Similarity NPC2413
0.8113 Intermediate Similarity NPC189266
0.8113 Intermediate Similarity NPC127674
0.8113 Intermediate Similarity NPC39701
0.8108 Intermediate Similarity NPC160692
0.8098 Intermediate Similarity NPC306669
0.8089 Intermediate Similarity NPC220858
0.8089 Intermediate Similarity NPC192768
0.8089 Intermediate Similarity NPC151895
0.8089 Intermediate Similarity NPC97221
0.8089 Intermediate Similarity NPC88249
0.8077 Intermediate Similarity NPC130941
0.8075 Intermediate Similarity NPC118804
0.8072 Intermediate Similarity NPC149090
0.8072 Intermediate Similarity NPC19520
0.8067 Intermediate Similarity NPC301050
0.8067 Intermediate Similarity NPC131204
0.8059 Intermediate Similarity NPC275132
0.8059 Intermediate Similarity NPC248642
0.8047 Intermediate Similarity NPC27887
0.8047 Intermediate Similarity NPC267408
0.8038 Intermediate Similarity NPC76213
0.8038 Intermediate Similarity NPC476568
0.8038 Intermediate Similarity NPC277669
0.8037 Intermediate Similarity NPC233650
0.8036 Intermediate Similarity NPC287588
0.8025 Intermediate Similarity NPC92541
0.8012 Intermediate Similarity NPC156576
0.8012 Intermediate Similarity NPC6152
0.8 Intermediate Similarity NPC11147
0.8 Intermediate Similarity NPC179704
0.8 Intermediate Similarity NPC301189
0.8 Intermediate Similarity NPC298186
0.7988 Intermediate Similarity NPC114364
0.7988 Intermediate Similarity NPC320223
0.7988 Intermediate Similarity NPC134858
0.7987 Intermediate Similarity NPC470924
0.7976 Intermediate Similarity NPC229166
0.7976 Intermediate Similarity NPC199465

  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 NPC148898 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
0.8707 High Similarity NPD4664 Clinical (unspecified phase)
0.8487 Intermediate Similarity NPD4584 Approved
0.8355 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8289 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD4773 Phase 2
0.828 Intermediate Similarity NPD4772 Phase 2
0.8153 Intermediate Similarity NPD4017 Approved
0.8141 Intermediate Similarity NPD3639 Approved
0.8141 Intermediate Similarity NPD3640 Phase 3
0.8141 Intermediate Similarity NPD3641 Approved
0.8027 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6030 Approved
0.8025 Intermediate Similarity NPD6031 Approved
0.7988 Intermediate Similarity NPD6107 Approved
0.7939 Intermediate Similarity NPD6071 Discontinued
0.7919 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD2563 Approved
0.7901 Intermediate Similarity NPD2560 Approved
0.7888 Intermediate Similarity NPD7298 Approved
0.7852 Intermediate Similarity NPD5718 Phase 2
0.7821 Intermediate Similarity NPD5241 Discontinued
0.7778 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD2492 Phase 1
0.7738 Intermediate Similarity NPD4481 Phase 3
0.7738 Intermediate Similarity NPD2898 Approved
0.7725 Intermediate Similarity NPD4166 Phase 2
0.7718 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD5313 Approved
0.7706 Intermediate Similarity NPD5312 Approved
0.7679 Intermediate Similarity NPD2969 Approved
0.7679 Intermediate Similarity NPD2970 Approved
0.7667 Intermediate Similarity NPD4420 Approved
0.7633 Intermediate Similarity NPD2489 Approved
0.7633 Intermediate Similarity NPD27 Approved
0.7622 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3051 Approved
0.761 Intermediate Similarity NPD3124 Discontinued
0.7602 Intermediate Similarity NPD8156 Discontinued
0.7596 Intermediate Similarity NPD5005 Approved
0.7596 Intermediate Similarity NPD5006 Approved
0.759 Intermediate Similarity NPD7833 Phase 2
0.759 Intermediate Similarity NPD7831 Phase 2
0.759 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7280 Phase 3
0.7586 Intermediate Similarity NPD7281 Phase 3
0.7544 Intermediate Similarity NPD8099 Discontinued
0.7544 Intermediate Similarity NPD8252 Approved
0.7544 Intermediate Similarity NPD8251 Approved
0.7531 Intermediate Similarity NPD4210 Discontinued
0.753 Intermediate Similarity NPD6788 Approved
0.7515 Intermediate Similarity NPD2978 Approved
0.7515 Intermediate Similarity NPD4010 Discontinued
0.7515 Intermediate Similarity NPD2977 Approved
0.75 Intermediate Similarity NPD2161 Phase 2
0.7484 Intermediate Similarity NPD6896 Approved
0.7484 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6895 Approved
0.747 Intermediate Similarity NPD5977 Approved
0.747 Intermediate Similarity NPD5978 Approved
0.7456 Intermediate Similarity NPD7802 Discontinued
0.7453 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1424 Approved
0.7381 Intermediate Similarity NPD5604 Discontinued
0.7378 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD5582 Discontinued
0.7362 Intermediate Similarity NPD4727 Phase 1
0.7358 Intermediate Similarity NPD4236 Phase 3
0.7358 Intermediate Similarity NPD4237 Approved
0.7358 Intermediate Similarity NPD5177 Phase 3
0.7349 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD1375 Discontinued
0.7338 Intermediate Similarity NPD4474 Approved
0.7338 Intermediate Similarity NPD4475 Approved
0.7314 Intermediate Similarity NPD6297 Approved
0.7312 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7296 Approved
0.729 Intermediate Similarity NPD3110 Approved
0.729 Intermediate Similarity NPD3109 Approved
0.7283 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6687 Approved
0.7267 Intermediate Similarity NPD6688 Approved
0.7257 Intermediate Similarity NPD3885 Approved
0.725 Intermediate Similarity NPD4162 Approved
0.7248 Intermediate Similarity NPD3705 Approved
0.7247 Intermediate Similarity NPD6853 Approved
0.7247 Intermediate Similarity NPD8054 Approved
0.7247 Intermediate Similarity NPD6851 Approved
0.7247 Intermediate Similarity NPD8053 Approved
0.7226 Intermediate Similarity NPD2674 Phase 3
0.7225 Intermediate Similarity NPD6365 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5773 Approved
0.7202 Intermediate Similarity NPD5772 Approved
0.7191 Intermediate Similarity NPD2971 Approved
0.7191 Intermediate Similarity NPD7310 Approved
0.7191 Intermediate Similarity NPD7311 Approved
0.7191 Intermediate Similarity NPD7312 Approved
0.7191 Intermediate Similarity NPD2968 Approved
0.7191 Intermediate Similarity NPD7313 Approved
0.7186 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7110 Phase 1
0.7171 Intermediate Similarity NPD4098 Discontinued
0.7152 Intermediate Similarity NPD5976 Discontinued
0.7151 Intermediate Similarity NPD7309 Approved
0.7143 Intermediate Similarity NPD3383 Approved
0.7143 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3384 Approved
0.7143 Intermediate Similarity NPD3382 Approved
0.7143 Intermediate Similarity NPD3060 Approved
0.7127 Intermediate Similarity NPD3349 Phase 2
0.7127 Intermediate Similarity NPD7906 Approved
0.7126 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD3656 Approved
0.7117 Intermediate Similarity NPD7124 Phase 2
0.7115 Intermediate Similarity NPD3532 Approved
0.7115 Intermediate Similarity NPD3531 Approved
0.7115 Intermediate Similarity NPD3530 Approved
0.7114 Intermediate Similarity NPD2668 Approved
0.7114 Intermediate Similarity NPD2667 Approved
0.7107 Intermediate Similarity NPD1753 Discontinued
0.7107 Intermediate Similarity NPD4108 Discontinued
0.7099 Intermediate Similarity NPD6748 Discontinued
0.7099 Intermediate Similarity NPD5754 Discontinued
0.7099 Intermediate Similarity NPD6331 Phase 2
0.7095 Intermediate Similarity NPD4578 Approved
0.7095 Intermediate Similarity NPD4577 Approved
0.7091 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD2420 Approved
0.7073 Intermediate Similarity NPD2421 Approved
0.707 Intermediate Similarity NPD2238 Phase 2
0.7051 Intermediate Similarity NPD3145 Approved
0.7051 Intermediate Similarity NPD3144 Approved
0.7048 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5720 Discontinued
0.7039 Intermediate Similarity NPD1421 Approved
0.7039 Intermediate Similarity NPD1420 Approved
0.7035 Intermediate Similarity NPD7400 Phase 3
0.7033 Intermediate Similarity NPD7291 Discontinued
0.7031 Intermediate Similarity NPD4859 Phase 1
0.703 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD7247 Discontinued
0.7013 Intermediate Similarity NPD7905 Discontinued
0.7012 Intermediate Similarity NPD3845 Phase 1
0.7012 Intermediate Similarity NPD2120 Phase 2
0.7 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.6995 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5677 Discontinued
0.6994 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6989 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6981 Remote Similarity NPD2653 Approved
0.6981 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6978 Remote Similarity NPD4663 Approved
0.6975 Remote Similarity NPD7153 Discontinued
0.6974 Remote Similarity NPD2233 Approved
0.6974 Remote Similarity NPD3816 Phase 1
0.6974 Remote Similarity NPD2232 Approved
0.6974 Remote Similarity NPD2230 Approved
0.6974 Remote Similarity NPD3815 Phase 1
0.6966 Remote Similarity NPD3920 Phase 2
0.6961 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5967 Approved
0.6959 Remote Similarity NPD2358 Clinical (unspecified phase)
0.6957 Remote Similarity NPD2490 Approved
0.6957 Remote Similarity NPD2488 Approved
0.6957 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6951 Remote Similarity NPD3692 Discontinued
0.6943 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6943 Remote Similarity NPD1336 Approved
0.694 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6937 Remote Similarity NPD6111 Discontinued
0.6933 Remote Similarity NPD1357 Approved
0.6927 Remote Similarity NPD7607 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6875 Approved
0.6923 Remote Similarity NPD6876 Approved
0.6909 Remote Similarity NPD2422 Clinical (unspecified phase)
0.6902 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6879 Remote Similarity NPD4055 Discovery
0.6871 Remote Similarity NPD5283 Phase 1
0.6868 Remote Similarity NPD6618 Phase 2
0.6867 Remote Similarity NPD7598 Phase 2
0.6864 Remote Similarity NPD4005 Discontinued
0.6864 Remote Similarity NPD6357 Discontinued
0.6854 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6854 Remote Similarity NPD5708 Clinical (unspecified phase)
0.6852 Remote Similarity NPD3156 Discontinued
0.6851 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5160 Discontinued
0.6835 Remote Similarity NPD1039 Discontinued
0.6832 Remote Similarity NPD7119 Phase 2
0.6828 Remote Similarity NPD3923 Approved
0.6828 Remote Similarity NPD3922 Approved
0.6828 Remote Similarity NPD3924 Approved
0.6828 Remote Similarity NPD3921 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