Structure

Physi-Chem Properties

Molecular Weight:  339.15
Volume:  342.033
LogP:  2.799
LogD:  2.861
LogS:  -3.607
# Rotatable Bonds:  2
TPSA:  40.16
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.84
Synthetic Accessibility Score:  3.171
Fsp3:  0.4
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:  -4.935
MDCK Permeability:  3.00308529403992e-05
Pgp-inhibitor:  0.385
Pgp-substrate:  0.728
Human Intestinal Absorption (HIA):  0.001
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.975
Plasma Protein Binding (PPB):  83.27702331542969%
Volume Distribution (VD):  1.844
Pgp-substrate:  8.192462921142578%

ADMET: Metabolism

CYP1A2-inhibitor:  0.626
CYP1A2-substrate:  0.96
CYP2C19-inhibitor:  0.481
CYP2C19-substrate:  0.938
CYP2C9-inhibitor:  0.027
CYP2C9-substrate:  0.85
CYP2D6-inhibitor:  0.555
CYP2D6-substrate:  0.938
CYP3A4-inhibitor:  0.759
CYP3A4-substrate:  0.923

ADMET: Excretion

Clearance (CL):  14.495
Half-life (T1/2):  0.154

ADMET: Toxicity

hERG Blockers:  0.439
Human Hepatotoxicity (H-HT):  0.196
Drug-inuced Liver Injury (DILI):  0.49
AMES Toxicity:  0.65
Rat Oral Acute Toxicity:  0.834
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.192
Carcinogencity:  0.71
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.943

Download Data

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

  Natural Product: NPC247389

Natural Product ID:  NPC247389
Common Name*:   GDVPELGSXTWKDA-ZDUSSCGKSA-N
IUPAC Name:   n.a.
Synonyms:   O-Methylbulbocapnine
Standard InCHIKey:  GDVPELGSXTWKDA-ZDUSSCGKSA-N
Standard InCHI:  InChI=1S/C20H21NO4/c1-21-7-6-12-9-15-20(25-10-24-15)18-16(12)13(21)8-11-4-5-14(22-2)19(23-3)17(11)18/h4-5,9,13H,6-8,10H2,1-3H3/t13-/m0/s1
SMILES:  CN1CCc2cc3c(c4-c5c(ccc(c5OC)OC)C[C@H]1c24)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464955
PubChem CID:   10246564
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota tubers n.a. n.a. PMID[20594848]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22737858]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23194502]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. rhizome n.a. PMID[25277281]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. tuber n.a. PMID[25670016]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[32058719]
NPO23076 Illigera luzonensis Species Hernandiaceae Eukaryota n.a. n.a. n.a. PMID[9214740]
NPO2204 Lindera megaphylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2204 Lindera megaphylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2204 Lindera megaphylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO827 Corydalis yanhusuo Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25345 Corydalis ternata Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22727 Avena fatua Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23076 Illigera luzonensis Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16798 Piper sylvaticum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2204 Lindera megaphylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13962 Corydalis turtschaninovii Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21569 Helichrysum fulvum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO827 Corydalis yanhusuo Species Papaveraceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 47.9 % PMID[514577]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[514577]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 75.1 % PMID[514577]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 50.4 % PMID[514577]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 72.5 % PMID[514577]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 83.4 % PMID[514577]
NPT20967 CELL-LINE Platelet n.a. Activity = 73.0 % PMID[514578]
NPT20967 CELL-LINE Platelet n.a. Activity = 60.8 % PMID[514578]
NPT177 Tissue Aorta Rattus norvegicus Activity = 22.9 % PMID[514578]
NPT177 Tissue Aorta Rattus norvegicus Activity = 68.1 % PMID[514578]
NPT177 Tissue Aorta Rattus norvegicus Activity = 55.2 % PMID[514578]
NPT177 Tissue Aorta Rattus norvegicus Activity = 88.5 % PMID[514578]
NPT26819 SINGLE PROTEIN Sclerostin Homo sapiens IC50 = 1500.0 nM PMID[514579]

☑ 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 NPC247389 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
0.9935 High Similarity NPC476432
0.9935 High Similarity NPC219341
0.9935 High Similarity NPC24264
0.987 High Similarity NPC16805
0.987 High Similarity NPC167546
0.987 High Similarity NPC225774
0.987 High Similarity NPC302527
0.9744 High Similarity NPC210918
0.9675 High Similarity NPC232924
0.9675 High Similarity NPC160298
0.9675 High Similarity NPC306902
0.9675 High Similarity NPC266753
0.9675 High Similarity NPC477559
0.9565 High Similarity NPC320223
0.9565 High Similarity NPC114364
0.956 High Similarity NPC149090
0.956 High Similarity NPC19520
0.9545 High Similarity NPC476572
0.9497 High Similarity NPC6152
0.9441 High Similarity NPC128560
0.9441 High Similarity NPC199465
0.9441 High Similarity NPC229166
0.9416 High Similarity NPC325871
0.9416 High Similarity NPC99659
0.939 High Similarity NPC248642
0.9371 High Similarity NPC298979
0.9333 High Similarity NPC156576
0.9329 High Similarity NPC32413
0.9329 High Similarity NPC474506
0.9313 High Similarity NPC241055
0.9308 High Similarity NPC304659
0.9308 High Similarity NPC86144
0.9268 High Similarity NPC258695
0.9268 High Similarity NPC126284
0.9268 High Similarity NPC470879
0.9245 High Similarity NPC168409
0.9221 High Similarity NPC81733
0.9221 High Similarity NPC326316
0.9217 High Similarity NPC135772
0.9207 High Similarity NPC23219
0.9182 High Similarity NPC189470
0.9157 High Similarity NPC116284
0.9152 High Similarity NPC267408
0.9146 High Similarity NPC112575
0.913 High Similarity NPC117188
0.913 High Similarity NPC158376
0.913 High Similarity NPC205421
0.913 High Similarity NPC12053
0.913 High Similarity NPC145832
0.913 High Similarity NPC306555
0.913 High Similarity NPC81218
0.913 High Similarity NPC474931
0.9096 High Similarity NPC476574
0.9096 High Similarity NPC155442
0.9096 High Similarity NPC312918
0.9096 High Similarity NPC477561
0.9091 High Similarity NPC148693
0.9091 High Similarity NPC118633
0.9091 High Similarity NPC294790
0.9085 High Similarity NPC477558
0.9053 High Similarity NPC237579
0.9045 High Similarity NPC138487
0.9045 High Similarity NPC244112
0.9045 High Similarity NPC216459
0.9045 High Similarity NPC41178
0.9026 High Similarity NPC475959
0.9006 High Similarity NPC253043
0.9006 High Similarity NPC78222
0.9006 High Similarity NPC196447
0.9006 High Similarity NPC96603
0.9006 High Similarity NPC212794
0.9006 High Similarity NPC306843
0.9006 High Similarity NPC477563
0.9006 High Similarity NPC13504
0.9006 High Similarity NPC136508
0.8994 High Similarity NPC57036
0.8994 High Similarity NPC214116
0.8987 High Similarity NPC146288
0.8944 High Similarity NPC1229
0.8944 High Similarity NPC324144
0.8902 High Similarity NPC152212
0.8889 High Similarity NPC82763
0.8868 High Similarity NPC203784
0.8868 High Similarity NPC234392
0.8868 High Similarity NPC170503
0.8868 High Similarity NPC126519
0.8868 High Similarity NPC31311
0.8846 High Similarity NPC211296
0.883 High Similarity NPC186546
0.883 High Similarity NPC312531
0.883 High Similarity NPC476576
0.882 High Similarity NPC166014
0.882 High Similarity NPC27410
0.8817 High Similarity NPC476575
0.8805 High Similarity NPC76079
0.8797 High Similarity NPC210148
0.8797 High Similarity NPC233029
0.8795 High Similarity NPC477020
0.8795 High Similarity NPC66341
0.8795 High Similarity NPC192135
0.8795 High Similarity NPC2314
0.878 High Similarity NPC204947
0.8758 High Similarity NPC477080
0.8757 High Similarity NPC179704
0.8735 High Similarity NPC239775
0.8728 High Similarity NPC475754
0.8726 High Similarity NPC219162
0.8706 High Similarity NPC275132
0.8698 High Similarity NPC220961
0.869 High Similarity NPC287588
0.8688 High Similarity NPC93593
0.8678 High Similarity NPC117717
0.8675 High Similarity NPC26240
0.8675 High Similarity NPC69712
0.8675 High Similarity NPC118274
0.8675 High Similarity NPC477562
0.8675 High Similarity NPC168753
0.8662 High Similarity NPC130941
0.8659 High Similarity NPC276944
0.8659 High Similarity NPC238530
0.8659 High Similarity NPC232514
0.8599 High Similarity NPC253883
0.8599 High Similarity NPC106295
0.8599 High Similarity NPC95075
0.8599 High Similarity NPC476144
0.8599 High Similarity NPC51957
0.8599 High Similarity NPC90844
0.8599 High Similarity NPC16107
0.8599 High Similarity NPC210437
0.8596 High Similarity NPC249405
0.859 High Similarity NPC145304
0.8571 High Similarity NPC470925
0.8571 High Similarity NPC328750
0.8571 High Similarity NPC474915
0.8571 High Similarity NPC213206
0.8571 High Similarity NPC188163
0.8554 High Similarity NPC150879
0.8544 High Similarity NPC7467
0.8537 High Similarity NPC60186
0.8528 High Similarity NPC111485
0.8519 High Similarity NPC180756
0.8519 High Similarity NPC323443
0.8506 High Similarity NPC474904
0.8506 High Similarity NPC314682
0.8494 Intermediate Similarity NPC35627
0.8494 Intermediate Similarity NPC476573
0.8494 Intermediate Similarity NPC81247
0.8491 Intermediate Similarity NPC92541
0.8488 Intermediate Similarity NPC73492
0.8488 Intermediate Similarity NPC299990
0.8488 Intermediate Similarity NPC233718
0.848 Intermediate Similarity NPC474507
0.8466 Intermediate Similarity NPC302001
0.8462 Intermediate Similarity NPC476567
0.8462 Intermediate Similarity NPC128019
0.8462 Intermediate Similarity NPC136860
0.8452 Intermediate Similarity NPC75958
0.8447 Intermediate Similarity NPC470924
0.8443 Intermediate Similarity NPC474324
0.8443 Intermediate Similarity NPC57812
0.8439 Intermediate Similarity NPC302275
0.8421 Intermediate Similarity NPC190461
0.8402 Intermediate Similarity NPC65403
0.8393 Intermediate Similarity NPC475845
0.8373 Intermediate Similarity NPC233650
0.8373 Intermediate Similarity NPC320104
0.8365 Intermediate Similarity NPC144863
0.8363 Intermediate Similarity NPC173416
0.8363 Intermediate Similarity NPC148709
0.8363 Intermediate Similarity NPC476577
0.8344 Intermediate Similarity NPC78733
0.8344 Intermediate Similarity NPC123323
0.8343 Intermediate Similarity NPC14507
0.8343 Intermediate Similarity NPC311991
0.8343 Intermediate Similarity NPC474708
0.8343 Intermediate Similarity NPC47077
0.8333 Intermediate Similarity NPC26601
0.8333 Intermediate Similarity NPC181653
0.8333 Intermediate Similarity NPC148898
0.8333 Intermediate Similarity NPC190332
0.8323 Intermediate Similarity NPC180306
0.8323 Intermediate Similarity NPC134858
0.8314 Intermediate Similarity NPC477560
0.8313 Intermediate Similarity NPC59907
0.8313 Intermediate Similarity NPC37144
0.8312 Intermediate Similarity NPC7018
0.8304 Intermediate Similarity NPC187678
0.8294 Intermediate Similarity NPC477640
0.8294 Intermediate Similarity NPC225597
0.8294 Intermediate Similarity NPC470739
0.8293 Intermediate Similarity NPC186063
0.8284 Intermediate Similarity NPC266176
0.8284 Intermediate Similarity NPC158148
0.8284 Intermediate Similarity NPC290759
0.8284 Intermediate Similarity NPC82533
0.8278 Intermediate Similarity NPC23080
0.8278 Intermediate Similarity NPC193906
0.8268 Intermediate Similarity NPC162653
0.8256 Intermediate Similarity NPC241704
0.825 Intermediate Similarity NPC476151

  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 NPC247389 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
0.8599 High Similarity NPD4584 Approved
0.8571 High Similarity NPD4664 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD4481 Phase 3
0.8383 Intermediate Similarity NPD3051 Approved
0.8291 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD2970 Approved
0.8225 Intermediate Similarity NPD2969 Approved
0.8081 Intermediate Similarity NPD8099 Discontinued
0.8081 Intermediate Similarity NPD8252 Approved
0.8081 Intermediate Similarity NPD8251 Approved
0.8075 Intermediate Similarity NPD2421 Approved
0.8075 Intermediate Similarity NPD2420 Approved
0.807 Intermediate Similarity NPD27 Approved
0.807 Intermediate Similarity NPD2489 Approved
0.8035 Intermediate Similarity NPD8156 Discontinued
0.8034 Intermediate Similarity NPD7906 Approved
0.8012 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD6788 Approved
0.7939 Intermediate Similarity NPD4017 Approved
0.791 Intermediate Similarity NPD7311 Approved
0.791 Intermediate Similarity NPD7312 Approved
0.791 Intermediate Similarity NPD2968 Approved
0.791 Intermediate Similarity NPD4577 Approved
0.791 Intermediate Similarity NPD2971 Approved
0.791 Intermediate Similarity NPD7313 Approved
0.791 Intermediate Similarity NPD4578 Approved
0.791 Intermediate Similarity NPD7310 Approved
0.7904 Intermediate Similarity NPD7298 Approved
0.788 Intermediate Similarity NPD4420 Approved
0.7877 Intermediate Similarity NPD4663 Approved
0.7865 Intermediate Similarity NPD7309 Approved
0.7857 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3110 Approved
0.7771 Intermediate Similarity NPD3109 Approved
0.7765 Intermediate Similarity NPD8053 Approved
0.7765 Intermediate Similarity NPD8054 Approved
0.773 Intermediate Similarity NPD5241 Discontinued
0.7713 Intermediate Similarity NPD5005 Approved
0.7713 Intermediate Similarity NPD5006 Approved
0.7711 Intermediate Similarity NPD3639 Approved
0.7711 Intermediate Similarity NPD6030 Approved
0.7711 Intermediate Similarity NPD3640 Phase 3
0.7711 Intermediate Similarity NPD3641 Approved
0.7711 Intermediate Similarity NPD6031 Approved
0.7711 Intermediate Similarity NPD4727 Phase 1
0.7688 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD2898 Approved
0.7644 Intermediate Similarity NPD6071 Discontinued
0.7634 Intermediate Similarity NPD2973 Approved
0.7634 Intermediate Similarity NPD2975 Approved
0.7634 Intermediate Similarity NPD2974 Approved
0.7616 Intermediate Similarity NPD7831 Phase 2
0.7616 Intermediate Similarity NPD7833 Phase 2
0.7616 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD2563 Approved
0.7602 Intermediate Similarity NPD2560 Approved
0.758 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD5754 Discontinued
0.7554 Intermediate Similarity NPD2488 Approved
0.7554 Intermediate Similarity NPD2490 Approved
0.7544 Intermediate Similarity NPD2978 Approved
0.7544 Intermediate Similarity NPD2977 Approved
0.7532 Intermediate Similarity NPD5718 Phase 2
0.7529 Intermediate Similarity NPD4772 Phase 2
0.7529 Intermediate Similarity NPD4773 Phase 2
0.7515 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD5604 Discontinued
0.7513 Intermediate Similarity NPD4580 Approved
0.7487 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD7802 Discontinued
0.7484 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD2494 Approved
0.7474 Intermediate Similarity NPD3452 Approved
0.7474 Intermediate Similarity NPD3450 Approved
0.7474 Intermediate Similarity NPD2493 Approved
0.7443 Intermediate Similarity NPD4010 Discontinued
0.7414 Intermediate Similarity NPD4055 Discovery
0.7396 Intermediate Similarity NPD5976 Discontinued
0.7386 Intermediate Similarity NPD6107 Approved
0.7381 Intermediate Similarity NPD1424 Approved
0.7375 Intermediate Similarity NPD4475 Approved
0.7375 Intermediate Similarity NPD4474 Approved
0.7371 Intermediate Similarity NPD7400 Phase 3
0.7365 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD3845 Phase 1
0.7363 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4582 Approved
0.7358 Intermediate Similarity NPD4583 Approved
0.7356 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4166 Phase 2
0.7337 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4859 Phase 1
0.733 Intermediate Similarity NPD4107 Approved
0.7322 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7322 Intermediate Similarity NPD7281 Phase 3
0.7322 Intermediate Similarity NPD7280 Phase 3
0.7321 Intermediate Similarity NPD3124 Discontinued
0.7318 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD3763 Approved
0.7306 Intermediate Similarity NPD4002 Approved
0.7306 Intermediate Similarity NPD4004 Approved
0.7301 Intermediate Similarity NPD6895 Approved
0.7301 Intermediate Similarity NPD6896 Approved
0.7296 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD8095 Phase 1
0.7262 Intermediate Similarity NPD7124 Phase 2
0.7258 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD6297 Approved
0.7239 Intermediate Similarity NPD2492 Phase 1
0.7232 Intermediate Similarity NPD5677 Discontinued
0.7228 Intermediate Similarity NPD5917 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7598 Phase 2
0.7211 Intermediate Similarity NPD5582 Discontinued
0.7202 Intermediate Similarity NPD4482 Phase 3
0.72 Intermediate Similarity NPD5977 Approved
0.72 Intermediate Similarity NPD5978 Approved
0.7189 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD4236 Phase 3
0.7186 Intermediate Similarity NPD4237 Approved
0.7186 Intermediate Similarity NPD5177 Phase 3
0.7179 Intermediate Similarity NPD3705 Approved
0.7176 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7047 Phase 3
0.7158 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4108 Discontinued
0.7143 Intermediate Similarity NPD5312 Approved
0.7143 Intermediate Similarity NPD5313 Approved
0.7143 Intermediate Similarity NPD6748 Discontinued
0.7135 Intermediate Similarity NPD6037 Discontinued
0.7122 Intermediate Similarity NPD6997 Phase 2
0.7111 Intermediate Similarity NPD6687 Approved
0.7111 Intermediate Similarity NPD6688 Approved
0.71 Intermediate Similarity NPD3816 Phase 1
0.71 Intermediate Similarity NPD7827 Phase 1
0.71 Intermediate Similarity NPD3815 Phase 1
0.7099 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6851 Approved
0.7097 Intermediate Similarity NPD6853 Approved
0.7086 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD3384 Approved
0.7086 Intermediate Similarity NPD3382 Approved
0.7086 Intermediate Similarity NPD3383 Approved
0.7077 Intermediate Similarity NPD3057 Approved
0.7074 Intermediate Similarity NPD3349 Phase 2
0.7066 Intermediate Similarity NPD1375 Discontinued
0.7052 Intermediate Similarity NPD4210 Discontinued
0.7049 Intermediate Similarity NPD6042 Phase 2
0.7049 Intermediate Similarity NPD42 Phase 2
0.7048 Intermediate Similarity NPD1753 Discontinued
0.7045 Intermediate Similarity NPD5772 Approved
0.7045 Intermediate Similarity NPD5773 Approved
0.7041 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD5155 Approved
0.7037 Intermediate Similarity NPD5156 Approved
0.7035 Intermediate Similarity NPD6090 Discontinued
0.703 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6386 Approved
0.7029 Intermediate Similarity NPD6385 Approved
0.7029 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7110 Phase 1
0.7022 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3885 Approved
0.7011 Intermediate Similarity NPD4005 Discontinued
0.7005 Intermediate Similarity NPD4040 Phase 1
0.6994 Remote Similarity NPD1914 Approved
0.699 Remote Similarity NPD3533 Approved
0.699 Remote Similarity NPD2972 Approved
0.6984 Remote Similarity NPD7291 Discontinued
0.6982 Remote Similarity NPD6674 Discontinued
0.6982 Remote Similarity NPD3060 Approved
0.6977 Remote Similarity NPD4123 Phase 3
0.6975 Remote Similarity NPD2606 Approved
0.6975 Remote Similarity NPD2605 Approved
0.6975 Remote Similarity NPD3594 Approved
0.6975 Remote Similarity NPD3595 Approved
0.6974 Remote Similarity NPD5457 Discontinued
0.6964 Remote Similarity NPD4726 Approved
0.6964 Remote Similarity NPD4721 Approved
0.6964 Remote Similarity NPD4725 Approved
0.6961 Remote Similarity NPD6747 Phase 1
0.6959 Remote Similarity NPD6667 Approved
0.6959 Remote Similarity NPD6666 Approved
0.6957 Remote Similarity NPD7247 Discontinued
0.6949 Remote Similarity NPD4585 Approved
0.6947 Remote Similarity NPD3408 Clinical (unspecified phase)
0.6941 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3635 Approved
0.6914 Remote Similarity NPD3636 Approved
0.6914 Remote Similarity NPD3637 Approved
0.6905 Remote Similarity NPD1632 Clinical (unspecified phase)

  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