Structure

Physi-Chem Properties

Molecular Weight:  353.13
Volume:  342.267
LogP:  2.614
LogD:  2.624
LogS:  -3.941
# Rotatable Bonds:  0
TPSA:  60.39
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.784
Synthetic Accessibility Score:  3.87
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:  -4.873
MDCK Permeability:  3.2356681913370267e-05
Pgp-inhibitor:  0.029
Pgp-substrate:  0.182
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.981
Plasma Protein Binding (PPB):  89.73221588134766%
Volume Distribution (VD):  2.16
Pgp-substrate:  9.911900520324707%

ADMET: Metabolism

CYP1A2-inhibitor:  0.914
CYP1A2-substrate:  0.609
CYP2C19-inhibitor:  0.948
CYP2C19-substrate:  0.868
CYP2C9-inhibitor:  0.234
CYP2C9-substrate:  0.854
CYP2D6-inhibitor:  0.951
CYP2D6-substrate:  0.894
CYP3A4-inhibitor:  0.962
CYP3A4-substrate:  0.899

ADMET: Excretion

Clearance (CL):  17.024
Half-life (T1/2):  0.221

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.159
Drug-inuced Liver Injury (DILI):  0.531
AMES Toxicity:  0.168
Rat Oral Acute Toxicity:  0.647
Maximum Recommended Daily Dose:  0.956
Skin Sensitization:  0.407
Carcinogencity:  0.915
Eye Corrosion:  0.004
Eye Irritation:  0.017
Respiratory Toxicity:  0.963

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

  Natural Product: NPC294790

Natural Product ID:  NPC294790
Common Name*:   Chelidonine
IUPAC Name:   n.a.
Synonyms:   (+)-Chelidonine; Chelidonine
Standard InCHIKey:  GHKISGDRQRSCII-ZOCIIQOWSA-N
Standard InCHI:  InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
SMILES:  CN1Cc2c([C@@H]3[C@H]1c1cc4OCOc4cc1C[C@@H]3O)ccc1c2OCO1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL496867
PubChem CID:   197810
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002665] Benzophenanthridine alkaloids
        • [CHEMONTID:0002666] Hexahydrobenzophenanthridine alkaloids

*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
NPO11457 Chelidonium majus Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11457 Chelidonium majus Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11457 Chelidonium majus Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11457 Chelidonium majus Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 < 200.0 ug.mL-1 PMID[541417]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 7300.0 nM PMID[541418]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 29.78 % PMID[541419]
NPT65 Cell Line HepG2 Homo sapiens IC50 > 40000.0 nM PMID[541420]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[541420]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 40000.0 nM PMID[541420]
NPT111 Cell Line K562 Homo sapiens IC50 = 17650.0 nM PMID[541420]
NPT927 Cell Line PBMC Homo sapiens IC50 > 40000.0 nM PMID[541420]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 6.72 % PMID[541419]
NPT21742 CELL-LINE L02 Homo sapiens IC50 > 40000.0 nM PMID[541420]

☑ 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 NPC294790 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 NPC148693
1.0 High Similarity NPC118633
0.9578 High Similarity NPC275132
0.9231 High Similarity NPC248642
0.9226 High Similarity NPC126284
0.9207 High Similarity NPC210918
0.9176 High Similarity NPC156576
0.9146 High Similarity NPC24264
0.9146 High Similarity NPC476432
0.9141 High Similarity NPC320104
0.9102 High Similarity NPC2314
0.9096 High Similarity NPC311991
0.9091 High Similarity NPC190332
0.9091 High Similarity NPC247389
0.9091 High Similarity NPC181653
0.9085 High Similarity NPC225774
0.9085 High Similarity NPC16805
0.9085 High Similarity NPC302527
0.9085 High Similarity NPC167546
0.9053 High Similarity NPC320223
0.9053 High Similarity NPC114364
0.9048 High Similarity NPC229166
0.9048 High Similarity NPC199465
0.9048 High Similarity NPC128560
0.9048 High Similarity NPC187678
0.903 High Similarity NPC219341
0.8976 High Similarity NPC298979
0.8976 High Similarity NPC100566
0.896 High Similarity NPC214116
0.8935 High Similarity NPC304675
0.8922 High Similarity NPC82533
0.8922 High Similarity NPC158148
0.8922 High Similarity NPC266176
0.8922 High Similarity NPC290759
0.8902 High Similarity NPC266753
0.8902 High Similarity NPC306902
0.8902 High Similarity NPC160298
0.8902 High Similarity NPC232924
0.8902 High Similarity NPC477559
0.8882 High Similarity NPC237044
0.8834 High Similarity NPC234392
0.8834 High Similarity NPC31311
0.8834 High Similarity NPC146288
0.883 High Similarity NPC474325
0.883 High Similarity NPC15919
0.8817 High Similarity NPC19520
0.8817 High Similarity NPC470739
0.8817 High Similarity NPC149090
0.8817 High Similarity NPC477640
0.8817 High Similarity NPC225597
0.881 High Similarity NPC58766
0.881 High Similarity NPC475686
0.8786 High Similarity NPC476575
0.8786 High Similarity NPC116284
0.8779 High Similarity NPC474745
0.8779 High Similarity NPC244554
0.8773 High Similarity NPC41178
0.8773 High Similarity NPC138487
0.8773 High Similarity NPC216459
0.8757 High Similarity NPC474475
0.8757 High Similarity NPC6152
0.875 High Similarity NPC57812
0.875 High Similarity NPC474324
0.8743 High Similarity NPC238530
0.8743 High Similarity NPC232514
0.8743 High Similarity NPC276944
0.8736 High Similarity NPC135772
0.8728 High Similarity NPC312918
0.8728 High Similarity NPC477561
0.8728 High Similarity NPC155442
0.8728 High Similarity NPC476574
0.8713 High Similarity NPC477558
0.8706 High Similarity NPC65403
0.8698 High Similarity NPC475845
0.8686 High Similarity NPC9867
0.8675 High Similarity NPC215829
0.8675 High Similarity NPC97072
0.8671 High Similarity NPC267408
0.8667 High Similarity NPC476572
0.8663 High Similarity NPC474470
0.8659 High Similarity NPC325871
0.8659 High Similarity NPC99659
0.8652 High Similarity NPC117717
0.865 High Similarity NPC233029
0.865 High Similarity NPC210148
0.8647 High Similarity NPC474708
0.8647 High Similarity NPC75958
0.8639 High Similarity NPC158376
0.8639 High Similarity NPC12053
0.8639 High Similarity NPC81218
0.8639 High Similarity NPC145832
0.8639 High Similarity NPC306555
0.8639 High Similarity NPC150879
0.8639 High Similarity NPC205421
0.8639 High Similarity NPC117188
0.8639 High Similarity NPC474931
0.8634 High Similarity NPC475959
0.8631 High Similarity NPC78222
0.8631 High Similarity NPC136508
0.8631 High Similarity NPC212794
0.8631 High Similarity NPC196447
0.8631 High Similarity NPC13504
0.8631 High Similarity NPC96603
0.8631 High Similarity NPC306843
0.8631 High Similarity NPC477563
0.8631 High Similarity NPC253043
0.8629 High Similarity NPC474746
0.8629 High Similarity NPC475981
0.8614 High Similarity NPC477080
0.8596 High Similarity NPC475754
0.8588 High Similarity NPC237579
0.8588 High Similarity NPC241055
0.858 High Similarity NPC304659
0.858 High Similarity NPC86144
0.858 High Similarity NPC476002
0.8571 High Similarity NPC233718
0.8571 High Similarity NPC324144
0.8563 High Similarity NPC4304
0.8563 High Similarity NPC249274
0.8563 High Similarity NPC205167
0.8545 High Similarity NPC78733
0.8539 High Similarity NPC82763
0.8538 High Similarity NPC152212
0.8531 High Similarity NPC57036
0.8531 High Similarity NPC230098
0.8521 High Similarity NPC168409
0.8514 High Similarity NPC474506
0.8514 High Similarity NPC32413
0.8506 High Similarity NPC23219
0.8503 High Similarity NPC111485
0.8483 Intermediate Similarity NPC186546
0.8483 Intermediate Similarity NPC476576
0.8476 Intermediate Similarity NPC81733
0.8476 Intermediate Similarity NPC326316
0.8462 Intermediate Similarity NPC233650
0.8462 Intermediate Similarity NPC1229
0.8462 Intermediate Similarity NPC189470
0.8457 Intermediate Similarity NPC470879
0.8457 Intermediate Similarity NPC258695
0.8453 Intermediate Similarity NPC162653
0.8452 Intermediate Similarity NPC166014
0.8452 Intermediate Similarity NPC27410
0.8448 Intermediate Similarity NPC112575
0.8434 Intermediate Similarity NPC76079
0.8434 Intermediate Similarity NPC244112
0.8434 Intermediate Similarity NPC93593
0.8424 Intermediate Similarity NPC148898
0.8412 Intermediate Similarity NPC247972
0.8412 Intermediate Similarity NPC134858
0.8405 Intermediate Similarity NPC7467
0.8402 Intermediate Similarity NPC60186
0.8391 Intermediate Similarity NPC49353
0.8382 Intermediate Similarity NPC239775
0.8353 Intermediate Similarity NPC218614
0.8352 Intermediate Similarity NPC99179
0.8344 Intermediate Similarity NPC476151
0.8344 Intermediate Similarity NPC210437
0.8344 Intermediate Similarity NPC476144
0.8344 Intermediate Similarity NPC51957
0.8344 Intermediate Similarity NPC106295
0.8344 Intermediate Similarity NPC16107
0.8343 Intermediate Similarity NPC241704
0.8333 Intermediate Similarity NPC192135
0.8333 Intermediate Similarity NPC477020
0.8333 Intermediate Similarity NPC66341
0.8324 Intermediate Similarity NPC168753
0.8324 Intermediate Similarity NPC26240
0.8324 Intermediate Similarity NPC477562
0.8324 Intermediate Similarity NPC118274
0.8324 Intermediate Similarity NPC69712
0.8323 Intermediate Similarity NPC193949
0.8323 Intermediate Similarity NPC207757
0.8323 Intermediate Similarity NPC278799
0.8323 Intermediate Similarity NPC5238
0.8323 Intermediate Similarity NPC204828
0.8323 Intermediate Similarity NPC469817
0.8323 Intermediate Similarity NPC39701
0.8323 Intermediate Similarity NPC172765
0.8323 Intermediate Similarity NPC110416
0.8323 Intermediate Similarity NPC189266
0.8323 Intermediate Similarity NPC54379
0.8323 Intermediate Similarity NPC2413
0.8323 Intermediate Similarity NPC127674
0.8323 Intermediate Similarity NPC276588
0.8323 Intermediate Similarity NPC184026
0.8323 Intermediate Similarity NPC249797
0.8323 Intermediate Similarity NPC295691
0.8314 Intermediate Similarity NPC210140
0.8314 Intermediate Similarity NPC252960
0.8305 Intermediate Similarity NPC179704
0.8304 Intermediate Similarity NPC180306
0.8304 Intermediate Similarity NPC169743
0.8286 Intermediate Similarity NPC329969
0.8284 Intermediate Similarity NPC59028
0.8284 Intermediate Similarity NPC92191
0.8274 Intermediate Similarity NPC323443
0.8274 Intermediate Similarity NPC180756
0.8258 Intermediate Similarity NPC73492
0.8258 Intermediate Similarity NPC299990
0.8256 Intermediate Similarity NPC264850

  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 NPC294790 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
0.869 High Similarity NPD3051 Approved
0.8529 High Similarity NPD2970 Approved
0.8529 High Similarity NPD2969 Approved
0.8372 Intermediate Similarity NPD2489 Approved
0.8372 Intermediate Similarity NPD27 Approved
0.8344 Intermediate Similarity NPD4584 Approved
0.8272 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD4481 Phase 3
0.8199 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8066 Intermediate Similarity NPD4663 Approved
0.8059 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD4773 Phase 2
0.8047 Intermediate Similarity NPD4772 Phase 2
0.8022 Intermediate Similarity NPD7906 Approved
0.8 Intermediate Similarity NPD7313 Approved
0.8 Intermediate Similarity NPD4577 Approved
0.8 Intermediate Similarity NPD4578 Approved
0.8 Intermediate Similarity NPD7312 Approved
0.8 Intermediate Similarity NPD7310 Approved
0.8 Intermediate Similarity NPD7311 Approved
0.7956 Intermediate Similarity NPD7309 Approved
0.7943 Intermediate Similarity NPD6071 Discontinued
0.7939 Intermediate Similarity NPD5241 Discontinued
0.7921 Intermediate Similarity NPD8156 Discontinued
0.7907 Intermediate Similarity NPD2563 Approved
0.7907 Intermediate Similarity NPD2560 Approved
0.7892 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD4420 Approved
0.7865 Intermediate Similarity NPD8251 Approved
0.7865 Intermediate Similarity NPD8252 Approved
0.7865 Intermediate Similarity NPD8099 Discontinued
0.7857 Intermediate Similarity NPD8053 Approved
0.7857 Intermediate Similarity NPD8054 Approved
0.7829 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD7831 Phase 2
0.7816 Intermediate Similarity NPD7833 Phase 2
0.7802 Intermediate Similarity NPD2971 Approved
0.7802 Intermediate Similarity NPD2968 Approved
0.7801 Intermediate Similarity NPD5006 Approved
0.7801 Intermediate Similarity NPD5005 Approved
0.7759 Intermediate Similarity NPD6788 Approved
0.7746 Intermediate Similarity NPD2977 Approved
0.7746 Intermediate Similarity NPD2978 Approved
0.7742 Intermediate Similarity NPD2488 Approved
0.7742 Intermediate Similarity NPD2490 Approved
0.7738 Intermediate Similarity NPD2421 Approved
0.7738 Intermediate Similarity NPD2420 Approved
0.7705 Intermediate Similarity NPD7280 Phase 3
0.7705 Intermediate Similarity NPD7281 Phase 3
0.7688 Intermediate Similarity NPD7298 Approved
0.7672 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD2973 Approved
0.7632 Intermediate Similarity NPD2975 Approved
0.7632 Intermediate Similarity NPD2974 Approved
0.7616 Intermediate Similarity NPD4017 Approved
0.7605 Intermediate Similarity NPD4237 Approved
0.7605 Intermediate Similarity NPD4236 Phase 3
0.7604 Intermediate Similarity NPD4580 Approved
0.7602 Intermediate Similarity NPD4727 Phase 1
0.7579 Intermediate Similarity NPD5582 Discontinued
0.7576 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD2898 Approved
0.7514 Intermediate Similarity NPD5604 Discontinued
0.75 Intermediate Similarity NPD3641 Approved
0.75 Intermediate Similarity NPD5177 Phase 3
0.75 Intermediate Similarity NPD3639 Approved
0.75 Intermediate Similarity NPD6031 Approved
0.75 Intermediate Similarity NPD3640 Phase 3
0.75 Intermediate Similarity NPD6030 Approved
0.7486 Intermediate Similarity NPD6107 Approved
0.7474 Intermediate Similarity NPD2494 Approved
0.7474 Intermediate Similarity NPD3452 Approved
0.7474 Intermediate Similarity NPD3450 Approved
0.7474 Intermediate Similarity NPD2493 Approved
0.7461 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD7827 Phase 1
0.7449 Intermediate Similarity NPD4583 Approved
0.7449 Intermediate Similarity NPD4582 Approved
0.7447 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD4010 Discontinued
0.7439 Intermediate Similarity NPD3110 Approved
0.7439 Intermediate Similarity NPD3109 Approved
0.7426 Intermediate Similarity NPD7047 Phase 3
0.7398 Intermediate Similarity NPD4004 Approved
0.7398 Intermediate Similarity NPD4002 Approved
0.7384 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD6997 Phase 2
0.7368 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4040 Phase 1
0.7345 Intermediate Similarity NPD5773 Approved
0.7345 Intermediate Similarity NPD5772 Approved
0.733 Intermediate Similarity NPD7296 Approved
0.7326 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD3060 Approved
0.7288 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD3057 Approved
0.7258 Intermediate Similarity NPD6297 Approved
0.7257 Intermediate Similarity NPD4210 Discontinued
0.7256 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD5754 Discontinued
0.7243 Intermediate Similarity NPD5312 Approved
0.7243 Intermediate Similarity NPD5313 Approved
0.7229 Intermediate Similarity NPD2238 Phase 2
0.7228 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4055 Discovery
0.7216 Intermediate Similarity NPD4005 Discontinued
0.7212 Intermediate Similarity NPD5718 Phase 2
0.7209 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD5160 Discontinued
0.72 Intermediate Similarity NPD5976 Discontinued
0.7198 Intermediate Similarity NPD7802 Discontinued
0.7196 Intermediate Similarity NPD6853 Approved
0.7196 Intermediate Similarity NPD6851 Approved
0.7193 Intermediate Similarity NPD6674 Discontinued
0.7184 Intermediate Similarity NPD1424 Approved
0.7182 Intermediate Similarity NPD7400 Phase 3
0.7181 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD2972 Approved
0.7172 Intermediate Similarity NPD3533 Approved
0.7169 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4475 Approved
0.7169 Intermediate Similarity NPD4474 Approved
0.7168 Intermediate Similarity NPD6667 Approved
0.7168 Intermediate Similarity NPD6666 Approved
0.7168 Intermediate Similarity NPD3845 Phase 1
0.7167 Intermediate Similarity NPD4967 Phase 2
0.7167 Intermediate Similarity NPD4965 Approved
0.7167 Intermediate Similarity NPD4966 Approved
0.7158 Intermediate Similarity NPD4166 Phase 2
0.7157 Intermediate Similarity NPD4107 Approved
0.715 Intermediate Similarity NPD3763 Approved
0.715 Intermediate Similarity NPD6723 Discontinued
0.7143 Intermediate Similarity NPD6090 Discontinued
0.7126 Intermediate Similarity NPD3124 Discontinued
0.7118 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD8095 Phase 1
0.7101 Intermediate Similarity NPD6896 Approved
0.7101 Intermediate Similarity NPD6895 Approved
0.7098 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD37 Approved
0.7093 Intermediate Similarity NPD4162 Approved
0.7091 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD7549 Discontinued
0.7088 Intermediate Similarity NPD5709 Phase 3
0.7086 Intermediate Similarity NPD7019 Approved
0.7086 Intermediate Similarity NPD7020 Approved
0.7085 Intermediate Similarity NPD3448 Approved
0.7085 Intermediate Similarity NPD2491 Approved
0.7079 Intermediate Similarity NPD4859 Phase 1
0.7069 Intermediate Similarity NPD7124 Phase 2
0.7068 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6042 Phase 2
0.7059 Intermediate Similarity NPD4108 Discontinued
0.7059 Intermediate Similarity NPD42 Phase 2
0.7059 Intermediate Similarity NPD1753 Discontinued
0.7052 Intermediate Similarity NPD6748 Discontinued
0.7052 Intermediate Similarity NPD6331 Phase 2
0.705 Intermediate Similarity NPD7497 Discontinued
0.7049 Intermediate Similarity NPD4666 Phase 3
0.7048 Intermediate Similarity NPD5156 Approved
0.7048 Intermediate Similarity NPD5155 Approved
0.7047 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD4482 Phase 3
0.7035 Intermediate Similarity NPD7037 Approved
0.7029 Intermediate Similarity NPD7598 Phase 2
0.7027 Intermediate Similarity NPD6688 Approved
0.7027 Intermediate Similarity NPD6687 Approved
0.7021 Intermediate Similarity NPD7479 Phase 2
0.7017 Intermediate Similarity NPD5977 Approved
0.7017 Intermediate Similarity NPD5978 Approved
0.7014 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD2677 Approved
0.701 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7228 Approved
0.7 Intermediate Similarity NPD3382 Approved
0.7 Intermediate Similarity NPD3384 Approved
0.7 Intermediate Similarity NPD3383 Approved
0.6995 Remote Similarity NPD6234 Discontinued
0.6991 Remote Similarity NPD6625 Approved
0.6989 Remote Similarity NPD4123 Phase 3
0.6989 Remote Similarity NPD6365 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2605 Approved
0.6988 Remote Similarity NPD3594 Approved
0.6988 Remote Similarity NPD3595 Approved
0.6988 Remote Similarity NPD2606 Approved
0.6984 Remote Similarity NPD7007 Discovery
0.6977 Remote Similarity NPD4725 Approved
0.6977 Remote Similarity NPD1375 Discontinued
0.6977 Remote Similarity NPD4726 Approved
0.6977 Remote Similarity NPD4721 Approved
0.6976 Remote Similarity NPD5676 Approved
0.6951 Remote Similarity NPD7258 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