Structure

Physi-Chem Properties

Molecular Weight:  839.27
Volume:  766.391
LogP:  0.307
LogD:  1.29
LogS:  -2.971
# Rotatable Bonds:  7
TPSA:  265.27
# H-Bond Aceptor:  19
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  21

MedChem Properties

QED Drug-Likeness Score:  0.159
Synthetic Accessibility Score:  6.285
Fsp3:  0.639
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.419
MDCK Permeability:  2.763683141893125e-06
Pgp-inhibitor:  0.103
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.83
20% Bioavailability (F20%):  0.991
30% Bioavailability (F30%):  0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  62.3876953125%
Volume Distribution (VD):  0.299
Pgp-substrate:  41.37214660644531%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.018
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.094
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.043
CYP3A4-inhibitor:  0.147
CYP3A4-substrate:  0.043

ADMET: Excretion

Clearance (CL):  2.395
Half-life (T1/2):  0.29

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.889
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.098
Maximum Recommended Daily Dose:  0.448
Skin Sensitization:  0.299
Carcinogencity:  0.024
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.035

Download Data

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

  Natural Product: NPC275132

Natural Product ID:  NPC275132
Common Name*:   Norchelidonine
IUPAC Name:   n.a.
Synonyms:   Norchelidonine
Standard InCHIKey:  DBJHCHBDQALOAS-XWIAVFTESA-N
Standard InCHI:  InChI=1S/C19H17NO5/c21-13-3-9-4-15-16(24-7-23-15)5-11(9)18-17(13)10-1-2-14-19(25-8-22-14)12(10)6-20-18/h1-2,4-5,13,17-18,20-21H,3,6-8H2/t13-,17-,18+/m1/s1
SMILES:  O[C@@H]1Cc2cc3OCOc3cc2[C@H]2[C@@H]1c1ccc3c(c1CN2)OCO3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1922603
PubChem CID:   57396731
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
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 16500.0 nM PMID[574183]

☑ 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 NPC275132 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
0.9578 High Similarity NPC294790
0.9578 High Similarity NPC118633
0.9578 High Similarity NPC148693
0.9181 High Similarity NPC476575
0.9112 High Similarity NPC477558
0.9048 High Similarity NPC6152
0.9017 High Similarity NPC135772
0.9012 High Similarity NPC477561
0.9012 High Similarity NPC155442
0.9012 High Similarity NPC312918
0.9012 High Similarity NPC476574
0.8953 High Similarity NPC267408
0.8935 High Similarity NPC152212
0.8927 High Similarity NPC117717
0.887 High Similarity NPC475754
0.8869 High Similarity NPC86144
0.8869 High Similarity NPC304659
0.8862 High Similarity NPC320104
0.8862 High Similarity NPC189470
0.8851 High Similarity NPC248642
0.8844 High Similarity NPC126284
0.8824 High Similarity NPC311991
0.8817 High Similarity NPC190332
0.8817 High Similarity NPC181653
0.8817 High Similarity NPC210918
0.8807 High Similarity NPC57036
0.88 High Similarity NPC156576
0.8793 High Similarity NPC474506
0.8793 High Similarity NPC32413
0.8786 High Similarity NPC23219
0.8757 High Similarity NPC24264
0.8757 High Similarity NPC476576
0.8757 High Similarity NPC186546
0.8757 High Similarity NPC476432
0.8736 High Similarity NPC470879
0.8736 High Similarity NPC258695
0.8728 High Similarity NPC112575
0.8721 High Similarity NPC2314
0.8706 High Similarity NPC247389
0.8698 High Similarity NPC225774
0.8698 High Similarity NPC167546
0.8698 High Similarity NPC16805
0.8698 High Similarity NPC302527
0.8678 High Similarity NPC320223
0.8678 High Similarity NPC114364
0.8671 High Similarity NPC128560
0.8671 High Similarity NPC199465
0.8671 High Similarity NPC229166
0.8671 High Similarity NPC187678
0.8647 High Similarity NPC219341
0.8613 High Similarity NPC192135
0.8613 High Similarity NPC66341
0.8613 High Similarity NPC477020
0.8605 High Similarity NPC477562
0.8605 High Similarity NPC69712
0.8605 High Similarity NPC26240
0.8596 High Similarity NPC214116
0.8596 High Similarity NPC298979
0.8596 High Similarity NPC100566
0.8571 High Similarity NPC15919
0.8563 High Similarity NPC304675
0.8563 High Similarity NPC329969
0.8563 High Similarity NPC234392
0.8563 High Similarity NPC31311
0.8547 High Similarity NPC475686
0.8547 High Similarity NPC158148
0.8547 High Similarity NPC58766
0.8547 High Similarity NPC290759
0.8547 High Similarity NPC266176
0.8547 High Similarity NPC82533
0.8521 High Similarity NPC266753
0.8521 High Similarity NPC477559
0.8521 High Similarity NPC160298
0.8521 High Similarity NPC306902
0.8521 High Similarity NPC232924
0.8514 High Similarity NPC237044
0.8497 Intermediate Similarity NPC474475
0.8466 Intermediate Similarity NPC474325
0.8452 Intermediate Similarity NPC203784
0.8452 Intermediate Similarity NPC146288
0.8452 Intermediate Similarity NPC170503
0.8452 Intermediate Similarity NPC126519
0.8448 Intermediate Similarity NPC19520
0.8448 Intermediate Similarity NPC477640
0.8448 Intermediate Similarity NPC470739
0.8448 Intermediate Similarity NPC149090
0.8448 Intermediate Similarity NPC225597
0.843 Intermediate Similarity NPC476573
0.843 Intermediate Similarity NPC81247
0.843 Intermediate Similarity NPC35627
0.8427 Intermediate Similarity NPC116284
0.8418 Intermediate Similarity NPC244554
0.8418 Intermediate Similarity NPC474745
0.8418 Intermediate Similarity NPC474507
0.8412 Intermediate Similarity NPC215829
0.8412 Intermediate Similarity NPC97072
0.8393 Intermediate Similarity NPC41178
0.8393 Intermediate Similarity NPC216459
0.8393 Intermediate Similarity NPC138487
0.8382 Intermediate Similarity NPC204947
0.8382 Intermediate Similarity NPC474324
0.8382 Intermediate Similarity NPC57812
0.8372 Intermediate Similarity NPC232514
0.8372 Intermediate Similarity NPC276944
0.8372 Intermediate Similarity NPC238530
0.8343 Intermediate Similarity NPC65403
0.8333 Intermediate Similarity NPC475845
0.8333 Intermediate Similarity NPC9867
0.8305 Intermediate Similarity NPC474470
0.8305 Intermediate Similarity NPC173416
0.8305 Intermediate Similarity NPC148709
0.8305 Intermediate Similarity NPC476577
0.8294 Intermediate Similarity NPC476572
0.8286 Intermediate Similarity NPC474708
0.8286 Intermediate Similarity NPC75958
0.8284 Intermediate Similarity NPC99659
0.8284 Intermediate Similarity NPC325871
0.8278 Intermediate Similarity NPC474746
0.8278 Intermediate Similarity NPC475981
0.8276 Intermediate Similarity NPC474931
0.8276 Intermediate Similarity NPC306555
0.8276 Intermediate Similarity NPC12053
0.8276 Intermediate Similarity NPC81218
0.8276 Intermediate Similarity NPC158376
0.8276 Intermediate Similarity NPC205421
0.8276 Intermediate Similarity NPC150879
0.8276 Intermediate Similarity NPC145832
0.8276 Intermediate Similarity NPC117188
0.8274 Intermediate Similarity NPC233029
0.8274 Intermediate Similarity NPC210148
0.8266 Intermediate Similarity NPC96603
0.8266 Intermediate Similarity NPC212794
0.8266 Intermediate Similarity NPC168409
0.8266 Intermediate Similarity NPC78222
0.8266 Intermediate Similarity NPC477563
0.8266 Intermediate Similarity NPC13504
0.8266 Intermediate Similarity NPC136508
0.8266 Intermediate Similarity NPC196447
0.8266 Intermediate Similarity NPC306843
0.8266 Intermediate Similarity NPC253043
0.8253 Intermediate Similarity NPC475959
0.8246 Intermediate Similarity NPC477080
0.8242 Intermediate Similarity NPC237579
0.8229 Intermediate Similarity NPC241055
0.8225 Intermediate Similarity NPC477564
0.8225 Intermediate Similarity NPC2295
0.8222 Intermediate Similarity NPC233718
0.8218 Intermediate Similarity NPC476002
0.8208 Intermediate Similarity NPC324144
0.8204 Intermediate Similarity NPC60538
0.8204 Intermediate Similarity NPC207824
0.8198 Intermediate Similarity NPC205167
0.8198 Intermediate Similarity NPC249274
0.8198 Intermediate Similarity NPC4304
0.8197 Intermediate Similarity NPC281581
0.8197 Intermediate Similarity NPC82763
0.8187 Intermediate Similarity NPC230098
0.8176 Intermediate Similarity NPC78733
0.8161 Intermediate Similarity NPC247972
0.814 Intermediate Similarity NPC111485
0.8118 Intermediate Similarity NPC162653
0.8114 Intermediate Similarity NPC195392
0.8107 Intermediate Similarity NPC326316
0.8107 Intermediate Similarity NPC76213
0.8107 Intermediate Similarity NPC81733
0.8107 Intermediate Similarity NPC277669
0.8103 Intermediate Similarity NPC233650
0.8103 Intermediate Similarity NPC1229
0.8092 Intermediate Similarity NPC27410
0.8092 Intermediate Similarity NPC166014
0.8083 Intermediate Similarity NPC46990
0.807 Intermediate Similarity NPC93593
0.807 Intermediate Similarity NPC244112
0.807 Intermediate Similarity NPC76079
0.8063 Intermediate Similarity NPC244606
0.8063 Intermediate Similarity NPC156728
0.8059 Intermediate Similarity NPC148898
0.8057 Intermediate Similarity NPC134858
0.8046 Intermediate Similarity NPC60186
0.8045 Intermediate Similarity NPC49353
0.8036 Intermediate Similarity NPC7467
0.8034 Intermediate Similarity NPC239775
0.8011 Intermediate Similarity NPC56887
0.8011 Intermediate Similarity NPC193853
0.8011 Intermediate Similarity NPC99179
0.8011 Intermediate Similarity NPC223077
0.8 Intermediate Similarity NPC241704
0.8 Intermediate Similarity NPC218614
0.8 Intermediate Similarity NPC283999
0.7979 Intermediate Similarity NPC11708
0.7978 Intermediate Similarity NPC118274
0.7978 Intermediate Similarity NPC168753
0.7976 Intermediate Similarity NPC476144
0.7976 Intermediate Similarity NPC210437
0.7976 Intermediate Similarity NPC106295
0.7976 Intermediate Similarity NPC51957
0.7976 Intermediate Similarity NPC16107
0.7976 Intermediate Similarity NPC476151
0.7967 Intermediate Similarity NPC179704
0.7966 Intermediate Similarity NPC210140

  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 NPC275132 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
0.8324 Intermediate Similarity NPD3051 Approved
0.8171 Intermediate Similarity NPD2969 Approved
0.8171 Intermediate Similarity NPD2970 Approved
0.8023 Intermediate Similarity NPD2978 Approved
0.8023 Intermediate Similarity NPD2489 Approved
0.8023 Intermediate Similarity NPD27 Approved
0.8023 Intermediate Similarity NPD2977 Approved
0.8012 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD4584 Approved
0.7921 Intermediate Similarity NPD4481 Phase 3
0.7882 Intermediate Similarity NPD4727 Phase 1
0.7861 Intermediate Similarity NPD7298 Approved
0.7838 Intermediate Similarity NPD4663 Approved
0.7831 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6030 Approved
0.7778 Intermediate Similarity NPD6031 Approved
0.7772 Intermediate Similarity NPD4577 Approved
0.7772 Intermediate Similarity NPD4578 Approved
0.7751 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD4773 Phase 2
0.7701 Intermediate Similarity NPD7906 Approved
0.7701 Intermediate Similarity NPD4772 Phase 2
0.7688 Intermediate Similarity NPD7827 Phase 1
0.7676 Intermediate Similarity NPD7310 Approved
0.7676 Intermediate Similarity NPD7312 Approved
0.7676 Intermediate Similarity NPD7313 Approved
0.7676 Intermediate Similarity NPD7311 Approved
0.7647 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD7309 Approved
0.7627 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD6071 Discontinued
0.7596 Intermediate Similarity NPD8156 Discontinued
0.7588 Intermediate Similarity NPD5241 Discontinued
0.7588 Intermediate Similarity NPD5160 Discontinued
0.7574 Intermediate Similarity NPD3060 Approved
0.7571 Intermediate Similarity NPD2560 Approved
0.7571 Intermediate Similarity NPD2563 Approved
0.7565 Intermediate Similarity NPD4420 Approved
0.7556 Intermediate Similarity NPD6107 Approved
0.7544 Intermediate Similarity NPD3845 Phase 1
0.7541 Intermediate Similarity NPD8099 Discontinued
0.7541 Intermediate Similarity NPD8252 Approved
0.7541 Intermediate Similarity NPD8251 Approved
0.754 Intermediate Similarity NPD8054 Approved
0.754 Intermediate Similarity NPD8053 Approved
0.75 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5005 Approved
0.75 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5006 Approved
0.7487 Intermediate Similarity NPD2971 Approved
0.7487 Intermediate Similarity NPD2968 Approved
0.7486 Intermediate Similarity NPD7833 Phase 2
0.7486 Intermediate Similarity NPD7831 Phase 2
0.7486 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD5976 Discontinued
0.7455 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD2488 Approved
0.7435 Intermediate Similarity NPD2490 Approved
0.7433 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.743 Intermediate Similarity NPD6788 Approved
0.7424 Intermediate Similarity NPD4040 Phase 1
0.7419 Intermediate Similarity NPD6297 Approved
0.7399 Intermediate Similarity NPD2420 Approved
0.7399 Intermediate Similarity NPD2421 Approved
0.7394 Intermediate Similarity NPD7281 Phase 3
0.7394 Intermediate Similarity NPD7280 Phase 3
0.7371 Intermediate Similarity NPD6723 Discontinued
0.7371 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4162 Approved
0.736 Intermediate Similarity NPD3382 Approved
0.736 Intermediate Similarity NPD3383 Approved
0.736 Intermediate Similarity NPD3384 Approved
0.7356 Intermediate Similarity NPD1424 Approved
0.7354 Intermediate Similarity NPD6851 Approved
0.7354 Intermediate Similarity NPD6853 Approved
0.7348 Intermediate Similarity NPD5709 Phase 3
0.7333 Intermediate Similarity NPD2973 Approved
0.7333 Intermediate Similarity NPD2974 Approved
0.7333 Intermediate Similarity NPD2975 Approved
0.7316 Intermediate Similarity NPD5087 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD4580 Approved
0.7308 Intermediate Similarity NPD4666 Phase 3
0.7293 Intermediate Similarity NPD5604 Discontinued
0.7288 Intermediate Similarity NPD4017 Approved
0.7283 Intermediate Similarity NPD2677 Approved
0.7282 Intermediate Similarity NPD5582 Discontinued
0.7273 Intermediate Similarity NPD3452 Approved
0.7273 Intermediate Similarity NPD3450 Approved
0.7267 Intermediate Similarity NPD4236 Phase 3
0.7267 Intermediate Similarity NPD4237 Approved
0.7263 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD2898 Approved
0.7235 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD4166 Phase 2
0.7228 Intermediate Similarity NPD4859 Phase 1
0.7219 Intermediate Similarity NPD42 Phase 2
0.7219 Intermediate Similarity NPD6042 Phase 2
0.7202 Intermediate Similarity NPD2845 Phase 2
0.7202 Intermediate Similarity NPD2843 Phase 2
0.72 Intermediate Similarity NPD4002 Approved
0.72 Intermediate Similarity NPD4004 Approved
0.72 Intermediate Similarity NPD7598 Phase 2
0.719 Intermediate Similarity NPD6997 Phase 2
0.7186 Intermediate Similarity NPD2494 Approved
0.7186 Intermediate Similarity NPD2493 Approved
0.7181 Intermediate Similarity NPD7479 Phase 2
0.7175 Intermediate Similarity NPD3640 Phase 3
0.7175 Intermediate Similarity NPD3641 Approved
0.7175 Intermediate Similarity NPD3639 Approved
0.7168 Intermediate Similarity NPD5177 Phase 3
0.7164 Intermediate Similarity NPD4582 Approved
0.7164 Intermediate Similarity NPD4583 Approved
0.7159 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7047 Phase 3
0.7135 Intermediate Similarity NPD4010 Discontinued
0.7113 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7104 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3109 Approved
0.7101 Intermediate Similarity NPD3110 Approved
0.7062 Intermediate Similarity NPD7019 Approved
0.7062 Intermediate Similarity NPD7020 Approved
0.7062 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD3122 Phase 3
0.7041 Intermediate Similarity NPD7296 Approved
0.7039 Intermediate Similarity NPD3686 Approved
0.7039 Intermediate Similarity NPD3687 Approved
0.7037 Intermediate Similarity NPD4873 Discontinued
0.7035 Intermediate Similarity NPD2155 Approved
0.7035 Intermediate Similarity NPD2156 Approved
0.7035 Intermediate Similarity NPD2154 Approved
0.7033 Intermediate Similarity NPD5772 Approved
0.7033 Intermediate Similarity NPD5773 Approved
0.7031 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3977 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD823 Approved
0.7018 Intermediate Similarity NPD817 Approved
0.7016 Intermediate Similarity NPD7038 Approved
0.7016 Intermediate Similarity NPD7039 Approved
0.7011 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4055 Discovery
0.7011 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD1774 Approved
0.7 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4005 Discontinued
0.699 Remote Similarity NPD5525 Clinical (unspecified phase)
0.698 Remote Similarity NPD3057 Approved
0.6978 Remote Similarity NPD4227 Discontinued
0.6978 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6674 Discontinued
0.6971 Remote Similarity NPD5061 Approved
0.6971 Remote Similarity NPD5062 Approved
0.6967 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6966 Remote Similarity NPD2874 Phase 2
0.6965 Remote Similarity NPD5457 Discontinued
0.6957 Remote Similarity NPD4966 Approved
0.6957 Remote Similarity NPD4967 Phase 2
0.6957 Remote Similarity NPD4965 Approved
0.6947 Remote Similarity NPD5312 Approved
0.6947 Remote Similarity NPD3933 Discontinued
0.6947 Remote Similarity NPD5313 Approved
0.6947 Remote Similarity NPD5096 Phase 3
0.6947 Remote Similarity NPD5095 Phase 3
0.6944 Remote Similarity NPD4210 Discontinued
0.694 Remote Similarity NPD4585 Approved
0.6932 Remote Similarity NPD5754 Discontinued
0.6931 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6927 Remote Similarity NPD52 Approved
0.6927 Remote Similarity NPD7526 Approved
0.6927 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2669 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2238 Phase 2
0.6901 Remote Similarity NPD3059 Approved
0.6901 Remote Similarity NPD3062 Approved
0.6901 Remote Similarity NPD3061 Approved
0.6898 Remote Similarity NPD7802 Discontinued
0.6897 Remote Similarity NPD3533 Approved
0.6897 Remote Similarity NPD3448 Approved
0.6897 Remote Similarity NPD2972 Approved
0.6895 Remote Similarity NPD6625 Approved
0.6893 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6887 Remote Similarity NPD3763 Approved
0.6885 Remote Similarity NPD5722 Discontinued
0.6885 Remote Similarity NPD37 Approved
0.6882 Remote Similarity NPD7400 Phase 3
0.6882 Remote Similarity NPD5718 Phase 2
0.6881 Remote Similarity NPD4107 Approved
0.6878 Remote Similarity NPD7999 Approved
0.6872 Remote Similarity NPD8152 Approved
0.6872 Remote Similarity NPD3645 Discontinued
0.6872 Remote Similarity NPD8153 Approved
0.6866 Remote Similarity NPD6877 Discontinued
0.6854 Remote Similarity NPD6667 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