Structure

Physi-Chem Properties

Molecular Weight:  821.27
Volume:  772.032
LogP:  1.064
LogD:  0.701
LogS:  -3.667
# Rotatable Bonds:  13
TPSA:  272.98
# H-Bond Aceptor:  20
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.27
Synthetic Accessibility Score:  7.622
Fsp3:  0.658
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:  -5.316
MDCK Permeability:  0.00018983022891916335
Pgp-inhibitor:  0.992
Pgp-substrate:  0.396
Human Intestinal Absorption (HIA):  0.976
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.07
Plasma Protein Binding (PPB):  25.89312744140625%
Volume Distribution (VD):  1.171
Pgp-substrate:  35.23665237426758%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.004
CYP2D6-inhibitor:  0.907
CYP2D6-substrate:  0.02
CYP3A4-inhibitor:  0.61
CYP3A4-substrate:  0.227

ADMET: Excretion

Clearance (CL):  2.144
Half-life (T1/2):  0.726

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.974
Drug-inuced Liver Injury (DILI):  0.963
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.063
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.107
Carcinogencity:  0.081
Eye Corrosion:  0.003
Eye Irritation:  0.023
Respiratory Toxicity:  0.018

Download Data

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

  Natural Product: NPC146824

Natural Product ID:  NPC146824
Common Name*:   Alatusinine
IUPAC Name:   n.a.
Synonyms:   Alatusinine
Standard InCHIKey:  PDOVVPMFGOLGNT-GFPSWGCNSA-N
Standard InCHI:  InChI=1S/C38H47NO19/c1-17(40)50-16-37-30(55-21(5)44)26(52-18(2)41)25-28(54-20(4)43)38(37)36(9,49)29(27(53-19(3)42)31(37)56-22(6)45)57-33(47)34(7,48)13-12-24-23(11-10-14-39-24)32(46)51-15-35(25,8)58-38/h10-11,14,25-31,48-49H,12-13,15-16H2,1-9H3/t25-,26-,27+,28-,29+,30-,31+,34?,35+,36+,37-,38+/m1/s1
SMILES:  CC(=O)OC[C@]12[C@@H](OC(=O)C)[C@@H](OC(=O)C)[C@H]3[C@]([C@@]42O[C@@]([C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)[C@H]4OC(=O)C)(C)COC(=O)c1cccnc1CCC(C(=O)O3)(C)O)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508998
PubChem CID:   44566643
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO1333 Maytenus chiapensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12713421]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO1333 Maytenus chiapensis Species Celastraceae Eukaryota n.a. leaf n.a. PMID[14738378]
NPO1333 Maytenus chiapensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[14738378]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO1333 Maytenus chiapensis Species Celastraceae Eukaryota root bark;leaves Huayllabamba-Urquillos, Province of Urabamba, Cusco (Peru); Parque Nacional El Imposible, El Salvador n.a. PMID[16038541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1333 Maytenus chiapensis Species Celastraceae 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
NPT1161 Cell Line CHO Cricetulus griseus LD50 > 100.0 ug ml-1 PMID[543561]
NPT927 Cell Line PBMC Homo sapiens IC50 = 45910.0 nM PMID[543562]
NPT927 Cell Line PBMC Homo sapiens IC50 = 75680.0 nM PMID[543562]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis EC50 = 1.6 10'-4 ug/cm2 PMID[543561]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis Activity = 125.0 % PMID[543561]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis Activity = 111.0 % PMID[543561]
NPT27 Others Unspecified LD50 = 73.22 ug ml-1 PMID[543561]

☑ 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 NPC146824 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
0.995 High Similarity NPC475362
0.9853 High Similarity NPC292416
0.9853 High Similarity NPC473689
0.9851 High Similarity NPC250807
0.9851 High Similarity NPC57797
0.9805 High Similarity NPC244839
0.9805 High Similarity NPC320324
0.9805 High Similarity NPC319880
0.9802 High Similarity NPC473850
0.9757 High Similarity NPC237702
0.9752 High Similarity NPC76565
0.971 High Similarity NPC475406
0.9706 High Similarity NPC228377
0.9706 High Similarity NPC328186
0.9706 High Similarity NPC477787
0.9706 High Similarity NPC122968
0.9704 High Similarity NPC475137
0.9704 High Similarity NPC475498
0.9663 High Similarity NPC38959
0.9663 High Similarity NPC327904
0.961 High Similarity NPC476110
0.961 High Similarity NPC475600
0.961 High Similarity NPC87152
0.961 High Similarity NPC475631
0.9565 High Similarity NPC316841
0.9563 High Similarity NPC470486
0.9563 High Similarity NPC471977
0.9563 High Similarity NPC471190
0.9563 High Similarity NPC475644
0.9552 High Similarity NPC471016
0.9526 High Similarity NPC253482
0.9522 High Similarity NPC35208
0.951 High Similarity NPC477788
0.9502 High Similarity NPC470306
0.9471 High Similarity NPC475596
0.9471 High Similarity NPC475303
0.9466 High Similarity NPC473506
0.9455 High Similarity NPC471014
0.9455 High Similarity NPC475408
0.9426 High Similarity NPC30456
0.9417 High Similarity NPC328154
0.9393 High Similarity NPC475648
0.9363 High Similarity NPC301368
0.9363 High Similarity NPC84815
0.9336 High Similarity NPC327769
0.9336 High Similarity NPC475426
0.9336 High Similarity NPC170751
0.9327 High Similarity NPC475601
0.9272 High Similarity NPC477912
0.9265 High Similarity NPC6981
0.9227 High Similarity NPC127720
0.9227 High Similarity NPC127026
0.922 High Similarity NPC62367
0.922 High Similarity NPC294579
0.922 High Similarity NPC144779
0.9183 High Similarity NPC471980
0.9175 High Similarity NPC216428
0.9167 High Similarity NPC319128
0.9167 High Similarity NPC4421
0.9163 High Similarity NPC472553
0.9151 High Similarity NPC469748
0.9122 High Similarity NPC477910
0.9122 High Similarity NPC477909
0.9122 High Similarity NPC42678
0.9122 High Similarity NPC477907
0.9104 High Similarity NPC96801
0.9104 High Similarity NPC150698
0.9095 High Similarity NPC148860
0.9073 High Similarity NPC228331
0.9048 High Similarity NPC477902
0.9034 High Similarity NPC473115
0.9034 High Similarity NPC158020
0.9034 High Similarity NPC6576
0.9034 High Similarity NPC473089
0.9034 High Similarity NPC75600
0.9034 High Similarity NPC212768
0.9015 High Similarity NPC472550
0.9015 High Similarity NPC48042
0.9015 High Similarity NPC304179
0.8973 High Similarity NPC13603
0.8962 High Similarity NPC211920
0.8962 High Similarity NPC124029
0.8952 High Similarity NPC477911
0.8929 High Similarity NPC85879
0.8929 High Similarity NPC53255
0.89 High Similarity NPC472555
0.8889 High Similarity NPC264674
0.8873 High Similarity NPC63041
0.8844 High Similarity NPC326930
0.8844 High Similarity NPC475301
0.8815 High Similarity NPC477903
0.8804 High Similarity NPC206343
0.8804 High Similarity NPC477908
0.8777 High Similarity NPC471978
0.875 High Similarity NPC477906
0.8692 High Similarity NPC477900
0.8692 High Similarity NPC477899
0.869 High Similarity NPC473833
0.8685 High Similarity NPC235364
0.8664 High Similarity NPC471979
0.8616 High Similarity NPC475533
0.8615 High Similarity NPC328928
0.8611 High Similarity NPC14116
0.8611 High Similarity NPC285411
0.8605 High Similarity NPC26881
0.8592 High Similarity NPC477901
0.8584 High Similarity NPC238278
0.8578 High Similarity NPC475315
0.8578 High Similarity NPC324619
0.8571 High Similarity NPC311196
0.8571 High Similarity NPC134384
0.8524 High Similarity NPC476467
0.8469 Intermediate Similarity NPC472752
0.8455 Intermediate Similarity NPC213143
0.8447 Intermediate Similarity NPC91125
0.8391 Intermediate Similarity NPC471015
0.8349 Intermediate Similarity NPC280473
0.8349 Intermediate Similarity NPC323551
0.8349 Intermediate Similarity NPC233727
0.8326 Intermediate Similarity NPC471013
0.8326 Intermediate Similarity NPC148896
0.8326 Intermediate Similarity NPC180668
0.831 Intermediate Similarity NPC41724
0.831 Intermediate Similarity NPC51008
0.8216 Intermediate Similarity NPC470189
0.8216 Intermediate Similarity NPC40919
0.819 Intermediate Similarity NPC289086
0.8182 Intermediate Similarity NPC10904
0.8166 Intermediate Similarity NPC476090
0.816 Intermediate Similarity NPC470190
0.8157 Intermediate Similarity NPC187494
0.8148 Intermediate Similarity NPC30570
0.8111 Intermediate Similarity NPC162812
0.8093 Intermediate Similarity NPC292517
0.8086 Intermediate Similarity NPC470279
0.8073 Intermediate Similarity NPC319556
0.8065 Intermediate Similarity NPC193361
0.8065 Intermediate Similarity NPC62844
0.8056 Intermediate Similarity NPC165837
0.8028 Intermediate Similarity NPC475835
0.7982 Intermediate Similarity NPC207531
0.7731 Intermediate Similarity NPC309498
0.7725 Intermediate Similarity NPC37473
0.7723 Intermediate Similarity NPC253314
0.7714 Intermediate Similarity NPC103230
0.7642 Intermediate Similarity NPC109922
0.7628 Intermediate Similarity NPC32451
0.7628 Intermediate Similarity NPC328559
0.7576 Intermediate Similarity NPC471004
0.757 Intermediate Similarity NPC320748
0.757 Intermediate Similarity NPC324245
0.7543 Intermediate Similarity NPC70155
0.7523 Intermediate Similarity NPC111732
0.7511 Intermediate Similarity NPC314834
0.75 Intermediate Similarity NPC79223
0.7488 Intermediate Similarity NPC249614
0.7467 Intermediate Similarity NPC235885
0.7455 Intermediate Similarity NPC156044
0.7454 Intermediate Similarity NPC123395
0.7448 Intermediate Similarity NPC107123
0.7442 Intermediate Similarity NPC329024
0.7434 Intermediate Similarity NPC141385
0.7407 Intermediate Similarity NPC149708
0.7407 Intermediate Similarity NPC317672
0.7391 Intermediate Similarity NPC141428
0.7376 Intermediate Similarity NPC314297
0.7376 Intermediate Similarity NPC315545
0.7368 Intermediate Similarity NPC140311
0.7366 Intermediate Similarity NPC191310
0.7364 Intermediate Similarity NPC477043
0.7364 Intermediate Similarity NPC25442
0.7364 Intermediate Similarity NPC12944
0.7356 Intermediate Similarity NPC317010
0.7356 Intermediate Similarity NPC471997
0.7355 Intermediate Similarity NPC476516
0.7349 Intermediate Similarity NPC135950
0.7333 Intermediate Similarity NPC207851
0.733 Intermediate Similarity NPC315638
0.733 Intermediate Similarity NPC314855
0.733 Intermediate Similarity NPC313796
0.733 Intermediate Similarity NPC313345
0.7328 Intermediate Similarity NPC57690
0.7327 Intermediate Similarity NPC59033
0.7304 Intermediate Similarity NPC106593
0.7294 Intermediate Similarity NPC103361
0.7277 Intermediate Similarity NPC44354
0.7273 Intermediate Similarity NPC473667
0.7265 Intermediate Similarity NPC470280
0.7261 Intermediate Similarity NPC2395
0.7257 Intermediate Similarity NPC317752
0.7254 Intermediate Similarity NPC183537
0.7227 Intermediate Similarity NPC155792
0.722 Intermediate Similarity NPC15406
0.7217 Intermediate Similarity NPC282103
0.7213 Intermediate Similarity NPC134637
0.7212 Intermediate Similarity NPC318299
0.721 Intermediate Similarity NPC267926
0.7209 Intermediate Similarity NPC114974
0.7208 Intermediate Similarity NPC210296
0.7207 Intermediate Similarity NPC314648

  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 NPC146824 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
0.8451 Intermediate Similarity NPD8468 Phase 2
0.7933 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD3794 Approved
0.7568 Intermediate Similarity NPD3795 Approved
0.7523 Intermediate Similarity NPD7396 Approved
0.7512 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD5891 Approved
0.7477 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD6987 Phase 1
0.7395 Intermediate Similarity NPD1483 Discontinued
0.7364 Intermediate Similarity NPD3947 Discontinued
0.7321 Intermediate Similarity NPD4417 Approved
0.7294 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7069 Discontinued
0.7265 Intermediate Similarity NPD2510 Approved
0.7265 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD2509 Approved
0.7232 Intermediate Similarity NPD4506 Discontinued
0.7217 Intermediate Similarity NPD3280 Approved
0.7214 Intermediate Similarity NPD820 Phase 3
0.7193 Intermediate Similarity NPD3389 Approved
0.7193 Intermediate Similarity NPD3393 Approved
0.7193 Intermediate Similarity NPD3394 Approved
0.7174 Intermediate Similarity NPD6770 Approved
0.7162 Intermediate Similarity NPD8326 Phase 3
0.7162 Intermediate Similarity NPD8325 Phase 3
0.7162 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD7708 Approved
0.7116 Intermediate Similarity NPD7234 Approved
0.7116 Intermediate Similarity NPD7233 Approved
0.7098 Intermediate Similarity NPD7010 Phase 3
0.7091 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6529 Discontinued
0.7075 Intermediate Similarity NPD7803 Approved
0.7032 Intermediate Similarity NPD4427 Phase 2
0.7022 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD5475 Discontinued
0.7014 Intermediate Similarity NPD53 Approved
0.7014 Intermediate Similarity NPD7778 Approved
0.7014 Intermediate Similarity NPD7777 Approved
0.7012 Intermediate Similarity NPD7955 Approved
0.7012 Intermediate Similarity NPD7956 Approved
0.6996 Remote Similarity NPD8479 Phase 2
0.699 Remote Similarity NPD6635 Approved
0.6983 Remote Similarity NPD7878 Phase 2
0.6978 Remote Similarity NPD5901 Discontinued
0.6978 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6972 Remote Similarity NPD2336 Approved
0.6958 Remote Similarity NPD4373 Phase 2
0.6949 Remote Similarity NPD3925 Approved
0.6947 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6934 Remote Similarity NPD6641 Approved
0.6934 Remote Similarity NPD6642 Approved
0.6927 Remote Similarity NPD8063 Discontinued
0.6926 Remote Similarity NPD7707 Approved
0.6908 Remote Similarity NPD5088 Discontinued
0.69 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6894 Remote Similarity NPD4301 Approved
0.6889 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6885 Remote Similarity NPD7885 Phase 2
0.6885 Remote Similarity NPD7886 Phase 2
0.6883 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6962 Phase 2
0.6867 Remote Similarity NPD5482 Discontinued
0.6866 Remote Similarity NPD9271 Approved
0.6857 Remote Similarity NPD6790 Phase 1
0.6857 Remote Similarity NPD7417 Discontinued
0.6854 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6849 Remote Similarity NPD5640 Discontinued
0.6847 Remote Similarity NPD2307 Discontinued
0.684 Remote Similarity NPD5866 Approved
0.6835 Remote Similarity NPD4948 Discontinued
0.6833 Remote Similarity NPD4952 Phase 3
0.6833 Remote Similarity NPD5022 Discontinued
0.6832 Remote Similarity NPD8465 Approved
0.6832 Remote Similarity NPD8467 Approved
0.6832 Remote Similarity NPD8466 Approved
0.6828 Remote Similarity NPD2831 Approved
0.6816 Remote Similarity NPD5003 Discontinued
0.6816 Remote Similarity NPD8485 Approved
0.6803 Remote Similarity NPD5805 Approved
0.68 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7001 Phase 3
0.6798 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6797 Remote Similarity NPD7470 Discontinued
0.6795 Remote Similarity NPD4989 Phase 2
0.6795 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6787 Remote Similarity NPD4376 Phase 3
0.6787 Remote Similarity NPD3921 Approved
0.6787 Remote Similarity NPD3922 Approved
0.6787 Remote Similarity NPD3924 Approved
0.6787 Remote Similarity NPD3923 Approved
0.6778 Remote Similarity NPD8289 Discontinued
0.6774 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6772 Remote Similarity NPD8091 Phase 3
0.6771 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6763 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6762 Remote Similarity NPD3006 Discontinued
0.6758 Remote Similarity NPD7862 Clinical (unspecified phase)
0.6757 Remote Similarity NPD4526 Approved
0.6757 Remote Similarity NPD4528 Approved
0.6757 Remote Similarity NPD4529 Approved
0.6756 Remote Similarity NPD6999 Discontinued
0.6756 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6743 Remote Similarity NPD4889 Approved
0.674 Remote Similarity NPD7187 Phase 2
0.6736 Remote Similarity NPD7688 Phase 1
0.6729 Remote Similarity NPD8460 Approved
0.6729 Remote Similarity NPD8459 Approved
0.6729 Remote Similarity NPD8426 Approved
0.6729 Remote Similarity NPD8425 Approved
0.6726 Remote Similarity NPD4601 Approved
0.6726 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6726 Remote Similarity NPD4600 Approved
0.6723 Remote Similarity NPD6995 Phase 1
0.6723 Remote Similarity NPD8356 Approved
0.6705 Remote Similarity NPD8429 Approved
0.6705 Remote Similarity NPD8427 Approved
0.6705 Remote Similarity NPD8428 Approved
0.6698 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6697 Remote Similarity NPD8361 Approved
0.6697 Remote Similarity NPD8360 Approved
0.6697 Remote Similarity NPD8435 Approved
0.6694 Remote Similarity NPD6716 Phase 1
0.6683 Remote Similarity NPD9075 Approved
0.6683 Remote Similarity NPD9074 Approved
0.6682 Remote Similarity NPD3178 Discontinued
0.6681 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6681 Remote Similarity NPD8160 Phase 2
0.668 Remote Similarity NPD4086 Phase 1
0.668 Remote Similarity NPD6553 Clinical (unspecified phase)
0.668 Remote Similarity NPD2921 Clinical (unspecified phase)
0.668 Remote Similarity NPD6292 Clinical (unspecified phase)
0.668 Remote Similarity NPD4328 Approved
0.6667 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6026 Approved
0.6667 Remote Similarity NPD8407 Phase 2
0.6667 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1631 Approved
0.6667 Remote Similarity NPD7404 Approved
0.6654 Remote Similarity NPD6228 Discontinued
0.6653 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6653 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6653 Remote Similarity NPD6276 Discontinued
0.6652 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6652 Remote Similarity NPD4602 Approved
0.6638 Remote Similarity NPD6176 Phase 1
0.6638 Remote Similarity NPD4897 Phase 2
0.6638 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6665 Discontinued
0.6635 Remote Similarity NPD2582 Approved
0.6635 Remote Similarity NPD2581 Approved
0.6624 Remote Similarity NPD4429 Discontinued
0.6624 Remote Similarity NPD7395 Discontinued
0.6624 Remote Similarity NPD3815 Phase 1
0.6624 Remote Similarity NPD3816 Phase 1
0.6624 Remote Similarity NPD3354 Phase 2
0.6622 Remote Similarity NPD2564 Approved
0.6622 Remote Similarity NPD6281 Approved
0.6622 Remote Similarity NPD2565 Phase 2
0.662 Remote Similarity NPD1575 Approved
0.662 Remote Similarity NPD1573 Approved
0.6615 Remote Similarity NPD5450 Discontinued
0.6612 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6612 Remote Similarity NPD8430 Approved
0.6611 Remote Similarity NPD5507 Approved
0.6611 Remote Similarity NPD5506 Approved
0.6609 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6607 Remote Similarity NPD6361 Phase 2
0.6606 Remote Similarity NPD6791 Phase 2
0.6606 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6606 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6603 Remote Similarity NPD8364 Approved
0.6603 Remote Similarity NPD8363 Approved
0.6601 Remote Similarity NPD8101 Phase 3
0.6595 Remote Similarity NPD8399 Phase 1
0.6595 Remote Similarity NPD8423 Phase 2
0.6593 Remote Similarity NPD6206 Phase 1
0.6589 Remote Similarity NPD6531 Approved
0.6589 Remote Similarity NPD6530 Approved
0.6586 Remote Similarity NPD7576 Discontinued
0.6582 Remote Similarity NPD8404 Phase 2
0.6581 Remote Similarity NPD7703 Clinical (unspecified phase)
0.658 Remote Similarity NPD7958 Clinical (unspecified phase)
0.658 Remote Similarity NPD7957 Phase 1
0.6579 Remote Similarity NPD4500 Approved
0.6579 Remote Similarity NPD6479 Discontinued
0.6579 Remote Similarity NPD4501 Approved
0.6574 Remote Similarity NPD5100 Phase 3
0.657 Remote Similarity NPD7426 Phase 1
0.6569 Remote Similarity NPD1996 Discontinued
0.6568 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6567 Remote Similarity NPD107 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