Structure

Physi-Chem Properties

Molecular Weight:  173.11
Volume:  167.179
LogP:  -1.227
LogD:  -0.863
LogS:  0.038
# Rotatable Bonds:  0
TPSA:  63.93
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.419
Synthetic Accessibility Score:  3.825
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.134
MDCK Permeability:  4.229642581776716e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.981
Human Intestinal Absorption (HIA):  0.043
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.282
Plasma Protein Binding (PPB):  12.13682746887207%
Volume Distribution (VD):  1.003
Pgp-substrate:  84.06974029541016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.092
CYP2C19-inhibitor:  0.026
CYP2C19-substrate:  0.82
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.164
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.534
CYP3A4-inhibitor:  0.001
CYP3A4-substrate:  0.122

ADMET: Excretion

Clearance (CL):  2.588
Half-life (T1/2):  0.829

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.163
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.076
Rat Oral Acute Toxicity:  0.058
Maximum Recommended Daily Dose:  0.026
Skin Sensitization:  0.281
Carcinogencity:  0.087
Eye Corrosion:  0.023
Eye Irritation:  0.455
Respiratory Toxicity:  0.825

Download Data

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

  Natural Product: NPC233034

Natural Product ID:  NPC233034
Common Name*:   Tridolgosir
IUPAC Name:   (1S,2R,8R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,2,8-triol
Synonyms:   Swainsonine; Tridolgosir
Standard InCHIKey:  FXUAIOOAOAVCGD-WCTZXXKLSA-N
Standard InCHI:  InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1
SMILES:  O[C@@H]1CN2[C@@H]([C@@H]1O)[C@H](O)CCC2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL371197
PubChem CID:   51683
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000251] Indolizidines

*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
NPO40701 Ipomoea sp. Q6 [aff. calobra] Strain Convolvulaceae Eukaryota n.a. n.a. n.a. PMID[7673932]
NPO14272 Swainsona luteola Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14272 Swainsona luteola Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31538 Swailnsonia galegifolia n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30725 Swailnsonia canescens n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14272 Swainsona luteola Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT1053 Individual Protein Alpha-mannosidase 2C1 Rattus norvegicus IC50 = 1750.0 nM PMID[453459]
NPT504 Individual Protein Alpha-mannosidase Glycine max IC50 = 400.0 nM PMID[453460]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[453462]
NPT499 Individual Protein Lysosomal alpha-mannosidase Homo sapiens IC50 = 20000.0 nM PMID[453465]
NPT499 Individual Protein Lysosomal alpha-mannosidase Homo sapiens IC50 = 50.0 nM PMID[453465]
NPT499 Individual Protein Lysosomal alpha-mannosidase Homo sapiens IC50 = 10.0 nM PMID[453465]
NPT5276 Individual Protein Mannosyl-oligosaccharide alpha-1,2-mannosidase isoform B Drosophila melanogaster IC50 = 5.0 nM PMID[453467]
NPT5276 Individual Protein Mannosyl-oligosaccharide alpha-1,2-mannosidase isoform B Drosophila melanogaster Ki = 3.0 nM PMID[453467]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 85310.01 nM PMID[453470]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[453470]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 5.09 % PMID[453471]
NPT2 Others Unspecified Inhibition = 50.0 % PMID[453464]
NPT2 Others Unspecified IC50 = 40.0 nM PMID[453465]
NPT2 Others Unspecified Ki = 155.0 nM PMID[453465]
NPT2 Others Unspecified Ki = 20.0 nM PMID[453465]
NPT22710 PROTEIN FAMILY GH92 alpha-mannosidase Bacteroides thetaiotaomicron Ki = 14000.0 nM PMID[453466]
NPT22710 PROTEIN FAMILY GH92 alpha-mannosidase Bacteroides thetaiotaomicron Ki = 5000.0 nM PMID[453466]
NPT2 Others Unspecified IC50 = 11.0 nM PMID[453467]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9528.3 nM PMID[453468]
NPT2 Others Unspecified IC50 = 100.0 nM PMID[453469]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -2.04 % PMID[453471]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 2.0 n.a. PMID[453472]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 52.6 % PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (acute) = 1.0 n.a. PMID[453472]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (acute) = 10.5 % PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (cytolytic) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (choleostasis) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (severe hepatitis) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (chronic liver disease) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (cirrhosis) = 0.0 n.a. PMID[453472]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (granulomatous hepatitis) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (association with vascular disease) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (steatosis) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Hepatotoxicity (malignant tumour) = 0.0 n.a. PMID[453472]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (benign tumour) = 0.0 n.a. PMID[453472]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[453473]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -4.47 % PMID[453474]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 13.48 % PMID[453475]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.05 % PMID[453476]
NPT2 Others Unspecified Potency n.a. 26603.2 nM PubChem BioAssay data set

☑ 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 NPC233034 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
0.9516 High Similarity NPC126664
0.9516 High Similarity NPC34291
0.8615 High Similarity NPC474469
0.8594 High Similarity NPC294883
0.8594 High Similarity NPC12514
0.8485 Intermediate Similarity NPC475127
0.8485 Intermediate Similarity NPC475715
0.8485 Intermediate Similarity NPC473419
0.8462 Intermediate Similarity NPC141156
0.8462 Intermediate Similarity NPC59221
0.8462 Intermediate Similarity NPC184150
0.8333 Intermediate Similarity NPC254617
0.8333 Intermediate Similarity NPC266242
0.8333 Intermediate Similarity NPC74555
0.8333 Intermediate Similarity NPC306763
0.8281 Intermediate Similarity NPC163134
0.8281 Intermediate Similarity NPC471419
0.8167 Intermediate Similarity NPC275727
0.8088 Intermediate Similarity NPC163538
0.8088 Intermediate Similarity NPC115800
0.8 Intermediate Similarity NPC277072
0.8 Intermediate Similarity NPC178263
0.7971 Intermediate Similarity NPC255535
0.7971 Intermediate Similarity NPC285014
0.7971 Intermediate Similarity NPC299603
0.7971 Intermediate Similarity NPC137554
0.7971 Intermediate Similarity NPC28959
0.7937 Intermediate Similarity NPC170172
0.7794 Intermediate Similarity NPC471418
0.7794 Intermediate Similarity NPC171850
0.7681 Intermediate Similarity NPC268922
0.7656 Intermediate Similarity NPC76726
0.7656 Intermediate Similarity NPC143809
0.7656 Intermediate Similarity NPC471421
0.7656 Intermediate Similarity NPC290106
0.7656 Intermediate Similarity NPC193593
0.7656 Intermediate Similarity NPC233364
0.7612 Intermediate Similarity NPC223386
0.7612 Intermediate Similarity NPC142290
0.7612 Intermediate Similarity NPC471892
0.7612 Intermediate Similarity NPC75435
0.7612 Intermediate Similarity NPC471780
0.7612 Intermediate Similarity NPC198341
0.7612 Intermediate Similarity NPC474928
0.7571 Intermediate Similarity NPC475694
0.7571 Intermediate Similarity NPC473710
0.75 Intermediate Similarity NPC286851
0.75 Intermediate Similarity NPC303798
0.75 Intermediate Similarity NPC473952
0.75 Intermediate Similarity NPC69798
0.75 Intermediate Similarity NPC77191
0.75 Intermediate Similarity NPC116377
0.75 Intermediate Similarity NPC101746
0.7465 Intermediate Similarity NPC476696
0.7465 Intermediate Similarity NPC476694
0.7465 Intermediate Similarity NPC476695
0.7424 Intermediate Similarity NPC62507
0.7424 Intermediate Similarity NPC474014
0.7424 Intermediate Similarity NPC57846
0.7424 Intermediate Similarity NPC30126
0.7424 Intermediate Similarity NPC8087
0.7361 Intermediate Similarity NPC474468
0.7344 Intermediate Similarity NPC10262
0.7344 Intermediate Similarity NPC311668
0.7344 Intermediate Similarity NPC65832
0.7313 Intermediate Similarity NPC2432
0.7313 Intermediate Similarity NPC22774
0.7313 Intermediate Similarity NPC150680
0.7313 Intermediate Similarity NPC69669
0.7313 Intermediate Similarity NPC306462
0.7313 Intermediate Similarity NPC218150
0.7246 Intermediate Similarity NPC315980
0.7231 Intermediate Similarity NPC204709
0.7077 Intermediate Similarity NPC293551
0.7031 Intermediate Similarity NPC471423
0.7031 Intermediate Similarity NPC471442
0.6875 Remote Similarity NPC272396
0.6818 Remote Similarity NPC471443
0.6818 Remote Similarity NPC471605
0.6795 Remote Similarity NPC150557
0.6667 Remote Similarity NPC165119
0.6667 Remote Similarity NPC112398
0.6625 Remote Similarity NPC471420
0.6618 Remote Similarity NPC319991
0.6567 Remote Similarity NPC8979
0.65 Remote Similarity NPC100204
0.65 Remote Similarity NPC83248
0.6444 Remote Similarity NPC313821
0.6429 Remote Similarity NPC469363
0.6389 Remote Similarity NPC160661
0.6389 Remote Similarity NPC472609
0.6364 Remote Similarity NPC315806
0.6353 Remote Similarity NPC306838
0.6341 Remote Similarity NPC36927
0.6341 Remote Similarity NPC271772
0.6338 Remote Similarity NPC145627
0.6338 Remote Similarity NPC17455
0.6316 Remote Similarity NPC306973
0.631 Remote Similarity NPC277918
0.6296 Remote Similarity NPC90839
0.6279 Remote Similarity NPC52533
0.6173 Remote Similarity NPC98750
0.6154 Remote Similarity NPC126186
0.6145 Remote Similarity NPC31313
0.6145 Remote Similarity NPC45906
0.6145 Remote Similarity NPC288415
0.6145 Remote Similarity NPC81006
0.6145 Remote Similarity NPC149908
0.6125 Remote Similarity NPC329077
0.6119 Remote Similarity NPC270041
0.6105 Remote Similarity NPC314387
0.6098 Remote Similarity NPC70574
0.6071 Remote Similarity NPC93630
0.6026 Remote Similarity NPC29326
0.6 Remote Similarity NPC470782
0.6 Remote Similarity NPC477002
0.5974 Remote Similarity NPC327753
0.5974 Remote Similarity NPC327486
0.5974 Remote Similarity NPC223174
0.597 Remote Similarity NPC123814
0.5921 Remote Similarity NPC195165
0.5921 Remote Similarity NPC107224
0.5854 Remote Similarity NPC233108
0.5846 Remote Similarity NPC121062
0.5846 Remote Similarity NPC29222
0.5846 Remote Similarity NPC96966
0.5844 Remote Similarity NPC23721
0.5789 Remote Similarity NPC129100
0.5789 Remote Similarity NPC291650
0.5789 Remote Similarity NPC221764
0.5789 Remote Similarity NPC322801
0.5789 Remote Similarity NPC196359
0.5789 Remote Similarity NPC135539
0.5789 Remote Similarity NPC78312
0.5735 Remote Similarity NPC474322
0.5696 Remote Similarity NPC477200
0.5696 Remote Similarity NPC470781
0.5679 Remote Similarity NPC470993
0.5679 Remote Similarity NPC470992
0.5672 Remote Similarity NPC224624
0.5663 Remote Similarity NPC314772
0.5663 Remote Similarity NPC314968
0.5647 Remote Similarity NPC219340
0.5647 Remote Similarity NPC470783
0.5616 Remote Similarity NPC474627
0.5616 Remote Similarity NPC201338
0.5616 Remote Similarity NPC328786

  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 NPC233034 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
1.0 High Similarity NPD9440 Discontinued
0.9516 High Similarity NPD9443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD9444 Discontinued
0.8095 Intermediate Similarity NPD9455 Approved
0.7969 Intermediate Similarity NPD393 Approved
0.7763 Intermediate Similarity NPD883 Phase 2
0.7763 Intermediate Similarity NPD882 Phase 2
0.7313 Intermediate Similarity NPD9027 Phase 3
0.7313 Intermediate Similarity NPD9026 Phase 2
0.7313 Intermediate Similarity NPD9028 Phase 2
0.7313 Intermediate Similarity NPD9029 Phase 3
0.6912 Remote Similarity NPD9022 Phase 2
0.6912 Remote Similarity NPD9024 Phase 2
0.6522 Remote Similarity NPD9239 Approved
0.6522 Remote Similarity NPD9240 Approved
0.6506 Remote Similarity NPD9401 Discovery
0.6444 Remote Similarity NPD3191 Approved
0.6444 Remote Similarity NPD3190 Approved
0.6444 Remote Similarity NPD3189 Approved
0.6364 Remote Similarity NPD9653 Clinical (unspecified phase)
0.6329 Remote Similarity NPD372 Clinical (unspecified phase)
0.6105 Remote Similarity NPD3185 Approved
0.6105 Remote Similarity NPD3184 Approved
0.6105 Remote Similarity NPD3182 Approved
0.6105 Remote Similarity NPD3183 Approved
0.6047 Remote Similarity NPD394 Phase 3
0.6 Remote Similarity NPD9407 Approved
0.5974 Remote Similarity NPD9445 Approved
0.597 Remote Similarity NPD3215 Phase 1
0.5952 Remote Similarity NPD2691 Clinical (unspecified phase)
0.5857 Remote Similarity NPD6439 Phase 3
0.5823 Remote Similarity NPD6704 Discontinued
0.5789 Remote Similarity NPD9032 Approved
0.5789 Remote Similarity NPD8868 Approved
0.5789 Remote Similarity NPD9033 Approved
0.5789 Remote Similarity NPD9031 Approved
0.5789 Remote Similarity NPD9030 Approved
0.5769 Remote Similarity NPD2697 Approved
0.5769 Remote Similarity NPD2694 Approved
0.5769 Remote Similarity NPD2696 Approved
0.5769 Remote Similarity NPD2695 Approved
0.5714 Remote Similarity NPD6706 Discontinued
0.5714 Remote Similarity NPD9429 Discontinued
0.5686 Remote Similarity NPD3188 Approved
0.5672 Remote Similarity NPD3214 Discontinued
0.5663 Remote Similarity NPD9434 Approved
0.5663 Remote Similarity NPD9435 Approved
0.5625 Remote Similarity NPD9405 Approved
0.5625 Remote Similarity NPD3187 Discontinued
0.56 Remote Similarity NPD9211 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