Structure

Physi-Chem Properties

Molecular Weight:  163.08
Volume:  149.934
LogP:  -2.475
LogD:  -2.021
LogS:  -0.155
# Rotatable Bonds:  1
TPSA:  92.95
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.285
Synthetic Accessibility Score:  4.014
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:  -5.143
MDCK Permeability:  0.0018226291285827756
Pgp-inhibitor:  0.0
Pgp-substrate:  0.044
Human Intestinal Absorption (HIA):  0.829
20% Bioavailability (F20%):  0.026
30% Bioavailability (F30%):  0.731

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.316
Plasma Protein Binding (PPB):  10.470806121826172%
Volume Distribution (VD):  0.578
Pgp-substrate:  86.65034484863281%

ADMET: Metabolism

CYP1A2-inhibitor:  0.011
CYP1A2-substrate:  0.047
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.496
CYP2C9-inhibitor:  0.0
CYP2C9-substrate:  0.135
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.189
CYP3A4-inhibitor:  0.002
CYP3A4-substrate:  0.025

ADMET: Excretion

Clearance (CL):  2.434
Half-life (T1/2):  0.622

ADMET: Toxicity

hERG Blockers:  0.047
Human Hepatotoxicity (H-HT):  0.137
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.129
Maximum Recommended Daily Dose:  0.042
Skin Sensitization:  0.09
Carcinogencity:  0.023
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.519

Download Data

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

  Natural Product: NPC150680

Natural Product ID:  NPC150680
Common Name*:   2-(Hydroxymethyl)Piperidine-3,4,5-Triol;Hydrochloride
IUPAC Name:   2-(hydroxymethyl)piperidine-3,4,5-triol;hydrochloride
Synonyms:  
Standard InCHIKey:  ZJIHMALTJRDNQI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H13NO4.ClH/c8-2-3-5(10)6(11)4(9)1-7-3;/h3-11H,1-2H2;1H
SMILES:  OCC1NCC(C(C1O)O)O.Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1489392
PubChem CID:   377339
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000195] Piperidines

*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
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. root n.a. PMID[17396934]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9544568]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20128 Taxillus chinensis Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7784 Loranthus chinensis Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20128 Taxillus chinensis Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9275 Loranthus parasticus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20128 Taxillus chinensis Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16194 Morus bombycis Species Moraceae 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
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 199.5 nM PMID[519051]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency = 281.8 nM PMID[519051]
NPT60 Individual Protein Lysosomal alpha-glucosidase Homo sapiens Potency n.a. 79.4 nM PMID[519051]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 22.4 nM PMID[519051]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 22438.82 nM PMID[519052]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10000.0 nM PMID[519052]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[519052]
NPT2 Others Unspecified Potency = 316.2 nM PMID[519051]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 5623.4 nM PMID[519051]
NPT2 Others Unspecified Potency n.a. 4.0 nM PMID[519051]

☑ 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 NPC150680 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 NPC69669
1.0 High Similarity NPC306462
1.0 High Similarity NPC2432
1.0 High Similarity NPC22774
1.0 High Similarity NPC218150
0.9661 High Similarity NPC471892
0.9661 High Similarity NPC75435
0.9661 High Similarity NPC142290
0.9661 High Similarity NPC471780
0.9661 High Similarity NPC198341
0.9661 High Similarity NPC223386
0.95 High Similarity NPC315980
0.95 High Similarity NPC303798
0.95 High Similarity NPC286851
0.9474 High Similarity NPC143809
0.9474 High Similarity NPC76726
0.9474 High Similarity NPC290106
0.9474 High Similarity NPC193593
0.9194 High Similarity NPC471418
0.9048 High Similarity NPC268922
0.8966 High Similarity NPC204709
0.8814 High Similarity NPC170172
0.8769 High Similarity NPC137554
0.8769 High Similarity NPC476695
0.8769 High Similarity NPC299603
0.8769 High Similarity NPC28959
0.8769 High Similarity NPC476694
0.8769 High Similarity NPC285014
0.8769 High Similarity NPC255535
0.8769 High Similarity NPC476696
0.8281 Intermediate Similarity NPC116377
0.8281 Intermediate Similarity NPC473952
0.8281 Intermediate Similarity NPC69798
0.8281 Intermediate Similarity NPC101746
0.8281 Intermediate Similarity NPC77191
0.8254 Intermediate Similarity NPC163134
0.8254 Intermediate Similarity NPC471419
0.8226 Intermediate Similarity NPC62507
0.8226 Intermediate Similarity NPC8087
0.7937 Intermediate Similarity NPC57846
0.7937 Intermediate Similarity NPC474014
0.7937 Intermediate Similarity NPC30126
0.7917 Intermediate Similarity NPC98750
0.7869 Intermediate Similarity NPC10262
0.7869 Intermediate Similarity NPC65832
0.7869 Intermediate Similarity NPC311668
0.7846 Intermediate Similarity NPC474928
0.7808 Intermediate Similarity NPC70574
0.7794 Intermediate Similarity NPC473710
0.7794 Intermediate Similarity NPC475694
0.7761 Intermediate Similarity NPC126664
0.7761 Intermediate Similarity NPC34291
0.7619 Intermediate Similarity NPC471421
0.7619 Intermediate Similarity NPC233364
0.76 Intermediate Similarity NPC271772
0.76 Intermediate Similarity NPC36927
0.7571 Intermediate Similarity NPC474468
0.7467 Intermediate Similarity NPC219340
0.7377 Intermediate Similarity NPC272396
0.7353 Intermediate Similarity NPC322801
0.7353 Intermediate Similarity NPC129100
0.7353 Intermediate Similarity NPC291650
0.7333 Intermediate Similarity NPC100204
0.7333 Intermediate Similarity NPC83248
0.7313 Intermediate Similarity NPC233034
0.7246 Intermediate Similarity NPC107224
0.7215 Intermediate Similarity NPC469363
0.7051 Intermediate Similarity NPC165119
0.6984 Remote Similarity NPC275727
0.6849 Remote Similarity NPC185084
0.6769 Remote Similarity NPC8979
0.6761 Remote Similarity NPC171850
0.6753 Remote Similarity NPC150557
0.6712 Remote Similarity NPC306973
0.6707 Remote Similarity NPC306838
0.6582 Remote Similarity NPC471420
0.6575 Remote Similarity NPC115800
0.6575 Remote Similarity NPC163538
0.6528 Remote Similarity NPC474469
0.6479 Remote Similarity NPC294883
0.6479 Remote Similarity NPC12514
0.6438 Remote Similarity NPC475127
0.6438 Remote Similarity NPC475715
0.6438 Remote Similarity NPC473419
0.6389 Remote Similarity NPC141156
0.6389 Remote Similarity NPC184150
0.6364 Remote Similarity NPC244539
0.6364 Remote Similarity NPC477002
0.6351 Remote Similarity NPC223174
0.6351 Remote Similarity NPC327753
0.6351 Remote Similarity NPC327486
0.6338 Remote Similarity NPC472609
0.6324 Remote Similarity NPC268927
0.6324 Remote Similarity NPC276928
0.6324 Remote Similarity NPC64250
0.6308 Remote Similarity NPC178263
0.6308 Remote Similarity NPC277072
0.6301 Remote Similarity NPC306763
0.6301 Remote Similarity NPC254617
0.6301 Remote Similarity NPC74555
0.6301 Remote Similarity NPC266242
0.6282 Remote Similarity NPC313762
0.625 Remote Similarity NPC318258
0.6164 Remote Similarity NPC196359
0.6164 Remote Similarity NPC78312
0.6164 Remote Similarity NPC221764
0.6164 Remote Similarity NPC135539
0.6164 Remote Similarity NPC59221
0.6154 Remote Similarity NPC123814
0.6104 Remote Similarity NPC26932
0.6098 Remote Similarity NPC315969
0.6087 Remote Similarity NPC315170
0.6056 Remote Similarity NPC17455
0.6049 Remote Similarity NPC314762
0.6032 Remote Similarity NPC29222
0.6032 Remote Similarity NPC121062
0.6032 Remote Similarity NPC96966
0.6024 Remote Similarity NPC263058
0.6 Remote Similarity NPC314968
0.6 Remote Similarity NPC314772
0.6 Remote Similarity NPC68974
0.5974 Remote Similarity NPC55274
0.5972 Remote Similarity NPC88898
0.5972 Remote Similarity NPC106216
0.5909 Remote Similarity NPC474322
0.5851 Remote Similarity NPC471628
0.5851 Remote Similarity NPC56298
0.5851 Remote Similarity NPC315036
0.5833 Remote Similarity NPC145627
0.5797 Remote Similarity NPC293551
0.5789 Remote Similarity NPC223893
0.5775 Remote Similarity NPC319131
0.5747 Remote Similarity NPC313552
0.5732 Remote Similarity NPC473971
0.5732 Remote Similarity NPC475363
0.5732 Remote Similarity NPC316807
0.5732 Remote Similarity NPC473972
0.5696 Remote Similarity NPC208657
0.5696 Remote Similarity NPC315806
0.5682 Remote Similarity NPC214376
0.5682 Remote Similarity NPC123746
0.5682 Remote Similarity NPC314408
0.5682 Remote Similarity NPC314007
0.5682 Remote Similarity NPC43850
0.5682 Remote Similarity NPC477060
0.5682 Remote Similarity NPC470282
0.5676 Remote Similarity NPC41429
0.567 Remote Similarity NPC221148
0.5667 Remote Similarity NPC266553
0.5625 Remote Similarity NPC473588
0.5625 Remote Similarity NPC78562
0.5614 Remote Similarity NPC66052
0.5614 Remote Similarity NPC325034
0.5614 Remote Similarity NPC293908
0.5614 Remote Similarity NPC86412
0.5614 Remote Similarity NPC192065
0.561 Remote Similarity NPC37681
0.5606 Remote Similarity NPC224624

  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 NPC150680 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 NPD9028 Phase 2
1.0 High Similarity NPD9027 Phase 3
1.0 High Similarity NPD9026 Phase 2
1.0 High Similarity NPD9029 Phase 3
0.8667 High Similarity NPD9455 Approved
0.8525 High Similarity NPD393 Approved
0.8361 Intermediate Similarity NPD9239 Approved
0.8361 Intermediate Similarity NPD9240 Approved
0.7937 Intermediate Similarity NPD9022 Phase 2
0.7937 Intermediate Similarity NPD9024 Phase 2
0.7761 Intermediate Similarity NPD9443 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD9030 Approved
0.7353 Intermediate Similarity NPD9031 Approved
0.7353 Intermediate Similarity NPD9033 Approved
0.7353 Intermediate Similarity NPD9032 Approved
0.7313 Intermediate Similarity NPD9440 Discontinued
0.7308 Intermediate Similarity NPD9401 Discovery
0.679 Remote Similarity NPD394 Phase 3
0.6761 Remote Similarity NPD9444 Discontinued
0.6757 Remote Similarity NPD9034 Approved
0.6757 Remote Similarity NPD67 Phase 2
0.642 Remote Similarity NPD882 Phase 2
0.642 Remote Similarity NPD883 Phase 2
0.6351 Remote Similarity NPD9445 Approved
0.6282 Remote Similarity NPD372 Clinical (unspecified phase)
0.6184 Remote Similarity NPD6704 Discontinued
0.6164 Remote Similarity NPD8868 Approved
0.6154 Remote Similarity NPD3215 Phase 1
0.6 Remote Similarity NPD9435 Approved
0.6 Remote Similarity NPD9434 Approved
0.5978 Remote Similarity NPD4282 Approved
0.5873 Remote Similarity NPD400 Approved
0.5873 Remote Similarity NPD399 Approved
0.5873 Remote Similarity NPD398 Approved
0.5854 Remote Similarity NPD9429 Discontinued
0.5851 Remote Similarity NPD4837 Approved
0.5851 Remote Similarity NPD4838 Approved
0.5851 Remote Similarity NPD4836 Approved
0.5851 Remote Similarity NPD4835 Approved
0.5846 Remote Similarity NPD3214 Discontinued
0.5833 Remote Similarity NPD8045 Clinical (unspecified phase)
0.5811 Remote Similarity NPD9442 Clinical (unspecified phase)
0.5753 Remote Similarity NPD9211 Clinical (unspecified phase)
0.575 Remote Similarity NPD9407 Approved
0.5747 Remote Similarity NPD3200 Clinical (unspecified phase)
0.5696 Remote Similarity NPD9653 Clinical (unspecified phase)
0.5682 Remote Similarity NPD3208 Approved
0.5682 Remote Similarity NPD3202 Approved
0.5682 Remote Similarity NPD3201 Approved
0.5682 Remote Similarity NPD3203 Approved
0.5682 Remote Similarity NPD3207 Approved
0.5682 Remote Similarity NPD3209 Approved
0.5682 Remote Similarity NPD2698 Approved
0.567 Remote Similarity NPD1450 Approved
0.567 Remote Similarity NPD1449 Approved
0.5614 Remote Similarity NPD9052 Approved
0.5614 Remote Similarity NPD9053 Approved
0.5614 Remote Similarity NPD9051 Approved
0.5612 Remote Similarity NPD2700 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