Structure

Physi-Chem Properties

Molecular Weight:  169.07
Volume:  167.826
LogP:  -0.426
LogD:  -0.307
LogS:  -0.579
# Rotatable Bonds:  2
TPSA:  73.58
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.586
Synthetic Accessibility Score:  2.549
Fsp3:  0.375
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:  -4.769
MDCK Permeability:  6.786337962694233e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.173
30% Bioavailability (F30%):  0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  10.176501274108887%
Volume Distribution (VD):  1.128
Pgp-substrate:  73.54129791259766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.053
CYP1A2-substrate:  0.15
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.191
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.156
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.395
CYP3A4-inhibitor:  0.003
CYP3A4-substrate:  0.171

ADMET: Excretion

Clearance (CL):  6.201
Half-life (T1/2):  0.935

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.057
Drug-inuced Liver Injury (DILI):  0.183
AMES Toxicity:  0.123
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.701
Carcinogencity:  0.117
Eye Corrosion:  0.003
Eye Irritation:  0.079
Respiratory Toxicity:  0.048

Download Data

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

  Natural Product: NPC132680

Natural Product ID:  NPC132680
Common Name*:   Pyridoxine Hydrochloride
IUPAC Name:   4,5-bis(hydroxymethyl)-2-methylpyridin-3-ol;hydrochloride
Synonyms:   Beesix; Benadon; Comploment Continus; Hexa-Betalin; Kent B6; Lyphomed; Orovite Comploment B6; Pyrid-10; Pyrid-20; Pyridox HCl; Pyridox-Roche; Pyridoxine HCl; Pyridoxol Hcl; Vital Foods; Vitalife; Vitamin B6
Standard InCHIKey:  ZUFQODAHGAHPFQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H11NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,10-12H,3-4H2,1H3;1H
SMILES:  Cc1c(c(CO)c(cn1)CO)O.Cl
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1200756
PubChem CID:   6019
51064122
517312
88396073
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001948] Pyridoxines

*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
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. DOI[10.3923/pjbs.2013.1138.1144]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[17262437]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[18078747]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18326559]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Essential oil n.a. n.a. PMID[23163425]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[23865201]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[24508058]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[25650289]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota garlic skin n.a. n.a. PMID[25726329]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[8350088]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[8882438]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Bulb n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26542 Rubia cordifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7103 Allium sativum Species Amaryllidaceae 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 28183.8 nM PMID[450783]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 29092.9 nM PMID[450784]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency n.a. 100000.0 nM PMID[450783]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 1062.1 nM PMID[450784]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 35481.3 nM PMID[450784]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 50118.7 nM PMID[450784]
NPT2 Others Unspecified Ki = 8290000.0 nM PMID[450785]
NPT2 Others Unspecified Ki = 8670000.0 nM PMID[450785]
NPT2 Others Unspecified Ki = 5560000.0 nM PMID[450785]
NPT2 Others Unspecified Ki = 5050000.0 nM PMID[450785]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.1746 n.a. PMID[450786]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 4.95 % PMID[450787]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 10.52 % PMID[450788]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.25 % PMID[450789]
NPT2 Others Unspecified Potency n.a. 13685.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24544.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1096.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61652.4 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 NPC132680 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 NPC269919
0.9862 High Similarity NPC63562
0.9732 High Similarity NPC263439
0.9597 High Similarity NPC324203
0.9597 High Similarity NPC322976
0.9597 High Similarity NPC63338
0.9342 High Similarity NPC211187
0.9103 High Similarity NPC256828
0.8827 High Similarity NPC325705
0.8827 High Similarity NPC52831
0.8402 Intermediate Similarity NPC36498
0.8312 Intermediate Similarity NPC220523
0.7987 Intermediate Similarity NPC153769
0.7949 Intermediate Similarity NPC471598
0.7886 Intermediate Similarity NPC3715
0.7857 Intermediate Similarity NPC471596
0.7806 Intermediate Similarity NPC280853
0.7798 Intermediate Similarity NPC252590
0.7756 Intermediate Similarity NPC285016
0.7756 Intermediate Similarity NPC245657
0.7738 Intermediate Similarity NPC473764
0.7738 Intermediate Similarity NPC314940
0.7736 Intermediate Similarity NPC161292
0.7711 Intermediate Similarity NPC473057
0.7697 Intermediate Similarity NPC174421
0.7658 Intermediate Similarity NPC470394
0.7658 Intermediate Similarity NPC470404
0.7658 Intermediate Similarity NPC470403
0.7643 Intermediate Similarity NPC318935
0.7628 Intermediate Similarity NPC471594
0.7619 Intermediate Similarity NPC108469
0.7562 Intermediate Similarity NPC470395
0.7558 Intermediate Similarity NPC194724
0.755 Intermediate Similarity NPC165370
0.7456 Intermediate Similarity NPC471178
0.7434 Intermediate Similarity NPC212125
0.7384 Intermediate Similarity NPC253810
0.7365 Intermediate Similarity NPC138018
0.7354 Intermediate Similarity NPC316403
0.7337 Intermediate Similarity NPC224928
0.7333 Intermediate Similarity NPC284348
0.733 Intermediate Similarity NPC478032
0.732 Intermediate Similarity NPC477110
0.7288 Intermediate Similarity NPC219963
0.7278 Intermediate Similarity NPC25899
0.7278 Intermediate Similarity NPC328029
0.7278 Intermediate Similarity NPC29702
0.7267 Intermediate Similarity NPC44161
0.7262 Intermediate Similarity NPC116573
0.7258 Intermediate Similarity NPC476167
0.7235 Intermediate Similarity NPC124542
0.7235 Intermediate Similarity NPC59779
0.7235 Intermediate Similarity NPC471177
0.7219 Intermediate Similarity NPC84508
0.7208 Intermediate Similarity NPC306397
0.7207 Intermediate Similarity NPC207851
0.7204 Intermediate Similarity NPC192315
0.7193 Intermediate Similarity NPC97367
0.719 Intermediate Similarity NPC151489
0.7182 Intermediate Similarity NPC46580
0.7167 Intermediate Similarity NPC42591
0.7167 Intermediate Similarity NPC314002
0.7157 Intermediate Similarity NPC314270
0.7152 Intermediate Similarity NPC257142
0.715 Intermediate Similarity NPC5145
0.7135 Intermediate Similarity NPC48192
0.7134 Intermediate Similarity NPC256893
0.7121 Intermediate Similarity NPC315804
0.7121 Intermediate Similarity NPC313804
0.7119 Intermediate Similarity NPC96890
0.7111 Intermediate Similarity NPC320394
0.7111 Intermediate Similarity NPC204717
0.7095 Intermediate Similarity NPC266551
0.7095 Intermediate Similarity NPC161887
0.7081 Intermediate Similarity NPC226202
0.7073 Intermediate Similarity NPC471323
0.7072 Intermediate Similarity NPC295158
0.7069 Intermediate Similarity NPC319456
0.7062 Intermediate Similarity NPC150048
0.7062 Intermediate Similarity NPC203754
0.7056 Intermediate Similarity NPC220765
0.7056 Intermediate Similarity NPC8022
0.7056 Intermediate Similarity NPC470799
0.7053 Intermediate Similarity NPC470678
0.7047 Intermediate Similarity NPC18348
0.7047 Intermediate Similarity NPC477111
0.7033 Intermediate Similarity NPC171171
0.7022 Intermediate Similarity NPC184964
0.7017 Intermediate Similarity NPC284559
0.7011 Intermediate Similarity NPC41717
0.7005 Intermediate Similarity NPC251090
0.6994 Remote Similarity NPC102423
0.6989 Remote Similarity NPC273532
0.6989 Remote Similarity NPC158129
0.6989 Remote Similarity NPC329541
0.6989 Remote Similarity NPC289786
0.6983 Remote Similarity NPC42979
0.6979 Remote Similarity NPC470500
0.6978 Remote Similarity NPC241025
0.6978 Remote Similarity NPC62510
0.6968 Remote Similarity NPC267928
0.6966 Remote Similarity NPC224764
0.6957 Remote Similarity NPC75544
0.6951 Remote Similarity NPC60553
0.6943 Remote Similarity NPC477113
0.694 Remote Similarity NPC314573
0.6936 Remote Similarity NPC71079
0.6936 Remote Similarity NPC79911
0.6927 Remote Similarity NPC283152
0.6915 Remote Similarity NPC473053
0.6911 Remote Similarity NPC155792
0.6906 Remote Similarity NPC470474
0.69 Remote Similarity NPC173080
0.6897 Remote Similarity NPC474217
0.6893 Remote Similarity NPC302647
0.6893 Remote Similarity NPC249614
0.6891 Remote Similarity NPC47059
0.6891 Remote Similarity NPC118832
0.6891 Remote Similarity NPC264166
0.6891 Remote Similarity NPC165349
0.6891 Remote Similarity NPC274291
0.6891 Remote Similarity NPC472259
0.6891 Remote Similarity NPC329708
0.6882 Remote Similarity NPC114974
0.6879 Remote Similarity NPC120798
0.6878 Remote Similarity NPC244536
0.6868 Remote Similarity NPC48938
0.6865 Remote Similarity NPC32771
0.6857 Remote Similarity NPC85918
0.6855 Remote Similarity NPC315320
0.6854 Remote Similarity NPC313791
0.6845 Remote Similarity NPC99666
0.6845 Remote Similarity NPC195268
0.6845 Remote Similarity NPC133140
0.6842 Remote Similarity NPC263455
0.6842 Remote Similarity NPC472284
0.6839 Remote Similarity NPC200836
0.6839 Remote Similarity NPC475774
0.6839 Remote Similarity NPC177404
0.6836 Remote Similarity NPC126481
0.6831 Remote Similarity NPC62069
0.6825 Remote Similarity NPC242209
0.6821 Remote Similarity NPC113812
0.6821 Remote Similarity NPC230869
0.6818 Remote Similarity NPC278366
0.6818 Remote Similarity NPC127730
0.68 Remote Similarity NPC469813
0.68 Remote Similarity NPC476446
0.68 Remote Similarity NPC78375
0.6793 Remote Similarity NPC20249
0.6789 Remote Similarity NPC156704
0.6788 Remote Similarity NPC211813
0.6782 Remote Similarity NPC131718
0.6778 Remote Similarity NPC288943
0.6774 Remote Similarity NPC472289
0.6772 Remote Similarity NPC326634
0.6771 Remote Similarity NPC19872
0.6763 Remote Similarity NPC212742
0.676 Remote Similarity NPC471294
0.6758 Remote Similarity NPC317010
0.6755 Remote Similarity NPC56170
0.6753 Remote Similarity NPC53144
0.6751 Remote Similarity NPC185782
0.6735 Remote Similarity NPC88008
0.6734 Remote Similarity NPC26679
0.6734 Remote Similarity NPC112206
0.6734 Remote Similarity NPC202605
0.6733 Remote Similarity NPC473822
0.672 Remote Similarity NPC106937
0.672 Remote Similarity NPC307963
0.672 Remote Similarity NPC66083
0.6718 Remote Similarity NPC475070
0.6708 Remote Similarity NPC324611
0.6704 Remote Similarity NPC14651
0.6704 Remote Similarity NPC121658
0.6703 Remote Similarity NPC164340
0.6702 Remote Similarity NPC77555
0.6702 Remote Similarity NPC90229
0.6702 Remote Similarity NPC469390
0.6686 Remote Similarity NPC302159
0.6685 Remote Similarity NPC134586
0.6684 Remote Similarity NPC110741
0.6684 Remote Similarity NPC44354
0.6684 Remote Similarity NPC315491
0.6684 Remote Similarity NPC472287
0.6684 Remote Similarity NPC249040
0.6684 Remote Similarity NPC472286
0.6684 Remote Similarity NPC213308
0.6684 Remote Similarity NPC45459
0.6684 Remote Similarity NPC230805
0.6667 Remote Similarity NPC475870
0.6667 Remote Similarity NPC259545
0.6667 Remote Similarity NPC476138
0.6667 Remote Similarity NPC61350
0.6667 Remote Similarity NPC471311
0.6667 Remote Similarity NPC324149
0.6667 Remote Similarity NPC322488
0.6667 Remote Similarity NPC245816
0.6667 Remote Similarity NPC471313
0.6648 Remote Similarity NPC476518

  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 NPC132680 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 NPD9382 Approved
1.0 High Similarity NPD9383 Approved
0.9597 High Similarity NPD9398 Clinical (unspecified phase)
0.8827 High Similarity NPD9510 Approved
0.8688 High Similarity NPD2123 Phase 3
0.8402 Intermediate Similarity NPD9364 Phase 2
0.8402 Intermediate Similarity NPD9363 Approved
0.8229 Intermediate Similarity NPD1229 Phase 2
0.8208 Intermediate Similarity NPD5317 Clinical (unspecified phase)
0.8107 Intermediate Similarity NPD9362 Approved
0.7987 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD861 Approved
0.7605 Intermediate Similarity NPD863 Approved
0.7605 Intermediate Similarity NPD862 Approved
0.7602 Intermediate Similarity NPD9690 Approved
0.7584 Intermediate Similarity NPD1213 Phase 3
0.756 Intermediate Similarity NPD925 Approved
0.756 Intermediate Similarity NPD926 Approved
0.7452 Intermediate Similarity NPD9506 Approved
0.7434 Intermediate Similarity NPD9284 Approved
0.7425 Intermediate Similarity NPD5255 Approved
0.7414 Intermediate Similarity NPD6159 Phase 2
0.7414 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD425 Approved
0.7412 Intermediate Similarity NPD424 Approved
0.7381 Intermediate Similarity NPD112 Approved
0.7381 Intermediate Similarity NPD9705 Discontinued
0.7318 Intermediate Similarity NPD5256 Discontinued
0.7299 Intermediate Similarity NPD158 Discontinued
0.7293 Intermediate Similarity NPD5316 Approved
0.7208 Intermediate Similarity NPD9080 Approved
0.7205 Intermediate Similarity NPD1649 Discontinued
0.7188 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD1352 Discontinued
0.7174 Intermediate Similarity NPD9695 Approved
0.716 Intermediate Similarity NPD2582 Approved
0.716 Intermediate Similarity NPD2581 Approved
0.7088 Intermediate Similarity NPD1034 Phase 3
0.7088 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD1418 Phase 2
0.7074 Intermediate Similarity NPD2177 Approved
0.7074 Intermediate Similarity NPD2176 Approved
0.7074 Intermediate Similarity NPD2175 Phase 3
0.7073 Intermediate Similarity NPD3813 Approved
0.7069 Intermediate Similarity NPD2781 Approved
0.7069 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1622 Discontinued
0.7052 Intermediate Similarity NPD2780 Approved
0.7052 Intermediate Similarity NPD2782 Approved
0.7035 Intermediate Similarity NPD534 Phase 2
0.7035 Intermediate Similarity NPD537 Phase 2
0.7029 Intermediate Similarity NPD565 Phase 2
0.7027 Intermediate Similarity NPD9689 Approved
0.7027 Intermediate Similarity NPD6569 Phase 2
0.7012 Intermediate Similarity NPD3525 Discontinued
0.6995 Remote Similarity NPD796 Phase 2
0.6995 Remote Similarity NPD2383 Phase 1
0.6983 Remote Similarity NPD1620 Clinical (unspecified phase)
0.697 Remote Similarity NPD8823 Approved
0.6966 Remote Similarity NPD5100 Phase 3
0.6959 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6946 Remote Similarity NPD4703 Approved
0.6946 Remote Similarity NPD4702 Approved
0.6939 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8063 Discontinued
0.6891 Remote Similarity NPD4038 Approved
0.6891 Remote Similarity NPD4036 Approved
0.6891 Remote Similarity NPD32 Approved
0.6891 Remote Similarity NPD4034 Approved
0.6891 Remote Similarity NPD4122 Approved
0.6891 Remote Similarity NPD4033 Approved
0.6891 Remote Similarity NPD4039 Approved
0.6891 Remote Similarity NPD31 Approved
0.6891 Remote Similarity NPD4035 Approved
0.6891 Remote Similarity NPD4037 Approved
0.6879 Remote Similarity NPD687 Clinical (unspecified phase)
0.6878 Remote Similarity NPD2952 Discontinued
0.6878 Remote Similarity NPD4086 Phase 1
0.6855 Remote Similarity NPD9206 Approved
0.6855 Remote Similarity NPD9207 Approved
0.6845 Remote Similarity NPD3921 Approved
0.6845 Remote Similarity NPD3922 Approved
0.6845 Remote Similarity NPD3923 Approved
0.6845 Remote Similarity NPD3924 Approved
0.6831 Remote Similarity NPD1096 Discontinued
0.6828 Remote Similarity NPD3321 Discontinued
0.6825 Remote Similarity NPD3478 Clinical (unspecified phase)
0.6825 Remote Similarity NPD3477 Phase 2
0.6813 Remote Similarity NPD4204 Approved
0.6813 Remote Similarity NPD4203 Approved
0.6813 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6807 Remote Similarity NPD3717 Discontinued
0.6806 Remote Similarity NPD9688 Approved
0.6806 Remote Similarity NPD9687 Approved
0.6798 Remote Similarity NPD1078 Clinical (unspecified phase)
0.6798 Remote Similarity NPD485 Clinical (unspecified phase)
0.6793 Remote Similarity NPD3082 Discontinued
0.6791 Remote Similarity NPD4699 Discontinued
0.6774 Remote Similarity NPD4021 Phase 2
0.6772 Remote Similarity NPD3396 Approved
0.6772 Remote Similarity NPD3395 Approved
0.6771 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4131 Phase 3
0.6765 Remote Similarity NPD8356 Approved
0.6757 Remote Similarity NPD4375 Approved
0.6735 Remote Similarity NPD6290 Phase 2
0.6735 Remote Similarity NPD1392 Approved
0.6725 Remote Similarity NPD9595 Approved
0.6725 Remote Similarity NPD9596 Approved
0.6721 Remote Similarity NPD3386 Phase 2
0.672 Remote Similarity NPD4551 Phase 2
0.672 Remote Similarity NPD1038 Approved
0.672 Remote Similarity NPD802 Phase 2
0.672 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6703 Remote Similarity NPD1503 Clinical (unspecified phase)
0.6703 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6702 Remote Similarity NPD7948 Phase 1
0.6685 Remote Similarity NPD5862 Discovery
0.6684 Remote Similarity NPD9714 Clinical (unspecified phase)
0.6684 Remote Similarity NPD484 Approved
0.6683 Remote Similarity NPD4502 Phase 2
0.6683 Remote Similarity NPD5939 Approved
0.6683 Remote Similarity NPD3570 Phase 2
0.6683 Remote Similarity NPD4945 Discontinued
0.6683 Remote Similarity NPD5936 Approved
0.6667 Remote Similarity NPD3039 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9574 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2077 Approved
0.6667 Remote Similarity NPD2076 Approved
0.6649 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6649 Remote Similarity NPD2544 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4724 Clinical (unspecified phase)
0.6648 Remote Similarity NPD1684 Approved
0.6648 Remote Similarity NPD1685 Approved
0.6648 Remote Similarity NPD1032 Phase 2
0.6635 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6635 Remote Similarity NPD8430 Approved
0.6632 Remote Similarity NPD6361 Phase 2
0.6629 Remote Similarity NPD704 Clinical (unspecified phase)
0.6627 Remote Similarity NPD9074 Approved
0.6627 Remote Similarity NPD9075 Approved
0.6625 Remote Similarity NPD5352 Clinical (unspecified phase)
0.6617 Remote Similarity NPD2616 Phase 3
0.6617 Remote Similarity NPD2615 Phase 3
0.6613 Remote Similarity NPD4889 Approved
0.6609 Remote Similarity NPD1274 Clinical (unspecified phase)
0.6599 Remote Similarity NPD3932 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6389 Clinical (unspecified phase)
0.6589 Remote Similarity NPD2414 Clinical (unspecified phase)
0.658 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6579 Remote Similarity NPD4372 Phase 1
0.6566 Remote Similarity NPD7222 Phase 2
0.6566 Remote Similarity NPD3930 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4072 Approved
0.6557 Remote Similarity NPD4071 Approved
0.6546 Remote Similarity NPD5999 Phase 2
0.6545 Remote Similarity NPD4529 Approved
0.6545 Remote Similarity NPD4528 Approved
0.6545 Remote Similarity NPD4526 Approved
0.6541 Remote Similarity NPD1570 Approved
0.6538 Remote Similarity NPD1923 Clinical (unspecified phase)
0.6537 Remote Similarity NPD7203 Clinical (unspecified phase)
0.6531 Remote Similarity NPD3928 Approved
0.6531 Remote Similarity NPD3931 Approved
0.6526 Remote Similarity NPD4148 Approved
0.6513 Remote Similarity NPD1740 Approved
0.6513 Remote Similarity NPD1739 Approved
0.6512 Remote Similarity NPD3576 Approved
0.6512 Remote Similarity NPD3575 Approved
0.6507 Remote Similarity NPD5640 Discontinued
0.6507 Remote Similarity NPD7603 Discontinued
0.6505 Remote Similarity NPD5596 Phase 2
0.65 Remote Similarity NPD4437 Phase 3
0.6497 Remote Similarity NPD2511 Approved
0.6489 Remote Similarity NPD706 Phase 1
0.6488 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6486 Remote Similarity NPD2601 Approved
0.6486 Remote Similarity NPD2600 Approved
0.6486 Remote Similarity NPD2599 Approved
0.6485 Remote Similarity NPD3330 Phase 1
0.6474 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6473 Remote Similarity NPD7726 Phase 1
0.6471 Remote Similarity NPD5612 Discontinued
0.6471 Remote Similarity NPD751 Clinical (unspecified phase)
0.6467 Remote Similarity NPD6641 Approved
0.6467 Remote Similarity NPD6642 Approved
0.6467 Remote Similarity NPD1380 Discovery
0.6465 Remote Similarity NPD4795 Phase 2
0.6464 Remote Similarity NPD7474 Suspended
0.6458 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6455 Remote Similarity NPD8021 Approved
0.6455 Remote Similarity NPD8020 Approved
0.6448 Remote Similarity NPD5065 Approved
0.6442 Remote Similarity NPD1856 Discontinued
0.644 Remote Similarity NPD2334 Discontinued

  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