Structure

Physi-Chem Properties

Molecular Weight:  125.05
Volume:  124.444
LogP:  -0.371
LogD:  0.06
LogS:  -0.639
# Rotatable Bonds:  1
TPSA:  53.35
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.566
Synthetic Accessibility Score:  2.304
Fsp3:  0.167
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:  -4.474
MDCK Permeability:  1.1466014257166535e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.161
30% Bioavailability (F30%):  0.179

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.103
Plasma Protein Binding (PPB):  23.64856719970703%
Volume Distribution (VD):  1.406
Pgp-substrate:  77.52450561523438%

ADMET: Metabolism

CYP1A2-inhibitor:  0.097
CYP1A2-substrate:  0.116
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.098
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.575
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.586
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.144

ADMET: Excretion

Clearance (CL):  9.704
Half-life (T1/2):  0.846

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.06
Drug-inuced Liver Injury (DILI):  0.387
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.222
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.705
Carcinogencity:  0.311
Eye Corrosion:  0.045
Eye Irritation:  0.987
Respiratory Toxicity:  0.065

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

  Natural Product: NPC220523

Natural Product ID:  NPC220523
Common Name*:   3-Hydroxy-6-Pyridinemethanol
IUPAC Name:   6-(hydroxymethyl)pyridin-3-ol
Synonyms:  
Standard InCHIKey:  NESFDGDRYVANBC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H7NO2/c8-4-5-1-2-6(9)3-7-5/h1-3,8-9H,4H2
SMILES:  OCc1ccc(cn1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1917284
PubChem CID:   419490
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0004151] Hydroxypyridines

*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]
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]
NPO30786 Viola yedoensis Species Violaceae Eukaryota n.a. leaf n.a. PMID[25562805]
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]
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. 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]
NPO30786 Viola yedoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18120 Radix rehmanniae Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30786 Viola yedoensis Species Violaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7103 Allium sativum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae 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
NPT1211 Individual Protein Dual specificity protein phosphatase 3 Homo sapiens IC50 > 100000.0 nM PMID[458532]
NPT2570 Individual Protein Protein-tyrosine phosphatase LC-PTP Homo sapiens IC50 > 100000.0 nM PMID[458532]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[458532]

☑ 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 NPC220523 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
0.9051 High Similarity NPC174421
0.8811 High Similarity NPC318935
0.8699 High Similarity NPC470395
0.8562 High Similarity NPC470394
0.8562 High Similarity NPC470403
0.8562 High Similarity NPC470404
0.8421 Intermediate Similarity NPC63562
0.8345 Intermediate Similarity NPC151489
0.8312 Intermediate Similarity NPC269919
0.8312 Intermediate Similarity NPC132680
0.8302 Intermediate Similarity NPC253810
0.8205 Intermediate Similarity NPC322976
0.8205 Intermediate Similarity NPC63338
0.8205 Intermediate Similarity NPC324203
0.8187 Intermediate Similarity NPC252590
0.817 Intermediate Similarity NPC284348
0.8151 Intermediate Similarity NPC328029
0.8125 Intermediate Similarity NPC473764
0.8125 Intermediate Similarity NPC314940
0.8101 Intermediate Similarity NPC263439
0.7987 Intermediate Similarity NPC211187
0.7975 Intermediate Similarity NPC25899
0.7974 Intermediate Similarity NPC257142
0.7925 Intermediate Similarity NPC48192
0.7844 Intermediate Similarity NPC219963
0.7821 Intermediate Similarity NPC153769
0.7803 Intermediate Similarity NPC226202
0.7791 Intermediate Similarity NPC256828
0.7736 Intermediate Similarity NPC116573
0.7724 Intermediate Similarity NPC165370
0.7677 Intermediate Similarity NPC161292
0.7677 Intermediate Similarity NPC302159
0.7633 Intermediate Similarity NPC161887
0.7633 Intermediate Similarity NPC266551
0.763 Intermediate Similarity NPC3715
0.7574 Intermediate Similarity NPC52831
0.7574 Intermediate Similarity NPC325705
0.7399 Intermediate Similarity NPC20249
0.7394 Intermediate Similarity NPC471178
0.7378 Intermediate Similarity NPC124542
0.7378 Intermediate Similarity NPC59779
0.7378 Intermediate Similarity NPC79911
0.7378 Intermediate Similarity NPC471177
0.7365 Intermediate Similarity NPC306397
0.7365 Intermediate Similarity NPC212125
0.7349 Intermediate Similarity NPC108469
0.7333 Intermediate Similarity NPC473057
0.7321 Intermediate Similarity NPC121658
0.7321 Intermediate Similarity NPC14651
0.7317 Intermediate Similarity NPC120798
0.7297 Intermediate Similarity NPC316403
0.7285 Intermediate Similarity NPC256893
0.7262 Intermediate Similarity NPC476518
0.7256 Intermediate Similarity NPC84508
0.7241 Intermediate Similarity NPC156059
0.7216 Intermediate Similarity NPC36498
0.7209 Intermediate Similarity NPC149402
0.7209 Intermediate Similarity NPC42979
0.7208 Intermediate Similarity NPC29702
0.7202 Intermediate Similarity NPC44161
0.72 Intermediate Similarity NPC295158
0.7195 Intermediate Similarity NPC138018
0.7193 Intermediate Similarity NPC224764
0.7189 Intermediate Similarity NPC470500
0.7174 Intermediate Similarity NPC231655
0.7168 Intermediate Similarity NPC478032
0.7152 Intermediate Similarity NPC113812
0.7151 Intermediate Similarity NPC184964
0.7143 Intermediate Similarity NPC192315
0.7105 Intermediate Similarity NPC315320
0.7104 Intermediate Similarity NPC476167
0.7097 Intermediate Similarity NPC329708
0.7097 Intermediate Similarity NPC47059
0.7097 Intermediate Similarity NPC165349
0.7097 Intermediate Similarity NPC118832
0.7097 Intermediate Similarity NPC274291
0.7097 Intermediate Similarity NPC264166
0.7093 Intermediate Similarity NPC150048
0.7093 Intermediate Similarity NPC203754
0.7089 Intermediate Similarity NPC60553
0.7076 Intermediate Similarity NPC111624
0.7052 Intermediate Similarity NPC96890
0.7051 Intermediate Similarity NPC114310
0.7041 Intermediate Similarity NPC41717
0.7035 Intermediate Similarity NPC95898
0.7013 Intermediate Similarity NPC322488
0.7012 Intermediate Similarity NPC36168
0.7006 Intermediate Similarity NPC314002
0.7 Intermediate Similarity NPC471598
0.6995 Remote Similarity NPC477110
0.6989 Remote Similarity NPC220765
0.6984 Remote Similarity NPC477111
0.6968 Remote Similarity NPC477113
0.6949 Remote Similarity NPC207851
0.6949 Remote Similarity NPC204717
0.6927 Remote Similarity NPC46580
0.6923 Remote Similarity NPC314270
0.6923 Remote Similarity NPC97367
0.6923 Remote Similarity NPC102423
0.6919 Remote Similarity NPC273532
0.6911 Remote Similarity NPC5145
0.691 Remote Similarity NPC241025
0.6906 Remote Similarity NPC114974
0.6902 Remote Similarity NPC267928
0.6901 Remote Similarity NPC319456
0.6894 Remote Similarity NPC471323
0.6888 Remote Similarity NPC315804
0.6888 Remote Similarity NPC313804
0.6872 Remote Similarity NPC171171
0.6864 Remote Similarity NPC177404
0.6861 Remote Similarity NPC83987
0.6855 Remote Similarity NPC280853
0.6855 Remote Similarity NPC85443
0.6854 Remote Similarity NPC55038
0.6839 Remote Similarity NPC324611
0.6833 Remote Similarity NPC74382
0.6833 Remote Similarity NPC206251
0.6831 Remote Similarity NPC329541
0.6821 Remote Similarity NPC470799
0.6821 Remote Similarity NPC8022
0.6816 Remote Similarity NPC244536
0.6813 Remote Similarity NPC245657
0.6813 Remote Similarity NPC285016
0.6811 Remote Similarity NPC90229
0.6811 Remote Similarity NPC224928
0.6806 Remote Similarity NPC18348
0.6798 Remote Similarity NPC48938
0.6797 Remote Similarity NPC471311
0.6797 Remote Similarity NPC471313
0.6796 Remote Similarity NPC110741
0.6792 Remote Similarity NPC471596
0.6786 Remote Similarity NPC212742
0.6776 Remote Similarity NPC324149
0.6776 Remote Similarity NPC99666
0.6766 Remote Similarity NPC33229
0.6766 Remote Similarity NPC263455
0.6763 Remote Similarity NPC126481
0.6757 Remote Similarity NPC251090
0.6753 Remote Similarity NPC313823
0.6748 Remote Similarity NPC167400
0.6739 Remote Similarity NPC289786
0.6737 Remote Similarity NPC472259
0.6735 Remote Similarity NPC288349
0.6725 Remote Similarity NPC118511
0.6722 Remote Similarity NPC42591
0.6706 Remote Similarity NPC131718
0.6705 Remote Similarity NPC194724
0.6703 Remote Similarity NPC32771
0.6703 Remote Similarity NPC326634
0.6702 Remote Similarity NPC19872
0.6686 Remote Similarity NPC313791
0.6685 Remote Similarity NPC314573
0.6685 Remote Similarity NPC478023
0.6684 Remote Similarity NPC475774
0.6667 Remote Similarity NPC71079
0.6667 Remote Similarity NPC193238
0.6649 Remote Similarity NPC84853
0.6632 Remote Similarity NPC470678
0.6632 Remote Similarity NPC211813
0.6631 Remote Similarity NPC156704
0.6631 Remote Similarity NPC77555
0.6629 Remote Similarity NPC158129
0.6628 Remote Similarity NPC162268
0.6628 Remote Similarity NPC474217
0.6617 Remote Similarity NPC470501
0.6614 Remote Similarity NPC315491
0.6614 Remote Similarity NPC45459
0.6613 Remote Similarity NPC146724
0.6612 Remote Similarity NPC472289
0.6612 Remote Similarity NPC224327
0.6609 Remote Similarity NPC1527
0.6597 Remote Similarity NPC200836
0.6596 Remote Similarity NPC472284
0.6595 Remote Similarity NPC195268
0.6595 Remote Similarity NPC133140
0.6595 Remote Similarity NPC471448
0.6592 Remote Similarity NPC317010
0.659 Remote Similarity NPC85918
0.6583 Remote Similarity NPC173080
0.658 Remote Similarity NPC88008
0.6578 Remote Similarity NPC109922
0.6578 Remote Similarity NPC222018
0.6578 Remote Similarity NPC242209
0.6576 Remote Similarity NPC144381
0.6576 Remote Similarity NPC134079
0.6575 Remote Similarity NPC284559
0.6575 Remote Similarity NPC62069
0.6575 Remote Similarity NPC320394
0.6573 Remote Similarity NPC76540
0.6571 Remote Similarity NPC164664
0.6569 Remote Similarity NPC186351
0.6567 Remote Similarity NPC470502
0.6561 Remote Similarity NPC187558
0.6559 Remote Similarity NPC230403
0.6559 Remote Similarity NPC307963
0.6552 Remote Similarity NPC27802
0.6552 Remote Similarity NPC127730
0.6552 Remote Similarity NPC278366
0.655 Remote Similarity NPC230869
0.6546 Remote Similarity NPC287208

  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 NPC220523 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
0.8618 High Similarity NPD604 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD861 Approved
0.8333 Intermediate Similarity NPD863 Approved
0.8333 Intermediate Similarity NPD862 Approved
0.8312 Intermediate Similarity NPD9382 Approved
0.8312 Intermediate Similarity NPD9383 Approved
0.8288 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.8205 Intermediate Similarity NPD9398 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD158 Discontinued
0.7866 Intermediate Similarity NPD9690 Approved
0.775 Intermediate Similarity NPD112 Approved
0.775 Intermediate Similarity NPD9705 Discontinued
0.7744 Intermediate Similarity NPD2123 Phase 3
0.7683 Intermediate Similarity NPD565 Phase 2
0.7574 Intermediate Similarity NPD9510 Approved
0.7516 Intermediate Similarity NPD9574 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9695 Approved
0.7484 Intermediate Similarity NPD9595 Approved
0.7484 Intermediate Similarity NPD9596 Approved
0.7436 Intermediate Similarity NPD8823 Approved
0.7432 Intermediate Similarity NPD5352 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD9506 Approved
0.7365 Intermediate Similarity NPD9284 Approved
0.7365 Intermediate Similarity NPD9080 Approved
0.7362 Intermediate Similarity NPD5255 Approved
0.7349 Intermediate Similarity NPD424 Approved
0.7349 Intermediate Similarity NPD425 Approved
0.733 Intermediate Similarity NPD1213 Phase 3
0.7289 Intermediate Similarity NPD926 Approved
0.7289 Intermediate Similarity NPD925 Approved
0.7247 Intermediate Similarity NPD9689 Approved
0.7216 Intermediate Similarity NPD9363 Approved
0.7216 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD9364 Phase 2
0.7216 Intermediate Similarity NPD1034 Phase 3
0.7202 Intermediate Similarity NPD2781 Approved
0.7202 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2782 Approved
0.7186 Intermediate Similarity NPD2780 Approved
0.7182 Intermediate Similarity NPD1229 Phase 2
0.7174 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD9098 Phase 3
0.7151 Intermediate Similarity NPD6159 Phase 2
0.7118 Intermediate Similarity NPD9548 Phase 2
0.7115 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD1620 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1418 Phase 2
0.7105 Intermediate Similarity NPD9206 Approved
0.7105 Intermediate Similarity NPD9207 Approved
0.7104 Intermediate Similarity NPD2175 Phase 3
0.7104 Intermediate Similarity NPD2177 Approved
0.7104 Intermediate Similarity NPD2176 Approved
0.7097 Intermediate Similarity NPD31 Approved
0.7097 Intermediate Similarity NPD4037 Approved
0.7097 Intermediate Similarity NPD4034 Approved
0.7097 Intermediate Similarity NPD4038 Approved
0.7097 Intermediate Similarity NPD4033 Approved
0.7097 Intermediate Similarity NPD32 Approved
0.7097 Intermediate Similarity NPD4035 Approved
0.7097 Intermediate Similarity NPD4036 Approved
0.7097 Intermediate Similarity NPD4039 Approved
0.7097 Intermediate Similarity NPD4122 Approved
0.7091 Intermediate Similarity NPD2582 Approved
0.7091 Intermediate Similarity NPD2581 Approved
0.7086 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD5319 Approved
0.7059 Intermediate Similarity NPD5320 Approved
0.7056 Intermediate Similarity NPD6569 Phase 2
0.7056 Intermediate Similarity NPD5317 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5316 Approved
0.7025 Intermediate Similarity NPD1649 Discontinued
0.7011 Intermediate Similarity NPD9687 Approved
0.7011 Intermediate Similarity NPD9688 Approved
0.7006 Intermediate Similarity NPD852 Discontinued
0.7 Intermediate Similarity NPD1352 Discontinued
0.694 Remote Similarity NPD3478 Clinical (unspecified phase)
0.694 Remote Similarity NPD3477 Phase 2
0.6937 Remote Similarity NPD3717 Discontinued
0.6932 Remote Similarity NPD9362 Approved
0.6902 Remote Similarity NPD1622 Discontinued
0.6894 Remote Similarity NPD3813 Approved
0.6886 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6886 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6886 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6875 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6872 Remote Similarity NPD3039 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4375 Approved
0.6851 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6290 Phase 2
0.6836 Remote Similarity NPD3386 Phase 2
0.6836 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6832 Remote Similarity NPD3525 Discontinued
0.6816 Remote Similarity NPD4086 Phase 1
0.6796 Remote Similarity NPD4021 Phase 2
0.6793 Remote Similarity NPD3395 Approved
0.6793 Remote Similarity NPD3396 Approved
0.6768 Remote Similarity NPD4702 Approved
0.6768 Remote Similarity NPD4703 Approved
0.6758 Remote Similarity NPD3321 Discontinued
0.6748 Remote Similarity NPD9075 Approved
0.6748 Remote Similarity NPD9074 Approved
0.674 Remote Similarity NPD2383 Phase 1
0.672 Remote Similarity NPD2952 Discontinued
0.6702 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6701 Remote Similarity NPD5936 Approved
0.6701 Remote Similarity NPD4502 Phase 2
0.6701 Remote Similarity NPD5939 Approved
0.67 Remote Similarity NPD8356 Approved
0.6689 Remote Similarity NPD9396 Approved
0.6689 Remote Similarity NPD9392 Approved
0.6686 Remote Similarity NPD2076 Approved
0.6686 Remote Similarity NPD2077 Approved
0.6667 Remote Similarity NPD8063 Discontinued
0.6667 Remote Similarity NPD4805 Approved
0.6667 Remote Similarity NPD1096 Discontinued
0.6667 Remote Similarity NPD5083 Clinical (unspecified phase)
0.6649 Remote Similarity NPD5999 Phase 2
0.6649 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6649 Remote Similarity NPD6361 Phase 2
0.6648 Remote Similarity NPD1923 Clinical (unspecified phase)
0.6647 Remote Similarity NPD704 Clinical (unspecified phase)
0.6631 Remote Similarity NPD7948 Phase 1
0.663 Remote Similarity NPD4699 Discontinued
0.663 Remote Similarity NPD3082 Discontinued
0.663 Remote Similarity NPD4148 Approved
0.663 Remote Similarity NPD4889 Approved
0.6617 Remote Similarity NPD1856 Discontinued
0.6615 Remote Similarity NPD3570 Phase 2
0.6615 Remote Similarity NPD4131 Phase 3
0.6614 Remote Similarity NPD484 Approved
0.6613 Remote Similarity NPD1602 Discontinued
0.6609 Remote Similarity NPD5862 Discovery
0.6601 Remote Similarity NPD5640 Discontinued
0.6595 Remote Similarity NPD3923 Approved
0.6595 Remote Similarity NPD3921 Approved
0.6595 Remote Similarity NPD3924 Approved
0.6595 Remote Similarity NPD3922 Approved
0.6595 Remote Similarity NPD4372 Phase 1
0.6584 Remote Similarity NPD1380 Discovery
0.6573 Remote Similarity NPD4071 Approved
0.6573 Remote Similarity NPD4072 Approved
0.6569 Remote Similarity NPD8430 Approved
0.6559 Remote Similarity NPD4528 Approved
0.6559 Remote Similarity NPD4526 Approved
0.6559 Remote Similarity NPD4529 Approved
0.6559 Remote Similarity NPD4551 Phase 2
0.6559 Remote Similarity NPD1038 Approved
0.6556 Remote Similarity NPD4203 Approved
0.6556 Remote Similarity NPD1570 Approved
0.6556 Remote Similarity NPD4204 Approved
0.6556 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6548 Remote Similarity NPD2616 Phase 3
0.6548 Remote Similarity NPD2615 Phase 3
0.6545 Remote Similarity NPD3928 Approved
0.6545 Remote Similarity NPD3931 Approved
0.6545 Remote Similarity NPD6975 Discontinued
0.6543 Remote Similarity NPD4804 Approved
0.6541 Remote Similarity NPD2334 Discontinued
0.6529 Remote Similarity NPD1274 Clinical (unspecified phase)
0.6526 Remote Similarity NPD6389 Clinical (unspecified phase)
0.6517 Remote Similarity NPD5100 Phase 3
0.6509 Remote Similarity NPD180 Clinical (unspecified phase)
0.6503 Remote Similarity NPD107 Approved
0.65 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6495 Remote Similarity NPD1392 Approved
0.6488 Remote Similarity NPD6553 Clinical (unspecified phase)
0.6484 Remote Similarity NPD3569 Discontinued
0.6483 Remote Similarity NPD9376 Approved
0.6481 Remote Similarity NPD2896 Discontinued
0.648 Remote Similarity NPD1032 Phase 2
0.6474 Remote Similarity NPD1685 Approved
0.6474 Remote Similarity NPD1684 Approved
0.6467 Remote Similarity NPD1661 Suspended
0.6467 Remote Similarity NPD6393 Clinical (unspecified phase)
0.6463 Remote Similarity NPD1383 Phase 3
0.6463 Remote Similarity NPD1382 Phase 2
0.6463 Remote Similarity NPD4823 Approved
0.6463 Remote Similarity NPD4824 Approved
0.6461 Remote Similarity NPD5065 Approved
0.6455 Remote Similarity NPD2959 Phase 3
0.6453 Remote Similarity NPD3433 Clinical (unspecified phase)
0.6453 Remote Similarity NPD4945 Discontinued
0.6448 Remote Similarity NPD6344 Clinical (unspecified phase)
0.6437 Remote Similarity NPD5088 Discontinued
0.6432 Remote Similarity NPD408 Approved
0.6432 Remote Similarity NPD9714 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3576 Approved
0.6429 Remote Similarity NPD3575 Approved
0.6425 Remote Similarity NPD2382 Approved
0.6425 Remote Similarity NPD2381 Approved
0.6425 Remote Similarity NPD2380 Approved
0.6424 Remote Similarity NPD1427 Clinical (unspecified phase)
0.6421 Remote Similarity NPD712 Clinical (unspecified phase)
0.6416 Remote Similarity NPD687 Clinical (unspecified phase)
0.6414 Remote Similarity NPD3330 Phase 1
0.6413 Remote Similarity NPD706 Phase 1
0.641 Remote Similarity NPD796 Phase 2

  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