Structure

Physi-Chem Properties

Molecular Weight:  215.08
Volume:  203.802
LogP:  0.891
LogD:  1.213
LogS:  -2.424
# Rotatable Bonds:  2
TPSA:  82.86
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.668
Synthetic Accessibility Score:  3.447
Fsp3:  0.1
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.987
MDCK Permeability:  4.556739440886304e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.621
30% Bioavailability (F30%):  0.392

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.366
Plasma Protein Binding (PPB):  58.41645050048828%
Volume Distribution (VD):  1.856
Pgp-substrate:  57.72836685180664%

ADMET: Metabolism

CYP1A2-inhibitor:  0.801
CYP1A2-substrate:  0.194
CYP2C19-inhibitor:  0.456
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.068
CYP2C9-substrate:  0.421
CYP2D6-inhibitor:  0.772
CYP2D6-substrate:  0.03
CYP3A4-inhibitor:  0.286
CYP3A4-substrate:  0.487

ADMET: Excretion

Clearance (CL):  11.801
Half-life (T1/2):  0.929

ADMET: Toxicity

hERG Blockers:  0.057
Human Hepatotoxicity (H-HT):  0.668
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.972
Maximum Recommended Daily Dose:  0.594
Skin Sensitization:  0.859
Carcinogencity:  0.014
Eye Corrosion:  0.005
Eye Irritation:  0.248
Respiratory Toxicity:  0.979

Download Data

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

  Natural Product: NPC50511

Natural Product ID:  NPC50511
Common Name*:   Kinetin
IUPAC Name:   N-(furan-2-ylmethyl)-7H-purin-6-amine
Synonyms:   Kinetin
Standard InCHIKey:  QANMHLXAZMSUEX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H9N5O/c1-2-7(16-3-1)4-11-9-8-10(13-5-12-8)15-6-14-9/h1-3,5-6H,4H2,(H2,11,12,13,14,15)
SMILES:  c1coc(c1)CNc1nc[nH]c2c1ncn2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL228792
PubChem CID:   3830
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001797] Imidazopyrimidines
        • [CHEMONTID:0000245] Purines and purine derivatives
          • [CHEMONTID:0002987] 6-aminopurines
            • [CHEMONTID:0003454] 6-alkylaminopurines

*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
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[11678654]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15787451]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota Roots Anhui, China n.a. PMID[22694318]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31050 Isatis indigotica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2690 Carapichea ipecacuanha Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2690 Carapichea ipecacuanha Species Rubiaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 21900.0 nM PMID[520885]
NPT3098 Individual Protein Chitinase Aspergillus fumigatus IC50 > 1000000.0 nM PMID[520886]
NPT3099 Individual Protein Endochitinase Saccharomyces cerevisiae S288c Ki = 3200.0 nM PMID[520886]
NPT3100 Individual Protein Acidic mammalian chitinase Homo sapiens IC50 > 1000000.0 nM PMID[520886]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 5011.9 nM PMID[520888]
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 12589.3 nM PMID[520889]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 12589.3 nM PMID[520888]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 7943.28 nM PMID[520889]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 819.9 nM PMID[520888]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 58.0 nM PMID[520888]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = -5.12 % PMID[520890]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 25118864.3 nM PMID[520888]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 > 10000.0 nM PMID[520894]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 > 10000.0 nM PMID[520895]
NPT1970 Cell Line THP-1 Homo sapiens Activity = 106.87 % PMID[520897]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 45.94 % PMID[520897]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = -19.51 % PMID[520897]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[520887]
NPT2 Others Unspecified Potency = 15848.9 nM PMID[520888]
NPT2 Others Unspecified Potency = 7943.3 nM PMID[520889]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 10000.0 nM PMID[520888]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 25118.9 nM PMID[520888]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9285.0 nM PMID[520888]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[520888]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 3.13 % PMID[520890]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 96.48 % PMID[520891]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 100.56 % PMID[520891]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 10583.9 nM PMID[520892]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 23694.5 nM PMID[520892]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency n.a. 1677.4 nM PMID[520892]
NPT35 Others n.a. Activity = 0.71 equiv PMID[520898]
NPT3478 Organism Nicotiana tabacum Nicotiana tabacum Activity = 101.0 % PMID[520898]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 98.0 % PMID[520898]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition index = 0.01403 n.a. PMID[520899]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 3.99 % PMID[520900]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.2348 n.a. PMID[520901]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -3.89 % PMID[520902]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.06 % PMID[520903]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[520904]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[520904]
NPT27 Others Unspecified Stability = 83.0 % PMID[520905]
NPT27 Others Unspecified Stability = 78.0 % PMID[520905]
NPT27 Others Unspecified PPB = 12.9 % PMID[520905]
NPT27 Others Unspecified logPapp > -6.0 n.a. PMID[520905]
NPT27 Others Unspecified Papp = 7.6 10^-6 cm/s PMID[520905]
NPT27 Others Unspecified Papp = 16.3 10^-6 cm/s PMID[520905]
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24541.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT27036 ORGANISM Amaranthus caudatus Amaranthus caudatus Activity = 68.0 % PMID[520898]

☑ 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 NPC50511 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
0.7056 Intermediate Similarity NPC160666
0.6916 Remote Similarity NPC250178
0.6795 Remote Similarity NPC115595
0.6707 Remote Similarity NPC150447
0.6707 Remote Similarity NPC74619
0.6667 Remote Similarity NPC63109
0.6638 Remote Similarity NPC187145
0.6549 Remote Similarity NPC116555
0.6534 Remote Similarity NPC258048
0.6518 Remote Similarity NPC9729
0.6516 Remote Similarity NPC295452
0.6516 Remote Similarity NPC171393
0.6492 Remote Similarity NPC51854
0.6466 Remote Similarity NPC267811
0.6435 Remote Similarity NPC471603
0.642 Remote Similarity NPC235685
0.6417 Remote Similarity NPC21461
0.641 Remote Similarity NPC48317
0.6393 Remote Similarity NPC101350
0.6371 Remote Similarity NPC122436
0.6349 Remote Similarity NPC260434
0.6336 Remote Similarity NPC77101
0.6303 Remote Similarity NPC130570
0.63 Remote Similarity NPC103388
0.6293 Remote Similarity NPC118940
0.629 Remote Similarity NPC316756
0.6267 Remote Similarity NPC187558
0.6255 Remote Similarity NPC102593
0.6255 Remote Similarity NPC196718
0.625 Remote Similarity NPC242923
0.6245 Remote Similarity NPC323969
0.623 Remote Similarity NPC165964
0.6224 Remote Similarity NPC107160
0.621 Remote Similarity NPC148889
0.6197 Remote Similarity NPC282247
0.6188 Remote Similarity NPC84853
0.6172 Remote Similarity NPC53534
0.6171 Remote Similarity NPC210123
0.6154 Remote Similarity NPC152620
0.6148 Remote Similarity NPC470323
0.6134 Remote Similarity NPC168209
0.6129 Remote Similarity NPC314281
0.6129 Remote Similarity NPC40530
0.6129 Remote Similarity NPC30540
0.6128 Remote Similarity NPC476287
0.6122 Remote Similarity NPC267078
0.6122 Remote Similarity NPC935
0.6098 Remote Similarity NPC474357
0.6096 Remote Similarity NPC19872
0.6091 Remote Similarity NPC257851
0.6091 Remote Similarity NPC157931
0.6087 Remote Similarity NPC245816
0.6087 Remote Similarity NPC476138
0.6068 Remote Similarity NPC123839
0.6067 Remote Similarity NPC308906
0.6066 Remote Similarity NPC66777
0.6066 Remote Similarity NPC471762
0.6063 Remote Similarity NPC63971
0.6063 Remote Similarity NPC91868
0.6058 Remote Similarity NPC243633
0.6058 Remote Similarity NPC175150
0.6026 Remote Similarity NPC176538
0.6025 Remote Similarity NPC323244
0.6017 Remote Similarity NPC17305
0.6008 Remote Similarity NPC208898
0.6008 Remote Similarity NPC471615
0.6 Remote Similarity NPC232727
0.5991 Remote Similarity NPC132539
0.5991 Remote Similarity NPC77061
0.5983 Remote Similarity NPC266249
0.5977 Remote Similarity NPC26543
0.5968 Remote Similarity NPC180504
0.5966 Remote Similarity NPC477979
0.5966 Remote Similarity NPC50562
0.5964 Remote Similarity NPC313514
0.596 Remote Similarity NPC240384
0.5957 Remote Similarity NPC121772
0.5957 Remote Similarity NPC185782
0.5953 Remote Similarity NPC56271
0.595 Remote Similarity NPC60621
0.5949 Remote Similarity NPC26679
0.5944 Remote Similarity NPC39370
0.5941 Remote Similarity NPC67658
0.5935 Remote Similarity NPC314954
0.5932 Remote Similarity NPC113369
0.5927 Remote Similarity NPC328924
0.5927 Remote Similarity NPC473186
0.5927 Remote Similarity NPC207686
0.5902 Remote Similarity NPC229893
0.5882 Remote Similarity NPC161887
0.588 Remote Similarity NPC182222
0.5877 Remote Similarity NPC280638
0.587 Remote Similarity NPC156003
0.587 Remote Similarity NPC194740
0.5868 Remote Similarity NPC288987
0.5867 Remote Similarity NPC472289
0.5866 Remote Similarity NPC39092
0.5865 Remote Similarity NPC167860
0.5865 Remote Similarity NPC123976
0.5863 Remote Similarity NPC469554
0.5856 Remote Similarity NPC270834
0.5853 Remote Similarity NPC472067
0.5853 Remote Similarity NPC472066
0.5853 Remote Similarity NPC472031
0.5851 Remote Similarity NPC27041
0.585 Remote Similarity NPC471614
0.5847 Remote Similarity NPC287208
0.5847 Remote Similarity NPC476465
0.5843 Remote Similarity NPC477806
0.5843 Remote Similarity NPC477795
0.5843 Remote Similarity NPC477796
0.5843 Remote Similarity NPC477805
0.584 Remote Similarity NPC141053
0.584 Remote Similarity NPC187501
0.5837 Remote Similarity NPC472068
0.5833 Remote Similarity NPC15801
0.5833 Remote Similarity NPC473821
0.5833 Remote Similarity NPC153452
0.583 Remote Similarity NPC45190
0.5826 Remote Similarity NPC467439
0.5826 Remote Similarity NPC469717
0.5813 Remote Similarity NPC125597
0.5811 Remote Similarity NPC219963
0.5809 Remote Similarity NPC8022
0.5809 Remote Similarity NPC470799
0.5809 Remote Similarity NPC36405
0.5806 Remote Similarity NPC476518
0.5805 Remote Similarity NPC321428
0.5805 Remote Similarity NPC249583
0.5796 Remote Similarity NPC216612
0.5792 Remote Similarity NPC89508
0.5787 Remote Similarity NPC472259
0.5785 Remote Similarity NPC312645
0.5785 Remote Similarity NPC12100
0.5783 Remote Similarity NPC69843
0.5782 Remote Similarity NPC314222
0.5782 Remote Similarity NPC33229
0.5782 Remote Similarity NPC196449
0.5782 Remote Similarity NPC120070
0.5781 Remote Similarity NPC82548
0.5781 Remote Similarity NPC71238
0.578 Remote Similarity NPC54214
0.578 Remote Similarity NPC14651
0.578 Remote Similarity NPC121658
0.5776 Remote Similarity NPC284338
0.5773 Remote Similarity NPC286195
0.5771 Remote Similarity NPC472061
0.5771 Remote Similarity NPC134079
0.5763 Remote Similarity NPC175602
0.5759 Remote Similarity NPC284678
0.5758 Remote Similarity NPC267928
0.5758 Remote Similarity NPC74153
0.5756 Remote Similarity NPC174758
0.5756 Remote Similarity NPC174672
0.5755 Remote Similarity NPC315411
0.5753 Remote Similarity NPC111624
0.5749 Remote Similarity NPC212766
0.5749 Remote Similarity NPC289423
0.5744 Remote Similarity NPC177996
0.5744 Remote Similarity NPC322064
0.5744 Remote Similarity NPC147983
0.5744 Remote Similarity NPC62995
0.574 Remote Similarity NPC266551
0.574 Remote Similarity NPC118776
0.5738 Remote Similarity NPC208084
0.5737 Remote Similarity NPC101543
0.5736 Remote Similarity NPC178858
0.5733 Remote Similarity NPC20249
0.5728 Remote Similarity NPC124276
0.5727 Remote Similarity NPC296527
0.572 Remote Similarity NPC472285
0.572 Remote Similarity NPC305984
0.572 Remote Similarity NPC75179
0.572 Remote Similarity NPC223189
0.5714 Remote Similarity NPC161801
0.5714 Remote Similarity NPC102755
0.5714 Remote Similarity NPC329631
0.5709 Remote Similarity NPC322482
0.5708 Remote Similarity NPC103361
0.5708 Remote Similarity NPC476527
0.5708 Remote Similarity NPC146418
0.5708 Remote Similarity NPC54981
0.5703 Remote Similarity NPC478078
0.5703 Remote Similarity NPC303374
0.5702 Remote Similarity NPC76748
0.5702 Remote Similarity NPC472062
0.5702 Remote Similarity NPC472063
0.5702 Remote Similarity NPC472069
0.5697 Remote Similarity NPC131885
0.5696 Remote Similarity NPC326422
0.5696 Remote Similarity NPC472064
0.5693 Remote Similarity NPC23215
0.5691 Remote Similarity NPC90019
0.5691 Remote Similarity NPC198503
0.5691 Remote Similarity NPC473317
0.569 Remote Similarity NPC61038
0.569 Remote Similarity NPC472070
0.569 Remote Similarity NPC106824
0.5688 Remote Similarity NPC1527
0.5685 Remote Similarity NPC308137

  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 NPC50511 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 NPD429 Approved
0.8009 Intermediate Similarity NPD2547 Discontinued
0.7532 Intermediate Similarity NPD2777 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD2311 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6286 Phase 3
0.7384 Intermediate Similarity NPD1480 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1273 Discontinued
0.7311 Intermediate Similarity NPD3844 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5703 Discontinued
0.7174 Intermediate Similarity NPD1961 Clinical (unspecified phase)
0.7137 Intermediate Similarity NPD1927 Discontinued
0.7097 Intermediate Similarity NPD2130 Discontinued
0.7085 Intermediate Similarity NPD1960 Phase 2
0.7063 Intermediate Similarity NPD7198 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4713 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4714 Approved
0.7051 Intermediate Similarity NPD34 Approved
0.7051 Intermediate Similarity NPD4715 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD4654 Phase 1
0.7004 Intermediate Similarity NPD5041 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6760 Discontinued
0.6951 Remote Similarity NPD5116 Phase 1
0.6951 Remote Similarity NPD6202 Discontinued
0.6948 Remote Similarity NPD6023 Discontinued
0.6905 Remote Similarity NPD5509 Phase 1
0.686 Remote Similarity NPD4558 Phase 2
0.6858 Remote Similarity NPD2412 Clinical (unspecified phase)
0.6833 Remote Similarity NPD5802 Phase 2
0.6798 Remote Similarity NPD1623 Approved
0.6798 Remote Similarity NPD5459 Phase 2
0.6766 Remote Similarity NPD2062 Phase 2
0.6754 Remote Similarity NPD1744 Approved
0.6752 Remote Similarity NPD1571 Phase 2
0.6723 Remote Similarity NPD5479 Discontinued
0.6721 Remote Similarity NPD4896 Clinical (unspecified phase)
0.6694 Remote Similarity NPD4440 Clinical (unspecified phase)
0.668 Remote Similarity NPD1225 Phase 2
0.668 Remote Similarity NPD1224 Phase 2
0.6667 Remote Similarity NPD3590 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1572 Phase 2
0.6667 Remote Similarity NPD245 Suspended
0.6652 Remote Similarity NPD983 Clinical (unspecified phase)
0.6652 Remote Similarity NPD796 Phase 2
0.6651 Remote Similarity NPD774 Phase 3
0.6639 Remote Similarity NPD4306 Phase 1
0.6639 Remote Similarity NPD6186 Approved
0.6638 Remote Similarity NPD6643 Discontinued
0.6625 Remote Similarity NPD946 Discontinued
0.6614 Remote Similarity NPD4442 Phase 2
0.661 Remote Similarity NPD1624 Phase 2
0.6606 Remote Similarity NPD978 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5044 Phase 2
0.659 Remote Similarity NPD6231 Phase 3
0.6583 Remote Similarity NPD1259 Discontinued
0.658 Remote Similarity NPD703 Discontinued
0.6573 Remote Similarity NPD3811 Discontinued
0.6556 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6553 Remote Similarity NPD1258 Discontinued
0.6531 Remote Similarity NPD7176 Clinical (unspecified phase)
0.6525 Remote Similarity NPD7051 Phase 3
0.6525 Remote Similarity NPD4935 Phase 2
0.6525 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6528 Phase 1
0.6504 Remote Similarity NPD1506 Discontinued
0.6502 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6494 Remote Similarity NPD6772 Clinical (unspecified phase)
0.649 Remote Similarity NPD6573 Phase 3
0.649 Remote Similarity NPD6572 Phase 2
0.6485 Remote Similarity NPD1504 Discontinued
0.6476 Remote Similarity NPD1367 Phase 2
0.6468 Remote Similarity NPD1286 Suspended
0.6461 Remote Similarity NPD2414 Clinical (unspecified phase)
0.6448 Remote Similarity NPD7689 Approved
0.6444 Remote Similarity NPD1659 Phase 1
0.6432 Remote Similarity NPD6223 Clinical (unspecified phase)
0.6431 Remote Similarity NPD7165 Approved
0.6431 Remote Similarity NPD7166 Approved
0.6429 Remote Similarity NPD8049 Phase 2
0.6426 Remote Similarity NPD7588 Discontinued
0.6426 Remote Similarity NPD4923 Phase 1
0.6425 Remote Similarity NPD705 Clinical (unspecified phase)
0.6423 Remote Similarity NPD5018 Phase 3
0.6419 Remote Similarity NPD3392 Approved
0.6419 Remote Similarity NPD1334 Clinical (unspecified phase)
0.6418 Remote Similarity NPD3613 Discontinued
0.6417 Remote Similarity NPD5139 Phase 1
0.6416 Remote Similarity NPD2965 Clinical (unspecified phase)
0.6414 Remote Similarity NPD4132 Clinical (unspecified phase)
0.6414 Remote Similarity NPD4560 Suspended
0.6414 Remote Similarity NPD4353 Phase 2
0.6414 Remote Similarity NPD2954 Approved
0.6414 Remote Similarity NPD2955 Approved
0.6409 Remote Similarity NPD4569 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5949 Phase 3
0.6404 Remote Similarity NPD5529 Phase 1
0.6404 Remote Similarity NPD5528 Clinical (unspecified phase)
0.6397 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6388 Remote Similarity NPD2876 Phase 3
0.6388 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1603 Discontinued
0.6382 Remote Similarity NPD6473 Phase 1
0.6379 Remote Similarity NPD3338 Clinical (unspecified phase)
0.6371 Remote Similarity NPD5118 Phase 2
0.6367 Remote Similarity NPD7117 Phase 2
0.636 Remote Similarity NPD1910 Approved
0.636 Remote Similarity NPD1911 Approved
0.6356 Remote Similarity NPD4459 Clinical (unspecified phase)
0.6356 Remote Similarity NPD4458 Phase 2
0.634 Remote Similarity NPD537 Phase 2
0.634 Remote Similarity NPD534 Phase 2
0.6332 Remote Similarity NPD2824 Phase 2
0.6327 Remote Similarity NPD3331 Phase 3
0.632 Remote Similarity NPD4863 Approved
0.632 Remote Similarity NPD6172 Clinical (unspecified phase)
0.6318 Remote Similarity NPD5887 Clinical (unspecified phase)
0.6318 Remote Similarity NPD3467 Clinical (unspecified phase)
0.6316 Remote Similarity NPD7323 Phase 2
0.6296 Remote Similarity NPD2471 Approved
0.6296 Remote Similarity NPD2472 Approved
0.6295 Remote Similarity NPD5482 Discontinued
0.629 Remote Similarity NPD1941 Approved
0.6286 Remote Similarity NPD4316 Phase 3
0.6284 Remote Similarity NPD7408 Phase 2
0.6283 Remote Similarity NPD1955 Discontinued
0.6282 Remote Similarity NPD5079 Phase 2
0.6265 Remote Similarity NPD5749 Phase 2
0.6261 Remote Similarity NPD6036 Suspended
0.6261 Remote Similarity NPD460 Discontinued
0.626 Remote Similarity NPD8442 Discontinued
0.6256 Remote Similarity NPD565 Phase 2
0.6255 Remote Similarity NPD3343 Phase 3
0.6255 Remote Similarity NPD3960 Clinical (unspecified phase)
0.6255 Remote Similarity NPD5080 Phase 2
0.625 Remote Similarity NPD5883 Phase 2
0.625 Remote Similarity NPD4673 Phase 2
0.625 Remote Similarity NPD949 Phase 1
0.624 Remote Similarity NPD6460 Clinical (unspecified phase)
0.6234 Remote Similarity NPD1600 Suspended
0.6231 Remote Similarity NPD7407 Discontinued
0.6231 Remote Similarity NPD3781 Phase 2
0.623 Remote Similarity NPD6244 Phase 3
0.623 Remote Similarity NPD6243 Phase 3
0.6227 Remote Similarity NPD207 Discontinued
0.6223 Remote Similarity NPD3941 Clinical (unspecified phase)
0.6222 Remote Similarity NPD8525 Approved
0.6222 Remote Similarity NPD772 Phase 3
0.621 Remote Similarity NPD7757 Approved
0.621 Remote Similarity NPD7758 Approved
0.6207 Remote Similarity NPD4048 Approved
0.6203 Remote Similarity NPD2884 Phase 1
0.6203 Remote Similarity NPD4555 Clinical (unspecified phase)
0.6201 Remote Similarity NPD1287 Phase 2
0.62 Remote Similarity NPD7206 Clinical (unspecified phase)
0.619 Remote Similarity NPD2443 Approved
0.619 Remote Similarity NPD2442 Approved
0.619 Remote Similarity NPD5644 Phase 1
0.6186 Remote Similarity NPD5643 Phase 2
0.6183 Remote Similarity NPD3255 Phase 1
0.6183 Remote Similarity NPD3254 Phase 1
0.618 Remote Similarity NPD2540 Clinical (unspecified phase)
0.6176 Remote Similarity NPD1834 Clinical (unspecified phase)
0.6174 Remote Similarity NPD2008 Discontinued
0.6169 Remote Similarity NPD4858 Phase 2
0.6167 Remote Similarity NPD6197 Approved
0.6165 Remote Similarity NPD6153 Approved
0.6164 Remote Similarity NPD2408 Discontinued
0.6164 Remote Similarity NPD415 Discontinued
0.6163 Remote Similarity NPD4080 Discontinued
0.6161 Remote Similarity NPD1951 Clinical (unspecified phase)
0.616 Remote Similarity NPD6756 Phase 1
0.616 Remote Similarity NPD7067 Approved
0.616 Remote Similarity NPD7068 Approved
0.616 Remote Similarity NPD5732 Approved
0.616 Remote Similarity NPD5731 Approved
0.616 Remote Similarity NPD5948 Phase 2
0.6154 Remote Similarity NPD2152 Clinical (unspecified phase)
0.6151 Remote Similarity NPD7898 Clinical (unspecified phase)
0.6151 Remote Similarity NPD1464 Clinical (unspecified phase)
0.6151 Remote Similarity NPD4187 Clinical (unspecified phase)
0.6151 Remote Similarity NPD7897 Phase 3
0.615 Remote Similarity NPD1982 Phase 1
0.615 Remote Similarity NPD1567 Clinical (unspecified phase)
0.6141 Remote Similarity NPD3043 Approved
0.6141 Remote Similarity NPD3938 Phase 1
0.6141 Remote Similarity NPD3042 Approved
0.6137 Remote Similarity NPD4495 Phase 1
0.6136 Remote Similarity NPD5757 Discontinued
0.6135 Remote Similarity NPD3962 Phase 2
0.6135 Remote Similarity NPD3959 Phase 2
0.6129 Remote Similarity NPD6750 Phase 2
0.6129 Remote Similarity NPD6605 Phase 3
0.6129 Remote Similarity NPD8421 Discontinued
0.6126 Remote Similarity NPD2410 Phase 2
0.6118 Remote Similarity NPD7980 Clinical (unspecified phase)
0.6118 Remote Similarity NPD1591 Approved
0.6116 Remote Similarity NPD1059 Phase 2
0.6113 Remote Similarity NPD5861 Clinical (unspecified phase)
0.6111 Remote Similarity NPD5750 Clinical (unspecified phase)
0.6109 Remote Similarity NPD5911 Clinical (unspecified phase)
0.6109 Remote Similarity NPD6393 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