Structure

Physi-Chem Properties

Molecular Weight:  138.03
Volume:  136.897
LogP:  1.214
LogD:  0.863
LogS:  -1.018
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.448
Synthetic Accessibility Score:  2.195
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.709
MDCK Permeability:  1.0171662324864883e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.919
30% Bioavailability (F30%):  0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.176
Plasma Protein Binding (PPB):  79.56826782226562%
Volume Distribution (VD):  0.603
Pgp-substrate:  18.727224349975586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.376
CYP1A2-substrate:  0.101
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.058
CYP2C9-substrate:  0.657
CYP2D6-inhibitor:  0.034
CYP2D6-substrate:  0.354
CYP3A4-inhibitor:  0.036
CYP3A4-substrate:  0.151

ADMET: Excretion

Clearance (CL):  11.851
Half-life (T1/2):  0.907

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.026
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.257
Rat Oral Acute Toxicity:  0.038
Maximum Recommended Daily Dose:  0.036
Skin Sensitization:  0.88
Carcinogencity:  0.278
Eye Corrosion:  0.982
Eye Irritation:  0.985
Respiratory Toxicity:  0.968

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  Natural Product: NPC28169

Natural Product ID:  NPC28169
Common Name*:   2,3-Dihydroxybenzaldehyde
IUPAC Name:   2,3-dihydroxybenzaldehyde
Synonyms:   2,3-Dihydroxybenzaldehyde
Standard InCHIKey:  IXWOUPGDGMCKGT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H
SMILES:  c1cc(C=O)c(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL491995
PubChem CID:   90579
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000124] Aldehydes
            • [CHEMONTID:0003213] Aryl-aldehydes
              • [CHEMONTID:0001345] Benzaldehydes
                • [CHEMONTID:0003978] Hydroxybenzaldehydes

*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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344559]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10344578]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10348041]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10604756]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10695669]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10724004]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10994816]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11099231]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11132958]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11374972]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[11473415]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14738393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Australian n.a. PMID[15497950]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15813185]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844966]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15974616]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16180833]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[1666120]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724845]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16830891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16872146]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17125235]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17315965]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17551212]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17608531]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17844998]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17887721]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17917237]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18044841]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Indonesian n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18081255]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. Northwest Territories, Canada 1995 PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18666798]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18776684]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19007176]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19129624]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19191549]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19856955]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19883065]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20092333]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20545334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[20836523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028889]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21028891]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21090727]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21314175]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[21639131]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21728289]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21751787]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21807523]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21873059]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. latex n.a. PMID[21879726]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[22145663]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22574670]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22583058]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22591466]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22758660]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[22775474]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23387796]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[23662937]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24592993]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24754815]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24878306]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24964393]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25211234]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25455147]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25495422]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25537064]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25918793]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[25934225]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26035239]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26465675]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26798949]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[26905826]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31013087]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31298537]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[31894983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32298122]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8501018]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[8784423]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8931733]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8982334]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031666]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9031676]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066767]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9066768]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9186568]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[9531983]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. mycelium n.a. PMID[9711246]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16308 Citrus wilsonii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16308 Citrus wilsonii Species Rutaceae 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
NPT1890 Individual Protein Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens IC50 = 20250.0 nM PMID[460972]
NPT1890 Individual Protein Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens IC50 = 20250.0 nM PMID[460973]
NPT1890 Individual Protein Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens IC50 = 20250 nM Patent: US8614253 B2
NPT2 Others Unspecified IC50 = 0.45 ug.mL-1 PMID[460970]
NPT2 Others Unspecified LD50 = 5.0 ug PMID[460971]
NPT2 Others Unspecified FC = 2.1 n.a. PMID[460971]
NPT2 Others Unspecified LD50 = 3.0 ug PMID[460971]
NPT2 Others Unspecified FC = 1.0 n.a. PMID[460971]
NPT2 Others Unspecified MHC = 40.0 ug PMID[460971]
NPT2 Others Unspecified FC = 8.0 n.a. PMID[460971]
NPT35 Others n.a. LogP = 1.19 n.a. PMID[460971]
NPT2 Others Unspecified MHC = 10.0 ug PMID[460971]
NPT2 Others Unspecified FC = 2.0 n.a. PMID[460971]

☑ 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 NPC28169 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
0.9196 High Similarity NPC163154
0.9115 High Similarity NPC278102
0.9083 High Similarity NPC303264
0.9083 High Similarity NPC473787
0.9052 High Similarity NPC260837
0.8934 High Similarity NPC261759
0.8899 High Similarity NPC163734
0.8475 Intermediate Similarity NPC150919
0.8462 Intermediate Similarity NPC240163
0.8462 Intermediate Similarity NPC161304
0.8403 Intermediate Similarity NPC41567
0.839 Intermediate Similarity NPC108288
0.839 Intermediate Similarity NPC312800
0.8374 Intermediate Similarity NPC4012
0.8359 Intermediate Similarity NPC157478
0.8359 Intermediate Similarity NPC200422
0.8359 Intermediate Similarity NPC295406
0.8359 Intermediate Similarity NPC289572
0.8333 Intermediate Similarity NPC156654
0.8333 Intermediate Similarity NPC224584
0.8333 Intermediate Similarity NPC100551
0.832 Intermediate Similarity NPC214620
0.8319 Intermediate Similarity NPC269414
0.8319 Intermediate Similarity NPC19149
0.8319 Intermediate Similarity NPC187913
0.8268 Intermediate Similarity NPC117609
0.8264 Intermediate Similarity NPC216297
0.8264 Intermediate Similarity NPC473662
0.8264 Intermediate Similarity NPC294964
0.8264 Intermediate Similarity NPC7151
0.825 Intermediate Similarity NPC184527
0.825 Intermediate Similarity NPC283844
0.8246 Intermediate Similarity NPC34715
0.8231 Intermediate Similarity NPC176102
0.8231 Intermediate Similarity NPC267539
0.8231 Intermediate Similarity NPC71108
0.8231 Intermediate Similarity NPC204257
0.8231 Intermediate Similarity NPC254832
0.8231 Intermediate Similarity NPC29317
0.8231 Intermediate Similarity NPC229638
0.823 Intermediate Similarity NPC219913
0.8203 Intermediate Similarity NPC34070
0.8203 Intermediate Similarity NPC469526
0.8182 Intermediate Similarity NPC206207
0.8175 Intermediate Similarity NPC117237
0.8175 Intermediate Similarity NPC203719
0.814 Intermediate Similarity NPC135801
0.8125 Intermediate Similarity NPC26697
0.8115 Intermediate Similarity NPC206778
0.8115 Intermediate Similarity NPC285829
0.811 Intermediate Similarity NPC247250
0.811 Intermediate Similarity NPC767
0.8095 Intermediate Similarity NPC49647
0.8095 Intermediate Similarity NPC227741
0.8095 Intermediate Similarity NPC295202
0.8095 Intermediate Similarity NPC136342
0.8083 Intermediate Similarity NPC477453
0.8077 Intermediate Similarity NPC294226
0.8074 Intermediate Similarity NPC299154
0.8065 Intermediate Similarity NPC86900
0.8047 Intermediate Similarity NPC474546
0.8045 Intermediate Similarity NPC141368
0.8033 Intermediate Similarity NPC232178
0.803 Intermediate Similarity NPC324929
0.8017 Intermediate Similarity NPC125252
0.8017 Intermediate Similarity NPC230349
0.8016 Intermediate Similarity NPC131799
0.8 Intermediate Similarity NPC50763
0.7984 Intermediate Similarity NPC244441
0.7984 Intermediate Similarity NPC233056
0.7984 Intermediate Similarity NPC298268
0.7969 Intermediate Similarity NPC214553
0.7966 Intermediate Similarity NPC114682
0.7955 Intermediate Similarity NPC72918
0.7951 Intermediate Similarity NPC94637
0.7951 Intermediate Similarity NPC212743
0.7937 Intermediate Similarity NPC74507
0.7937 Intermediate Similarity NPC234890
0.7934 Intermediate Similarity NPC277394
0.7934 Intermediate Similarity NPC299252
0.7934 Intermediate Similarity NPC61062
0.7934 Intermediate Similarity NPC128825
0.7931 Intermediate Similarity NPC141523
0.7928 Intermediate Similarity NPC283711
0.792 Intermediate Similarity NPC307174
0.792 Intermediate Similarity NPC225710
0.792 Intermediate Similarity NPC300274
0.7917 Intermediate Similarity NPC81808
0.791 Intermediate Similarity NPC175552
0.7907 Intermediate Similarity NPC226855
0.7891 Intermediate Similarity NPC158654
0.7891 Intermediate Similarity NPC16651
0.7891 Intermediate Similarity NPC32163
0.7886 Intermediate Similarity NPC233165
0.7886 Intermediate Similarity NPC90522
0.7886 Intermediate Similarity NPC328459
0.7886 Intermediate Similarity NPC184579
0.7881 Intermediate Similarity NPC222084
0.7874 Intermediate Similarity NPC287473
0.7869 Intermediate Similarity NPC160199
0.7863 Intermediate Similarity NPC17843
0.7857 Intermediate Similarity NPC477153
0.7857 Intermediate Similarity NPC375356
0.7833 Intermediate Similarity NPC148969
0.7833 Intermediate Similarity NPC211421
0.7833 Intermediate Similarity NPC223004
0.7833 Intermediate Similarity NPC53953
0.7826 Intermediate Similarity NPC79672
0.7823 Intermediate Similarity NPC72977
0.7823 Intermediate Similarity NPC34634
0.7823 Intermediate Similarity NPC265454
0.7823 Intermediate Similarity NPC233282
0.782 Intermediate Similarity NPC258502
0.7812 Intermediate Similarity NPC51037
0.7797 Intermediate Similarity NPC98392
0.7795 Intermediate Similarity NPC310540
0.7795 Intermediate Similarity NPC68756
0.7795 Intermediate Similarity NPC152525
0.7778 Intermediate Similarity NPC61398
0.7778 Intermediate Similarity NPC112135
0.7778 Intermediate Similarity NPC416
0.7778 Intermediate Similarity NPC217756
0.7769 Intermediate Similarity NPC118288
0.7769 Intermediate Similarity NPC276111
0.7761 Intermediate Similarity NPC194764
0.7761 Intermediate Similarity NPC264112
0.7761 Intermediate Similarity NPC65005
0.776 Intermediate Similarity NPC244994
0.776 Intermediate Similarity NPC216216
0.776 Intermediate Similarity NPC272454
0.776 Intermediate Similarity NPC179092
0.776 Intermediate Similarity NPC35856
0.776 Intermediate Similarity NPC301987
0.776 Intermediate Similarity NPC98305
0.776 Intermediate Similarity NPC159760
0.776 Intermediate Similarity NPC26433
0.776 Intermediate Similarity NPC222876
0.776 Intermediate Similarity NPC178395
0.776 Intermediate Similarity NPC292665
0.776 Intermediate Similarity NPC115188
0.7754 Intermediate Similarity NPC199936
0.7752 Intermediate Similarity NPC107672
0.7752 Intermediate Similarity NPC71525
0.7744 Intermediate Similarity NPC144662
0.7744 Intermediate Similarity NPC204582
0.7737 Intermediate Similarity NPC84273
0.7734 Intermediate Similarity NPC240744
0.7734 Intermediate Similarity NPC103540
0.7734 Intermediate Similarity NPC167055
0.7731 Intermediate Similarity NPC471535
0.771 Intermediate Similarity NPC199253
0.771 Intermediate Similarity NPC136588
0.7705 Intermediate Similarity NPC4665
0.7704 Intermediate Similarity NPC170742
0.7704 Intermediate Similarity NPC147418
0.7704 Intermediate Similarity NPC290030
0.7704 Intermediate Similarity NPC62907
0.7698 Intermediate Similarity NPC295034
0.7698 Intermediate Similarity NPC198336
0.7692 Intermediate Similarity NPC294902
0.7692 Intermediate Similarity NPC1786
0.7692 Intermediate Similarity NPC165257
0.7692 Intermediate Similarity NPC234175
0.7692 Intermediate Similarity NPC237225
0.7692 Intermediate Similarity NPC1075
0.7686 Intermediate Similarity NPC98543
0.7674 Intermediate Similarity NPC231774
0.7674 Intermediate Similarity NPC3224
0.7674 Intermediate Similarity NPC306765
0.7674 Intermediate Similarity NPC96915
0.7674 Intermediate Similarity NPC8745
0.7672 Intermediate Similarity NPC52087
0.7669 Intermediate Similarity NPC474715
0.7669 Intermediate Similarity NPC239855
0.7667 Intermediate Similarity NPC54626
0.7667 Intermediate Similarity NPC212718
0.7664 Intermediate Similarity NPC203063
0.7664 Intermediate Similarity NPC476534
0.7664 Intermediate Similarity NPC50823
0.7661 Intermediate Similarity NPC63126
0.7661 Intermediate Similarity NPC241089
0.7656 Intermediate Similarity NPC288945
0.7656 Intermediate Similarity NPC117794
0.7656 Intermediate Similarity NPC142956
0.7656 Intermediate Similarity NPC13238
0.7652 Intermediate Similarity NPC85342
0.7652 Intermediate Similarity NPC110764
0.7647 Intermediate Similarity NPC325625
0.7638 Intermediate Similarity NPC283514
0.7638 Intermediate Similarity NPC114298
0.7638 Intermediate Similarity NPC244351
0.7634 Intermediate Similarity NPC94810
0.7632 Intermediate Similarity NPC131587
0.763 Intermediate Similarity NPC475111
0.7627 Intermediate Similarity NPC226699
0.7627 Intermediate Similarity NPC29883
0.7626 Intermediate Similarity NPC287722
0.7619 Intermediate Similarity NPC236520
0.7619 Intermediate Similarity NPC294361
0.7619 Intermediate Similarity NPC295317

  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 NPC28169 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
0.839 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD9266 Approved
0.8333 Intermediate Similarity NPD74 Approved
0.8246 Intermediate Similarity NPD9267 Approved
0.8246 Intermediate Similarity NPD9263 Approved
0.8246 Intermediate Similarity NPD9264 Approved
0.8175 Intermediate Similarity NPD9494 Approved
0.814 Intermediate Similarity NPD943 Approved
0.7934 Intermediate Similarity NPD9493 Approved
0.792 Intermediate Similarity NPD9269 Phase 2
0.7895 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD9261 Approved
0.7769 Intermediate Similarity NPD9281 Approved
0.7734 Intermediate Similarity NPD1470 Approved
0.7698 Intermediate Similarity NPD1201 Approved
0.7669 Intermediate Similarity NPD447 Suspended
0.7627 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD9268 Approved
0.7537 Intermediate Similarity NPD230 Phase 1
0.7518 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD1164 Approved
0.7244 Intermediate Similarity NPD9545 Approved
0.7232 Intermediate Similarity NPD9256 Approved
0.7232 Intermediate Similarity NPD9258 Approved
0.7231 Intermediate Similarity NPD9717 Approved
0.7203 Intermediate Similarity NPD1511 Approved
0.7197 Intermediate Similarity NPD1203 Approved
0.7194 Intermediate Similarity NPD1551 Phase 2
0.7185 Intermediate Similarity NPD411 Approved
0.7133 Intermediate Similarity NPD3882 Suspended
0.7132 Intermediate Similarity NPD520 Approved
0.7103 Intermediate Similarity NPD1512 Approved
0.7071 Intermediate Similarity NPD2935 Discontinued
0.7047 Intermediate Similarity NPD1934 Approved
0.7045 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1510 Phase 2
0.7 Intermediate Similarity NPD2801 Approved
0.696 Remote Similarity NPD228 Approved
0.6957 Remote Similarity NPD1240 Approved
0.6942 Remote Similarity NPD1237 Approved
0.6935 Remote Similarity NPD3021 Approved
0.6935 Remote Similarity NPD3022 Approved
0.6923 Remote Similarity NPD844 Approved
0.6923 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6897 Remote Similarity NPD3300 Phase 2
0.6889 Remote Similarity NPD258 Approved
0.6889 Remote Similarity NPD2798 Approved
0.6889 Remote Similarity NPD257 Approved
0.688 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6875 Remote Similarity NPD9257 Approved
0.6875 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6875 Remote Similarity NPD9259 Approved
0.6864 Remote Similarity NPD288 Approved
0.6857 Remote Similarity NPD1607 Approved
0.6838 Remote Similarity NPD9569 Approved
0.6835 Remote Similarity NPD825 Approved
0.6835 Remote Similarity NPD826 Approved
0.6833 Remote Similarity NPD289 Clinical (unspecified phase)
0.6831 Remote Similarity NPD5405 Approved
0.6831 Remote Similarity NPD5404 Approved
0.6831 Remote Similarity NPD5406 Approved
0.6831 Remote Similarity NPD9570 Approved
0.6831 Remote Similarity NPD5408 Approved
0.6828 Remote Similarity NPD6190 Approved
0.6812 Remote Similarity NPD2313 Discontinued
0.6807 Remote Similarity NPD9495 Approved
0.6786 Remote Similarity NPD555 Phase 2
0.6786 Remote Similarity NPD1933 Approved
0.6786 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6783 Remote Similarity NPD2344 Approved
0.6772 Remote Similarity NPD9379 Approved
0.6772 Remote Similarity NPD9377 Approved
0.6765 Remote Similarity NPD1019 Discontinued
0.6763 Remote Similarity NPD259 Phase 1
0.6759 Remote Similarity NPD8166 Discontinued
0.6736 Remote Similarity NPD970 Clinical (unspecified phase)
0.6736 Remote Similarity NPD1549 Phase 2
0.6733 Remote Similarity NPD3455 Phase 2
0.673 Remote Similarity NPD3818 Discontinued
0.669 Remote Similarity NPD9279 Approved
0.6688 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6832 Phase 2
0.6667 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2346 Discontinued
0.6667 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6643 Remote Similarity NPD2799 Discontinued
0.6637 Remote Similarity NPD111 Approved
0.6623 Remote Similarity NPD824 Approved
0.6619 Remote Similarity NPD9537 Phase 1
0.6619 Remote Similarity NPD9536 Phase 1
0.6617 Remote Similarity NPD9381 Approved
0.6617 Remote Similarity NPD9384 Approved
0.6604 Remote Similarity NPD6166 Phase 2
0.6604 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6599 Remote Similarity NPD2309 Approved
0.6589 Remote Similarity NPD1241 Discontinued
0.6579 Remote Similarity NPD4380 Phase 2
0.6571 Remote Similarity NPD3764 Approved
0.6552 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6549 Remote Similarity NPD275 Approved
0.6549 Remote Similarity NPD274 Approved
0.6529 Remote Similarity NPD9273 Approved
0.6516 Remote Similarity NPD5402 Approved
0.6516 Remote Similarity NPD3817 Phase 2
0.6515 Remote Similarity NPD5536 Phase 2
0.6507 Remote Similarity NPD75 Approved
0.6507 Remote Similarity NPD9277 Approved
0.6493 Remote Similarity NPD1778 Approved
0.6493 Remote Similarity NPD3019 Approved
0.6493 Remote Similarity NPD2932 Approved
0.6481 Remote Similarity NPD7054 Approved
0.6478 Remote Similarity NPD6232 Discontinued
0.6475 Remote Similarity NPD1238 Approved
0.6471 Remote Similarity NPD1202 Approved
0.6471 Remote Similarity NPD845 Approved
0.6466 Remote Similarity NPD9094 Approved
0.6466 Remote Similarity NPD1759 Phase 1
0.6452 Remote Similarity NPD1465 Phase 2
0.6442 Remote Similarity NPD7472 Approved
0.6442 Remote Similarity NPD7074 Phase 3
0.6438 Remote Similarity NPD9275 Approved
0.6438 Remote Similarity NPD9278 Suspended
0.6438 Remote Similarity NPD9274 Approved
0.6438 Remote Similarity NPD9276 Approved
0.6424 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6423 Remote Similarity NPD1242 Phase 1
0.6423 Remote Similarity NPD9622 Approved
0.6423 Remote Similarity NPD1755 Approved
0.6419 Remote Similarity NPD1196 Approved
0.6417 Remote Similarity NPD2934 Approved
0.6417 Remote Similarity NPD9260 Approved
0.6417 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6417 Remote Similarity NPD2933 Approved
0.6415 Remote Similarity NPD1247 Approved
0.6405 Remote Similarity NPD3226 Approved
0.6402 Remote Similarity NPD6797 Phase 2
0.64 Remote Similarity NPD6799 Approved
0.64 Remote Similarity NPD7390 Discontinued
0.6392 Remote Similarity NPD919 Approved
0.6391 Remote Similarity NPD1758 Phase 1
0.6387 Remote Similarity NPD6844 Discontinued
0.6382 Remote Similarity NPD5403 Approved
0.6378 Remote Similarity NPD290 Approved
0.6371 Remote Similarity NPD846 Approved
0.6371 Remote Similarity NPD940 Approved
0.637 Remote Similarity NPD2796 Approved
0.6364 Remote Similarity NPD256 Approved
0.6364 Remote Similarity NPD2859 Approved
0.6364 Remote Similarity NPD2860 Approved
0.6364 Remote Similarity NPD255 Approved
0.6364 Remote Similarity NPD7251 Discontinued
0.6358 Remote Similarity NPD2533 Approved
0.6358 Remote Similarity NPD4661 Approved
0.6358 Remote Similarity NPD642 Clinical (unspecified phase)
0.6358 Remote Similarity NPD7473 Discontinued
0.6358 Remote Similarity NPD2534 Approved
0.6358 Remote Similarity NPD5401 Approved
0.6358 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6358 Remote Similarity NPD4662 Approved
0.6358 Remote Similarity NPD2532 Approved
0.6351 Remote Similarity NPD1195 Approved
0.6341 Remote Similarity NPD3020 Approved
0.6333 Remote Similarity NPD643 Clinical (unspecified phase)
0.6329 Remote Similarity NPD7075 Discontinued
0.6329 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7266 Discontinued
0.6324 Remote Similarity NPD3496 Discontinued
0.6316 Remote Similarity NPD9568 Approved
0.6309 Remote Similarity NPD4628 Phase 3
0.6308 Remote Similarity NPD9508 Approved
0.6301 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6301 Remote Similarity NPD4308 Phase 3
0.6299 Remote Similarity NPD2651 Approved
0.6299 Remote Similarity NPD2649 Approved
0.6294 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6291 Remote Similarity NPD1543 Discontinued
0.6288 Remote Similarity NPD2629 Approved
0.6286 Remote Similarity NPD9620 Approved
0.6286 Remote Similarity NPD9621 Approved
0.6286 Remote Similarity NPD9619 Approved
0.6281 Remote Similarity NPD9296 Approved
0.6279 Remote Similarity NPD4750 Phase 3
0.627 Remote Similarity NPD164 Approved
0.6265 Remote Similarity NPD6559 Discontinued
0.6259 Remote Similarity NPD1876 Approved
0.6259 Remote Similarity NPD1283 Approved
0.625 Remote Similarity NPD4626 Approved
0.625 Remote Similarity NPD5494 Approved
0.625 Remote Similarity NPD1613 Approved
0.625 Remote Similarity NPD2342 Discontinued
0.625 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6242 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6242 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6242 Remote Similarity NPD7819 Suspended
0.6239 Remote Similarity NPD9087 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