Structure

Physi-Chem Properties

Molecular Weight:  354.07
Volume:  346.678
LogP:  3.531
LogD:  2.254
LogS:  -4.416
# Rotatable Bonds:  4
TPSA:  117.97
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.544
Synthetic Accessibility Score:  2.561
Fsp3:  0.158
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.026
MDCK Permeability:  1.7803151422413066e-05
Pgp-inhibitor:  0.509
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.229
20% Bioavailability (F20%):  0.019
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.07
Plasma Protein Binding (PPB):  98.13426971435547%
Volume Distribution (VD):  0.587
Pgp-substrate:  2.604203462600708%

ADMET: Metabolism

CYP1A2-inhibitor:  0.901
CYP1A2-substrate:  0.209
CYP2C19-inhibitor:  0.204
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.76
CYP2C9-substrate:  0.282
CYP2D6-inhibitor:  0.108
CYP2D6-substrate:  0.168
CYP3A4-inhibitor:  0.619
CYP3A4-substrate:  0.155

ADMET: Excretion

Clearance (CL):  4.238
Half-life (T1/2):  0.333

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.12
Drug-inuced Liver Injury (DILI):  0.969
AMES Toxicity:  0.896
Rat Oral Acute Toxicity:  0.101
Maximum Recommended Daily Dose:  0.065
Skin Sensitization:  0.385
Carcinogencity:  0.568
Eye Corrosion:  0.003
Eye Irritation:  0.349
Respiratory Toxicity:  0.044

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  Natural Product: NPC26924

Natural Product ID:  NPC26924
Common Name*:   Methyl 2-(3-Acetyl-4,5-Dihydroxy-9,10-Dioxoanthracen-2-Yl)Acetate
IUPAC Name:   methyl 2-(3-acetyl-4,5-dihydroxy-9,10-dioxoanthracen-2-yl)acetate
Synonyms:  
Standard InCHIKey:  XJIJYLAICXTKPT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H14O7/c1-8(20)14-9(7-13(22)26-2)6-11-16(18(14)24)19(25)15-10(17(11)23)4-3-5-12(15)21/h3-6,21,24H,7H2,1-2H3
SMILES:  COC(=O)Cc1cc2C(=O)c3cccc(c3C(=O)c2c(c1C(=O)C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL484027
PubChem CID:   2754656
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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]

☑ 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
NPT79 Organism Bacillus subtilis Bacillus subtilis LD99 = 3.0 ug ml-1 PMID[448812]

☑ 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 NPC26924 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
0.9925 High Similarity NPC315578
0.9474 High Similarity NPC288089
0.9338 High Similarity NPC4214
0.9281 High Similarity NPC66593
0.9254 High Similarity NPC115458
0.9231 High Similarity NPC315520
0.9197 High Similarity NPC13715
0.9167 High Similarity NPC282923
0.9118 High Similarity NPC80035
0.9051 High Similarity NPC272268
0.9037 High Similarity NPC70622
0.9021 High Similarity NPC119767
0.9 High Similarity NPC290550
0.8993 High Similarity NPC1268
0.8971 High Similarity NPC225051
0.8966 High Similarity NPC205766
0.8963 High Similarity NPC205992
0.8955 High Similarity NPC99731
0.8939 High Similarity NPC103540
0.8936 High Similarity NPC193555
0.8929 High Similarity NPC96421
0.8919 High Similarity NPC474861
0.8889 High Similarity NPC136588
0.8889 High Similarity NPC199253
0.8881 High Similarity NPC48248
0.8864 High Similarity NPC142956
0.8864 High Similarity NPC173978
0.8857 High Similarity NPC138099
0.8857 High Similarity NPC242994
0.8849 High Similarity NPC53414
0.8849 High Similarity NPC471905
0.8849 High Similarity NPC53206
0.8841 High Similarity NPC283088
0.8841 High Similarity NPC161632
0.8832 High Similarity NPC52407
0.8832 High Similarity NPC254603
0.8832 High Similarity NPC53896
0.8819 High Similarity NPC147250
0.8819 High Similarity NPC314437
0.8815 High Similarity NPC146647
0.8815 High Similarity NPC34414
0.8811 High Similarity NPC193703
0.8811 High Similarity NPC21599
0.8803 High Similarity NPC73061
0.8803 High Similarity NPC474300
0.8794 High Similarity NPC181560
0.8794 High Similarity NPC183345
0.8794 High Similarity NPC169452
0.8788 High Similarity NPC375356
0.8786 High Similarity NPC61590
0.8786 High Similarity NPC416
0.8786 High Similarity NPC61398
0.8784 High Similarity NPC470408
0.8784 High Similarity NPC218870
0.8784 High Similarity NPC182921
0.8784 High Similarity NPC474824
0.8777 High Similarity NPC141934
0.8777 High Similarity NPC474813
0.8777 High Similarity NPC155211
0.8777 High Similarity NPC254847
0.8777 High Similarity NPC472308
0.8768 High Similarity NPC50924
0.8759 High Similarity NPC309430
0.8759 High Similarity NPC58685
0.875 High Similarity NPC31799
0.8741 High Similarity NPC476473
0.8732 High Similarity NPC305845
0.8732 High Similarity NPC204045
0.8732 High Similarity NPC124365
0.8731 High Similarity NPC3224
0.8725 High Similarity NPC66029
0.8723 High Similarity NPC295339
0.8714 High Similarity NPC471452
0.8714 High Similarity NPC245923
0.8712 High Similarity NPC300274
0.8686 High Similarity NPC17083
0.8681 High Similarity NPC79627
0.8681 High Similarity NPC48762
0.8671 High Similarity NPC69755
0.8671 High Similarity NPC135524
0.8671 High Similarity NPC19631
0.8671 High Similarity NPC239136
0.8662 High Similarity NPC168471
0.8662 High Similarity NPC225243
0.8658 High Similarity NPC208806
0.8643 High Similarity NPC118919
0.8633 High Similarity NPC44437
0.8633 High Similarity NPC1249
0.863 High Similarity NPC245584
0.863 High Similarity NPC312929
0.863 High Similarity NPC126767
0.863 High Similarity NPC289042
0.863 High Similarity NPC118027
0.863 High Similarity NPC56433
0.863 High Similarity NPC190648
0.863 High Similarity NPC5568
0.8621 High Similarity NPC34482
0.8613 High Similarity NPC55949
0.8613 High Similarity NPC475741
0.8611 High Similarity NPC53016
0.8611 High Similarity NPC471682
0.8609 High Similarity NPC263483
0.8603 High Similarity NPC95537
0.8601 High Similarity NPC246638
0.86 High Similarity NPC318270
0.8593 High Similarity NPC96915
0.8593 High Similarity NPC231774
0.8592 High Similarity NPC306835
0.8592 High Similarity NPC29771
0.8592 High Similarity NPC190457
0.8592 High Similarity NPC476477
0.8592 High Similarity NPC471602
0.8592 High Similarity NPC256463
0.8592 High Similarity NPC143438
0.8592 High Similarity NPC216312
0.8592 High Similarity NPC111422
0.8592 High Similarity NPC299405
0.8582 High Similarity NPC305060
0.8581 High Similarity NPC255641
0.8581 High Similarity NPC290954
0.8571 High Similarity NPC94781
0.8571 High Similarity NPC307174
0.8571 High Similarity NPC258502
0.8571 High Similarity NPC471907
0.8562 High Similarity NPC470570
0.8562 High Similarity NPC285122
0.8562 High Similarity NPC300540
0.8561 High Similarity NPC267205
0.8561 High Similarity NPC48036
0.8561 High Similarity NPC314048
0.8552 High Similarity NPC471906
0.8552 High Similarity NPC244691
0.8551 High Similarity NPC244699
0.8551 High Similarity NPC72669
0.8551 High Similarity NPC93015
0.8551 High Similarity NPC474517
0.8543 High Similarity NPC313299
0.8542 High Similarity NPC257644
0.8531 High Similarity NPC32749
0.8531 High Similarity NPC147542
0.8531 High Similarity NPC37992
0.8531 High Similarity NPC327916
0.8531 High Similarity NPC42262
0.8531 High Similarity NPC220496
0.8531 High Similarity NPC241349
0.8523 High Similarity NPC302783
0.8523 High Similarity NPC473201
0.8514 High Similarity NPC44378
0.8514 High Similarity NPC120171
0.8514 High Similarity NPC280753
0.8511 High Similarity NPC193358
0.8511 High Similarity NPC191976
0.8511 High Similarity NPC86524
0.8511 High Similarity NPC315275
0.85 High Similarity NPC472262
0.85 High Similarity NPC12070
0.85 High Similarity NPC287604
0.85 High Similarity NPC282780
0.85 High Similarity NPC166480
0.85 High Similarity NPC161964
0.8493 Intermediate Similarity NPC471683
0.8493 Intermediate Similarity NPC170055
0.8487 Intermediate Similarity NPC317580
0.8483 Intermediate Similarity NPC21873
0.8478 Intermediate Similarity NPC31539
0.8478 Intermediate Similarity NPC198305
0.8477 Intermediate Similarity NPC3449
0.8472 Intermediate Similarity NPC257003
0.8472 Intermediate Similarity NPC471444
0.8467 Intermediate Similarity NPC165257
0.8462 Intermediate Similarity NPC103337
0.8462 Intermediate Similarity NPC114620
0.8456 Intermediate Similarity NPC294646
0.8456 Intermediate Similarity NPC470568
0.8456 Intermediate Similarity NPC160499
0.8456 Intermediate Similarity NPC473751
0.8456 Intermediate Similarity NPC147735
0.8451 Intermediate Similarity NPC62272
0.8446 Intermediate Similarity NPC172329
0.8446 Intermediate Similarity NPC2569
0.8444 Intermediate Similarity NPC236189
0.844 Intermediate Similarity NPC249272
0.8435 Intermediate Similarity NPC225173
0.8435 Intermediate Similarity NPC163846
0.8433 Intermediate Similarity NPC91478
0.8431 Intermediate Similarity NPC326084
0.8429 Intermediate Similarity NPC294226
0.8429 Intermediate Similarity NPC114183
0.8429 Intermediate Similarity NPC193169
0.8425 Intermediate Similarity NPC300684
0.8425 Intermediate Similarity NPC19896
0.8425 Intermediate Similarity NPC103910
0.8425 Intermediate Similarity NPC48130
0.8425 Intermediate Similarity NPC218866
0.8425 Intermediate Similarity NPC84568
0.8421 Intermediate Similarity NPC474360
0.8414 Intermediate Similarity NPC474961
0.8411 Intermediate Similarity NPC214632
0.8411 Intermediate Similarity NPC209393
0.8411 Intermediate Similarity NPC205172

  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 NPC26924 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
0.8939 High Similarity NPD1470 Approved
0.8897 High Similarity NPD3226 Approved
0.8777 High Similarity NPD1509 Clinical (unspecified phase)
0.8636 High Similarity NPD1201 Approved
0.8451 Intermediate Similarity NPD5404 Approved
0.8451 Intermediate Similarity NPD5406 Approved
0.8451 Intermediate Similarity NPD5408 Approved
0.8451 Intermediate Similarity NPD5405 Approved
0.8264 Intermediate Similarity NPD2346 Discontinued
0.8153 Intermediate Similarity NPD6232 Discontinued
0.8113 Intermediate Similarity NPD7473 Discontinued
0.8054 Intermediate Similarity NPD7390 Discontinued
0.8045 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8027 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD3764 Approved
0.7935 Intermediate Similarity NPD7819 Suspended
0.7823 Intermediate Similarity NPD2935 Discontinued
0.7806 Intermediate Similarity NPD7411 Suspended
0.7763 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD2534 Approved
0.7763 Intermediate Similarity NPD2532 Approved
0.7763 Intermediate Similarity NPD2533 Approved
0.774 Intermediate Similarity NPD1607 Approved
0.773 Intermediate Similarity NPD1164 Approved
0.7724 Intermediate Similarity NPD943 Approved
0.7718 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD2313 Discontinued
0.7635 Intermediate Similarity NPD1510 Phase 2
0.7635 Intermediate Similarity NPD2799 Discontinued
0.7633 Intermediate Similarity NPD8150 Discontinued
0.763 Intermediate Similarity NPD5951 Approved
0.7616 Intermediate Similarity NPD7003 Approved
0.7607 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD1240 Approved
0.7562 Intermediate Similarity NPD3749 Approved
0.7558 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD6959 Discontinued
0.7518 Intermediate Similarity NPD9493 Approved
0.75 Intermediate Similarity NPD3750 Approved
0.75 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD1551 Phase 2
0.7456 Intermediate Similarity NPD8312 Approved
0.7456 Intermediate Similarity NPD8313 Approved
0.7453 Intermediate Similarity NPD7075 Discontinued
0.7452 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD7458 Discontinued
0.7442 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD2798 Approved
0.7419 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD2344 Approved
0.7417 Intermediate Similarity NPD1471 Phase 3
0.7413 Intermediate Similarity NPD1283 Approved
0.741 Intermediate Similarity NPD9545 Approved
0.741 Intermediate Similarity NPD7177 Discontinued
0.7403 Intermediate Similarity NPD3300 Phase 2
0.74 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7768 Phase 2
0.7386 Intermediate Similarity NPD4628 Phase 3
0.7375 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1549 Phase 2
0.7365 Intermediate Similarity NPD5844 Phase 1
0.7313 Intermediate Similarity NPD74 Approved
0.7313 Intermediate Similarity NPD9266 Approved
0.7305 Intermediate Similarity NPD3019 Approved
0.7305 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4380 Phase 2
0.7296 Intermediate Similarity NPD6599 Discontinued
0.7285 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1608 Approved
0.7241 Intermediate Similarity NPD1203 Approved
0.7239 Intermediate Similarity NPD9264 Approved
0.7239 Intermediate Similarity NPD9263 Approved
0.7239 Intermediate Similarity NPD9267 Approved
0.7239 Intermediate Similarity NPD2342 Discontinued
0.7239 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD3268 Approved
0.7226 Intermediate Similarity NPD2309 Approved
0.7205 Intermediate Similarity NPD1934 Approved
0.7205 Intermediate Similarity NPD6801 Discontinued
0.7203 Intermediate Similarity NPD1281 Approved
0.7202 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD2932 Approved
0.7183 Intermediate Similarity NPD4626 Approved
0.7181 Intermediate Similarity NPD6663 Approved
0.7175 Intermediate Similarity NPD6535 Approved
0.7175 Intermediate Similarity NPD6534 Approved
0.7171 Intermediate Similarity NPD4308 Phase 3
0.7171 Intermediate Similarity NPD3748 Approved
0.7169 Intermediate Similarity NPD5711 Approved
0.7169 Intermediate Similarity NPD5710 Approved
0.7162 Intermediate Similarity NPD7008 Discontinued
0.7161 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD8166 Discontinued
0.716 Intermediate Similarity NPD2801 Approved
0.7143 Intermediate Similarity NPD7435 Discontinued
0.7143 Intermediate Similarity NPD5736 Approved
0.7134 Intermediate Similarity NPD1511 Approved
0.7134 Intermediate Similarity NPD6799 Approved
0.7124 Intermediate Similarity NPD2796 Approved
0.7119 Intermediate Similarity NPD6213 Phase 3
0.7119 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6212 Phase 3
0.7114 Intermediate Similarity NPD411 Approved
0.7104 Intermediate Similarity NPD8320 Phase 1
0.7104 Intermediate Similarity NPD8319 Approved
0.7086 Intermediate Similarity NPD230 Phase 1
0.7076 Intermediate Similarity NPD5953 Discontinued
0.7073 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD3882 Suspended
0.7072 Intermediate Similarity NPD6777 Approved
0.7072 Intermediate Similarity NPD6782 Approved
0.7072 Intermediate Similarity NPD6779 Approved
0.7072 Intermediate Similarity NPD6781 Approved
0.7072 Intermediate Similarity NPD6778 Approved
0.7072 Intermediate Similarity NPD6780 Approved
0.7072 Intermediate Similarity NPD6776 Approved
0.7068 Intermediate Similarity NPD1930 Approved
0.7068 Intermediate Similarity NPD1929 Approved
0.7068 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD17 Approved
0.7056 Intermediate Similarity NPD7700 Phase 2
0.7056 Intermediate Similarity NPD7699 Phase 2
0.7044 Intermediate Similarity NPD1512 Approved
0.7044 Intermediate Similarity NPD6273 Approved
0.7035 Intermediate Similarity NPD6559 Discontinued
0.7034 Intermediate Similarity NPD9717 Approved
0.7034 Intermediate Similarity NPD3972 Approved
0.7025 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD6099 Approved
0.7013 Intermediate Similarity NPD6100 Approved
0.7012 Intermediate Similarity NPD5402 Approved
0.7012 Intermediate Similarity NPD3817 Phase 2
0.7007 Intermediate Similarity NPD3266 Approved
0.7007 Intermediate Similarity NPD3267 Approved
0.7006 Intermediate Similarity NPD6190 Approved
0.7 Intermediate Similarity NPD920 Approved
0.7 Intermediate Similarity NPD9281 Approved
0.6993 Remote Similarity NPD1651 Approved
0.6992 Remote Similarity NPD1932 Approved
0.6987 Remote Similarity NPD2800 Approved
0.6987 Remote Similarity NPD1243 Approved
0.698 Remote Similarity NPD6832 Phase 2
0.6978 Remote Similarity NPD7635 Approved
0.6974 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6974 Remote Similarity NPD447 Suspended
0.6966 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7698 Approved
0.6957 Remote Similarity NPD7697 Approved
0.6957 Remote Similarity NPD7696 Phase 3
0.6951 Remote Similarity NPD1465 Phase 2
0.6948 Remote Similarity NPD7033 Discontinued
0.6946 Remote Similarity NPD5494 Approved
0.694 Remote Similarity NPD9261 Approved
0.6939 Remote Similarity NPD1876 Approved
0.6934 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6932 Remote Similarity NPD8434 Phase 2
0.6928 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6923 Remote Similarity NPD8285 Discontinued
0.6919 Remote Similarity NPD7870 Phase 2
0.6919 Remote Similarity NPD7871 Phase 2
0.6918 Remote Similarity NPD9269 Phase 2
0.6915 Remote Similarity NPD7874 Approved
0.6915 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6908 Remote Similarity NPD4307 Phase 2
0.6908 Remote Similarity NPD2979 Phase 3
0.6901 Remote Similarity NPD3818 Discontinued
0.6897 Remote Similarity NPD3026 Approved
0.6897 Remote Similarity NPD3023 Approved
0.6894 Remote Similarity NPD5403 Approved
0.6894 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6892 Remote Similarity NPD2797 Approved
0.6882 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6166 Phase 2
0.6882 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6875 Remote Similarity NPD642 Clinical (unspecified phase)
0.6875 Remote Similarity NPD9268 Approved
0.6875 Remote Similarity NPD3025 Approved
0.6875 Remote Similarity NPD3024 Approved
0.6875 Remote Similarity NPD5401 Approved
0.6875 Remote Similarity NPD5691 Approved
0.6862 Remote Similarity NPD8151 Discontinued
0.686 Remote Similarity NPD7286 Phase 2
0.6855 Remote Similarity NPD643 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6842 Remote Similarity NPD520 Approved
0.6828 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6824 Remote Similarity NPD3225 Approved
0.6821 Remote Similarity NPD4625 Phase 3
0.6818 Remote Similarity NPD6651 Approved
0.6812 Remote Similarity NPD2329 Discontinued
0.6809 Remote Similarity NPD7701 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