Structure

Physi-Chem Properties

Molecular Weight:  334.08
Volume:  337.837
LogP:  5.239
LogD:  2.794
LogS:  -3.516
# Rotatable Bonds:  1
TPSA:  101.15
# H-Bond Aceptor:  5
# H-Bond Donor:  5
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.264
Synthetic Accessibility Score:  2.833
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.317
MDCK Permeability:  7.301128334802343e-06
Pgp-inhibitor:  0.009
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.856
20% Bioavailability (F20%):  0.512
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  96.8868179321289%
Volume Distribution (VD):  0.466
Pgp-substrate:  10.013248443603516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.932
CYP1A2-substrate:  0.151
CYP2C19-inhibitor:  0.041
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.641
CYP2C9-substrate:  0.542
CYP2D6-inhibitor:  0.097
CYP2D6-substrate:  0.211
CYP3A4-inhibitor:  0.041
CYP3A4-substrate:  0.034

ADMET: Excretion

Clearance (CL):  5.379
Half-life (T1/2):  0.525

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.074
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.757
Rat Oral Acute Toxicity:  0.135
Maximum Recommended Daily Dose:  0.871
Skin Sensitization:  0.953
Carcinogencity:  0.771
Eye Corrosion:  0.004
Eye Irritation:  0.932
Respiratory Toxicity:  0.306

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  Natural Product: NPC474813

Natural Product ID:  NPC474813
Common Name*:   Bisanhydro-Gamma-Rhodomycinone
IUPAC Name:   8-ethyl-1,6,11-trihydroxytetracene-5,12-dione
Synonyms:   Bisanhydro-Gamma-Rhodomycinone
Standard InCHIKey:  IQQXEUJGABFGFT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H14O5/c1-2-9-6-7-10-12(8-9)19(24)15-16(17(10)22)20(25)14-11(18(15)23)4-3-5-13(14)21/h3-8,21-22,24H,2H2,1H3
SMILES:  CCC1=CC2=C(C=C1)C(=C3C(=C2O)C(=O)C4=C(C3=O)C(=CC=C4)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL483829
PubChem CID:   23260551
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000022] Naphthacenes
        • [CHEMONTID:0000155] Tetracenequinones

*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. n.a. n.a. PMID[18081255]
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[18205372]
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[18327911]
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[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 = 13.0 ug ml-1 PMID[479914]

☑ 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 NPC474813 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
0.9923 High Similarity NPC245923
0.9695 High Similarity NPC155211
0.9612 High Similarity NPC205992
0.9466 High Similarity NPC225051
0.9398 High Similarity NPC272268
0.938 High Similarity NPC282923
0.9323 High Similarity NPC283088
0.9313 High Similarity NPC72669
0.9313 High Similarity NPC474517
0.9237 High Similarity NPC55949
0.9231 High Similarity NPC48248
0.9225 High Similarity NPC96915
0.9209 High Similarity NPC471683
0.9185 High Similarity NPC305060
0.9173 High Similarity NPC115458
0.916 High Similarity NPC34414
0.916 High Similarity NPC99731
0.916 High Similarity NPC146647
0.9147 High Similarity NPC103540
0.9137 High Similarity NPC10764
0.913 High Similarity NPC239136
0.913 High Similarity NPC19631
0.9124 High Similarity NPC96421
0.9118 High Similarity NPC13715
0.9104 High Similarity NPC472262
0.9104 High Similarity NPC287604
0.9104 High Similarity NPC161964
0.9098 High Similarity NPC58685
0.9098 High Similarity NPC70622
0.907 High Similarity NPC173978
0.907 High Similarity NPC142956
0.9065 High Similarity NPC471682
0.9058 High Similarity NPC246638
0.9058 High Similarity NPC124365
0.9037 High Similarity NPC80035
0.9023 High Similarity NPC244699
0.8993 High Similarity NPC257644
0.8992 High Similarity NPC375356
0.8986 High Similarity NPC225243
0.8963 High Similarity NPC288089
0.8963 High Similarity NPC50924
0.8947 High Similarity NPC136588
0.8947 High Similarity NPC199253
0.8931 High Similarity NPC306765
0.8931 High Similarity NPC3224
0.8915 High Similarity NPC300274
0.8913 High Similarity NPC143438
0.8889 High Similarity NPC314048
0.8889 High Similarity NPC53896
0.8872 High Similarity NPC278928
0.8857 High Similarity NPC69755
0.8815 High Similarity NPC246693
0.8815 High Similarity NPC110609
0.8815 High Similarity NPC242358
0.8811 High Similarity NPC37709
0.8806 High Similarity NPC31539
0.8777 High Similarity NPC1268
0.8777 High Similarity NPC26924
0.8777 High Similarity NPC242994
0.8777 High Similarity NPC138099
0.8776 High Similarity NPC66029
0.8769 High Similarity NPC307174
0.8768 High Similarity NPC53414
0.8768 High Similarity NPC471905
0.8768 High Similarity NPC62272
0.8768 High Similarity NPC53206
0.8759 High Similarity NPC315520
0.8759 High Similarity NPC161632
0.875 High Similarity NPC52407
0.8741 High Similarity NPC147250
0.8741 High Similarity NPC300540
0.8722 High Similarity NPC471530
0.8714 High Similarity NPC181560
0.8714 High Similarity NPC169452
0.8714 High Similarity NPC315578
0.8705 High Similarity NPC61398
0.8705 High Similarity NPC416
0.8696 High Similarity NPC254847
0.8681 High Similarity NPC119767
0.8667 High Similarity NPC31799
0.8662 High Similarity NPC296752
0.8652 High Similarity NPC187843
0.8647 High Similarity NPC231774
0.8647 High Similarity NPC1991
0.8633 High Similarity NPC147418
0.863 High Similarity NPC205766
0.8603 High Similarity NPC85342
0.8601 High Similarity NPC227841
0.8592 High Similarity NPC469520
0.8592 High Similarity NPC474300
0.8592 High Similarity NPC193555
0.8581 High Similarity NPC474824
0.8581 High Similarity NPC470408
0.8581 High Similarity NPC182921
0.8581 High Similarity NPC218870
0.8571 High Similarity NPC4214
0.8561 High Similarity NPC141934
0.8561 High Similarity NPC472308
0.8561 High Similarity NPC193358
0.8551 High Similarity NPC12070
0.8551 High Similarity NPC44437
0.8538 High Similarity NPC285829
0.8538 High Similarity NPC206778
0.8531 High Similarity NPC476473
0.8531 High Similarity NPC313047
0.8531 High Similarity NPC474203
0.8531 High Similarity NPC451542
0.8531 High Similarity NPC295712
0.8521 High Similarity NPC204045
0.8521 High Similarity NPC305845
0.8521 High Similarity NPC477275
0.8511 High Similarity NPC190457
0.8507 High Similarity NPC136342
0.8507 High Similarity NPC295202
0.8507 High Similarity NPC160499
0.8507 High Similarity NPC227741
0.8507 High Similarity NPC49647
0.8496 Intermediate Similarity NPC152525
0.8496 Intermediate Similarity NPC310540
0.8496 Intermediate Similarity NPC68756
0.8489 Intermediate Similarity NPC258502
0.8489 Intermediate Similarity NPC249272
0.8478 Intermediate Similarity NPC114183
0.8478 Intermediate Similarity NPC267205
0.8473 Intermediate Similarity NPC472046
0.8472 Intermediate Similarity NPC244691
0.8472 Intermediate Similarity NPC193703
0.8472 Intermediate Similarity NPC79627
0.8472 Intermediate Similarity NPC471906
0.8472 Intermediate Similarity NPC21599
0.8467 Intermediate Similarity NPC474861
0.8467 Intermediate Similarity NPC17083
0.8462 Intermediate Similarity NPC232178
0.8462 Intermediate Similarity NPC135524
0.8462 Intermediate Similarity NPC85310
0.8433 Intermediate Similarity NPC131799
0.8429 Intermediate Similarity NPC191976
0.8425 Intermediate Similarity NPC290194
0.8417 Intermediate Similarity NPC282780
0.8417 Intermediate Similarity NPC1249
0.8417 Intermediate Similarity NPC270899
0.8417 Intermediate Similarity NPC166480
0.8414 Intermediate Similarity NPC68441
0.8414 Intermediate Similarity NPC12402
0.8406 Intermediate Similarity NPC309430
0.8403 Intermediate Similarity NPC238629
0.8403 Intermediate Similarity NPC293545
0.8403 Intermediate Similarity NPC174905
0.84 Intermediate Similarity NPC226656
0.84 Intermediate Similarity NPC66508
0.8394 Intermediate Similarity NPC198305
0.8394 Intermediate Similarity NPC475741
0.8392 Intermediate Similarity NPC290550
0.8382 Intermediate Similarity NPC96024
0.838 Intermediate Similarity NPC306835
0.838 Intermediate Similarity NPC476477
0.838 Intermediate Similarity NPC299405
0.838 Intermediate Similarity NPC111422
0.838 Intermediate Similarity NPC471602
0.838 Intermediate Similarity NPC216312
0.838 Intermediate Similarity NPC256463
0.838 Intermediate Similarity NPC29771
0.8378 Intermediate Similarity NPC294646
0.8369 Intermediate Similarity NPC44960
0.8369 Intermediate Similarity NPC53001
0.8369 Intermediate Similarity NPC474110
0.8358 Intermediate Similarity NPC164014
0.8358 Intermediate Similarity NPC236189
0.8358 Intermediate Similarity NPC234890
0.8358 Intermediate Similarity NPC74507
0.8357 Intermediate Similarity NPC22222
0.8357 Intermediate Similarity NPC281513
0.8356 Intermediate Similarity NPC110882
0.8356 Intermediate Similarity NPC314437
0.8356 Intermediate Similarity NPC85393
0.8356 Intermediate Similarity NPC285122
0.8356 Intermediate Similarity NPC271944
0.8355 Intermediate Similarity NPC324736
0.8346 Intermediate Similarity NPC91478
0.8345 Intermediate Similarity NPC48762
0.8345 Intermediate Similarity NPC294226
0.8333 Intermediate Similarity NPC474622
0.8333 Intermediate Similarity NPC474961
0.8333 Intermediate Similarity NPC93015
0.8333 Intermediate Similarity NPC474621
0.8333 Intermediate Similarity NPC73061
0.8322 Intermediate Similarity NPC37992
0.8322 Intermediate Similarity NPC183345
0.8322 Intermediate Similarity NPC32749
0.8322 Intermediate Similarity NPC35
0.8322 Intermediate Similarity NPC147542
0.8322 Intermediate Similarity NPC220496
0.8322 Intermediate Similarity NPC42262
0.8322 Intermediate Similarity NPC327916
0.8322 Intermediate Similarity NPC241349
0.8321 Intermediate Similarity NPC276238
0.831 Intermediate Similarity NPC87723
0.831 Intermediate Similarity NPC206207
0.8308 Intermediate Similarity NPC269414
0.8301 Intermediate Similarity NPC284495

  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 NPC474813 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
0.9147 High Similarity NPD1470 Approved
0.8837 High Similarity NPD1201 Approved
0.8768 High Similarity NPD5404 Approved
0.8768 High Similarity NPD5405 Approved
0.8768 High Similarity NPD5406 Approved
0.8768 High Similarity NPD5408 Approved
0.8696 High Similarity NPD1509 Clinical (unspecified phase)
0.8601 High Similarity NPD7390 Discontinued
0.8414 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8188 Intermediate Similarity NPD3226 Approved
0.8056 Intermediate Similarity NPD2346 Discontinued
0.7785 Intermediate Similarity NPD3300 Phase 2
0.774 Intermediate Similarity NPD2935 Discontinued
0.7736 Intermediate Similarity NPD6232 Discontinued
0.7702 Intermediate Similarity NPD7473 Discontinued
0.7674 Intermediate Similarity NPD2342 Discontinued
0.7673 Intermediate Similarity NPD6959 Discontinued
0.7652 Intermediate Similarity NPD7635 Approved
0.7651 Intermediate Similarity NPD7003 Approved
0.7643 Intermediate Similarity NPD1164 Approved
0.7639 Intermediate Similarity NPD943 Approved
0.7622 Intermediate Similarity NPD3764 Approved
0.7574 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2313 Discontinued
0.7464 Intermediate Similarity NPD3019 Approved
0.745 Intermediate Similarity NPD2344 Approved
0.7432 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD5951 Approved
0.7384 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD8313 Approved
0.7381 Intermediate Similarity NPD8312 Approved
0.7372 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD2798 Approved
0.7338 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD2932 Approved
0.7315 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD2799 Discontinued
0.7312 Intermediate Similarity NPD7768 Phase 2
0.7297 Intermediate Similarity NPD1607 Approved
0.7289 Intermediate Similarity NPD5844 Phase 1
0.7267 Intermediate Similarity NPD3749 Approved
0.7255 Intermediate Similarity NPD2309 Approved
0.7251 Intermediate Similarity NPD8150 Discontinued
0.7226 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6534 Approved
0.72 Intermediate Similarity NPD1510 Phase 2
0.72 Intermediate Similarity NPD6535 Approved
0.7192 Intermediate Similarity NPD7008 Discontinued
0.719 Intermediate Similarity NPD3750 Approved
0.7188 Intermediate Similarity NPD7819 Suspended
0.7162 Intermediate Similarity NPD1240 Approved
0.7153 Intermediate Similarity NPD497 Approved
0.7143 Intermediate Similarity NPD6212 Phase 3
0.7143 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6213 Phase 3
0.7143 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7177 Discontinued
0.7124 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD2532 Approved
0.7115 Intermediate Similarity NPD2534 Approved
0.7115 Intermediate Similarity NPD2533 Approved
0.7108 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4380 Phase 2
0.7105 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6776 Approved
0.7095 Intermediate Similarity NPD6777 Approved
0.7095 Intermediate Similarity NPD6779 Approved
0.7095 Intermediate Similarity NPD6782 Approved
0.7095 Intermediate Similarity NPD6781 Approved
0.7095 Intermediate Similarity NPD6780 Approved
0.7095 Intermediate Similarity NPD6778 Approved
0.709 Intermediate Similarity NPD9266 Approved
0.709 Intermediate Similarity NPD74 Approved
0.7083 Intermediate Similarity NPD1283 Approved
0.7081 Intermediate Similarity NPD2801 Approved
0.7081 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD495 Approved
0.708 Intermediate Similarity NPD498 Approved
0.708 Intermediate Similarity NPD496 Approved
0.7079 Intermediate Similarity NPD7699 Phase 2
0.7079 Intermediate Similarity NPD7700 Phase 2
0.7063 Intermediate Similarity NPD7411 Suspended
0.705 Intermediate Similarity NPD9493 Approved
0.7044 Intermediate Similarity NPD7458 Discontinued
0.7042 Intermediate Similarity NPD3023 Approved
0.7042 Intermediate Similarity NPD3026 Approved
0.7033 Intermediate Similarity NPD7870 Phase 2
0.7033 Intermediate Similarity NPD7871 Phase 2
0.7021 Intermediate Similarity NPD3024 Approved
0.7021 Intermediate Similarity NPD3025 Approved
0.7021 Intermediate Similarity NPD1651 Approved
0.7015 Intermediate Similarity NPD9267 Approved
0.7015 Intermediate Similarity NPD9263 Approved
0.7015 Intermediate Similarity NPD9264 Approved
0.6993 Remote Similarity NPD1471 Phase 3
0.6978 Remote Similarity NPD7697 Approved
0.6978 Remote Similarity NPD7698 Approved
0.6978 Remote Similarity NPD7696 Phase 3
0.6978 Remote Similarity NPD7435 Discontinued
0.6972 Remote Similarity NPD2286 Discontinued
0.697 Remote Similarity NPD5494 Approved
0.6968 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6968 Remote Similarity NPD8166 Discontinued
0.6959 Remote Similarity NPD6559 Discontinued
0.6959 Remote Similarity NPD5029 Approved
0.6959 Remote Similarity NPD5031 Approved
0.6959 Remote Similarity NPD5027 Approved
0.6948 Remote Similarity NPD1549 Phase 2
0.6948 Remote Similarity NPD970 Clinical (unspecified phase)
0.6947 Remote Similarity NPD289 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4878 Approved
0.6943 Remote Similarity NPD1511 Approved
0.6933 Remote Similarity NPD5402 Approved
0.6928 Remote Similarity NPD1551 Phase 2
0.6923 Remote Similarity NPD6823 Phase 2
0.6918 Remote Similarity NPD1203 Approved
0.6914 Remote Similarity NPD1934 Approved
0.6914 Remote Similarity NPD6844 Discontinued
0.6894 Remote Similarity NPD1932 Approved
0.6883 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1281 Approved
0.6875 Remote Similarity NPD1611 Approved
0.6863 Remote Similarity NPD3748 Approved
0.6863 Remote Similarity NPD4308 Phase 3
0.6855 Remote Similarity NPD1512 Approved
0.6855 Remote Similarity NPD6273 Approved
0.6849 Remote Similarity NPD1876 Approved
0.6846 Remote Similarity NPD4625 Phase 3
0.6846 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6846 Remote Similarity NPD288 Approved
0.6842 Remote Similarity NPD1930 Approved
0.6842 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1929 Approved
0.6829 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7701 Phase 2
0.6821 Remote Similarity NPD5026 Approved
0.6821 Remote Similarity NPD4954 Approved
0.6821 Remote Similarity NPD5034 Approved
0.6821 Remote Similarity NPD5028 Approved
0.6821 Remote Similarity NPD4955 Approved
0.6821 Remote Similarity NPD36 Approved
0.6811 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6166 Phase 2
0.6805 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6805 Remote Similarity NPD6167 Clinical (unspecified phase)
0.68 Remote Similarity NPD411 Approved
0.6795 Remote Similarity NPD2800 Approved
0.6792 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6788 Remote Similarity NPD4750 Phase 3
0.6786 Remote Similarity NPD9281 Approved
0.6776 Remote Similarity NPD447 Suspended
0.6769 Remote Similarity NPD844 Approved
0.6765 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6763 Remote Similarity NPD5030 Phase 2
0.6761 Remote Similarity NPD5038 Approved
0.6761 Remote Similarity NPD5037 Approved
0.6757 Remote Similarity NPD8320 Phase 1
0.6757 Remote Similarity NPD8319 Approved
0.6755 Remote Similarity NPD7874 Approved
0.6755 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6755 Remote Similarity NPD6663 Approved
0.6752 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6747 Remote Similarity NPD7075 Discontinued
0.6736 Remote Similarity NPD4626 Approved
0.6727 Remote Similarity NPD2296 Approved
0.6725 Remote Similarity NPD3751 Discontinued
0.672 Remote Similarity NPD7801 Approved
0.6716 Remote Similarity NPD9261 Approved
0.6715 Remote Similarity NPD2329 Discontinued
0.6715 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6714 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3972 Approved
0.6712 Remote Similarity NPD9717 Approved
0.6711 Remote Similarity NPD5736 Approved
0.6711 Remote Similarity NPD2979 Phase 3
0.671 Remote Similarity NPD6099 Approved
0.671 Remote Similarity NPD2796 Approved
0.671 Remote Similarity NPD6100 Approved
0.6705 Remote Similarity NPD5036 Approved
0.6702 Remote Similarity NPD8151 Discontinued
0.6687 Remote Similarity NPD3882 Suspended
0.6687 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6686 Remote Similarity NPD6020 Phase 2
0.6685 Remote Similarity NPD6836 Approved
0.6667 Remote Similarity NPD5033 Approved
0.6667 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1237 Approved
0.6667 Remote Similarity NPD1465 Phase 2
0.6647 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6646 Remote Similarity NPD3400 Discontinued
0.6646 Remote Similarity NPD4628 Phase 3
0.6643 Remote Similarity NPD7610 Discontinued
0.6627 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6622 Remote Similarity NPD6696 Suspended

  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