Structure

Physi-Chem Properties

Molecular Weight:  358.14
Volume:  364.193
LogP:  2.415
LogD:  2.248
LogS:  -4.422
# Rotatable Bonds:  2
TPSA:  79.78
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.578
Synthetic Accessibility Score:  3.209
Fsp3:  0.19
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.924
MDCK Permeability:  7.1942426984605845e-06
Pgp-inhibitor:  0.011
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.146
30% Bioavailability (F30%):  0.265

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.557
Plasma Protein Binding (PPB):  94.27840423583984%
Volume Distribution (VD):  1.359
Pgp-substrate:  3.459519624710083%

ADMET: Metabolism

CYP1A2-inhibitor:  0.369
CYP1A2-substrate:  0.458
CYP2C19-inhibitor:  0.903
CYP2C19-substrate:  0.221
CYP2C9-inhibitor:  0.818
CYP2C9-substrate:  0.83
CYP2D6-inhibitor:  0.51
CYP2D6-substrate:  0.634
CYP3A4-inhibitor:  0.932
CYP3A4-substrate:  0.614

ADMET: Excretion

Clearance (CL):  4.372
Half-life (T1/2):  0.281

ADMET: Toxicity

hERG Blockers:  0.054
Human Hepatotoxicity (H-HT):  0.916
Drug-inuced Liver Injury (DILI):  0.924
AMES Toxicity:  0.312
Rat Oral Acute Toxicity:  0.651
Maximum Recommended Daily Dose:  0.89
Skin Sensitization:  0.097
Carcinogencity:  0.35
Eye Corrosion:  0.003
Eye Irritation:  0.028
Respiratory Toxicity:  0.686

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

  Natural Product: NPC6865

Natural Product ID:  NPC6865
Common Name*:   Fumiquinazoline F
IUPAC Name:   (1S,4R)-4-(1H-indol-3-ylmethyl)-1-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-dione
Synonyms:  
Standard InCHIKey:  SUVZUTHVKIBYOH-KPZWWZAWSA-N
Standard InCHI:  InChI=1S/C21H18N4O2/c1-12-19-24-17-9-5-3-7-15(17)21(27)25(19)18(20(26)23-12)10-13-11-22-16-8-4-2-6-14(13)16/h2-9,11-12,18,22H,10H2,1H3,(H,23,26)/t12-,18+/m0/s1
SMILES:  OC1=N[C@@H](C)c2n([C@@H]1Cc1c[nH]c3c1cccc3)c(=O)c1c(n2)cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229117
PubChem CID:   10089772
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0004788] Diazanaphthalenes
        • [CHEMONTID:0004789] Benzodiazines
          • [CHEMONTID:0000485] Quinazolines

*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
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota rhizosphere Sonoran desert n.a. PMID[15620238]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17542490]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17564467]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17616609]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[17929896]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19053517]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19113967]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19159274]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19256529]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu 2003 PMID[20303767]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21366228]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21718031]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21854017]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21954885]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22106303]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota healthy leaf of Ginkgo biloba campus of Nanjing University, Nanjing, China 2008-OCT PMID[22196792]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota isolated from the sponge Xestospongia testudinaria n.a. n.a. PMID[22225637]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota Isolated from a sandy-loam soil sample 50 m inland from Waikiki Beach, Honolulu, Hawaii 2010-JUL PMID[22400916]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota stem bark of Melia azedarach n.a. n.a. PMID[22409377]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22703109]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23527875]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23557488]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23563483]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24050204]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25001296]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25581396]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[26273902]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31012585]
NPO31572 Aspergillus sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[33305943]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[7622436]
NPO10538 Aspergillus fumigatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10538 Aspergillus fumigatus Species Aspergillaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 100000.0 nM PMID[540246]
NPT111 Cell Line K562 Homo sapiens IC50 > 100000.0 nM PMID[540246]
NPT1769 Organism Mythimna separata Mythimna separata AFI = 30.0 % PMID[540245]
NPT176 Organism Artemia salina Artemia salina LC50 = 55.3 ug.mL-1 PMID[540245]
NPT1203 Organism Fusarium graminearum Fusarium graminearum MIC = 12.5 ug.mL-1 PMID[540245]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum MIC = 50.0 ug.mL-1 PMID[540245]
NPT5164 Organism Fusarium oxysporum f. sp. niveum Fusarium oxysporum f. sp. niveum MIC = 25.0 ug.mL-1 PMID[540245]
NPT2600 Organism Fusarium solani Fusarium solani MIC = 50.0 ug.mL-1 PMID[540245]
NPT562 Organism Colletotrichum gloeosporioides Colletotrichum gloeosporioides MIC = 12.5 ug.mL-1 PMID[540245]
NPT962 Organism Alternaria alternata Alternaria alternata MIC = 12.5 ug.mL-1 PMID[540245]
NPT2705 Organism Alternaria solani Alternaria solani MIC = 25.0 ug.mL-1 PMID[540245]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana MIC = 12.5 ug.mL-1 PMID[540245]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 100.0 ug.mL-1 PMID[540246]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 50.0 ug.mL-1 PMID[540246]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC > 100.0 ug.mL-1 PMID[540246]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC > 100.0 ug.mL-1 PMID[540246]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 100.0 ug.mL-1 PMID[540246]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[540246]
NPT2 Others Unspecified IC50 = 17350.0 nM PMID[540246]

☑ 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 NPC6865 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
1.0 High Similarity NPC153980
0.9947 High Similarity NPC72956
0.9789 High Similarity NPC471193
0.9789 High Similarity NPC471194
0.974 High Similarity NPC471192
0.9271 High Similarity NPC471191
0.8474 Intermediate Similarity NPC21429
0.8385 Intermediate Similarity NPC94752
0.8377 Intermediate Similarity NPC228835
0.8342 Intermediate Similarity NPC17059
0.8317 Intermediate Similarity NPC477714
0.8269 Intermediate Similarity NPC477715
0.8267 Intermediate Similarity NPC473376
0.8263 Intermediate Similarity NPC11126
0.8205 Intermediate Similarity NPC213629
0.8093 Intermediate Similarity NPC165495
0.8085 Intermediate Similarity NPC63751
0.8031 Intermediate Similarity NPC88110
0.8019 Intermediate Similarity NPC478158
0.801 Intermediate Similarity NPC54420
0.8 Intermediate Similarity NPC477003
0.797 Intermediate Similarity NPC171317
0.7959 Intermediate Similarity NPC133003
0.7959 Intermediate Similarity NPC308931
0.7959 Intermediate Similarity NPC99939
0.7952 Intermediate Similarity NPC54744
0.7941 Intermediate Similarity NPC471944
0.7938 Intermediate Similarity NPC91179
0.7937 Intermediate Similarity NPC474561
0.7937 Intermediate Similarity NPC49954
0.7933 Intermediate Similarity NPC162860
0.7931 Intermediate Similarity NPC293917
0.7929 Intermediate Similarity NPC321708
0.7927 Intermediate Similarity NPC59269
0.7919 Intermediate Similarity NPC141612
0.7919 Intermediate Similarity NPC17273
0.7919 Intermediate Similarity NPC135601
0.7915 Intermediate Similarity NPC478157
0.7907 Intermediate Similarity NPC220851
0.7905 Intermediate Similarity NPC75634
0.7887 Intermediate Similarity NPC248041
0.7887 Intermediate Similarity NPC126709
0.7876 Intermediate Similarity NPC267885
0.7872 Intermediate Similarity NPC282231
0.7868 Intermediate Similarity NPC15102
0.7864 Intermediate Similarity NPC317701
0.7857 Intermediate Similarity NPC320968
0.785 Intermediate Similarity NPC476460
0.7835 Intermediate Similarity NPC84827
0.7835 Intermediate Similarity NPC14113
0.7835 Intermediate Similarity NPC145885
0.7833 Intermediate Similarity NPC227582
0.7824 Intermediate Similarity NPC203468
0.7824 Intermediate Similarity NPC110500
0.7824 Intermediate Similarity NPC149155
0.7822 Intermediate Similarity NPC202812
0.7819 Intermediate Similarity NPC279918
0.7804 Intermediate Similarity NPC281049
0.78 Intermediate Similarity NPC154339
0.7795 Intermediate Similarity NPC283219
0.7794 Intermediate Similarity NPC470499
0.7794 Intermediate Similarity NPC473640
0.7773 Intermediate Similarity NPC54981
0.7772 Intermediate Similarity NPC267343
0.7767 Intermediate Similarity NPC475506
0.7763 Intermediate Similarity NPC157931
0.7761 Intermediate Similarity NPC473763
0.7761 Intermediate Similarity NPC117244
0.7758 Intermediate Similarity NPC477549
0.7756 Intermediate Similarity NPC106118
0.7756 Intermediate Similarity NPC100321
0.7749 Intermediate Similarity NPC160105
0.7744 Intermediate Similarity NPC284775
0.7739 Intermediate Similarity NPC235684
0.7737 Intermediate Similarity NPC194640
0.7736 Intermediate Similarity NPC31385
0.7736 Intermediate Similarity NPC75726
0.7736 Intermediate Similarity NPC110602
0.7734 Intermediate Similarity NPC294693
0.7729 Intermediate Similarity NPC155143
0.7727 Intermediate Similarity NPC471762
0.7718 Intermediate Similarity NPC252338
0.7708 Intermediate Similarity NPC78020
0.7704 Intermediate Similarity NPC213468
0.7703 Intermediate Similarity NPC89987
0.7677 Intermediate Similarity NPC470205
0.7667 Intermediate Similarity NPC471155
0.7665 Intermediate Similarity NPC16659
0.7656 Intermediate Similarity NPC54988
0.7633 Intermediate Similarity NPC470497
0.763 Intermediate Similarity NPC71238
0.763 Intermediate Similarity NPC270241
0.7626 Intermediate Similarity NPC229893
0.7626 Intermediate Similarity NPC64216
0.7624 Intermediate Similarity NPC324091
0.7621 Intermediate Similarity NPC131887
0.7619 Intermediate Similarity NPC225400
0.7614 Intermediate Similarity NPC265710
0.7612 Intermediate Similarity NPC278434
0.7602 Intermediate Similarity NPC257851
0.7602 Intermediate Similarity NPC476491
0.7596 Intermediate Similarity NPC300183
0.7594 Intermediate Similarity NPC107077
0.7594 Intermediate Similarity NPC223791
0.759 Intermediate Similarity NPC314603
0.7583 Intermediate Similarity NPC472538
0.7583 Intermediate Similarity NPC470786
0.7573 Intermediate Similarity NPC167710
0.757 Intermediate Similarity NPC473218
0.757 Intermediate Similarity NPC470702
0.7568 Intermediate Similarity NPC66777
0.7563 Intermediate Similarity NPC248454
0.756 Intermediate Similarity NPC476874
0.7557 Intermediate Similarity NPC319232
0.7557 Intermediate Similarity NPC24370
0.7549 Intermediate Similarity NPC473342
0.7549 Intermediate Similarity NPC477167
0.7538 Intermediate Similarity NPC233936
0.7538 Intermediate Similarity NPC191415
0.7535 Intermediate Similarity NPC470703
0.7534 Intermediate Similarity NPC69843
0.7534 Intermediate Similarity NPC326363
0.7525 Intermediate Similarity NPC55772
0.7525 Intermediate Similarity NPC219336
0.7524 Intermediate Similarity NPC11445
0.7513 Intermediate Similarity NPC42372
0.7512 Intermediate Similarity NPC326422
0.7512 Intermediate Similarity NPC304203
0.75 Intermediate Similarity NPC74413
0.75 Intermediate Similarity NPC477004
0.7489 Intermediate Similarity NPC56109
0.7489 Intermediate Similarity NPC191382
0.7488 Intermediate Similarity NPC262898
0.7487 Intermediate Similarity NPC471943
0.7476 Intermediate Similarity NPC157828
0.7476 Intermediate Similarity NPC195239
0.7475 Intermediate Similarity NPC15573
0.7475 Intermediate Similarity NPC111275
0.7475 Intermediate Similarity NPC217372
0.7475 Intermediate Similarity NPC62749
0.7475 Intermediate Similarity NPC473380
0.7475 Intermediate Similarity NPC240088
0.7475 Intermediate Similarity NPC183662
0.7474 Intermediate Similarity NPC114637
0.7463 Intermediate Similarity NPC47190
0.7462 Intermediate Similarity NPC469529
0.7462 Intermediate Similarity NPC293216
0.7462 Intermediate Similarity NPC469938
0.746 Intermediate Similarity NPC469760
0.746 Intermediate Similarity NPC259644
0.746 Intermediate Similarity NPC469763
0.746 Intermediate Similarity NPC25008
0.746 Intermediate Similarity NPC469765
0.746 Intermediate Similarity NPC469786
0.746 Intermediate Similarity NPC73952
0.7455 Intermediate Similarity NPC477175
0.7455 Intermediate Similarity NPC470730
0.7454 Intermediate Similarity NPC282247
0.7452 Intermediate Similarity NPC474916
0.7442 Intermediate Similarity NPC82370
0.744 Intermediate Similarity NPC179701
0.7437 Intermediate Similarity NPC248462
0.7422 Intermediate Similarity NPC475859
0.7422 Intermediate Similarity NPC475969
0.7421 Intermediate Similarity NPC70922
0.7421 Intermediate Similarity NPC211572
0.7421 Intermediate Similarity NPC80597
0.7421 Intermediate Similarity NPC75540
0.7421 Intermediate Similarity NPC155444
0.7421 Intermediate Similarity NPC212376
0.7416 Intermediate Similarity NPC153123
0.7416 Intermediate Similarity NPC475914
0.7416 Intermediate Similarity NPC220797
0.7416 Intermediate Similarity NPC474318
0.7416 Intermediate Similarity NPC201266
0.7416 Intermediate Similarity NPC268744
0.7415 Intermediate Similarity NPC138370
0.7413 Intermediate Similarity NPC102755
0.7413 Intermediate Similarity NPC163055
0.7404 Intermediate Similarity NPC471199
0.7401 Intermediate Similarity NPC325976
0.7397 Intermediate Similarity NPC475736
0.7393 Intermediate Similarity NPC260900
0.7393 Intermediate Similarity NPC476073
0.7393 Intermediate Similarity NPC193761
0.7391 Intermediate Similarity NPC220151
0.7391 Intermediate Similarity NPC19692
0.7389 Intermediate Similarity NPC165743
0.7387 Intermediate Similarity NPC64436
0.7385 Intermediate Similarity NPC470731
0.7383 Intermediate Similarity NPC116555
0.7383 Intermediate Similarity NPC266249
0.7382 Intermediate Similarity NPC285469
0.7382 Intermediate Similarity NPC84317
0.7381 Intermediate Similarity NPC269203
0.7381 Intermediate Similarity NPC13456
0.7381 Intermediate Similarity NPC23420
0.7381 Intermediate Similarity NPC205254
0.7381 Intermediate Similarity NPC303820
0.7381 Intermediate Similarity NPC77241

  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 NPC6865 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
0.8424 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.809 Intermediate Similarity NPD7618 Phase 3
0.809 Intermediate Similarity NPD7619 Phase 3
0.8029 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD6664 Approved
0.8 Intermediate Similarity NPD5901 Discontinued
0.7981 Intermediate Similarity NPD6204 Clinical (unspecified phase)
0.797 Intermediate Similarity NPD3961 Discontinued
0.794 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD6165 Phase 2
0.7926 Intermediate Similarity NPD6164 Phase 2
0.79 Intermediate Similarity NPD4922 Phase 2
0.7854 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7854 Intermediate Similarity NPD7817 Phase 1
0.784 Intermediate Similarity NPD8000 Clinical (unspecified phase)
0.783 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7828 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD482 Approved
0.7822 Intermediate Similarity NPD7944 Discontinued
0.782 Intermediate Similarity NPD8093 Discontinued
0.781 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7804 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD2095 Phase 2
0.7766 Intermediate Similarity NPD2094 Phase 2
0.7766 Intermediate Similarity NPD2092 Phase 2
0.7755 Intermediate Similarity NPD6595 Phase 3
0.7746 Intermediate Similarity NPD7971 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD7970 Approved
0.7732 Intermediate Similarity NPD4128 Approved
0.7727 Intermediate Similarity NPD2091 Phase 2
0.7727 Intermediate Similarity NPD7564 Discontinued
0.7727 Intermediate Similarity NPD2096 Phase 2
0.7718 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD2442 Approved
0.7714 Intermediate Similarity NPD2443 Approved
0.7692 Intermediate Similarity NPD4075 Phase 2
0.7689 Intermediate Similarity NPD7470 Discontinued
0.7688 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD750 Phase 2
0.7668 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD8272 Phase 2
0.7626 Intermediate Similarity NPD6753 Phase 1
0.7626 Intermediate Similarity NPD6752 Phase 1
0.7617 Intermediate Similarity NPD8094 Discontinued
0.7612 Intermediate Similarity NPD4988 Discontinued
0.7612 Intermediate Similarity NPD8431 Approved
0.761 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD4863 Approved
0.7571 Intermediate Similarity NPD8114 Approved
0.7571 Intermediate Similarity NPD5426 Phase 3
0.7571 Intermediate Similarity NPD8115 Approved
0.7563 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD2008 Discontinued
0.7524 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD4848 Phase 1
0.7523 Intermediate Similarity NPD5198 Approved
0.7523 Intermediate Similarity NPD5199 Approved
0.7512 Intermediate Similarity NPD2408 Discontinued
0.7512 Intermediate Similarity NPD5017 Discontinued
0.7512 Intermediate Similarity NPD3968 Approved
0.75 Intermediate Similarity NPD5592 Clinical (unspecified phase)
0.7489 Intermediate Similarity NPD7781 Approved
0.7489 Intermediate Similarity NPD7780 Approved
0.7488 Intermediate Similarity NPD7175 Phase 1
0.7488 Intermediate Similarity NPD2411 Approved
0.7488 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD4181 Approved
0.7466 Intermediate Similarity NPD6173 Approved
0.7465 Intermediate Similarity NPD7665 Phase 2
0.7465 Intermediate Similarity NPD7666 Phase 3
0.7465 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD5065 Approved
0.7453 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD7957 Phase 1
0.7452 Intermediate Similarity NPD1982 Phase 1
0.7442 Intermediate Similarity NPD4614 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7434 Intermediate Similarity NPD7950 Approved
0.7434 Intermediate Similarity NPD7952 Approved
0.7434 Intermediate Similarity NPD7789 Approved
0.7434 Intermediate Similarity NPD7953 Approved
0.7434 Intermediate Similarity NPD7951 Approved
0.7434 Intermediate Similarity NPD7790 Approved
0.7434 Intermediate Similarity NPD7791 Approved
0.7418 Intermediate Similarity NPD3410 Approved
0.7418 Intermediate Similarity NPD3411 Phase 2
0.7407 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7406 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD7603 Discontinued
0.7395 Intermediate Similarity NPD4051 Discontinued
0.7393 Intermediate Similarity NPD8073 Approved
0.7389 Intermediate Similarity NPD5820 Clinical (unspecified phase)
0.7387 Intermediate Similarity NPD6850 Phase 2
0.7387 Intermediate Similarity NPD6849 Phase 2
0.7383 Intermediate Similarity NPD2509 Approved
0.7383 Intermediate Similarity NPD7232 Discontinued
0.7383 Intermediate Similarity NPD2510 Approved
0.7373 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD3967 Approved
0.7366 Intermediate Similarity NPD7730 Approved
0.7366 Intermediate Similarity NPD7731 Approved
0.7361 Intermediate Similarity NPD3915 Approved
0.7358 Intermediate Similarity NPD8072 Approved
0.7358 Intermediate Similarity NPD6176 Phase 1
0.7356 Intermediate Similarity NPD6226 Phase 3
0.7354 Intermediate Similarity NPD7271 Approved
0.7353 Intermediate Similarity NPD4948 Discontinued
0.735 Intermediate Similarity NPD4076 Approved
0.735 Intermediate Similarity NPD4079 Approved
0.7349 Intermediate Similarity NPD5510 Approved
0.7346 Intermediate Similarity NPD7727 Phase 2
0.7336 Intermediate Similarity NPD1506 Discontinued
0.7333 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6999 Discontinued
0.733 Intermediate Similarity NPD6242 Discontinued
0.7327 Intermediate Similarity NPD3917 Approved
0.7327 Intermediate Similarity NPD7657 Approved
0.7327 Intermediate Similarity NPD3916 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7656 Approved
0.7327 Intermediate Similarity NPD3918 Approved
0.7324 Intermediate Similarity NPD6288 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6987 Phase 1
0.7321 Intermediate Similarity NPD8289 Discontinued
0.7315 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD7187 Phase 2
0.7308 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.7306 Intermediate Similarity NPD3394 Approved
0.7306 Intermediate Similarity NPD3393 Approved
0.7306 Intermediate Similarity NPD3389 Approved
0.7304 Intermediate Similarity NPD7026 Phase 2
0.7301 Intermediate Similarity NPD7824 Approved
0.73 Intermediate Similarity NPD3505 Approved
0.73 Intermediate Similarity NPD3506 Approved
0.7295 Intermediate Similarity NPD5505 Discontinued
0.729 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD5489 Phase 1
0.729 Intermediate Similarity NPD5491 Phase 3
0.7289 Intermediate Similarity NPD4845 Discontinued
0.7282 Intermediate Similarity NPD4499 Approved
0.7281 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7027 Phase 3
0.7264 Intermediate Similarity NPD8386 Phase 2
0.7252 Intermediate Similarity NPD6210 Phase 3
0.7251 Intermediate Similarity NPD7308 Discontinued
0.7246 Intermediate Similarity NPD2336 Approved
0.7243 Intermediate Similarity NPD7209 Approved
0.7243 Intermediate Similarity NPD7207 Approved
0.7243 Intermediate Similarity NPD7208 Approved
0.7243 Intermediate Similarity NPD3947 Discontinued
0.7241 Intermediate Similarity NPD3320 Approved
0.7241 Intermediate Similarity NPD3319 Phase 1
0.7241 Intermediate Similarity NPD3318 Approved
0.724 Intermediate Similarity NPD6470 Phase 3
0.7238 Intermediate Similarity NPD5446 Phase 2
0.7228 Intermediate Similarity NPD5473 Discontinued
0.7222 Intermediate Similarity NPD6487 Approved
0.7222 Intermediate Similarity NPD6486 Approved
0.722 Intermediate Similarity NPD5809 Phase 3
0.722 Intermediate Similarity NPD6217 Discontinued
0.7211 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.721 Intermediate Similarity NPD3914 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7001 Phase 3
0.7203 Intermediate Similarity NPD4558 Phase 2
0.7202 Intermediate Similarity NPD5475 Discontinued
0.72 Intermediate Similarity NPD7269 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD2812 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD2813 Phase 3
0.7195 Intermediate Similarity NPD3805 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD3178 Discontinued
0.7188 Intermediate Similarity NPD5001 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5854 Approved
0.7168 Intermediate Similarity NPD7711 Discontinued
0.7156 Intermediate Similarity NPD7948 Phase 1
0.715 Intermediate Similarity NPD2881 Approved
0.715 Intermediate Similarity NPD2879 Approved
0.7149 Intermediate Similarity NPD3353 Approved
0.7143 Intermediate Similarity NPD2479 Phase 3
0.7143 Intermediate Similarity NPD5855 Phase 3
0.7143 Intermediate Similarity NPD5853 Phase 3
0.7143 Intermediate Similarity NPD2481 Approved
0.7143 Intermediate Similarity NPD4882 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD4601 Approved
0.7136 Intermediate Similarity NPD4600 Approved
0.713 Intermediate Similarity NPD8047 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD2144 Approved
0.7123 Intermediate Similarity NPD7204 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD6178 Phase 3

  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