Structure

Physi-Chem Properties

Molecular Weight:  528.26
Volume:  550.269
LogP:  3.042
LogD:  3.006
LogS:  -4.217
# Rotatable Bonds:  2
TPSA:  116.33
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.313
Synthetic Accessibility Score:  6.105
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.005
MDCK Permeability:  9.0171351985191e-06
Pgp-inhibitor:  0.04
Pgp-substrate:  0.668
Human Intestinal Absorption (HIA):  0.017
20% Bioavailability (F20%):  0.034
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.209
Plasma Protein Binding (PPB):  95.82595825195312%
Volume Distribution (VD):  0.373
Pgp-substrate:  3.848545551300049%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.51
CYP2C19-inhibitor:  0.547
CYP2C19-substrate:  0.681
CYP2C9-inhibitor:  0.411
CYP2C9-substrate:  0.137
CYP2D6-inhibitor:  0.116
CYP2D6-substrate:  0.15
CYP3A4-inhibitor:  0.951
CYP3A4-substrate:  0.428

ADMET: Excretion

Clearance (CL):  8.625
Half-life (T1/2):  0.097

ADMET: Toxicity

hERG Blockers:  0.088
Human Hepatotoxicity (H-HT):  0.333
Drug-inuced Liver Injury (DILI):  0.293
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.931
Maximum Recommended Daily Dose:  0.968
Skin Sensitization:  0.103
Carcinogencity:  0.142
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.985

Download Data

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

  Natural Product: NPC147446

Natural Product ID:  NPC147446
Common Name*:   Cytoglobosin A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VROGJHMZKMLYET-NKUOSLKNSA-N
Standard InCHI:  InChI=1S/C32H36N2O5/c1-15-8-7-10-22-28(36)17(3)16(2)27-24(12-19-14-33-23-11-6-5-9-20(19)23)34-31(39)32(22,27)25(35)13-21-26(15)18(4)29(37)30(21)38/h5-7,9-11,14-16,21-22,24,26-28,33,36-37H,3,8,12-13H2,1-2,4H3,(H,34,39)/b10-7+/t15-,16+,21+,22-,24-,26-,27-,28+,32+/m0/s1
SMILES:  C=C1[C@@H](C)[C@H]2[C@@H](N=C([C@]32[C@H]([C@@H]1O)/C=C/C[C@@H]([C@@H]1[C@@H](CC3=O)C(=O)C(=C1C)O)C)O)Cc1c[nH]c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097577
PubChem CID:   46209792
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001819] Isoindoles and derivatives
        • [CHEMONTID:0002496] Isoindolines
          • [CHEMONTID:0001820] Isoindolones

*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
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[12357398]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[12483566]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[15497948]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[15921417]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16209910]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16499339]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16872138]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[16904330]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[17125234]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[17827664]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota Ginkgo biloba n.a. n.a. PMID[19246197]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[19246197]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[19427327]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[20225834]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[20814854]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota isolated from the leaves of Viguiera robusta n.a. n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. mycelium n.a. PMID[21548578]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21640594]
NPO997 Peltodon longipes Species Lamiaceae Eukaryota roots Santa Maria, South Brazil 2007-Dec PMID[21775156]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[21854043]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[22112725]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[22593034]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[23072467]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. Xichang of Sichuan Province, China n.a. PMID[26125976]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[26343828]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[5066072]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. PMID[7116505]
NPO2853 Eschweilera coriacea Species Lecythidaceae Eukaryota bark Suriname rainforest n.a. PMID[9677272]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[CiteXplore Id]
NPO5665 Ulva pertusa Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5665 Ulva pertusa Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3809 Eucalyptus cladocalyx Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5665 Ulva pertusa Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO997 Peltodon longipes Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5665 Ulva pertusa Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23741 Aspergillus violaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1920 Podocarpus elongata Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6621 Salvadora persica Species Salvadoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3809 Eucalyptus cladocalyx Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2853 Eschweilera coriacea Species Lecythidaceae 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 > 10000.0 nM PMID[486715]

☑ 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 NPC147446 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
0.945 High Similarity NPC203614
0.942 High Similarity NPC290529
0.9257 High Similarity NPC204491
0.9204 High Similarity NPC87856
0.9179 High Similarity NPC141428
0.9163 High Similarity NPC132211
0.9091 High Similarity NPC57690
0.9087 High Similarity NPC235885
0.9064 High Similarity NPC267965
0.9015 High Similarity NPC151976
0.9005 High Similarity NPC258062
0.8955 High Similarity NPC225821
0.8952 High Similarity NPC267926
0.8867 High Similarity NPC271862
0.8857 High Similarity NPC266192
0.8852 High Similarity NPC2395
0.8818 High Similarity NPC127677
0.8806 High Similarity NPC98715
0.8768 High Similarity NPC46225
0.855 High Similarity NPC11445
0.85 High Similarity NPC157828
0.85 High Similarity NPC195239
0.8341 Intermediate Similarity NPC300183
0.8117 Intermediate Similarity NPC70155
0.8047 Intermediate Similarity NPC474412
0.7964 Intermediate Similarity NPC476818
0.7943 Intermediate Similarity NPC252338
0.79 Intermediate Similarity NPC300688
0.7877 Intermediate Similarity NPC477043
0.7864 Intermediate Similarity NPC47190
0.7847 Intermediate Similarity NPC477041
0.7847 Intermediate Similarity NPC477044
0.7826 Intermediate Similarity NPC267343
0.78 Intermediate Similarity NPC151939
0.7799 Intermediate Similarity NPC227582
0.7783 Intermediate Similarity NPC260900
0.7761 Intermediate Similarity NPC213468
0.7725 Intermediate Similarity NPC477045
0.7707 Intermediate Similarity NPC99428
0.7681 Intermediate Similarity NPC154339
0.7678 Intermediate Similarity NPC131887
0.7677 Intermediate Similarity NPC201700
0.7642 Intermediate Similarity NPC74413
0.7636 Intermediate Similarity NPC471284
0.7621 Intermediate Similarity NPC315555
0.7617 Intermediate Similarity NPC476874
0.7615 Intermediate Similarity NPC234999
0.7596 Intermediate Similarity NPC206967
0.7591 Intermediate Similarity NPC229348
0.7545 Intermediate Similarity NPC235900
0.7535 Intermediate Similarity NPC123019
0.7535 Intermediate Similarity NPC476073
0.7535 Intermediate Similarity NPC155143
0.7533 Intermediate Similarity NPC472762
0.7512 Intermediate Similarity NPC95783
0.7489 Intermediate Similarity NPC162860
0.7489 Intermediate Similarity NPC96131
0.7488 Intermediate Similarity NPC475506
0.7466 Intermediate Similarity NPC475778
0.7466 Intermediate Similarity NPC219087
0.7463 Intermediate Similarity NPC198339
0.7442 Intermediate Similarity NPC49196
0.7442 Intermediate Similarity NPC195461
0.7442 Intermediate Similarity NPC79129
0.7442 Intermediate Similarity NPC81654
0.7442 Intermediate Similarity NPC249150
0.7442 Intermediate Similarity NPC313985
0.7437 Intermediate Similarity NPC311276
0.743 Intermediate Similarity NPC50503
0.7415 Intermediate Similarity NPC55772
0.7409 Intermediate Similarity NPC223791
0.7409 Intermediate Similarity NPC107077
0.7397 Intermediate Similarity NPC88008
0.7397 Intermediate Similarity NPC54420
0.7389 Intermediate Similarity NPC97525
0.7389 Intermediate Similarity NPC314603
0.7378 Intermediate Similarity NPC264285
0.7368 Intermediate Similarity NPC235684
0.7363 Intermediate Similarity NPC160105
0.7358 Intermediate Similarity NPC67551
0.7352 Intermediate Similarity NPC18661
0.7349 Intermediate Similarity NPC473640
0.7349 Intermediate Similarity NPC473747
0.7343 Intermediate Similarity NPC71037
0.733 Intermediate Similarity NPC478158
0.7325 Intermediate Similarity NPC16352
0.7324 Intermediate Similarity NPC474177
0.7323 Intermediate Similarity NPC469762
0.7321 Intermediate Similarity NPC280290
0.7321 Intermediate Similarity NPC163421
0.7321 Intermediate Similarity NPC188387
0.7317 Intermediate Similarity NPC267885
0.7313 Intermediate Similarity NPC61813
0.7308 Intermediate Similarity NPC469358
0.7304 Intermediate Similarity NPC24370
0.7304 Intermediate Similarity NPC319232
0.7301 Intermediate Similarity NPC477714
0.7301 Intermediate Similarity NPC281049
0.7301 Intermediate Similarity NPC473310
0.7299 Intermediate Similarity NPC321708
0.7294 Intermediate Similarity NPC193761
0.729 Intermediate Similarity NPC181502
0.729 Intermediate Similarity NPC85066
0.7282 Intermediate Similarity NPC111275
0.7281 Intermediate Similarity NPC470497
0.7277 Intermediate Similarity NPC49954
0.7277 Intermediate Similarity NPC474561
0.7273 Intermediate Similarity NPC469785
0.7269 Intermediate Similarity NPC67288
0.7268 Intermediate Similarity NPC203468
0.7268 Intermediate Similarity NPC149155
0.7268 Intermediate Similarity NPC110500
0.7265 Intermediate Similarity NPC250129
0.7265 Intermediate Similarity NPC323752
0.7264 Intermediate Similarity NPC40779
0.726 Intermediate Similarity NPC302191
0.7246 Intermediate Similarity NPC248041
0.7246 Intermediate Similarity NPC283219
0.7246 Intermediate Similarity NPC126709
0.7244 Intermediate Similarity NPC478157
0.7241 Intermediate Similarity NPC78020
0.7241 Intermediate Similarity NPC154293
0.7237 Intermediate Similarity NPC276657
0.7235 Intermediate Similarity NPC293917
0.7235 Intermediate Similarity NPC100321
0.7232 Intermediate Similarity NPC75634
0.7231 Intermediate Similarity NPC476516
0.7225 Intermediate Similarity NPC19679
0.7222 Intermediate Similarity NPC80597
0.7222 Intermediate Similarity NPC156704
0.7222 Intermediate Similarity NPC75540
0.7222 Intermediate Similarity NPC211572
0.7222 Intermediate Similarity NPC212376
0.7222 Intermediate Similarity NPC70922
0.722 Intermediate Similarity NPC475165
0.7217 Intermediate Similarity NPC213629
0.7212 Intermediate Similarity NPC471997
0.7209 Intermediate Similarity NPC133366
0.7207 Intermediate Similarity NPC314957
0.7205 Intermediate Similarity NPC473317
0.7204 Intermediate Similarity NPC94752
0.7202 Intermediate Similarity NPC475151
0.72 Intermediate Similarity NPC230869
0.7198 Intermediate Similarity NPC476491
0.7192 Intermediate Similarity NPC54988
0.7189 Intermediate Similarity NPC171317
0.7188 Intermediate Similarity NPC320968
0.7181 Intermediate Similarity NPC472285
0.7181 Intermediate Similarity NPC477715
0.7176 Intermediate Similarity NPC231342
0.7175 Intermediate Similarity NPC469743
0.7175 Intermediate Similarity NPC284102
0.7172 Intermediate Similarity NPC259644
0.7172 Intermediate Similarity NPC469763
0.7172 Intermediate Similarity NPC469786
0.7172 Intermediate Similarity NPC73952
0.7172 Intermediate Similarity NPC25008
0.7172 Intermediate Similarity NPC469760
0.7172 Intermediate Similarity NPC469765
0.717 Intermediate Similarity NPC119700
0.717 Intermediate Similarity NPC317030
0.7168 Intermediate Similarity NPC313640
0.7163 Intermediate Similarity NPC176199
0.7163 Intermediate Similarity NPC472443
0.7163 Intermediate Similarity NPC215795
0.7162 Intermediate Similarity NPC323927
0.7157 Intermediate Similarity NPC63751
0.7155 Intermediate Similarity NPC79107
0.7155 Intermediate Similarity NPC112547
0.7155 Intermediate Similarity NPC475424
0.7143 Intermediate Similarity NPC229332
0.7143 Intermediate Similarity NPC77555
0.7143 Intermediate Similarity NPC472444
0.7137 Intermediate Similarity NPC326363
0.7136 Intermediate Similarity NPC65215
0.7136 Intermediate Similarity NPC34508
0.7136 Intermediate Similarity NPC474116
0.7136 Intermediate Similarity NPC313791
0.7136 Intermediate Similarity NPC173028
0.713 Intermediate Similarity NPC171787
0.7129 Intermediate Similarity NPC477042
0.7129 Intermediate Similarity NPC282231
0.7124 Intermediate Similarity NPC475602
0.7123 Intermediate Similarity NPC214428
0.7123 Intermediate Similarity NPC213308
0.7123 Intermediate Similarity NPC315491
0.7123 Intermediate Similarity NPC45459
0.7117 Intermediate Similarity NPC187456
0.7116 Intermediate Similarity NPC99666
0.7115 Intermediate Similarity NPC84827
0.7115 Intermediate Similarity NPC14113
0.7115 Intermediate Similarity NPC68354
0.7115 Intermediate Similarity NPC145885
0.7112 Intermediate Similarity NPC125597
0.7111 Intermediate Similarity NPC82370
0.711 Intermediate Similarity NPC149708
0.7109 Intermediate Similarity NPC165201
0.7109 Intermediate Similarity NPC228835
0.7106 Intermediate Similarity NPC282033
0.7106 Intermediate Similarity NPC474877

  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 NPC147446 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
0.7593 Intermediate Similarity NPD7957 Phase 1
0.7593 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD5426 Phase 3
0.7524 Intermediate Similarity NPD2096 Phase 2
0.7524 Intermediate Similarity NPD2091 Phase 2
0.7523 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD2092 Phase 2
0.7476 Intermediate Similarity NPD2094 Phase 2
0.7476 Intermediate Similarity NPD2095 Phase 2
0.7476 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4601 Approved
0.7442 Intermediate Similarity NPD4600 Approved
0.7399 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7352 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7001 Phase 3
0.7268 Intermediate Similarity NPD482 Approved
0.7265 Intermediate Similarity NPD7470 Discontinued
0.726 Intermediate Similarity NPD8072 Approved
0.7251 Intermediate Similarity NPD8431 Approved
0.7244 Intermediate Similarity NPD7707 Approved
0.7235 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD6999 Discontinued
0.7235 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD5901 Discontinued
0.7225 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6595 Phase 3
0.72 Intermediate Similarity NPD8094 Discontinued
0.7163 Intermediate Similarity NPD4076 Approved
0.7163 Intermediate Similarity NPD4079 Approved
0.7156 Intermediate Similarity NPD8093 Discontinued
0.7143 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7948 Phase 1
0.7137 Intermediate Similarity NPD7824 Approved
0.7136 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD8073 Approved
0.7136 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD2510 Approved
0.713 Intermediate Similarity NPD7944 Discontinued
0.713 Intermediate Similarity NPD2509 Approved
0.7123 Intermediate Similarity NPD484 Approved
0.7123 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD3505 Approved
0.7115 Intermediate Similarity NPD3506 Approved
0.7115 Intermediate Similarity NPD2144 Approved
0.7111 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD3038 Discontinued
0.7085 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6987 Phase 1
0.7072 Intermediate Similarity NPD8272 Phase 2
0.707 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD7665 Phase 2
0.7054 Intermediate Similarity NPD7666 Phase 3
0.7053 Intermediate Similarity NPD750 Phase 2
0.7051 Intermediate Similarity NPD7730 Approved
0.7051 Intermediate Similarity NPD7731 Approved
0.7046 Intermediate Similarity NPD7791 Approved
0.7046 Intermediate Similarity NPD7790 Approved
0.7046 Intermediate Similarity NPD7789 Approved
0.7046 Intermediate Similarity NPD7952 Approved
0.7046 Intermediate Similarity NPD7953 Approved
0.7046 Intermediate Similarity NPD7950 Approved
0.7046 Intermediate Similarity NPD7951 Approved
0.7019 Intermediate Similarity NPD5065 Approved
0.7009 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.6996 Remote Similarity NPD8283 Approved
0.6996 Remote Similarity NPD8282 Approved
0.6996 Remote Similarity NPD56 Approved
0.699 Remote Similarity NPD2844 Phase 3
0.699 Remote Similarity NPD5069 Clinical (unspecified phase)
0.6987 Remote Similarity NPD3389 Approved
0.6987 Remote Similarity NPD3393 Approved
0.6987 Remote Similarity NPD3394 Approved
0.6978 Remote Similarity NPD8423 Phase 2
0.6978 Remote Similarity NPD8399 Phase 1
0.6977 Remote Similarity NPD7233 Approved
0.6977 Remote Similarity NPD7234 Approved
0.6966 Remote Similarity NPD7271 Approved
0.6955 Remote Similarity NPD7777 Approved
0.6955 Remote Similarity NPD53 Approved
0.6955 Remote Similarity NPD7778 Approved
0.694 Remote Similarity NPD6242 Discontinued
0.693 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5575 Clinical (unspecified phase)
0.692 Remote Similarity NPD8098 Approved
0.692 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6909 Remote Similarity NPD5003 Discontinued
0.6909 Remote Similarity NPD6664 Approved
0.6895 Remote Similarity NPD7619 Phase 3
0.6895 Remote Similarity NPD7618 Phase 3
0.6887 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6887 Remote Similarity NPD5897 Approved
0.6887 Remote Similarity NPD5898 Approved
0.6887 Remote Similarity NPD5899 Approved
0.6886 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6883 Remote Similarity NPD8327 Clinical (unspecified phase)
0.6883 Remote Similarity NPD8326 Phase 3
0.6883 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6883 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6883 Remote Similarity NPD8325 Phase 3
0.688 Remote Similarity NPD6995 Phase 1
0.6878 Remote Similarity NPD7781 Approved
0.6878 Remote Similarity NPD7780 Approved
0.6875 Remote Similarity NPD1326 Approved
0.6875 Remote Similarity NPD1325 Approved
0.6875 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6864 Remote Similarity NPD7603 Discontinued
0.6864 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6856 Remote Similarity NPD4852 Phase 2
0.6853 Remote Similarity NPD7878 Phase 2
0.6852 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6847 Remote Similarity NPD6026 Approved
0.6835 Remote Similarity NPD6164 Phase 2
0.6835 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6835 Remote Similarity NPD6165 Phase 2
0.6825 Remote Similarity NPD6375 Clinical (unspecified phase)
0.682 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6798 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6789 Remote Similarity NPD4499 Approved
0.6786 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6783 Remote Similarity NPD8096 Phase 3
0.6783 Remote Similarity NPD8097 Phase 3
0.6773 Remote Similarity NPD1038 Approved
0.6767 Remote Similarity NPD5612 Discontinued
0.6763 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6761 Remote Similarity NPD8386 Phase 2
0.6756 Remote Similarity NPD7187 Phase 2
0.6746 Remote Similarity NPD4638 Approved
0.6746 Remote Similarity NPD4640 Approved
0.6746 Remote Similarity NPD4639 Approved
0.6745 Remote Similarity NPD4075 Phase 2
0.6742 Remote Similarity NPD4427 Phase 2
0.6741 Remote Similarity NPD4501 Approved
0.6741 Remote Similarity NPD4500 Approved
0.6731 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6728 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6176 Phase 1
0.6723 Remote Similarity NPD7711 Discontinued
0.6712 Remote Similarity NPD2565 Phase 2
0.6712 Remote Similarity NPD2564 Approved
0.6711 Remote Similarity NPD8322 Phase 2
0.6697 Remote Similarity NPD802 Phase 2
0.6696 Remote Similarity NPD8114 Approved
0.6696 Remote Similarity NPD8115 Approved
0.6683 Remote Similarity NPD6635 Approved
0.6681 Remote Similarity NPD2916 Discontinued
0.6667 Remote Similarity NPD7070 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6479 Discontinued
0.6667 Remote Similarity NPD5596 Phase 2
0.6653 Remote Similarity NPD8289 Discontinued
0.6652 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6652 Remote Similarity NPD7970 Approved
0.6652 Remote Similarity NPD7946 Pre-registration
0.665 Remote Similarity NPD4462 Approved
0.665 Remote Similarity NPD4463 Approved
0.665 Remote Similarity NPD2172 Phase 1
0.6636 Remote Similarity NPD8123 Approved
0.6636 Remote Similarity NPD8122 Approved
0.6636 Remote Similarity NPD4181 Approved
0.6636 Remote Similarity NPD3871 Clinical (unspecified phase)
0.6636 Remote Similarity NPD3870 Clinical (unspecified phase)
0.6627 Remote Similarity NPD8468 Phase 2
0.6625 Remote Similarity NPD4845 Discontinued
0.6623 Remote Similarity NPD4051 Discontinued
0.6623 Remote Similarity NPD3947 Discontinued
0.6622 Remote Similarity NPD1304 Clinical (unspecified phase)
0.6621 Remote Similarity NPD3961 Discontinued
0.662 Remote Similarity NPD3178 Discontinued
0.662 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6616 Remote Similarity NPD786 Approved
0.6612 Remote Similarity NPD7688 Phase 1
0.6609 Remote Similarity NPD6376 Discontinued
0.6609 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6606 Remote Similarity NPD2336 Approved
0.6606 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6603 Remote Similarity NPD5088 Discontinued
0.6603 Remote Similarity NPD3323 Discontinued
0.6595 Remote Similarity NPD4614 Clinical (unspecified phase)
0.6589 Remote Similarity NPD5100 Phase 3
0.6587 Remote Similarity NPD2511 Approved
0.6584 Remote Similarity NPD5151 Clinical (unspecified phase)
0.658 Remote Similarity NPD7941 Phase 3
0.6579 Remote Similarity NPD2920 Discontinued
0.6577 Remote Similarity NPD6665 Discontinued
0.6574 Remote Similarity NPD5473 Discontinued
0.6567 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6565 Remote Similarity NPD1392 Approved
0.6564 Remote Similarity NPD7817 Phase 1
0.656 Remote Similarity NPD6178 Phase 3
0.6559 Remote Similarity NPD4561 Discontinued
0.6557 Remote Similarity NPD7558 Phase 2
0.6553 Remote Similarity NPD8160 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