Structure

Physi-Chem Properties

Molecular Weight:  546.27
Volume:  567.616
LogP:  3.376
LogD:  2.546
LogS:  -4.044
# Rotatable Bonds:  2
TPSA:  136.56
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.259
Synthetic Accessibility Score:  6.007
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:  -5.0
MDCK Permeability:  1.1956755770370364e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.914
Human Intestinal Absorption (HIA):  0.649
20% Bioavailability (F20%):  0.285
30% Bioavailability (F30%):  0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.273
Plasma Protein Binding (PPB):  94.73754119873047%
Volume Distribution (VD):  0.27
Pgp-substrate:  3.0213565826416016%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.19
CYP2C19-inhibitor:  0.162
CYP2C19-substrate:  0.442
CYP2C9-inhibitor:  0.206
CYP2C9-substrate:  0.565
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.113
CYP3A4-inhibitor:  0.908
CYP3A4-substrate:  0.252

ADMET: Excretion

Clearance (CL):  3.752
Half-life (T1/2):  0.678

ADMET: Toxicity

hERG Blockers:  0.085
Human Hepatotoxicity (H-HT):  0.697
Drug-inuced Liver Injury (DILI):  0.368
AMES Toxicity:  0.057
Rat Oral Acute Toxicity:  0.866
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.145
Carcinogencity:  0.044
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.931

Download Data

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

  Natural Product: NPC141428

Natural Product ID:  NPC141428
Common Name*:   Chaetoglobosin Q
IUPAC Name:   n.a.
Synonyms:   Chaetoglobosin Q
Standard InCHIKey:  GXXPQGPTEVHUTJ-VOXRAUTJSA-N
Standard InCHI:  InChI=1S/C32H38N2O6/c1-17-8-7-10-22-29(38)31(4,40)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(39)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-14,16-17,19,22,24,27-29,33,37-38,40H,8,15H2,1-4H3,(H,34,39)/b10-7+,13-12+,18-14+/t17-,19-,22-,24-,27-,28+,29-,31+,32+/m0/s1
SMILES:  C[C@H]1C/C=C/[C@H]2[C@@H]([C@@](C)([C@@H](C)[C@H]3[C@H](Cc4c[nH]c5ccccc45)N=C([C@@]23C(=O)/C=C/C(=O)[C@@H](/C(=C/1)/C)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443917
PubChem CID:   11261310
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 n.a. n.a. n.a. PMID[19246197]
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[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. mycelium n.a. PMID[21548578]
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. n.a. n.a. PMID[21640594]
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]
NPO24171 Chaetomium globosum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[CiteXplore Id]
NPO24171 Chaetomium globosum Species Chaetomiaceae 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
NPT168 Cell Line P388 Mus musculus IC50 = 2.19 ug.mL-1 PMID[565904]

☑ 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 NPC141428 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
0.9608 High Similarity NPC57690
0.9598 High Similarity NPC203614
0.9598 High Similarity NPC204491
0.9369 High Similarity NPC267926
0.935 High Similarity NPC151976
0.935 High Similarity NPC87856
0.9307 High Similarity NPC132211
0.9227 High Similarity NPC235885
0.9179 High Similarity NPC147446
0.9179 High Similarity NPC266192
0.915 High Similarity NPC258062
0.915 High Similarity NPC127677
0.9113 High Similarity NPC267965
0.91 High Similarity NPC46225
0.91 High Similarity NPC225821
0.9009 High Similarity NPC290529
0.899 High Similarity NPC2395
0.895 High Similarity NPC98715
0.8916 High Similarity NPC271862
0.86 High Similarity NPC11445
0.855 High Similarity NPC195239
0.855 High Similarity NPC157828
0.839 Intermediate Similarity NPC300183
0.8326 Intermediate Similarity NPC70155
0.7928 Intermediate Similarity NPC476818
0.7926 Intermediate Similarity NPC471284
0.7874 Intermediate Similarity NPC267343
0.7861 Intermediate Similarity NPC300688
0.784 Intermediate Similarity NPC477043
0.7834 Intermediate Similarity NPC235900
0.7826 Intermediate Similarity NPC47190
0.782 Intermediate Similarity NPC252338
0.7773 Intermediate Similarity NPC96131
0.7761 Intermediate Similarity NPC151939
0.7756 Intermediate Similarity NPC315555
0.7729 Intermediate Similarity NPC154339
0.7725 Intermediate Similarity NPC477041
0.7725 Intermediate Similarity NPC477044
0.7723 Intermediate Similarity NPC213468
0.7712 Intermediate Similarity NPC476516
0.7682 Intermediate Similarity NPC474412
0.7678 Intermediate Similarity NPC227582
0.767 Intermediate Similarity NPC99428
0.7664 Intermediate Similarity NPC260900
0.7664 Intermediate Similarity NPC123019
0.7664 Intermediate Similarity NPC476874
0.7661 Intermediate Similarity NPC234999
0.7655 Intermediate Similarity NPC472762
0.7652 Intermediate Similarity NPC35208
0.7642 Intermediate Similarity NPC131887
0.7639 Intermediate Similarity NPC18661
0.7638 Intermediate Similarity NPC201700
0.7606 Intermediate Similarity NPC477045
0.7597 Intermediate Similarity NPC253482
0.7591 Intermediate Similarity NPC219087
0.7589 Intermediate Similarity NPC61813
0.756 Intermediate Similarity NPC206967
0.7557 Intermediate Similarity NPC229348
0.7523 Intermediate Similarity NPC74413
0.7523 Intermediate Similarity NPC88008
0.7511 Intermediate Similarity NPC475778
0.75 Intermediate Similarity NPC155143
0.75 Intermediate Similarity NPC475648
0.7487 Intermediate Similarity NPC40779
0.7477 Intermediate Similarity NPC149708
0.7476 Intermediate Similarity NPC95783
0.7467 Intermediate Similarity NPC476491
0.7465 Intermediate Similarity NPC231342
0.7463 Intermediate Similarity NPC472443
0.7455 Intermediate Similarity NPC472285
0.7454 Intermediate Similarity NPC475506
0.7452 Intermediate Similarity NPC188387
0.7452 Intermediate Similarity NPC163421
0.7446 Intermediate Similarity NPC96801
0.7446 Intermediate Similarity NPC150698
0.7444 Intermediate Similarity NPC313640
0.744 Intermediate Similarity NPC469358
0.744 Intermediate Similarity NPC472444
0.7435 Intermediate Similarity NPC475362
0.7429 Intermediate Similarity NPC209917
0.7427 Intermediate Similarity NPC198339
0.7425 Intermediate Similarity NPC475426
0.7422 Intermediate Similarity NPC473310
0.7419 Intermediate Similarity NPC476073
0.7416 Intermediate Similarity NPC235684
0.7407 Intermediate Similarity NPC79129
0.7407 Intermediate Similarity NPC249150
0.7407 Intermediate Similarity NPC49196
0.7407 Intermediate Similarity NPC195461
0.7407 Intermediate Similarity NPC313985
0.7407 Intermediate Similarity NPC470497
0.7407 Intermediate Similarity NPC81654
0.74 Intermediate Similarity NPC311276
0.7395 Intermediate Similarity NPC50503
0.7395 Intermediate Similarity NPC476517
0.7391 Intermediate Similarity NPC475601
0.7391 Intermediate Similarity NPC146824
0.7391 Intermediate Similarity NPC71037
0.7383 Intermediate Similarity NPC205403
0.7382 Intermediate Similarity NPC237702
0.738 Intermediate Similarity NPC475137
0.738 Intermediate Similarity NPC475498
0.7379 Intermediate Similarity NPC270009
0.7379 Intermediate Similarity NPC55772
0.7376 Intermediate Similarity NPC162860
0.7371 Intermediate Similarity NPC292416
0.7371 Intermediate Similarity NPC473689
0.7368 Intermediate Similarity NPC280290
0.7359 Intermediate Similarity NPC470486
0.7359 Intermediate Similarity NPC475644
0.7359 Intermediate Similarity NPC471190
0.7359 Intermediate Similarity NPC471977
0.7357 Intermediate Similarity NPC276657
0.7353 Intermediate Similarity NPC314603
0.7348 Intermediate Similarity NPC475424
0.7348 Intermediate Similarity NPC112547
0.7348 Intermediate Similarity NPC79107
0.7345 Intermediate Similarity NPC281049
0.7339 Intermediate Similarity NPC319880
0.7339 Intermediate Similarity NPC244839
0.7339 Intermediate Similarity NPC469748
0.7339 Intermediate Similarity NPC320324
0.7336 Intermediate Similarity NPC76565
0.7336 Intermediate Similarity NPC133366
0.7333 Intermediate Similarity NPC30570
0.733 Intermediate Similarity NPC314957
0.7327 Intermediate Similarity NPC160105
0.7317 Intermediate Similarity NPC472586
0.7316 Intermediate Similarity NPC124029
0.7316 Intermediate Similarity NPC87152
0.7316 Intermediate Similarity NPC475631
0.7316 Intermediate Similarity NPC476110
0.7316 Intermediate Similarity NPC211920
0.7316 Intermediate Similarity NPC475600
0.7315 Intermediate Similarity NPC473640
0.7315 Intermediate Similarity NPC473747
0.7308 Intermediate Similarity NPC323752
0.7308 Intermediate Similarity NPC302191
0.7304 Intermediate Similarity NPC473850
0.7297 Intermediate Similarity NPC223791
0.7297 Intermediate Similarity NPC478158
0.7297 Intermediate Similarity NPC107077
0.729 Intermediate Similarity NPC474177
0.7286 Intermediate Similarity NPC469762
0.7285 Intermediate Similarity NPC54420
0.7282 Intermediate Similarity NPC267885
0.7281 Intermediate Similarity NPC100321
0.7277 Intermediate Similarity NPC475406
0.7273 Intermediate Similarity NPC319232
0.7273 Intermediate Similarity NPC473506
0.7273 Intermediate Similarity NPC24370
0.7269 Intermediate Similarity NPC264285
0.7265 Intermediate Similarity NPC30456
0.7264 Intermediate Similarity NPC321708
0.7261 Intermediate Similarity NPC250807
0.7261 Intermediate Similarity NPC57797
0.726 Intermediate Similarity NPC193761
0.7257 Intermediate Similarity NPC476114
0.7256 Intermediate Similarity NPC181502
0.7256 Intermediate Similarity NPC85066
0.7252 Intermediate Similarity NPC171787
0.7246 Intermediate Similarity NPC327904
0.7246 Intermediate Similarity NPC38959
0.7246 Intermediate Similarity NPC111275
0.7243 Intermediate Similarity NPC67551
0.7241 Intermediate Similarity NPC328186
0.7241 Intermediate Similarity NPC49954
0.7241 Intermediate Similarity NPC228377
0.7241 Intermediate Similarity NPC122968
0.7241 Intermediate Similarity NPC476492
0.7241 Intermediate Similarity NPC474561
0.7241 Intermediate Similarity NPC477787
0.7236 Intermediate Similarity NPC469785
0.7235 Intermediate Similarity NPC67288
0.7235 Intermediate Similarity NPC470499
0.7235 Intermediate Similarity NPC102008
0.7233 Intermediate Similarity NPC110500
0.7233 Intermediate Similarity NPC149155
0.7233 Intermediate Similarity NPC203468
0.7232 Intermediate Similarity NPC250129
0.7232 Intermediate Similarity NPC320968
0.7229 Intermediate Similarity NPC477902
0.7229 Intermediate Similarity NPC328154
0.7225 Intermediate Similarity NPC249428
0.7222 Intermediate Similarity NPC477906
0.7222 Intermediate Similarity NPC475596
0.7222 Intermediate Similarity NPC282033
0.7222 Intermediate Similarity NPC475303
0.7217 Intermediate Similarity NPC119700
0.7217 Intermediate Similarity NPC278434
0.7217 Intermediate Similarity NPC16352
0.7212 Intermediate Similarity NPC176199
0.7212 Intermediate Similarity NPC478157
0.7212 Intermediate Similarity NPC215795
0.7212 Intermediate Similarity NPC248041
0.7212 Intermediate Similarity NPC126709
0.7212 Intermediate Similarity NPC283219
0.7206 Intermediate Similarity NPC154293
0.7206 Intermediate Similarity NPC78020
0.7203 Intermediate Similarity NPC327769

  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 NPC141428 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
0.765 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7573 Intermediate Similarity NPD2096 Phase 2
0.7573 Intermediate Similarity NPD2091 Phase 2
0.7558 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7957 Phase 1
0.7524 Intermediate Similarity NPD2094 Phase 2
0.7524 Intermediate Similarity NPD2095 Phase 2
0.7524 Intermediate Similarity NPD2092 Phase 2
0.7477 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD5426 Phase 3
0.7407 Intermediate Similarity NPD4601 Approved
0.7407 Intermediate Similarity NPD4600 Approved
0.7387 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD8325 Phase 3
0.7378 Intermediate Similarity NPD8326 Phase 3
0.7378 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7352 Intermediate Similarity NPD5901 Discontinued
0.7309 Intermediate Similarity NPD7470 Discontinued
0.7265 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD2510 Approved
0.7252 Intermediate Similarity NPD2509 Approved
0.7244 Intermediate Similarity NPD8094 Discontinued
0.724 Intermediate Similarity NPD7001 Phase 3
0.7235 Intermediate Similarity NPD7778 Approved
0.7235 Intermediate Similarity NPD7777 Approved
0.7235 Intermediate Similarity NPD53 Approved
0.7233 Intermediate Similarity NPD482 Approved
0.7227 Intermediate Similarity NPD8072 Approved
0.7222 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD8431 Approved
0.7212 Intermediate Similarity NPD7707 Approved
0.7202 Intermediate Similarity NPD6999 Discontinued
0.7202 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD8093 Discontinued
0.7198 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD8073 Approved
0.7177 Intermediate Similarity NPD6595 Phase 3
0.7177 Intermediate Similarity NPD5897 Approved
0.7177 Intermediate Similarity NPD5899 Approved
0.7177 Intermediate Similarity NPD5898 Approved
0.7169 Intermediate Similarity NPD8248 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD8468 Phase 2
0.713 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD4076 Approved
0.7129 Intermediate Similarity NPD4079 Approved
0.7123 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD7878 Phase 2
0.7117 Intermediate Similarity NPD6987 Phase 1
0.7111 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7948 Phase 1
0.7105 Intermediate Similarity NPD3393 Approved
0.7105 Intermediate Similarity NPD3389 Approved
0.7105 Intermediate Similarity NPD3394 Approved
0.7103 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD8399 Phase 1
0.7098 Intermediate Similarity NPD8423 Phase 2
0.7097 Intermediate Similarity NPD7944 Discontinued
0.7091 Intermediate Similarity NPD484 Approved
0.7081 Intermediate Similarity NPD2144 Approved
0.7081 Intermediate Similarity NPD3505 Approved
0.7081 Intermediate Similarity NPD3506 Approved
0.708 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD5065 Approved
0.7062 Intermediate Similarity NPD3038 Discontinued
0.704 Intermediate Similarity NPD8272 Phase 2
0.7039 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD2844 Phase 3
0.7037 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD7824 Approved
0.7032 Intermediate Similarity NPD5003 Discontinued
0.7022 Intermediate Similarity NPD7665 Phase 2
0.7022 Intermediate Similarity NPD7666 Phase 3
0.7019 Intermediate Similarity NPD750 Phase 2
0.6996 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6983 Remote Similarity NPD6242 Discontinued
0.6978 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6964 Remote Similarity NPD8282 Approved
0.6964 Remote Similarity NPD8283 Approved
0.6964 Remote Similarity NPD56 Approved
0.6949 Remote Similarity NPD7730 Approved
0.6949 Remote Similarity NPD7731 Approved
0.6946 Remote Similarity NPD7953 Approved
0.6946 Remote Similarity NPD7791 Approved
0.6946 Remote Similarity NPD7952 Approved
0.6946 Remote Similarity NPD7951 Approved
0.6946 Remote Similarity NPD7950 Approved
0.6946 Remote Similarity NPD7789 Approved
0.6946 Remote Similarity NPD7790 Approved
0.6944 Remote Similarity NPD7233 Approved
0.6944 Remote Similarity NPD7234 Approved
0.6941 Remote Similarity NPD4427 Phase 2
0.6937 Remote Similarity NPD4500 Approved
0.6937 Remote Similarity NPD4501 Approved
0.6926 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1326 Approved
0.6923 Remote Similarity NPD1325 Approved
0.6905 Remote Similarity NPD7708 Approved
0.6895 Remote Similarity NPD5575 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6884 Remote Similarity NPD6610 Clinical (unspecified phase)
0.6883 Remote Similarity NPD5612 Discontinued
0.6878 Remote Similarity NPD6164 Phase 2
0.6878 Remote Similarity NPD6664 Approved
0.6878 Remote Similarity NPD6165 Phase 2
0.6875 Remote Similarity NPD7187 Phase 2
0.6864 Remote Similarity NPD7619 Phase 3
0.6864 Remote Similarity NPD7271 Approved
0.6864 Remote Similarity NPD7618 Phase 3
0.6856 Remote Similarity NPD7070 Clinical (unspecified phase)
0.6853 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2125 Clinical (unspecified phase)
0.684 Remote Similarity NPD6203 Clinical (unspecified phase)
0.6838 Remote Similarity NPD6530 Approved
0.6838 Remote Similarity NPD6531 Approved
0.6835 Remote Similarity NPD2565 Phase 2
0.6835 Remote Similarity NPD7603 Discontinued
0.6835 Remote Similarity NPD2564 Approved
0.6833 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6826 Remote Similarity NPD4852 Phase 2
0.682 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6248 Phase 2
0.6816 Remote Similarity NPD6249 Phase 2
0.6814 Remote Similarity NPD8098 Approved
0.6804 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7955 Approved
0.6798 Remote Similarity NPD7956 Approved
0.6797 Remote Similarity NPD7803 Approved
0.6797 Remote Similarity NPD3794 Approved
0.6797 Remote Similarity NPD3795 Approved
0.6792 Remote Similarity NPD6375 Clinical (unspecified phase)
0.6778 Remote Similarity NPD7780 Approved
0.6778 Remote Similarity NPD7781 Approved
0.6776 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4426 Clinical (unspecified phase)
0.677 Remote Similarity NPD6176 Phase 1
0.6765 Remote Similarity NPD8289 Discontinued
0.6758 Remote Similarity NPD4499 Approved
0.6756 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6749 Remote Similarity NPD3006 Discontinued
0.6744 Remote Similarity NPD3178 Discontinued
0.6742 Remote Similarity NPD1038 Approved
0.674 Remote Similarity NPD8115 Approved
0.674 Remote Similarity NPD3947 Discontinued
0.674 Remote Similarity NPD8114 Approved
0.6739 Remote Similarity NPD8321 Discontinued
0.6736 Remote Similarity NPD7558 Phase 2
0.6736 Remote Similarity NPD5040 Clinical (unspecified phase)
0.6736 Remote Similarity NPD4845 Discontinued
0.6729 Remote Similarity NPD8386 Phase 2
0.6714 Remote Similarity NPD4638 Approved
0.6714 Remote Similarity NPD4640 Approved
0.6714 Remote Similarity NPD4075 Phase 2
0.6714 Remote Similarity NPD4639 Approved
0.6713 Remote Similarity NPD5596 Phase 2
0.6709 Remote Similarity NPD6995 Phase 1
0.6708 Remote Similarity NPD8329 Phase 3
0.67 Remote Similarity NPD4463 Approved
0.67 Remote Similarity NPD4462 Approved
0.6699 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6698 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6698 Remote Similarity NPD43 Approved
0.6698 Remote Similarity NPD6182 Approved
0.6696 Remote Similarity NPD5487 Phase 1
0.6696 Remote Similarity NPD2920 Discontinued
0.6692 Remote Similarity NPD8467 Approved
0.6692 Remote Similarity NPD8427 Approved
0.6692 Remote Similarity NPD8466 Approved
0.6692 Remote Similarity NPD8429 Approved
0.6692 Remote Similarity NPD8428 Approved
0.6692 Remote Similarity NPD8465 Approved
0.6681 Remote Similarity NPD1392 Approved
0.6681 Remote Similarity NPD8096 Phase 3
0.6681 Remote Similarity NPD8097 Phase 3
0.668 Remote Similarity NPD8374 Phase 3
0.6667 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4948 Discontinued
0.6667 Remote Similarity NPD4051 Discontinued
0.6667 Remote Similarity NPD802 Phase 2
0.6654 Remote Similarity NPD8364 Approved
0.6654 Remote Similarity NPD8363 Approved
0.6653 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6652 Remote Similarity NPD2336 Approved
0.6652 Remote Similarity NPD7191 Phase 2
0.6652 Remote Similarity NPD2916 Discontinued
0.6652 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6651 Remote Similarity NPD5088 Discontinued
0.664 Remote Similarity NPD7576 Discontinued
0.6638 Remote Similarity NPD4614 Clinical (unspecified phase)
0.6638 Remote Similarity NPD5067 Phase 2
0.6638 Remote Similarity NPD5066 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