Structure

Physi-Chem Properties

Molecular Weight:  654.43
Volume:  738.928
LogP:  9.672
LogD:  6.58
LogS:  -4.33
# Rotatable Bonds:  14
TPSA:  88.51
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.122
Synthetic Accessibility Score:  5.815
Fsp3:  0.535
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.128
MDCK Permeability:  1.703330417512916e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.132
Human Intestinal Absorption (HIA):  0.113
20% Bioavailability (F20%):  0.983
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.036
Plasma Protein Binding (PPB):  98.57759857177734%
Volume Distribution (VD):  3.103
Pgp-substrate:  7.249374866485596%

ADMET: Metabolism

CYP1A2-inhibitor:  0.04
CYP1A2-substrate:  0.158
CYP2C19-inhibitor:  0.697
CYP2C19-substrate:  0.763
CYP2C9-inhibitor:  0.866
CYP2C9-substrate:  0.954
CYP2D6-inhibitor:  0.667
CYP2D6-substrate:  0.009
CYP3A4-inhibitor:  0.912
CYP3A4-substrate:  0.87

ADMET: Excretion

Clearance (CL):  13.781
Half-life (T1/2):  0.06

ADMET: Toxicity

hERG Blockers:  0.049
Human Hepatotoxicity (H-HT):  0.868
Drug-inuced Liver Injury (DILI):  0.927
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.92
Maximum Recommended Daily Dose:  0.033
Skin Sensitization:  0.055
Carcinogencity:  0.29
Eye Corrosion:  0.018
Eye Irritation:  0.057
Respiratory Toxicity:  0.95

Download Data

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

  Natural Product: NPC25736

Natural Product ID:  NPC25736
Common Name*:   Garcicowin B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  XTFPCLRYUHLWLA-LYQFBJAVSA-N
Standard InCHI:  InChI=1S/C43H58O5/c1-28(2)14-11-16-32(9)19-20-34-27-42(24-21-30(5)6)38(46)36(37(45)33-17-12-18-35(44)26-33)39(47)43(40(42)48,25-22-31(7)8)41(34,10)23-13-15-29(3)4/h12,14-15,17-19,21-22,26,34,44,46H,11,13,16,20,23-25,27H2,1-10H3/b32-19+/t34-,41+,42+,43-/m1/s1
SMILES:  CC(=CCC/C(=C/C[C@@H]1C[C@@]2(CC=C(C)C)C(=C(C(=O)c3cccc(c3)O)C(=O)[C@](CC=C(C)C)(C2=O)[C@@]1(C)CCC=C(C)C)O)/C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1077054
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1071/CH03175]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[16724839]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19113969]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20058933]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota leaves Bobai, Guangxi Province, China 2005-Dec PMID[24679044]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota Barks n.a. n.a. PMID[24754786]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota flowers Pakook, Muang District, Chiang Rai Province, Thailand 2013-Feb PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota young fruits Khokkhon, Tha Bo District, Nong Khai Province, Thailand 2011-Aug PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota Leaves n.a. n.a. PMID[31860303]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11471 Garcinia oblongifolia Species Clusiaceae 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
NPT165 Cell Line HeLa Homo sapiens Inhibition = 50.0 % PMID[516819]
NPT165 Cell Line HeLa Homo sapiens IC50 = 10800.0 nM PMID[516819]
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 12600.0 nM PMID[516819]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 6200.0 nM PMID[516819]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 10800.0 nM PMID[516819]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 19100.0 nM PMID[516819]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 6000.0 nM PMID[516819]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 3.0 n.a. PMID[516819]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 9600.0 nM PMID[516819]

☑ 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 NPC25736 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
0.9385 High Similarity NPC118366
0.9313 High Similarity NPC23667
0.9313 High Similarity NPC149773
0.9313 High Similarity NPC114333
0.9313 High Similarity NPC51531
0.9313 High Similarity NPC473779
0.9313 High Similarity NPC91887
0.9313 High Similarity NPC165191
0.9313 High Similarity NPC50615
0.9313 High Similarity NPC473479
0.9313 High Similarity NPC469857
0.9313 High Similarity NPC245760
0.9313 High Similarity NPC46242
0.9313 High Similarity NPC157284
0.9313 High Similarity NPC5014
0.9313 High Similarity NPC477849
0.9313 High Similarity NPC42384
0.9313 High Similarity NPC28592
0.9313 High Similarity NPC289358
0.9313 High Similarity NPC297797
0.9242 High Similarity NPC294330
0.9173 High Similarity NPC473527
0.916 High Similarity NPC7464
0.9037 High Similarity NPC469855
0.9037 High Similarity NPC30846
0.9037 High Similarity NPC471971
0.9037 High Similarity NPC471972
0.8905 High Similarity NPC8493
0.8905 High Similarity NPC469375
0.8905 High Similarity NPC145301
0.8905 High Similarity NPC144247
0.8905 High Similarity NPC469856
0.8905 High Similarity NPC469854
0.8905 High Similarity NPC294679
0.8881 High Similarity NPC469681
0.8881 High Similarity NPC471974
0.8881 High Similarity NPC469680
0.8777 High Similarity NPC471970
0.876 High Similarity NPC471530
0.8731 High Similarity NPC193358
0.8682 High Similarity NPC3224
0.8652 High Similarity NPC264229
0.8652 High Similarity NPC132810
0.8652 High Similarity NPC46549
0.8647 High Similarity NPC115458
0.8636 High Similarity NPC17083
0.8615 High Similarity NPC72667
0.8607 High Similarity NPC234637
0.8607 High Similarity NPC130591
0.8593 High Similarity NPC472308
0.8593 High Similarity NPC474311
0.8592 High Similarity NPC237441
0.855 High Similarity NPC48248
0.8538 High Similarity NPC306765
0.8538 High Similarity NPC254492
0.8538 High Similarity NPC15837
0.8525 High Similarity NPC471481
0.8511 High Similarity NPC273798
0.8507 High Similarity NPC53896
0.8485 Intermediate Similarity NPC146647
0.8485 Intermediate Similarity NPC34414
0.8485 Intermediate Similarity NPC171460
0.8473 Intermediate Similarity NPC176130
0.8473 Intermediate Similarity NPC78364
0.8473 Intermediate Similarity NPC69424
0.8473 Intermediate Similarity NPC84672
0.8456 Intermediate Similarity NPC272268
0.845 Intermediate Similarity NPC375356
0.8443 Intermediate Similarity NPC218855
0.8433 Intermediate Similarity NPC58685
0.8425 Intermediate Similarity NPC285829
0.8425 Intermediate Similarity NPC206778
0.8421 Intermediate Similarity NPC108129
0.8409 Intermediate Similarity NPC96024
0.8403 Intermediate Similarity NPC48949
0.8397 Intermediate Similarity NPC231774
0.8397 Intermediate Similarity NPC71610
0.8394 Intermediate Similarity NPC475957
0.8385 Intermediate Similarity NPC310540
0.8385 Intermediate Similarity NPC199273
0.8382 Intermediate Similarity NPC80035
0.8382 Intermediate Similarity NPC249272
0.8372 Intermediate Similarity NPC91478
0.8372 Intermediate Similarity NPC300274
0.8372 Intermediate Similarity NPC307174
0.837 Intermediate Similarity NPC477139
0.8358 Intermediate Similarity NPC244699
0.8356 Intermediate Similarity NPC305710
0.8346 Intermediate Similarity NPC276238
0.8346 Intermediate Similarity NPC117899
0.8333 Intermediate Similarity NPC87723
0.8321 Intermediate Similarity NPC103540
0.8309 Intermediate Similarity NPC12070
0.8309 Intermediate Similarity NPC270899
0.8309 Intermediate Similarity NPC202225
0.8309 Intermediate Similarity NPC50924
0.8295 Intermediate Similarity NPC154696
0.8295 Intermediate Similarity NPC120545
0.8284 Intermediate Similarity NPC55949
0.8271 Intermediate Similarity NPC282923
0.8271 Intermediate Similarity NPC193203
0.8261 Intermediate Similarity NPC53001
0.8258 Intermediate Similarity NPC474106
0.8258 Intermediate Similarity NPC96915
0.8254 Intermediate Similarity NPC477453
0.8252 Intermediate Similarity NPC143685
0.8248 Intermediate Similarity NPC283088
0.8244 Intermediate Similarity NPC74507
0.8244 Intermediate Similarity NPC234890
0.8244 Intermediate Similarity NPC142956
0.8235 Intermediate Similarity NPC474715
0.8235 Intermediate Similarity NPC138472
0.8235 Intermediate Similarity NPC225051
0.8235 Intermediate Similarity NPC114183
0.8235 Intermediate Similarity NPC4170
0.8231 Intermediate Similarity NPC282577
0.8227 Intermediate Similarity NPC193555
0.8222 Intermediate Similarity NPC18798
0.8222 Intermediate Similarity NPC471851
0.8217 Intermediate Similarity NPC259703
0.8217 Intermediate Similarity NPC32322
0.8214 Intermediate Similarity NPC315578
0.8209 Intermediate Similarity NPC303910
0.8209 Intermediate Similarity NPC99731
0.8209 Intermediate Similarity NPC471832
0.8201 Intermediate Similarity NPC13715
0.8201 Intermediate Similarity NPC4214
0.8175 Intermediate Similarity NPC288089
0.8175 Intermediate Similarity NPC161304
0.8175 Intermediate Similarity NPC322197
0.8175 Intermediate Similarity NPC475088
0.8168 Intermediate Similarity NPC275145
0.8162 Intermediate Similarity NPC110609
0.8162 Intermediate Similarity NPC242358
0.8162 Intermediate Similarity NPC175738
0.8162 Intermediate Similarity NPC246693
0.8148 Intermediate Similarity NPC475741
0.8148 Intermediate Similarity NPC199253
0.8148 Intermediate Similarity NPC136588
0.8143 Intermediate Similarity NPC26924
0.814 Intermediate Similarity NPC318552
0.814 Intermediate Similarity NPC190501
0.8134 Intermediate Similarity NPC3009
0.8134 Intermediate Similarity NPC237225
0.8134 Intermediate Similarity NPC229894
0.8129 Intermediate Similarity NPC36868
0.8129 Intermediate Similarity NPC277559
0.8116 Intermediate Similarity NPC43353
0.8116 Intermediate Similarity NPC477596
0.8115 Intermediate Similarity NPC34715
0.811 Intermediate Similarity NPC108288
0.8106 Intermediate Similarity NPC474766
0.8106 Intermediate Similarity NPC173978
0.8102 Intermediate Similarity NPC475346
0.8102 Intermediate Similarity NPC475457
0.8102 Intermediate Similarity NPC111845
0.8102 Intermediate Similarity NPC171968
0.8102 Intermediate Similarity NPC18982
0.8102 Intermediate Similarity NPC78307
0.8102 Intermediate Similarity NPC475627
0.8092 Intermediate Similarity NPC68167
0.8088 Intermediate Similarity NPC205992
0.8085 Intermediate Similarity NPC169452
0.8085 Intermediate Similarity NPC181560
0.8074 Intermediate Similarity NPC109123
0.8071 Intermediate Similarity NPC230811
0.8071 Intermediate Similarity NPC473622
0.8065 Intermediate Similarity NPC222905
0.8062 Intermediate Similarity NPC31296
0.8062 Intermediate Similarity NPC258366
0.8062 Intermediate Similarity NPC79933
0.8062 Intermediate Similarity NPC42657
0.8062 Intermediate Similarity NPC473974
0.8058 Intermediate Similarity NPC155211
0.8047 Intermediate Similarity NPC269414
0.8045 Intermediate Similarity NPC478107
0.8045 Intermediate Similarity NPC470649
0.8045 Intermediate Similarity NPC123506
0.8043 Intermediate Similarity NPC282780
0.8043 Intermediate Similarity NPC477594
0.8043 Intermediate Similarity NPC472262
0.8043 Intermediate Similarity NPC166480
0.8043 Intermediate Similarity NPC161964
0.8043 Intermediate Similarity NPC287604
0.8042 Intermediate Similarity NPC199936
0.803 Intermediate Similarity NPC198014
0.803 Intermediate Similarity NPC477153
0.803 Intermediate Similarity NPC135062
0.8029 Intermediate Similarity NPC70622
0.8016 Intermediate Similarity NPC294458
0.8015 Intermediate Similarity NPC27659
0.8015 Intermediate Similarity NPC167323
0.8015 Intermediate Similarity NPC269923
0.8015 Intermediate Similarity NPC117609
0.8015 Intermediate Similarity NPC31799
0.8015 Intermediate Similarity NPC198305
0.8014 Intermediate Similarity NPC138099
0.8014 Intermediate Similarity NPC242994
0.8 Intermediate Similarity NPC95537
0.8 Intermediate Similarity NPC110882

  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 NPC25736 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
0.8321 Intermediate Similarity NPD1470 Approved
0.8281 Intermediate Similarity NPD2932 Approved
0.8154 Intermediate Similarity NPD1201 Approved
0.814 Intermediate Similarity NPD3019 Approved
0.811 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD8166 Discontinued
0.7671 Intermediate Similarity NPD3300 Phase 2
0.7669 Intermediate Similarity NPD3026 Approved
0.7669 Intermediate Similarity NPD3023 Approved
0.7652 Intermediate Similarity NPD3024 Approved
0.7652 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD3025 Approved
0.7619 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD5951 Approved
0.75 Intermediate Similarity NPD5406 Approved
0.75 Intermediate Similarity NPD5404 Approved
0.75 Intermediate Similarity NPD5408 Approved
0.75 Intermediate Similarity NPD5405 Approved
0.7483 Intermediate Similarity NPD3226 Approved
0.7464 Intermediate Similarity NPD2798 Approved
0.7448 Intermediate Similarity NPD2346 Discontinued
0.7447 Intermediate Similarity NPD6663 Approved
0.7426 Intermediate Similarity NPD3972 Approved
0.741 Intermediate Similarity NPD5736 Approved
0.7394 Intermediate Similarity NPD943 Approved
0.7383 Intermediate Similarity NPD7390 Discontinued
0.7333 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD2799 Discontinued
0.7299 Intermediate Similarity NPD4878 Approved
0.7266 Intermediate Similarity NPD1164 Approved
0.726 Intermediate Similarity NPD2935 Discontinued
0.7254 Intermediate Similarity NPD3764 Approved
0.7246 Intermediate Similarity NPD1755 Approved
0.7219 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD1471 Phase 3
0.7211 Intermediate Similarity NPD2344 Approved
0.7185 Intermediate Similarity NPD3091 Approved
0.7181 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD7003 Approved
0.7143 Intermediate Similarity NPD6099 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD6100 Approved
0.7134 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2313 Discontinued
0.7133 Intermediate Similarity NPD3268 Approved
0.7121 Intermediate Similarity NPD7635 Approved
0.712 Intermediate Similarity NPD3020 Approved
0.7111 Intermediate Similarity NPD7610 Discontinued
0.7087 Intermediate Similarity NPD1930 Approved
0.7087 Intermediate Similarity NPD1929 Approved
0.7087 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8032 Phase 2
0.708 Intermediate Similarity NPD4059 Approved
0.7077 Intermediate Similarity NPD74 Approved
0.7077 Intermediate Similarity NPD9266 Approved
0.7075 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD1876 Approved
0.707 Intermediate Similarity NPD7819 Suspended
0.7059 Intermediate Similarity NPD6273 Approved
0.7045 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD9493 Approved
0.7023 Intermediate Similarity NPD3022 Approved
0.7023 Intermediate Similarity NPD3021 Approved
0.702 Intermediate Similarity NPD2309 Approved
0.702 Intermediate Similarity NPD7910 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD9267 Approved
0.7 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD9263 Approved
0.7 Intermediate Similarity NPD9264 Approved
0.6984 Remote Similarity NPD2066 Phase 3
0.6978 Remote Similarity NPD3092 Approved
0.697 Remote Similarity NPD4141 Clinical (unspecified phase)
0.696 Remote Similarity NPD3495 Discontinued
0.696 Remote Similarity NPD288 Approved
0.6959 Remote Similarity NPD1510 Phase 2
0.6957 Remote Similarity NPD3095 Discontinued
0.6954 Remote Similarity NPD4628 Phase 3
0.6951 Remote Similarity NPD7473 Discontinued
0.695 Remote Similarity NPD1283 Approved
0.6944 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6939 Remote Similarity NPD1607 Approved
0.6939 Remote Similarity NPD6651 Approved
0.6935 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6934 Remote Similarity NPD7009 Phase 2
0.6929 Remote Similarity NPD289 Clinical (unspecified phase)
0.6918 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1240 Approved
0.6901 Remote Similarity NPD3094 Phase 2
0.6899 Remote Similarity NPD1237 Approved
0.6894 Remote Similarity NPD4750 Phase 3
0.6887 Remote Similarity NPD2800 Approved
0.6884 Remote Similarity NPD1651 Approved
0.6883 Remote Similarity NPD4378 Clinical (unspecified phase)
0.688 Remote Similarity NPD844 Approved
0.688 Remote Similarity NPD2860 Approved
0.688 Remote Similarity NPD2859 Approved
0.687 Remote Similarity NPD2342 Discontinued
0.6863 Remote Similarity NPD7236 Approved
0.6863 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6842 Remote Similarity NPD8150 Discontinued
0.6842 Remote Similarity NPD8434 Phase 2
0.6842 Remote Similarity NPD3750 Approved
0.6828 Remote Similarity NPD7008 Discontinued
0.6821 Remote Similarity NPD970 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6812 Remote Similarity NPD9545 Approved
0.6809 Remote Similarity NPD1608 Approved
0.68 Remote Similarity NPD2933 Approved
0.68 Remote Similarity NPD2934 Approved
0.6786 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4879 Approved
0.6783 Remote Similarity NPD3266 Approved
0.6783 Remote Similarity NPD3267 Approved
0.6783 Remote Similarity NPD1203 Approved
0.6783 Remote Similarity NPD2797 Approved
0.6774 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7631 Approved
0.6772 Remote Similarity NPD7028 Phase 2
0.6768 Remote Similarity NPD6232 Discontinued
0.6767 Remote Similarity NPD1792 Phase 2
0.6765 Remote Similarity NPD9281 Approved
0.6765 Remote Similarity NPD2629 Approved
0.6761 Remote Similarity NPD4379 Clinical (unspecified phase)
0.675 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5031 Approved
0.6746 Remote Similarity NPD5027 Approved
0.6746 Remote Similarity NPD5029 Approved
0.6744 Remote Similarity NPD1932 Approved
0.6738 Remote Similarity NPD1281 Approved
0.6738 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6738 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6738 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6735 Remote Similarity NPD7961 Discontinued
0.6733 Remote Similarity NPD4308 Phase 3
0.673 Remote Similarity NPD7411 Suspended
0.672 Remote Similarity NPD5122 Clinical (unspecified phase)
0.672 Remote Similarity NPD845 Approved
0.6714 Remote Similarity NPD1751 Approved
0.6711 Remote Similarity NPD1549 Phase 2
0.6706 Remote Similarity NPD5026 Approved
0.6706 Remote Similarity NPD5034 Approved
0.6706 Remote Similarity NPD36 Approved
0.6706 Remote Similarity NPD5028 Approved
0.6706 Remote Similarity NPD4955 Approved
0.6706 Remote Similarity NPD4954 Approved
0.6694 Remote Similarity NPD7609 Phase 3
0.6692 Remote Similarity NPD2329 Discontinued
0.6692 Remote Similarity NPD9261 Approved
0.669 Remote Similarity NPD9269 Phase 2
0.669 Remote Similarity NPD9494 Approved
0.669 Remote Similarity NPD9717 Approved
0.6687 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2532 Approved
0.6667 Remote Similarity NPD2533 Approved
0.6667 Remote Similarity NPD8312 Approved
0.6667 Remote Similarity NPD2534 Approved
0.6667 Remote Similarity NPD4380 Phase 2
0.6667 Remote Similarity NPD7768 Phase 2
0.6667 Remote Similarity NPD411 Approved
0.6667 Remote Similarity NPD8313 Approved
0.6647 Remote Similarity NPD5030 Phase 2
0.6647 Remote Similarity NPD5033 Approved
0.6646 Remote Similarity NPD5760 Phase 2
0.6646 Remote Similarity NPD2801 Approved
0.6646 Remote Similarity NPD7239 Suspended
0.6646 Remote Similarity NPD5761 Phase 2
0.6645 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6645 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6645 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6644 Remote Similarity NPD447 Suspended
0.6644 Remote Similarity NPD6832 Phase 2
0.6643 Remote Similarity NPD9268 Approved
0.6643 Remote Similarity NPD4093 Discontinued
0.6626 Remote Similarity NPD7075 Discontinued
0.6623 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6614 Remote Similarity NPD1809 Phase 2
0.6608 Remote Similarity NPD5032 Approved
0.6606 Remote Similarity NPD6959 Discontinued
0.6603 Remote Similarity NPD1511 Approved
0.6599 Remote Similarity NPD7095 Approved
0.6596 Remote Similarity NPD17 Approved
0.6596 Remote Similarity NPD4626 Approved
0.6584 Remote Similarity NPD1934 Approved
0.6584 Remote Similarity NPD6844 Discontinued
0.6579 Remote Similarity NPD2796 Approved
0.6577 Remote Similarity NPD6346 Approved
0.6577 Remote Similarity NPD2979 Phase 3
0.6575 Remote Similarity NPD3637 Approved
0.6575 Remote Similarity NPD3636 Approved
0.6575 Remote Similarity NPD3635 Approved
0.6571 Remote Similarity NPD6836 Approved
0.657 Remote Similarity NPD5035 Approved
0.6569 Remote Similarity NPD1241 Discontinued
0.6564 Remote Similarity NPD3882 Suspended
0.6562 Remote Similarity NPD6599 Discontinued

  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