Structure

Physi-Chem Properties

Molecular Weight:  484.32
Volume:  518.059
LogP:  3.01
LogD:  2.724
LogS:  -4.46
# Rotatable Bonds:  2
TPSA:  88.51
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.39
Synthetic Accessibility Score:  5.179
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.357
MDCK Permeability:  2.253129059681669e-05
Pgp-inhibitor:  0.087
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.957
Plasma Protein Binding (PPB):  78.4603500366211%
Volume Distribution (VD):  0.569
Pgp-substrate:  9.89721393585205%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.849
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.763
CYP2C9-inhibitor:  0.059
CYP2C9-substrate:  0.055
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.061
CYP3A4-inhibitor:  0.332
CYP3A4-substrate:  0.345

ADMET: Excretion

Clearance (CL):  1.345
Half-life (T1/2):  0.287

ADMET: Toxicity

hERG Blockers:  0.064
Human Hepatotoxicity (H-HT):  0.162
Drug-inuced Liver Injury (DILI):  0.068
AMES Toxicity:  0.042
Rat Oral Acute Toxicity:  0.04
Maximum Recommended Daily Dose:  0.098
Skin Sensitization:  0.952
Carcinogencity:  0.166
Eye Corrosion:  0.21
Eye Irritation:  0.593
Respiratory Toxicity:  0.86

Download Data

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

  Natural Product: NPC252737

Natural Product ID:  NPC252737
Common Name*:   Cangoronine
IUPAC Name:   (2R,4aS,6aR,6aR,8aR,14aS,14bR)-8a-formyl-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-3,4,5,6,6b,7,8,12,12a,13,14,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:   Cangoronine
Standard InCHIKey:  CDOKUYLTAYCBST-GKMFGOQDSA-N
Standard InCHI:  InChI=1S/C30H44O5/c1-18-23(33)19(32)15-21-27(4)12-14-29(6)22-16-26(3,24(34)35)10-9-25(22,2)11-13-28(29,5)20(27)7-8-30(18,21)17-31/h17,20-22,33H,7-16H2,1-6H3,(H,34,35)/t20?,21?,22-,25-,26-,27-,28-,29+,30+/m1/s1
SMILES:  CC1=C(C(=O)CC2[C@]3(C)CC[C@@]4(C)[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@]4(C)C3CC[C@]12C=O)C(=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1651341
PubChem CID:   9869964
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO25224 Maytenus retusa Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21090801]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15853 Euphorbia poisonii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15853 Euphorbia poisonii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25224 Maytenus retusa Species Celastraceae 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
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 15.0 % PMID[502364]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 9.0 % PMID[502364]
NPT83 Cell Line MCF7 Homo sapiens Inhibition = 16.0 % PMID[502364]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 60.0 % PMID[502364]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 48.0 % PMID[502364]
NPT116 Cell Line HL-60 Homo sapiens Inhibition = 40.0 % PMID[502364]

☑ 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 NPC252737 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
0.881 High Similarity NPC18955
0.8778 High Similarity NPC230064
0.869 High Similarity NPC192329
0.8652 High Similarity NPC474474
0.8636 High Similarity NPC229717
0.8621 High Similarity NPC96095
0.8571 High Similarity NPC174167
0.8571 High Similarity NPC470036
0.8556 High Similarity NPC112454
0.8478 Intermediate Similarity NPC263780
0.8462 Intermediate Similarity NPC46441
0.8444 Intermediate Similarity NPC230387
0.837 Intermediate Similarity NPC233455
0.837 Intermediate Similarity NPC4036
0.837 Intermediate Similarity NPC65120
0.837 Intermediate Similarity NPC145067
0.837 Intermediate Similarity NPC158030
0.837 Intermediate Similarity NPC474525
0.8352 Intermediate Similarity NPC184663
0.8352 Intermediate Similarity NPC469546
0.8333 Intermediate Similarity NPC158141
0.8333 Intermediate Similarity NPC173089
0.8315 Intermediate Similarity NPC474680
0.8298 Intermediate Similarity NPC777
0.8295 Intermediate Similarity NPC105803
0.8295 Intermediate Similarity NPC53733
0.828 Intermediate Similarity NPC295643
0.828 Intermediate Similarity NPC214756
0.828 Intermediate Similarity NPC272075
0.8276 Intermediate Similarity NPC162632
0.8276 Intermediate Similarity NPC274050
0.8276 Intermediate Similarity NPC263272
0.8276 Intermediate Similarity NPC267691
0.8276 Intermediate Similarity NPC471898
0.8242 Intermediate Similarity NPC474511
0.8242 Intermediate Similarity NPC1753
0.8229 Intermediate Similarity NPC471966
0.8222 Intermediate Similarity NPC56588
0.8191 Intermediate Similarity NPC74751
0.8182 Intermediate Similarity NPC251779
0.8182 Intermediate Similarity NPC69101
0.8161 Intermediate Similarity NPC474956
0.8152 Intermediate Similarity NPC477973
0.8152 Intermediate Similarity NPC474700
0.8152 Intermediate Similarity NPC281524
0.8111 Intermediate Similarity NPC474537
0.8105 Intermediate Similarity NPC147232
0.8105 Intermediate Similarity NPC139570
0.8105 Intermediate Similarity NPC148523
0.809 Intermediate Similarity NPC200752
0.809 Intermediate Similarity NPC70834
0.8085 Intermediate Similarity NPC298554
0.8085 Intermediate Similarity NPC211230
0.8068 Intermediate Similarity NPC278459
0.8068 Intermediate Similarity NPC90055
0.8068 Intermediate Similarity NPC3915
0.8065 Intermediate Similarity NPC291028
0.8065 Intermediate Similarity NPC198818
0.8065 Intermediate Similarity NPC193750
0.8046 Intermediate Similarity NPC16394
0.8043 Intermediate Similarity NPC182797
0.8043 Intermediate Similarity NPC52169
0.8022 Intermediate Similarity NPC158393
0.8022 Intermediate Similarity NPC72638
0.8021 Intermediate Similarity NPC98874
0.8021 Intermediate Similarity NPC157113
0.8021 Intermediate Similarity NPC62516
0.8 Intermediate Similarity NPC23170
0.8 Intermediate Similarity NPC222047
0.8 Intermediate Similarity NPC171789
0.8 Intermediate Similarity NPC209868
0.8 Intermediate Similarity NPC474882
0.7979 Intermediate Similarity NPC38754
0.7979 Intermediate Similarity NPC471588
0.7979 Intermediate Similarity NPC6255
0.7979 Intermediate Similarity NPC105189
0.7978 Intermediate Similarity NPC310989
0.7957 Intermediate Similarity NPC225585
0.7957 Intermediate Similarity NPC68148
0.7957 Intermediate Similarity NPC130520
0.7957 Intermediate Similarity NPC121798
0.7957 Intermediate Similarity NPC234346
0.7957 Intermediate Similarity NPC64872
0.7957 Intermediate Similarity NPC274330
0.7957 Intermediate Similarity NPC143232
0.7957 Intermediate Similarity NPC30522
0.7957 Intermediate Similarity NPC293048
0.7957 Intermediate Similarity NPC61543
0.7957 Intermediate Similarity NPC290972
0.7957 Intermediate Similarity NPC25906
0.7957 Intermediate Similarity NPC270768
0.7957 Intermediate Similarity NPC263393
0.7957 Intermediate Similarity NPC65615
0.7957 Intermediate Similarity NPC198664
0.7957 Intermediate Similarity NPC127689
0.7957 Intermediate Similarity NPC59263
0.7955 Intermediate Similarity NPC477057
0.7955 Intermediate Similarity NPC267517
0.7955 Intermediate Similarity NPC104545
0.7955 Intermediate Similarity NPC37038
0.7938 Intermediate Similarity NPC26413
0.7935 Intermediate Similarity NPC171203
0.7935 Intermediate Similarity NPC130577
0.7935 Intermediate Similarity NPC18064
0.7935 Intermediate Similarity NPC88716
0.7935 Intermediate Similarity NPC98442
0.7935 Intermediate Similarity NPC307426
0.7935 Intermediate Similarity NPC293564
0.7935 Intermediate Similarity NPC242468
0.7935 Intermediate Similarity NPC68160
0.7935 Intermediate Similarity NPC142415
0.7935 Intermediate Similarity NPC102683
0.7935 Intermediate Similarity NPC51700
0.7931 Intermediate Similarity NPC260385
0.7931 Intermediate Similarity NPC476808
0.7931 Intermediate Similarity NPC30321
0.7931 Intermediate Similarity NPC476810
0.7931 Intermediate Similarity NPC280654
0.7931 Intermediate Similarity NPC110094
0.7912 Intermediate Similarity NPC473038
0.7912 Intermediate Similarity NPC469993
0.7912 Intermediate Similarity NPC33881
0.7907 Intermediate Similarity NPC92080
0.7907 Intermediate Similarity NPC89294
0.79 Intermediate Similarity NPC179208
0.7895 Intermediate Similarity NPC118490
0.7895 Intermediate Similarity NPC151722
0.7895 Intermediate Similarity NPC169343
0.7889 Intermediate Similarity NPC307258
0.7872 Intermediate Similarity NPC120968
0.7872 Intermediate Similarity NPC477872
0.7872 Intermediate Similarity NPC7260
0.7872 Intermediate Similarity NPC273621
0.7872 Intermediate Similarity NPC111110
0.7872 Intermediate Similarity NPC210037
0.7872 Intermediate Similarity NPC126369
0.7872 Intermediate Similarity NPC227467
0.7872 Intermediate Similarity NPC470589
0.7872 Intermediate Similarity NPC474728
0.7872 Intermediate Similarity NPC49320
0.7872 Intermediate Similarity NPC130278
0.7872 Intermediate Similarity NPC120840
0.7872 Intermediate Similarity NPC290614
0.7872 Intermediate Similarity NPC18872
0.7872 Intermediate Similarity NPC113989
0.7865 Intermediate Similarity NPC221647
0.7849 Intermediate Similarity NPC40552
0.7849 Intermediate Similarity NPC17733
0.7849 Intermediate Similarity NPC473242
0.7849 Intermediate Similarity NPC290690
0.7849 Intermediate Similarity NPC470629
0.7849 Intermediate Similarity NPC181225
0.7849 Intermediate Similarity NPC474512
0.7849 Intermediate Similarity NPC246708
0.7841 Intermediate Similarity NPC199595
0.7841 Intermediate Similarity NPC231431
0.7826 Intermediate Similarity NPC475181
0.7826 Intermediate Similarity NPC235341
0.7826 Intermediate Similarity NPC95594
0.7826 Intermediate Similarity NPC477579
0.7826 Intermediate Similarity NPC324063
0.7822 Intermediate Similarity NPC213366
0.7816 Intermediate Similarity NPC471899
0.7816 Intermediate Similarity NPC107039
0.7816 Intermediate Similarity NPC165711
0.7816 Intermediate Similarity NPC476811
0.7816 Intermediate Similarity NPC471897
0.7812 Intermediate Similarity NPC474328
0.7812 Intermediate Similarity NPC148964
0.7812 Intermediate Similarity NPC474529
0.7802 Intermediate Similarity NPC209882
0.7802 Intermediate Similarity NPC180834
0.7802 Intermediate Similarity NPC312660
0.7789 Intermediate Similarity NPC71074
0.7789 Intermediate Similarity NPC187722
0.7789 Intermediate Similarity NPC306541
0.7789 Intermediate Similarity NPC966
0.7789 Intermediate Similarity NPC472149
0.7789 Intermediate Similarity NPC155120
0.7789 Intermediate Similarity NPC235704
0.7789 Intermediate Similarity NPC228784
0.7789 Intermediate Similarity NPC282616
0.7789 Intermediate Similarity NPC77099
0.7789 Intermediate Similarity NPC235884
0.7789 Intermediate Similarity NPC300351
0.7789 Intermediate Similarity NPC288833
0.7789 Intermediate Similarity NPC60755
0.7789 Intermediate Similarity NPC84319
0.7789 Intermediate Similarity NPC475708
0.7789 Intermediate Similarity NPC470590
0.7789 Intermediate Similarity NPC25299
0.7789 Intermediate Similarity NPC52021
0.7789 Intermediate Similarity NPC285184
0.7789 Intermediate Similarity NPC324341
0.7778 Intermediate Similarity NPC469325
0.7778 Intermediate Similarity NPC103486
0.7778 Intermediate Similarity NPC302661
0.7778 Intermediate Similarity NPC238991
0.7766 Intermediate Similarity NPC95246
0.7766 Intermediate Similarity NPC474972

  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 NPC252737 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
0.8556 High Similarity NPD7285 Clinical (unspecified phase)
0.837 Intermediate Similarity NPD7515 Phase 2
0.8191 Intermediate Similarity NPD7748 Approved
0.7938 Intermediate Similarity NPD7902 Approved
0.7931 Intermediate Similarity NPD3617 Approved
0.7835 Intermediate Similarity NPD7614 Phase 1
0.7753 Intermediate Similarity NPD4695 Discontinued
0.7677 Intermediate Similarity NPD5696 Approved
0.766 Intermediate Similarity NPD5737 Approved
0.766 Intermediate Similarity NPD6672 Approved
0.7629 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD7900 Approved
0.7576 Intermediate Similarity NPD6084 Phase 2
0.7576 Intermediate Similarity NPD6083 Phase 2
0.7475 Intermediate Similarity NPD7732 Phase 3
0.7474 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4753 Phase 2
0.7374 Intermediate Similarity NPD5695 Phase 3
0.7374 Intermediate Similarity NPD4629 Approved
0.7374 Intermediate Similarity NPD5210 Approved
0.734 Intermediate Similarity NPD5329 Approved
0.73 Intermediate Similarity NPD4697 Phase 3
0.7263 Intermediate Similarity NPD6409 Approved
0.7263 Intermediate Similarity NPD5330 Approved
0.7263 Intermediate Similarity NPD7334 Approved
0.7263 Intermediate Similarity NPD6684 Approved
0.7263 Intermediate Similarity NPD7146 Approved
0.7263 Intermediate Similarity NPD7521 Approved
0.7234 Intermediate Similarity NPD3133 Approved
0.7234 Intermediate Similarity NPD3666 Approved
0.7234 Intermediate Similarity NPD4197 Approved
0.7234 Intermediate Similarity NPD3665 Phase 1
0.7216 Intermediate Similarity NPD6904 Approved
0.7216 Intermediate Similarity NPD6673 Approved
0.7216 Intermediate Similarity NPD6080 Approved
0.7172 Intermediate Similarity NPD6399 Phase 3
0.7158 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD6903 Approved
0.7083 Intermediate Similarity NPD3618 Phase 1
0.7083 Intermediate Similarity NPD5279 Phase 3
0.7075 Intermediate Similarity NPD7128 Approved
0.7075 Intermediate Similarity NPD6675 Approved
0.7075 Intermediate Similarity NPD6402 Approved
0.7075 Intermediate Similarity NPD5739 Approved
0.7053 Intermediate Similarity NPD4786 Approved
0.7045 Intermediate Similarity NPD6081 Approved
0.7041 Intermediate Similarity NPD5328 Approved
0.7021 Intermediate Similarity NPD4223 Phase 3
0.7021 Intermediate Similarity NPD4221 Approved
0.7021 Intermediate Similarity NPD3667 Approved
0.6961 Remote Similarity NPD5222 Approved
0.6961 Remote Similarity NPD5221 Approved
0.6961 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6947 Remote Similarity NPD4788 Approved
0.6944 Remote Similarity NPD7320 Approved
0.6944 Remote Similarity NPD6899 Approved
0.6944 Remote Similarity NPD6881 Approved
0.6907 Remote Similarity NPD6098 Approved
0.6907 Remote Similarity NPD5690 Phase 2
0.6907 Remote Similarity NPD4694 Approved
0.6907 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5280 Approved
0.69 Remote Similarity NPD8034 Phase 2
0.69 Remote Similarity NPD5281 Approved
0.69 Remote Similarity NPD5693 Phase 1
0.69 Remote Similarity NPD5284 Approved
0.69 Remote Similarity NPD8035 Phase 2
0.69 Remote Similarity NPD6050 Approved
0.69 Remote Similarity NPD6079 Approved
0.6893 Remote Similarity NPD5173 Approved
0.6893 Remote Similarity NPD4755 Approved
0.6881 Remote Similarity NPD6373 Approved
0.6881 Remote Similarity NPD6372 Approved
0.6852 Remote Similarity NPD5697 Approved
0.6852 Remote Similarity NPD5701 Approved
0.6837 Remote Similarity NPD3573 Approved
0.6818 Remote Similarity NPD7102 Approved
0.6818 Remote Similarity NPD6883 Approved
0.6818 Remote Similarity NPD7290 Approved
0.68 Remote Similarity NPD5692 Phase 3
0.6789 Remote Similarity NPD6011 Approved
0.6762 Remote Similarity NPD4700 Approved
0.6762 Remote Similarity NPD5286 Approved
0.6762 Remote Similarity NPD4696 Approved
0.6762 Remote Similarity NPD5285 Approved
0.6757 Remote Similarity NPD6649 Approved
0.6757 Remote Similarity NPD6847 Approved
0.6757 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6650 Approved
0.6757 Remote Similarity NPD8130 Phase 1
0.6757 Remote Similarity NPD6869 Approved
0.6757 Remote Similarity NPD6617 Approved
0.6742 Remote Similarity NPD4789 Approved
0.6735 Remote Similarity NPD4693 Phase 3
0.6735 Remote Similarity NPD4689 Approved
0.6735 Remote Similarity NPD5205 Approved
0.6735 Remote Similarity NPD4519 Discontinued
0.6735 Remote Similarity NPD4688 Approved
0.6735 Remote Similarity NPD4138 Approved
0.6735 Remote Similarity NPD4623 Approved
0.6735 Remote Similarity NPD4690 Approved
0.6733 Remote Similarity NPD5694 Approved
0.6727 Remote Similarity NPD6014 Approved
0.6727 Remote Similarity NPD6012 Approved
0.6727 Remote Similarity NPD6013 Approved
0.6702 Remote Similarity NPD7645 Phase 2
0.6701 Remote Similarity NPD3668 Phase 3
0.6699 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6698 Remote Similarity NPD5223 Approved
0.6696 Remote Similarity NPD8297 Approved
0.6696 Remote Similarity NPD6882 Approved
0.6695 Remote Similarity NPD8328 Phase 3
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4224 Phase 2
0.6667 Remote Similarity NPD4202 Approved
0.6667 Remote Similarity NPD7638 Approved
0.6636 Remote Similarity NPD5091 Approved
0.6636 Remote Similarity NPD5224 Approved
0.6636 Remote Similarity NPD5226 Approved
0.6636 Remote Similarity NPD5211 Phase 2
0.6636 Remote Similarity NPD5225 Approved
0.6636 Remote Similarity NPD4633 Approved
0.6609 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7640 Approved
0.6604 Remote Similarity NPD7639 Approved
0.66 Remote Similarity NPD5208 Approved
0.6577 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6574 Remote Similarity NPD4754 Approved
0.6574 Remote Similarity NPD5175 Approved
0.6574 Remote Similarity NPD5174 Approved
0.6562 Remote Similarity NPD4692 Approved
0.6562 Remote Similarity NPD4139 Approved
0.6559 Remote Similarity NPD6117 Approved
0.6552 Remote Similarity NPD7341 Phase 2
0.6545 Remote Similarity NPD6614 Approved
0.6545 Remote Similarity NPD6412 Phase 2
0.6538 Remote Similarity NPD5654 Approved
0.6522 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6522 Remote Similarity NPD6868 Approved
0.6514 Remote Similarity NPD5141 Approved
0.6505 Remote Similarity NPD5133 Approved
0.6491 Remote Similarity NPD4632 Approved
0.6489 Remote Similarity NPD6116 Phase 1
0.6481 Remote Similarity NPD7632 Discontinued
0.6455 Remote Similarity NPD4767 Approved
0.6455 Remote Similarity NPD4768 Approved
0.6444 Remote Similarity NPD4137 Phase 3
0.6421 Remote Similarity NPD6114 Approved
0.6421 Remote Similarity NPD6115 Approved
0.6421 Remote Similarity NPD6697 Approved
0.6421 Remote Similarity NPD6118 Approved
0.6415 Remote Similarity NPD5959 Approved
0.641 Remote Similarity NPD6335 Approved
0.6408 Remote Similarity NPD6411 Approved
0.6392 Remote Similarity NPD8028 Phase 2
0.6379 Remote Similarity NPD6274 Approved
0.6374 Remote Similarity NPD4691 Approved
0.6374 Remote Similarity NPD4244 Approved
0.6374 Remote Similarity NPD4747 Approved
0.6374 Remote Similarity NPD4245 Approved
0.6356 Remote Similarity NPD7101 Approved
0.6356 Remote Similarity NPD7100 Approved
0.6354 Remote Similarity NPD4195 Approved
0.6339 Remote Similarity NPD5128 Approved
0.6339 Remote Similarity NPD4730 Approved
0.6339 Remote Similarity NPD4729 Approved
0.6339 Remote Similarity NPD5168 Approved
0.6325 Remote Similarity NPD6009 Approved
0.6325 Remote Similarity NPD7115 Discovery
0.6325 Remote Similarity NPD6317 Approved
0.6311 Remote Similarity NPD5207 Approved
0.6304 Remote Similarity NPD5777 Approved
0.6304 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6304 Remote Similarity NPD4809 Clinical (unspecified phase)
0.63 Remote Similarity NPD1694 Approved
0.6292 Remote Similarity NPD3704 Approved
0.6289 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6286 Remote Similarity NPD6001 Approved
0.6283 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6271 Remote Similarity NPD6313 Approved
0.6271 Remote Similarity NPD6314 Approved
0.6264 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3698 Phase 2
0.625 Remote Similarity NPD6908 Approved
0.625 Remote Similarity NPD6909 Approved
0.6228 Remote Similarity NPD5249 Phase 3
0.6228 Remote Similarity NPD5169 Approved
0.6228 Remote Similarity NPD5135 Approved
0.6228 Remote Similarity NPD5251 Approved
0.6228 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6228 Remote Similarity NPD4634 Approved
0.6228 Remote Similarity NPD5247 Approved
0.6228 Remote Similarity NPD5248 Approved
0.6228 Remote Similarity NPD5250 Approved
0.6228 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6214 Remote Similarity NPD6101 Approved
0.621 Remote Similarity NPD7736 Approved
0.6195 Remote Similarity NPD6686 Approved

  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