Structure

Physi-Chem Properties

Molecular Weight:  698.29
Volume:  705.474
LogP:  3.844
LogD:  2.433
LogS:  -4.067
# Rotatable Bonds:  13
TPSA:  174.87
# H-Bond Aceptor:  13
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.225
Synthetic Accessibility Score:  5.693
Fsp3:  0.541
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.145
MDCK Permeability:  6.82922764099203e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.873
20% Bioavailability (F20%):  0.723
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.05
Plasma Protein Binding (PPB):  75.76679229736328%
Volume Distribution (VD):  2.294
Pgp-substrate:  16.829065322875977%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.137
CYP2C9-substrate:  0.031
CYP2D6-inhibitor:  0.887
CYP2D6-substrate:  0.044
CYP3A4-inhibitor:  0.796
CYP3A4-substrate:  0.376

ADMET: Excretion

Clearance (CL):  2.927
Half-life (T1/2):  0.443

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.986
Drug-inuced Liver Injury (DILI):  0.968
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.75
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.082
Carcinogencity:  0.089
Eye Corrosion:  0.037
Eye Irritation:  0.096
Respiratory Toxicity:  0.946

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

  Natural Product: NPC475262

Natural Product ID:  NPC475262
Common Name*:   (2S*,3S*,4R*,5R*,7S*,8S*, 9S*,13S*,15R*)-5Alpha,7Beta,8Alpha,9Alpha,15Beta-Pentaacetoxy-3Beta-Benzoyloxyjatropha-6(17),11E-Dien-14-One
IUPAC Name:   [(1S,2S,3aR,5S,6E,9S,10S,11S,13R,13aR)-3a,9,10,11,13-pentaacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4-oxo-2,3,5,9,10,11,13,13a-octahydro-1H-cyclopenta[12]annulen-1-yl] benzoate
Synonyms:  
Standard InCHIKey:  WGRSFLGHEJKNBQ-YXHNETSESA-N
Standard InCHI:  InChI=1S/C37H46O13/c1-19-16-17-36(9,10)34(48-25(7)41)32(47-24(6)40)31(46-23(5)39)21(3)30(45-22(4)38)28-29(49-35(44)27-14-12-11-13-15-27)20(2)18-37(28,33(19)43)50-26(8)42/h11-17,19-20,28-32,34H,3,18H2,1-2,4-10H3/b17-16+/t19-,20-,28+,29-,30-,31-,32+,34+,37+/m0/s1
SMILES:  CC1CC2(C(C1OC(=O)C3=CC=CC=C3)C(C(=C)C(C(C(C(C=CC(C2=O)C)(C)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL502207
PubChem CID:   10417294
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO18344 Euphorbia mongolica Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[12880317]
NPO18344 Euphorbia mongolica Species Euphorbiaceae 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
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 31.46 n.a. PMID[495863]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 217.81 n.a. PMID[495863]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 2.6 n.a. PMID[495863]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 18.02 n.a. PMID[495863]

☑ 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 NPC475262 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC265459
1.0 High Similarity NPC290833
0.9922 High Similarity NPC285221
0.9922 High Similarity NPC194769
0.9921 High Similarity NPC472250
0.9845 High Similarity NPC86772
0.9769 High Similarity NPC272523
0.9769 High Similarity NPC325805
0.9695 High Similarity NPC475660
0.969 High Similarity NPC270364
0.9621 High Similarity NPC473497
0.9538 High Similarity NPC79699
0.9478 High Similarity NPC477094
0.9478 High Similarity NPC477096
0.9478 High Similarity NPC45307
0.9478 High Similarity NPC82467
0.9474 High Similarity NPC474303
0.9474 High Similarity NPC475413
0.947 High Similarity NPC276652
0.9398 High Similarity NPC251294
0.9328 High Similarity NPC473654
0.9302 High Similarity NPC42234
0.9302 High Similarity NPC475508
0.927 High Similarity NPC477095
0.927 High Similarity NPC170668
0.9242 High Similarity NPC472247
0.9203 High Similarity NPC205389
0.9191 High Similarity NPC153214
0.9185 High Similarity NPC187566
0.9167 High Similarity NPC153617
0.916 High Similarity NPC477360
0.916 High Similarity NPC233860
0.9154 High Similarity NPC272946
0.9091 High Similarity NPC472248
0.9071 High Similarity NPC477099
0.9071 High Similarity NPC25484
0.9071 High Similarity NPC477097
0.9071 High Similarity NPC477101
0.9071 High Similarity NPC232583
0.903 High Similarity NPC477358
0.9023 High Similarity NPC134937
0.9023 High Similarity NPC324898
0.9023 High Similarity NPC298547
0.9023 High Similarity NPC477368
0.9023 High Similarity NPC28836
0.9015 High Similarity NPC239358
0.9008 High Similarity NPC122504
0.9008 High Similarity NPC3450
0.9008 High Similarity NPC475452
0.9008 High Similarity NPC475671
0.8955 High Similarity NPC200154
0.8955 High Similarity NPC477367
0.8955 High Similarity NPC279637
0.8955 High Similarity NPC232888
0.8955 High Similarity NPC149401
0.8947 High Similarity NPC477364
0.8905 High Similarity NPC242355
0.8889 High Similarity NPC202729
0.8881 High Similarity NPC477359
0.8881 High Similarity NPC477098
0.8881 High Similarity NPC477100
0.8881 High Similarity NPC311492
0.8872 High Similarity NPC233692
0.8837 High Similarity NPC8990
0.8824 High Similarity NPC27721
0.8824 High Similarity NPC327511
0.8824 High Similarity NPC205305
0.8803 High Similarity NPC125033
0.8769 High Similarity NPC477369
0.8759 High Similarity NPC473301
0.8759 High Similarity NPC121268
0.8759 High Similarity NPC53361
0.8705 High Similarity NPC475135
0.863 High Similarity NPC70344
0.8511 High Similarity NPC191387
0.8511 High Similarity NPC131966
0.8467 Intermediate Similarity NPC55744
0.8433 Intermediate Similarity NPC477370
0.8421 Intermediate Similarity NPC477366
0.8421 Intermediate Similarity NPC477363
0.8409 Intermediate Similarity NPC477362
0.8392 Intermediate Similarity NPC471100
0.8392 Intermediate Similarity NPC471107
0.838 Intermediate Similarity NPC95449
0.837 Intermediate Similarity NPC37968
0.8358 Intermediate Similarity NPC477365
0.8358 Intermediate Similarity NPC477357
0.8311 Intermediate Similarity NPC469456
0.8288 Intermediate Similarity NPC254558
0.8231 Intermediate Similarity NPC51602
0.8222 Intermediate Similarity NPC472706
0.8207 Intermediate Similarity NPC475552
0.8201 Intermediate Similarity NPC471911
0.8201 Intermediate Similarity NPC4242
0.8194 Intermediate Similarity NPC470231
0.8188 Intermediate Similarity NPC475569
0.8188 Intermediate Similarity NPC472394
0.8182 Intermediate Similarity NPC182869
0.8176 Intermediate Similarity NPC22571
0.8176 Intermediate Similarity NPC283875
0.8176 Intermediate Similarity NPC469647
0.8176 Intermediate Similarity NPC469648
0.8176 Intermediate Similarity NPC138641
0.8169 Intermediate Similarity NPC87934
0.8169 Intermediate Similarity NPC162613
0.8162 Intermediate Similarity NPC472707
0.8148 Intermediate Similarity NPC476599
0.8138 Intermediate Similarity NPC127857
0.8138 Intermediate Similarity NPC134131
0.8138 Intermediate Similarity NPC25043
0.8134 Intermediate Similarity NPC472704
0.8112 Intermediate Similarity NPC266374
0.8108 Intermediate Similarity NPC472398
0.8108 Intermediate Similarity NPC471103
0.8106 Intermediate Similarity NPC473243
0.8099 Intermediate Similarity NPC9905
0.8095 Intermediate Similarity NPC473403
0.8067 Intermediate Similarity NPC21410
0.8067 Intermediate Similarity NPC473611
0.8067 Intermediate Similarity NPC473670
0.8067 Intermediate Similarity NPC282239
0.806 Intermediate Similarity NPC472703
0.8056 Intermediate Similarity NPC192658
0.8056 Intermediate Similarity NPC183540
0.8056 Intermediate Similarity NPC472546
0.8054 Intermediate Similarity NPC233581
0.8054 Intermediate Similarity NPC145649
0.8041 Intermediate Similarity NPC7095
0.8041 Intermediate Similarity NPC112216
0.8014 Intermediate Similarity NPC472577
0.8014 Intermediate Similarity NPC195647
0.8014 Intermediate Similarity NPC17877
0.8014 Intermediate Similarity NPC66761
0.8014 Intermediate Similarity NPC291638
0.8013 Intermediate Similarity NPC11410
0.8013 Intermediate Similarity NPC106895
0.8013 Intermediate Similarity NPC217091
0.7987 Intermediate Similarity NPC306799
0.7987 Intermediate Similarity NPC161955
0.7987 Intermediate Similarity NPC101043
0.7973 Intermediate Similarity NPC81698
0.7973 Intermediate Similarity NPC60509
0.7973 Intermediate Similarity NPC250046
0.7972 Intermediate Similarity NPC170718
0.7961 Intermediate Similarity NPC472393
0.7959 Intermediate Similarity NPC478263
0.7959 Intermediate Similarity NPC312393
0.7958 Intermediate Similarity NPC52523
0.7958 Intermediate Similarity NPC217673
0.7947 Intermediate Similarity NPC469730
0.7947 Intermediate Similarity NPC473632
0.7947 Intermediate Similarity NPC132599
0.7947 Intermediate Similarity NPC251139
0.7945 Intermediate Similarity NPC34943
0.7943 Intermediate Similarity NPC474608
0.7941 Intermediate Similarity NPC246166
0.7931 Intermediate Similarity NPC51181
0.7929 Intermediate Similarity NPC469499
0.7919 Intermediate Similarity NPC473214
0.7919 Intermediate Similarity NPC198455
0.7919 Intermediate Similarity NPC470245
0.7919 Intermediate Similarity NPC161239
0.7919 Intermediate Similarity NPC165260
0.7917 Intermediate Similarity NPC184747
0.7917 Intermediate Similarity NPC183270
0.7917 Intermediate Similarity NPC48017
0.7917 Intermediate Similarity NPC147880
0.7917 Intermediate Similarity NPC473112
0.7917 Intermediate Similarity NPC473109
0.7917 Intermediate Similarity NPC211137
0.7917 Intermediate Similarity NPC473081
0.7917 Intermediate Similarity NPC4341
0.7917 Intermediate Similarity NPC473613
0.7917 Intermediate Similarity NPC477904
0.7917 Intermediate Similarity NPC473060
0.7917 Intermediate Similarity NPC476094
0.7917 Intermediate Similarity NPC200592
0.7917 Intermediate Similarity NPC43241
0.7917 Intermediate Similarity NPC473758
0.7917 Intermediate Similarity NPC473440
0.7917 Intermediate Similarity NPC473085
0.7914 Intermediate Similarity NPC82712
0.7914 Intermediate Similarity NPC147561
0.7908 Intermediate Similarity NPC471102
0.7905 Intermediate Similarity NPC327031
0.7902 Intermediate Similarity NPC475373
0.7902 Intermediate Similarity NPC184109
0.7898 Intermediate Similarity NPC161151
0.7891 Intermediate Similarity NPC125882
0.7891 Intermediate Similarity NPC478264
0.7891 Intermediate Similarity NPC471162
0.7887 Intermediate Similarity NPC477893
0.7881 Intermediate Similarity NPC242262
0.7881 Intermediate Similarity NPC256142
0.7881 Intermediate Similarity NPC472030
0.7881 Intermediate Similarity NPC249471
0.7881 Intermediate Similarity NPC77719
0.7881 Intermediate Similarity NPC473414
0.7881 Intermediate Similarity NPC257213
0.7881 Intermediate Similarity NPC158333

  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 NPC475262 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
0.8138 Intermediate Similarity NPD7236 Approved
0.7987 Intermediate Similarity NPD7239 Suspended
0.7862 Intermediate Similarity NPD7799 Discontinued
0.7746 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD2067 Discontinued
0.7516 Intermediate Similarity NPD7057 Phase 3
0.7516 Intermediate Similarity NPD7058 Phase 2
0.7462 Intermediate Similarity NPD2182 Approved
0.7388 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD7961 Discontinued
0.7176 Intermediate Similarity NPD6685 Approved
0.7154 Intermediate Similarity NPD164 Approved
0.7143 Intermediate Similarity NPD8368 Discontinued
0.7118 Intermediate Similarity NPD8407 Phase 2
0.7071 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD4628 Phase 3
0.7055 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7685 Pre-registration
0.7007 Intermediate Similarity NPD2629 Approved
0.6994 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6858 Approved
0.6985 Remote Similarity NPD7094 Approved
0.6981 Remote Similarity NPD6599 Discontinued
0.6972 Remote Similarity NPD6287 Discontinued
0.6966 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6085 Phase 2
0.6957 Remote Similarity NPD4198 Discontinued
0.6947 Remote Similarity NPD5765 Approved
0.6941 Remote Similarity NPD6764 Approved
0.6941 Remote Similarity NPD6765 Approved
0.6936 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6936 Remote Similarity NPD8434 Phase 2
0.6929 Remote Similarity NPD7741 Discontinued
0.6912 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6912 Remote Similarity NPD6912 Phase 3
0.6863 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6005 Phase 3
0.6863 Remote Similarity NPD6004 Phase 3
0.6863 Remote Similarity NPD6002 Phase 3
0.6857 Remote Similarity NPD8435 Approved
0.6852 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6846 Remote Similarity NPD1238 Approved
0.6829 Remote Similarity NPD7075 Discontinued
0.6818 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6815 Remote Similarity NPD6799 Approved
0.6809 Remote Similarity NPD9545 Approved
0.6795 Remote Similarity NPD6190 Approved
0.6795 Remote Similarity NPD3887 Approved
0.6782 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6782 Remote Similarity NPD6784 Approved
0.6782 Remote Similarity NPD6785 Approved
0.6765 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6761 Remote Similarity NPD8360 Approved
0.6761 Remote Similarity NPD8361 Approved
0.6755 Remote Similarity NPD6355 Discontinued
0.6748 Remote Similarity NPD5761 Phase 2
0.6748 Remote Similarity NPD5760 Phase 2
0.6712 Remote Similarity NPD5667 Approved
0.6711 Remote Similarity NPD6653 Approved
0.6692 Remote Similarity NPD6647 Phase 2
0.6691 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7137 Phase 2
0.6687 Remote Similarity NPD6801 Discontinued
0.6667 Remote Similarity NPD3764 Approved
0.6667 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6648 Remote Similarity NPD8150 Discontinued
0.6645 Remote Similarity NPD5763 Approved
0.6645 Remote Similarity NPD5762 Approved
0.6645 Remote Similarity NPD230 Phase 1
0.6645 Remote Similarity NPD7702 Clinical (unspecified phase)
0.663 Remote Similarity NPD8485 Approved
0.6625 Remote Similarity NPD6273 Approved
0.6623 Remote Similarity NPD7305 Phase 1
0.6622 Remote Similarity NPD5647 Approved
0.6607 Remote Similarity NPD8127 Discontinued
0.6606 Remote Similarity NPD3817 Phase 2
0.6606 Remote Similarity NPD5402 Approved
0.66 Remote Similarity NPD7008 Discontinued
0.6599 Remote Similarity NPD1876 Approved
0.6584 Remote Similarity NPD5403 Approved
0.6584 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6575 Remote Similarity NPD3972 Approved
0.6575 Remote Similarity NPD6637 Approved
0.6562 Remote Similarity NPD5401 Approved
0.6554 Remote Similarity NPD6362 Approved
0.6545 Remote Similarity NPD7819 Suspended
0.6538 Remote Similarity NPD2353 Approved
0.6538 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6832 Phase 2
0.6522 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1237 Approved
0.6513 Remote Similarity NPD7713 Phase 3
0.6507 Remote Similarity NPD4806 Approved
0.6507 Remote Similarity NPD4807 Approved
0.6503 Remote Similarity NPD7458 Discontinued
0.65 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6483 Remote Similarity NPD5306 Approved
0.6483 Remote Similarity NPD5305 Approved
0.6483 Remote Similarity NPD17 Approved
0.6474 Remote Similarity NPD2796 Approved
0.6467 Remote Similarity NPD3662 Phase 3
0.6467 Remote Similarity NPD3663 Approved
0.6467 Remote Similarity NPD3664 Approved
0.6467 Remote Similarity NPD3661 Approved
0.6466 Remote Similarity NPD7798 Approved
0.646 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6456 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2569 Approved
0.6452 Remote Similarity NPD2567 Approved
0.645 Remote Similarity NPD5494 Approved
0.6444 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6444 Remote Similarity NPD1929 Approved
0.6444 Remote Similarity NPD1930 Approved
0.6433 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6429 Remote Similarity NPD969 Suspended
0.6424 Remote Similarity NPD6386 Approved
0.6424 Remote Similarity NPD7055 Discontinued
0.6424 Remote Similarity NPD6385 Approved
0.6408 Remote Similarity NPD5951 Approved
0.6408 Remote Similarity NPD4766 Approved
0.6407 Remote Similarity NPD5353 Approved
0.6405 Remote Similarity NPD8032 Phase 2
0.6405 Remote Similarity NPD6663 Approved
0.6403 Remote Similarity NPD4233 Approved
0.6403 Remote Similarity NPD4234 Approved
0.6391 Remote Similarity NPD9495 Approved
0.6391 Remote Similarity NPD919 Approved
0.638 Remote Similarity NPD920 Approved
0.6379 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6375 Remote Similarity NPD2354 Approved
0.6369 Remote Similarity NPD3882 Suspended
0.6369 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4380 Phase 2
0.6358 Remote Similarity NPD2533 Approved
0.6358 Remote Similarity NPD2534 Approved
0.6358 Remote Similarity NPD5736 Approved
0.6358 Remote Similarity NPD2532 Approved
0.6357 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6351 Remote Similarity NPD1608 Approved
0.635 Remote Similarity NPD5048 Discontinued
0.6345 Remote Similarity NPD7009 Phase 2
0.6343 Remote Similarity NPD2066 Phase 3
0.6337 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6336 Remote Similarity NPD1202 Approved
0.6335 Remote Similarity NPD6652 Clinical (unspecified phase)
0.633 Remote Similarity NPD7497 Discontinued
0.6327 Remote Similarity NPD4106 Approved
0.6327 Remote Similarity NPD4135 Approved
0.6327 Remote Similarity NPD4136 Approved
0.6321 Remote Similarity NPD8462 Phase 1
0.6312 Remote Similarity NPD8297 Approved
0.6312 Remote Similarity NPD8166 Discontinued
0.6312 Remote Similarity NPD2575 Approved
0.6312 Remote Similarity NPD6398 Clinical (unspecified phase)
0.631 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6307 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6306 Remote Similarity NPD7033 Discontinued
0.6306 Remote Similarity NPD2799 Discontinued
0.6306 Remote Similarity NPD3748 Approved
0.6304 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6301 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6299 Remote Similarity NPD6233 Phase 2
0.6299 Remote Similarity NPD9259 Approved
0.6299 Remote Similarity NPD9257 Approved
0.6288 Remote Similarity NPD1693 Approved
0.6277 Remote Similarity NPD5909 Discontinued
0.6276 Remote Similarity NPD7610 Discontinued
0.6275 Remote Similarity NPD6039 Approved
0.6275 Remote Similarity NPD7095 Approved
0.6267 Remote Similarity NPD2198 Approved
0.6267 Remote Similarity NPD2199 Approved
0.6266 Remote Similarity NPD2438 Suspended
0.6264 Remote Similarity NPD7473 Discontinued
0.6259 Remote Similarity NPD5126 Approved
0.6259 Remote Similarity NPD5125 Phase 3
0.6258 Remote Similarity NPD642 Clinical (unspecified phase)
0.6258 Remote Similarity NPD4378 Clinical (unspecified phase)
0.625 Remote Similarity NPD5204 Approved
0.625 Remote Similarity NPD7084 Phase 3
0.6243 Remote Similarity NPD3926 Phase 2
0.6243 Remote Similarity NPD5242 Approved
0.6241 Remote Similarity NPD1989 Approved
0.6235 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6234 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6234 Remote Similarity NPD2313 Discontinued
0.6234 Remote Similarity NPD6798 Discontinued
0.6231 Remote Similarity NPD3672 Approved
0.6231 Remote Similarity NPD3673 Approved
0.6229 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6228 Remote Similarity NPD7411 Suspended
0.6226 Remote Similarity NPD1471 Phase 3
0.6225 Remote Similarity NPD3267 Approved
0.6225 Remote Similarity NPD3266 Approved
0.6224 Remote Similarity NPD2652 Approved
0.6224 Remote Similarity NPD2650 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