Structure

Physi-Chem Properties

Molecular Weight:  654.27
Volume:  662.092
LogP:  3.144
LogD:  2.354
LogS:  -4.193
# Rotatable Bonds:  11
TPSA:  165.64
# H-Bond Aceptor:  12
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.247
Synthetic Accessibility Score:  5.584
Fsp3:  0.514
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:  -5.181
MDCK Permeability:  7.396400906145573e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.739
20% Bioavailability (F20%):  0.961
30% Bioavailability (F30%):  0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  78.63457489013672%
Volume Distribution (VD):  2.068
Pgp-substrate:  18.135967254638672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.016
CYP1A2-substrate:  0.032
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.211
CYP2C9-substrate:  0.032
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.038
CYP3A4-inhibitor:  0.878
CYP3A4-substrate:  0.387

ADMET: Excretion

Clearance (CL):  3.766
Half-life (T1/2):  0.632

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.981
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.94
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.073
Carcinogencity:  0.253
Eye Corrosion:  0.113
Eye Irritation:  0.113
Respiratory Toxicity:  0.942

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

  Natural Product: NPC86772

Natural Product ID:  NPC86772
Common Name*:   3Beta,5Alpha,8Alpha,15Beta-Tetraacetoxy-7Beta-Benzoyloxyjatropha-6(17)-11E-Dien-9,14-Dione
IUPAC Name:   [(1S,2S,3aR,5S,6E,10R,11S,13R,13aR)-1,3a,10,13-tetraacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1,2,3,5,10,11,13,13a-octahydrocyclopenta[12]annulen-11-yl] benzoate
Synonyms:  
Standard InCHIKey:  YOAHCTQIURAMTM-PISILSIWSA-N
Standard InCHI:  InChI=1S/C35H42O12/c1-18-15-16-34(8,9)32(41)30(45-23(6)38)29(46-33(42)25-13-11-10-12-14-25)20(3)28(44-22(5)37)26-27(43-21(4)36)19(2)17-35(26,31(18)40)47-24(7)39/h10-16,18-19,26-30H,3,17H2,1-2,4-9H3/b16-15+/t18-,19-,26+,27-,28-,29-,30+,35+/m0/s1
SMILES:  CC(=O)O[C@@H]1[C@@H](OC(=O)c2ccccc2)C(=C)[C@H](OC(=O)C)[C@H]2[C@@H](OC(=O)C)[C@H](C[C@]2(OC(=O)C)C(=O)[C@H](/C=C/C(C1=O)(C)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL500267
PubChem CID:   11767492
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
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota n.a. stem n.a. DOI[10.1016/0014-2999(92)90156-X]
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota n.a. stem n.a. DOI[10.1039/C39820001150]
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota n.a. root n.a. DOI[10.1039/C39820001150]
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota Leaves n.a. n.a. PMID[11170675]
NPO9973 Euphorbia turczaninowii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11520228]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. from the rhizosphere of Opuntia versicolor of the Sonoran Desert n.a. PMID[14695798]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16124769]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[18271552]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22360613]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24534845]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25671343]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[2921224]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[30207465]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32163285]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32897070]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[8984154]
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[9214732]
NPO10244 Aglaia elliptifolia Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO68 Paracynoglossum imeretinum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9973 Euphorbia turczaninowii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5818 Cordyceps confragosa Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9716 Encephalartos villosus Species Zamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7624 Callitris tasmanica Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2595 Aspergillus terreus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8236 Phakellia aruensis Species Bubaridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10244 Aglaia elliptifolia Species Meliaceae 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
NPT319 Cell Line B16 Mus musculus IC50 > 5.0 ug.mL-1 PMID[537375]
NPT32 Organism Mus musculus Mus musculus ID50 > 100.0 ug PMID[537375]

☑ 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 NPC86772 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
0.9923 High Similarity NPC272523
0.9923 High Similarity NPC325805
0.9845 High Similarity NPC265459
0.9845 High Similarity NPC475262
0.9845 High Similarity NPC290833
0.9773 High Similarity NPC473497
0.9769 High Similarity NPC194769
0.9769 High Similarity NPC285221
0.9767 High Similarity NPC472250
0.9692 High Similarity NPC79699
0.9627 High Similarity NPC477096
0.9627 High Similarity NPC45307
0.9627 High Similarity NPC82467
0.9627 High Similarity NPC477094
0.9624 High Similarity NPC475413
0.9624 High Similarity NPC474303
0.9549 High Similarity NPC475660
0.9542 High Similarity NPC270364
0.9416 High Similarity NPC170668
0.9416 High Similarity NPC477095
0.9348 High Similarity NPC205389
0.9333 High Similarity NPC187566
0.9328 High Similarity NPC276652
0.9318 High Similarity NPC153617
0.9259 High Similarity NPC251294
0.9214 High Similarity NPC232583
0.9214 High Similarity NPC25484
0.9214 High Similarity NPC477101
0.9214 High Similarity NPC477097
0.9214 High Similarity NPC477099
0.9191 High Similarity NPC473654
0.916 High Similarity NPC475508
0.916 High Similarity NPC42234
0.9104 High Similarity NPC472247
0.9058 High Similarity NPC153214
0.9051 High Similarity NPC242355
0.9023 High Similarity NPC233860
0.9023 High Similarity NPC477360
0.9021 High Similarity NPC477098
0.9021 High Similarity NPC477100
0.9015 High Similarity NPC272946
0.8955 High Similarity NPC472248
0.8897 High Similarity NPC477358
0.8889 High Similarity NPC324898
0.8889 High Similarity NPC477368
0.8889 High Similarity NPC134937
0.8889 High Similarity NPC298547
0.8889 High Similarity NPC28836
0.8881 High Similarity NPC239358
0.8872 High Similarity NPC475671
0.8872 High Similarity NPC475452
0.8872 High Similarity NPC122504
0.8872 High Similarity NPC3450
0.8824 High Similarity NPC232888
0.8824 High Similarity NPC149401
0.8824 High Similarity NPC279637
0.8824 High Similarity NPC200154
0.8824 High Similarity NPC477367
0.8815 High Similarity NPC477364
0.8759 High Similarity NPC202729
0.875 High Similarity NPC311492
0.875 High Similarity NPC477359
0.8741 High Similarity NPC233692
0.8702 High Similarity NPC8990
0.8696 High Similarity NPC27721
0.8696 High Similarity NPC205305
0.8696 High Similarity NPC327511
0.8681 High Similarity NPC125033
0.8636 High Similarity NPC477369
0.8633 High Similarity NPC53361
0.8633 High Similarity NPC473301
0.8633 High Similarity NPC121268
0.86 High Similarity NPC55744
0.8582 High Similarity NPC475135
0.8531 High Similarity NPC471100
0.8531 High Similarity NPC471107
0.8514 High Similarity NPC70344
0.8425 Intermediate Similarity NPC254558
0.8392 Intermediate Similarity NPC191387
0.8392 Intermediate Similarity NPC131966
0.837 Intermediate Similarity NPC472706
0.8367 Intermediate Similarity NPC51602
0.8345 Intermediate Similarity NPC475552
0.8309 Intermediate Similarity NPC472707
0.8309 Intermediate Similarity NPC477370
0.8296 Intermediate Similarity NPC477363
0.8296 Intermediate Similarity NPC477366
0.8284 Intermediate Similarity NPC472704
0.8284 Intermediate Similarity NPC477362
0.8276 Intermediate Similarity NPC134131
0.8276 Intermediate Similarity NPC127857
0.8276 Intermediate Similarity NPC25043
0.8264 Intermediate Similarity NPC95449
0.8248 Intermediate Similarity NPC37968
0.8243 Intermediate Similarity NPC471103
0.8235 Intermediate Similarity NPC477365
0.8235 Intermediate Similarity NPC477357
0.8231 Intermediate Similarity NPC473403
0.8209 Intermediate Similarity NPC472703
0.82 Intermediate Similarity NPC473670
0.82 Intermediate Similarity NPC21410
0.82 Intermediate Similarity NPC469456
0.82 Intermediate Similarity NPC282239
0.8176 Intermediate Similarity NPC7095
0.8176 Intermediate Similarity NPC112216
0.8146 Intermediate Similarity NPC106895
0.8146 Intermediate Similarity NPC217091
0.8146 Intermediate Similarity NPC11410
0.8121 Intermediate Similarity NPC306799
0.8121 Intermediate Similarity NPC101043
0.8108 Intermediate Similarity NPC60509
0.8108 Intermediate Similarity NPC81698
0.8108 Intermediate Similarity NPC250046
0.8099 Intermediate Similarity NPC52523
0.8099 Intermediate Similarity NPC217673
0.8092 Intermediate Similarity NPC472393
0.8085 Intermediate Similarity NPC4242
0.8085 Intermediate Similarity NPC471911
0.8082 Intermediate Similarity NPC470231
0.8079 Intermediate Similarity NPC251139
0.8071 Intermediate Similarity NPC469499
0.8071 Intermediate Similarity NPC472394
0.8071 Intermediate Similarity NPC475569
0.8069 Intermediate Similarity NPC182869
0.8067 Intermediate Similarity NPC469648
0.8067 Intermediate Similarity NPC138641
0.8067 Intermediate Similarity NPC469647
0.8067 Intermediate Similarity NPC22571
0.8067 Intermediate Similarity NPC283875
0.8056 Intermediate Similarity NPC87934
0.8056 Intermediate Similarity NPC183270
0.8056 Intermediate Similarity NPC162613
0.8056 Intermediate Similarity NPC477904
0.8054 Intermediate Similarity NPC198455
0.8054 Intermediate Similarity NPC165260
0.8054 Intermediate Similarity NPC161239
0.8042 Intermediate Similarity NPC184109
0.8039 Intermediate Similarity NPC471102
0.8029 Intermediate Similarity NPC476599
0.8027 Intermediate Similarity NPC471162
0.8013 Intermediate Similarity NPC473414
0.8013 Intermediate Similarity NPC237549
0.8013 Intermediate Similarity NPC256142
0.8013 Intermediate Similarity NPC472022
0.8013 Intermediate Similarity NPC304876
0.8013 Intermediate Similarity NPC257213
0.8013 Intermediate Similarity NPC265395
0.8013 Intermediate Similarity NPC1173
0.8013 Intermediate Similarity NPC77719
0.8013 Intermediate Similarity NPC242262
0.8013 Intermediate Similarity NPC158333
0.8013 Intermediate Similarity NPC219419
0.8013 Intermediate Similarity NPC249471
0.8013 Intermediate Similarity NPC472005
0.8013 Intermediate Similarity NPC472030
0.8 Intermediate Similarity NPC266374
0.8 Intermediate Similarity NPC472398
0.7986 Intermediate Similarity NPC9905
0.7985 Intermediate Similarity NPC473243
0.7973 Intermediate Similarity NPC477737
0.7961 Intermediate Similarity NPC114357
0.7961 Intermediate Similarity NPC473611
0.7961 Intermediate Similarity NPC112523
0.7961 Intermediate Similarity NPC472549
0.7961 Intermediate Similarity NPC26033
0.7961 Intermediate Similarity NPC228204
0.7961 Intermediate Similarity NPC259144
0.7961 Intermediate Similarity NPC155329
0.7961 Intermediate Similarity NPC114410
0.7947 Intermediate Similarity NPC233581
0.7947 Intermediate Similarity NPC145649
0.7945 Intermediate Similarity NPC183540
0.7945 Intermediate Similarity NPC192658
0.7945 Intermediate Similarity NPC63737
0.7945 Intermediate Similarity NPC472546
0.7935 Intermediate Similarity NPC329997
0.7902 Intermediate Similarity NPC195647
0.7902 Intermediate Similarity NPC66761
0.7902 Intermediate Similarity NPC17877
0.7902 Intermediate Similarity NPC291638
0.7902 Intermediate Similarity NPC472577
0.7895 Intermediate Similarity NPC248265
0.7895 Intermediate Similarity NPC11588
0.7895 Intermediate Similarity NPC134685
0.7895 Intermediate Similarity NPC229545
0.7881 Intermediate Similarity NPC161955
0.7877 Intermediate Similarity NPC282973
0.7862 Intermediate Similarity NPC170718
0.7862 Intermediate Similarity NPC40138
0.7857 Intermediate Similarity NPC469771
0.7852 Intermediate Similarity NPC478263
0.7852 Intermediate Similarity NPC312393
0.7848 Intermediate Similarity NPC324769
0.7848 Intermediate Similarity NPC325732
0.7843 Intermediate Similarity NPC469730
0.7843 Intermediate Similarity NPC132599
0.7843 Intermediate Similarity NPC473632
0.7838 Intermediate Similarity NPC80895
0.7838 Intermediate Similarity NPC34943
0.7838 Intermediate Similarity NPC471912

  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 NPC86772 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
0.8027 Intermediate Similarity NPD7236 Approved
0.7987 Intermediate Similarity NPD7799 Discontinued
0.7887 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD7239 Suspended
0.75 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD2067 Discontinued
0.7421 Intermediate Similarity NPD7057 Phase 3
0.7421 Intermediate Similarity NPD7058 Phase 2
0.7348 Intermediate Similarity NPD2182 Approved
0.7279 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD8368 Discontinued
0.7235 Intermediate Similarity NPD8407 Phase 2
0.7163 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6599 Discontinued
0.7103 Intermediate Similarity NPD5740 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD6085 Phase 2
0.7095 Intermediate Similarity NPD7961 Discontinued
0.7068 Intermediate Similarity NPD6685 Approved
0.7052 Intermediate Similarity NPD8434 Phase 2
0.7045 Intermediate Similarity NPD164 Approved
0.6975 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6972 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6971 Remote Similarity NPD8435 Approved
0.6968 Remote Similarity NPD4628 Phase 3
0.6959 Remote Similarity NPD7685 Pre-registration
0.6959 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6951 Remote Similarity NPD7075 Discontinued
0.6943 Remote Similarity NPD6799 Approved
0.6906 Remote Similarity NPD2629 Approved
0.6884 Remote Similarity NPD6858 Approved
0.6884 Remote Similarity NPD7094 Approved
0.6875 Remote Similarity NPD8360 Approved
0.6875 Remote Similarity NPD8361 Approved
0.6875 Remote Similarity NPD6287 Discontinued
0.6871 Remote Similarity NPD5761 Phase 2
0.6871 Remote Similarity NPD5760 Phase 2
0.686 Remote Similarity NPD6765 Approved
0.686 Remote Similarity NPD6764 Approved
0.6857 Remote Similarity NPD4198 Discontinued
0.6857 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5765 Approved
0.6831 Remote Similarity NPD7741 Discontinued
0.6812 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6812 Remote Similarity NPD6912 Phase 3
0.681 Remote Similarity NPD6801 Discontinued
0.6792 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6002 Phase 3
0.6774 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6004 Phase 3
0.6774 Remote Similarity NPD6005 Phase 3
0.6774 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6761 Remote Similarity NPD8150 Discontinued
0.6757 Remote Similarity NPD5647 Approved
0.6742 Remote Similarity NPD1238 Approved
0.674 Remote Similarity NPD8485 Approved
0.6727 Remote Similarity NPD3817 Phase 2
0.6727 Remote Similarity NPD5402 Approved
0.6716 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6713 Remote Similarity NPD9545 Approved
0.6709 Remote Similarity NPD3887 Approved
0.6709 Remote Similarity NPD6190 Approved
0.6708 Remote Similarity NPD5403 Approved
0.6705 Remote Similarity NPD6785 Approved
0.6705 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6784 Approved
0.6687 Remote Similarity NPD5401 Approved
0.6686 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD6832 Phase 2
0.6667 Remote Similarity NPD7819 Suspended
0.663 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6653 Approved
0.6622 Remote Similarity NPD5667 Approved
0.6611 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6603 Remote Similarity NPD7137 Phase 2
0.6603 Remote Similarity NPD2796 Approved
0.6594 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6593 Remote Similarity NPD6647 Phase 2
0.6581 Remote Similarity NPD2567 Approved
0.6581 Remote Similarity NPD2569 Approved
0.6579 Remote Similarity NPD3764 Approved
0.6568 Remote Similarity NPD5494 Approved
0.6561 Remote Similarity NPD5763 Approved
0.6561 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6561 Remote Similarity NPD5762 Approved
0.6558 Remote Similarity NPD230 Phase 1
0.6543 Remote Similarity NPD6273 Approved
0.6538 Remote Similarity NPD7305 Phase 1
0.6529 Remote Similarity NPD8127 Discontinued
0.6513 Remote Similarity NPD7008 Discontinued
0.651 Remote Similarity NPD1876 Approved
0.6509 Remote Similarity NPD919 Approved
0.6503 Remote Similarity NPD920 Approved
0.6503 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6496 Remote Similarity NPD5048 Discontinued
0.6494 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6488 Remote Similarity NPD3882 Suspended
0.6486 Remote Similarity NPD3972 Approved
0.6486 Remote Similarity NPD6637 Approved
0.6485 Remote Similarity NPD4380 Phase 2
0.6481 Remote Similarity NPD2533 Approved
0.6481 Remote Similarity NPD2532 Approved
0.6481 Remote Similarity NPD2534 Approved
0.6467 Remote Similarity NPD6362 Approved
0.6456 Remote Similarity NPD2353 Approved
0.6456 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6438 Remote Similarity NPD2575 Approved
0.6433 Remote Similarity NPD2799 Discontinued
0.6433 Remote Similarity NPD7033 Discontinued
0.6429 Remote Similarity NPD7713 Phase 3
0.6429 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6425 Remote Similarity NPD8462 Phase 1
0.6424 Remote Similarity NPD7458 Discontinued
0.6423 Remote Similarity NPD1237 Approved
0.6419 Remote Similarity NPD4806 Approved
0.6419 Remote Similarity NPD4807 Approved
0.6416 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6395 Remote Similarity NPD5305 Approved
0.6395 Remote Similarity NPD5306 Approved
0.6395 Remote Similarity NPD17 Approved
0.6382 Remote Similarity NPD3663 Approved
0.6382 Remote Similarity NPD3661 Approved
0.6382 Remote Similarity NPD3662 Phase 3
0.6382 Remote Similarity NPD3664 Approved
0.638 Remote Similarity NPD7004 Clinical (unspecified phase)
0.638 Remote Similarity NPD4378 Clinical (unspecified phase)
0.638 Remote Similarity NPD642 Clinical (unspecified phase)
0.6379 Remote Similarity NPD7473 Discontinued
0.6375 Remote Similarity NPD7421 Clinical (unspecified phase)
0.637 Remote Similarity NPD7798 Approved
0.6364 Remote Similarity NPD2652 Approved
0.6364 Remote Similarity NPD2650 Approved
0.6364 Remote Similarity NPD2313 Discontinued
0.6358 Remote Similarity NPD3926 Phase 2
0.6353 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6352 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6352 Remote Similarity NPD1471 Phase 3
0.635 Remote Similarity NPD1930 Approved
0.635 Remote Similarity NPD1931 Clinical (unspecified phase)
0.635 Remote Similarity NPD1929 Approved
0.6347 Remote Similarity NPD6386 Approved
0.6347 Remote Similarity NPD7411 Suspended
0.6347 Remote Similarity NPD6385 Approved
0.6345 Remote Similarity NPD9493 Approved
0.6343 Remote Similarity NPD7893 Clinical (unspecified phase)
0.634 Remote Similarity NPD7055 Discontinued
0.6338 Remote Similarity NPD969 Suspended
0.6337 Remote Similarity NPD1247 Approved
0.6335 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6331 Remote Similarity NPD5353 Approved
0.6325 Remote Similarity NPD3226 Approved
0.6323 Remote Similarity NPD6663 Approved
0.6323 Remote Similarity NPD8032 Phase 2
0.6322 Remote Similarity NPD2403 Approved
0.6319 Remote Similarity NPD5951 Approved
0.6319 Remote Similarity NPD4766 Approved
0.6316 Remote Similarity NPD8320 Phase 1
0.6316 Remote Similarity NPD8319 Approved
0.6316 Remote Similarity NPD2798 Approved
0.6316 Remote Similarity NPD1019 Discontinued
0.6313 Remote Similarity NPD8313 Approved
0.6313 Remote Similarity NPD8312 Approved
0.6312 Remote Similarity NPD4233 Approved
0.6312 Remote Similarity NPD4234 Approved
0.6312 Remote Similarity NPD970 Clinical (unspecified phase)
0.6296 Remote Similarity NPD9495 Approved
0.6296 Remote Similarity NPD2354 Approved
0.6294 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5736 Approved
0.6273 Remote Similarity NPD1243 Approved
0.6273 Remote Similarity NPD2800 Approved
0.6272 Remote Similarity NPD7972 Discontinued
0.6268 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6267 Remote Similarity NPD1608 Approved
0.6264 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7497 Discontinued
0.6259 Remote Similarity NPD7009 Phase 2
0.6259 Remote Similarity NPD6319 Approved
0.6258 Remote Similarity NPD643 Clinical (unspecified phase)
0.6258 Remote Similarity NPD6652 Clinical (unspecified phase)
0.6257 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6257 Remote Similarity NPD7808 Phase 3
0.625 Remote Similarity NPD2346 Discontinued
0.625 Remote Similarity NPD6010 Discontinued
0.625 Remote Similarity NPD2066 Phase 3
0.625 Remote Similarity NPD3818 Discontinued
0.6242 Remote Similarity NPD4106 Approved
0.6242 Remote Similarity NPD4136 Approved
0.6242 Remote Similarity NPD4135 Approved
0.6242 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6242 Remote Similarity NPD447 Suspended
0.6241 Remote Similarity NPD1202 Approved
0.6236 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6235 Remote Similarity NPD8166 Discontinued
0.6235 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6229 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6229 Remote Similarity NPD6168 Clinical (unspecified phase)

  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