Structure

Physi-Chem Properties

Molecular Weight:  612.26
Volume:  621.346
LogP:  3.084
LogD:  2.396
LogS:  -4.24
# Rotatable Bonds:  9
TPSA:  159.57
# H-Bond Aceptor:  11
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  5.505
Fsp3:  0.515
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:  -5.183
MDCK Permeability:  7.169372838689014e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.528
20% Bioavailability (F20%):  0.902
30% Bioavailability (F30%):  0.912

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.062
Plasma Protein Binding (PPB):  80.50399017333984%
Volume Distribution (VD):  1.957
Pgp-substrate:  18.054304122924805%

ADMET: Metabolism

CYP1A2-inhibitor:  0.021
CYP1A2-substrate:  0.045
CYP2C19-inhibitor:  0.032
CYP2C19-substrate:  0.085
CYP2C9-inhibitor:  0.144
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.05
CYP3A4-inhibitor:  0.868
CYP3A4-substrate:  0.338

ADMET: Excretion

Clearance (CL):  3.901
Half-life (T1/2):  0.416

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.973
Drug-inuced Liver Injury (DILI):  0.971
AMES Toxicity:  0.032
Rat Oral Acute Toxicity:  0.898
Maximum Recommended Daily Dose:  0.015
Skin Sensitization:  0.07
Carcinogencity:  0.347
Eye Corrosion:  0.056
Eye Irritation:  0.101
Respiratory Toxicity:  0.942

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

  Natural Product: NPC473497

Natural Product ID:  NPC473497
Common Name*:   (2S*,3S*,4R*,5R*,7S*,8R*,13S*,15R*)-5Alpha,7Beta,8Alpha-Triacetoxy-3Beta-Benzoyloxy-15Beta-Hydroxyjatropha-6(17),11E-Diene-9,14-Dione
IUPAC Name:   [(1S,2S,3aR,5S,6E,10R,11S,13R,13aR)-10,11,13-triacetyloxy-3a-hydroxy-2,5,8,8-tetramethyl-12-methylidene-4,9-dioxo-1,2,3,5,10,11,13,13a-octahydrocyclopenta[12]annulen-1-yl] benzoate
Synonyms:  
Standard InCHIKey:  WIIHXTZBFPAMCQ-ARERDINJSA-N
Standard InCHI:  InChI=1S/C33H40O11/c1-17-14-15-32(7,8)30(38)28(43-22(6)36)27(42-21(5)35)19(3)26(41-20(4)34)24-25(18(2)16-33(24,40)29(17)37)44-31(39)23-12-10-9-11-13-23/h9-15,17-18,24-28,40H,3,16H2,1-2,4-8H3/b15-14+/t17-,18-,24+,25-,26-,27-,28+,33+/m0/s1
SMILES:  CC1CC2(C(C1OC(=O)C3=CC=CC=C3)C(C(=C)C(C(C(=O)C(C=CC(C2=O)C)(C)C)OC(=O)C)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443723
PubChem CID:   10054505
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 = 148.64 n.a. PMID[519206]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 277.08 n.a. PMID[519206]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 12.29 n.a. PMID[519206]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 22.92 n.a. PMID[519206]

☑ 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 NPC473497 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
0.9851 High Similarity NPC45307
0.985 High Similarity NPC474303
0.985 High Similarity NPC475413
0.9773 High Similarity NPC86772
0.9699 High Similarity NPC272523
0.9699 High Similarity NPC325805
0.9635 High Similarity NPC170668
0.9621 High Similarity NPC475262
0.9621 High Similarity NPC265459
0.9621 High Similarity NPC290833
0.9565 High Similarity NPC205389
0.9549 High Similarity NPC194769
0.9549 High Similarity NPC285221
0.9545 High Similarity NPC472250
0.9474 High Similarity NPC79699
0.9429 High Similarity NPC477099
0.9429 High Similarity NPC25484
0.9429 High Similarity NPC477097
0.9429 High Similarity NPC477101
0.9429 High Similarity NPC232583
0.9416 High Similarity NPC477096
0.9416 High Similarity NPC82467
0.9416 High Similarity NPC477094
0.9338 High Similarity NPC475660
0.9328 High Similarity NPC472247
0.9328 High Similarity NPC270364
0.9275 High Similarity NPC153214
0.927 High Similarity NPC242355
0.9248 High Similarity NPC233860
0.9242 High Similarity NPC272946
0.9231 High Similarity NPC477098
0.9231 High Similarity NPC477100
0.9214 High Similarity NPC477095
0.9179 High Similarity NPC472248
0.913 High Similarity NPC187566
0.9124 High Similarity NPC276652
0.9111 High Similarity NPC153617
0.9111 High Similarity NPC28836
0.9111 High Similarity NPC477368
0.9104 High Similarity NPC239358
0.9058 High Similarity NPC251294
0.9044 High Similarity NPC200154
0.9044 High Similarity NPC477367
0.9044 High Similarity NPC232888
0.9037 High Similarity NPC477364
0.8993 High Similarity NPC473654
0.8978 High Similarity NPC202729
0.8971 High Similarity NPC311492
0.8971 High Similarity NPC477359
0.8963 High Similarity NPC233692
0.8955 High Similarity NPC475508
0.8955 High Similarity NPC42234
0.8913 High Similarity NPC27721
0.8889 High Similarity NPC125033
0.8849 High Similarity NPC473301
0.8824 High Similarity NPC477360
0.88 High Similarity NPC55744
0.8716 High Similarity NPC70344
0.8705 High Similarity NPC477358
0.8696 High Similarity NPC324898
0.8696 High Similarity NPC134937
0.8696 High Similarity NPC298547
0.8676 High Similarity NPC475452
0.8676 High Similarity NPC475671
0.8676 High Similarity NPC3450
0.8676 High Similarity NPC122504
0.8633 High Similarity NPC149401
0.8633 High Similarity NPC279637
0.8593 High Similarity NPC472706
0.8571 High Similarity NPC51602
0.8529 High Similarity NPC472707
0.8529 High Similarity NPC477370
0.8519 High Similarity NPC477363
0.8519 High Similarity NPC477366
0.8511 High Similarity NPC327511
0.8511 High Similarity NPC205305
0.8507 High Similarity NPC477362
0.8507 High Similarity NPC472704
0.8507 High Similarity NPC8990
0.8483 Intermediate Similarity NPC25043
0.8483 Intermediate Similarity NPC127857
0.8483 Intermediate Similarity NPC134131
0.8472 Intermediate Similarity NPC95449
0.8467 Intermediate Similarity NPC37968
0.8456 Intermediate Similarity NPC477365
0.8456 Intermediate Similarity NPC477357
0.8451 Intermediate Similarity NPC53361
0.8451 Intermediate Similarity NPC121268
0.8446 Intermediate Similarity NPC471103
0.8444 Intermediate Similarity NPC477369
0.8433 Intermediate Similarity NPC472703
0.8403 Intermediate Similarity NPC475135
0.84 Intermediate Similarity NPC469456
0.84 Intermediate Similarity NPC473670
0.84 Intermediate Similarity NPC21410
0.84 Intermediate Similarity NPC282239
0.8378 Intermediate Similarity NPC7095
0.8378 Intermediate Similarity NPC112216
0.8356 Intermediate Similarity NPC471100
0.8356 Intermediate Similarity NPC471107
0.8344 Intermediate Similarity NPC217091
0.8344 Intermediate Similarity NPC106895
0.8344 Intermediate Similarity NPC11410
0.8322 Intermediate Similarity NPC306799
0.8322 Intermediate Similarity NPC101043
0.8311 Intermediate Similarity NPC60509
0.8311 Intermediate Similarity NPC81698
0.8311 Intermediate Similarity NPC250046
0.831 Intermediate Similarity NPC217673
0.831 Intermediate Similarity NPC52523
0.8289 Intermediate Similarity NPC472393
0.8278 Intermediate Similarity NPC251139
0.8276 Intermediate Similarity NPC182869
0.8267 Intermediate Similarity NPC469647
0.8267 Intermediate Similarity NPC469648
0.8267 Intermediate Similarity NPC138641
0.8267 Intermediate Similarity NPC22571
0.8267 Intermediate Similarity NPC283875
0.8264 Intermediate Similarity NPC162613
0.8264 Intermediate Similarity NPC87934
0.8255 Intermediate Similarity NPC161239
0.8255 Intermediate Similarity NPC198455
0.8255 Intermediate Similarity NPC254558
0.8255 Intermediate Similarity NPC165260
0.8235 Intermediate Similarity NPC471102
0.8231 Intermediate Similarity NPC471162
0.8219 Intermediate Similarity NPC191387
0.8219 Intermediate Similarity NPC131966
0.8212 Intermediate Similarity NPC237549
0.8212 Intermediate Similarity NPC219419
0.8212 Intermediate Similarity NPC77719
0.8212 Intermediate Similarity NPC1173
0.8212 Intermediate Similarity NPC472030
0.8212 Intermediate Similarity NPC265395
0.8212 Intermediate Similarity NPC473414
0.8212 Intermediate Similarity NPC249471
0.8212 Intermediate Similarity NPC257213
0.8212 Intermediate Similarity NPC242262
0.8212 Intermediate Similarity NPC256142
0.8212 Intermediate Similarity NPC472022
0.8212 Intermediate Similarity NPC304876
0.8212 Intermediate Similarity NPC472005
0.8212 Intermediate Similarity NPC158333
0.8207 Intermediate Similarity NPC266374
0.82 Intermediate Similarity NPC472398
0.8194 Intermediate Similarity NPC9905
0.8176 Intermediate Similarity NPC477737
0.8176 Intermediate Similarity NPC475552
0.8158 Intermediate Similarity NPC473611
0.8158 Intermediate Similarity NPC228204
0.8158 Intermediate Similarity NPC472549
0.8158 Intermediate Similarity NPC112523
0.8158 Intermediate Similarity NPC26033
0.8158 Intermediate Similarity NPC155329
0.8158 Intermediate Similarity NPC114357
0.8158 Intermediate Similarity NPC114410
0.8158 Intermediate Similarity NPC259144
0.8151 Intermediate Similarity NPC192658
0.8151 Intermediate Similarity NPC63737
0.8151 Intermediate Similarity NPC183540
0.8151 Intermediate Similarity NPC472546
0.8146 Intermediate Similarity NPC145649
0.8146 Intermediate Similarity NPC233581
0.8129 Intermediate Similarity NPC329997
0.8092 Intermediate Similarity NPC11588
0.8092 Intermediate Similarity NPC134685
0.8092 Intermediate Similarity NPC229545
0.8092 Intermediate Similarity NPC248265
0.8079 Intermediate Similarity NPC161955
0.8069 Intermediate Similarity NPC170718
0.8067 Intermediate Similarity NPC473403
0.8054 Intermediate Similarity NPC478263
0.8054 Intermediate Similarity NPC312393
0.8052 Intermediate Similarity NPC469771
0.805 Intermediate Similarity NPC40138
0.8043 Intermediate Similarity NPC246166
0.8041 Intermediate Similarity NPC80895
0.8041 Intermediate Similarity NPC34943
0.8041 Intermediate Similarity NPC471912
0.8039 Intermediate Similarity NPC132599
0.8039 Intermediate Similarity NPC473632
0.8039 Intermediate Similarity NPC469730
0.8038 Intermediate Similarity NPC324769
0.8038 Intermediate Similarity NPC325732
0.8027 Intermediate Similarity NPC51181
0.8026 Intermediate Similarity NPC477905
0.8026 Intermediate Similarity NPC472548
0.8014 Intermediate Similarity NPC82712
0.8014 Intermediate Similarity NPC473440
0.8013 Intermediate Similarity NPC470245
0.8013 Intermediate Similarity NPC91730
0.8013 Intermediate Similarity NPC473214
0.8 Intermediate Similarity NPC327031
0.8 Intermediate Similarity NPC132652
0.7987 Intermediate Similarity NPC301946
0.7987 Intermediate Similarity NPC277053
0.7987 Intermediate Similarity NPC32
0.7987 Intermediate Similarity NPC125882
0.7987 Intermediate Similarity NPC122491
0.7987 Intermediate Similarity NPC161151

  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 NPC473497 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
0.8231 Intermediate Similarity NPD7236 Approved
0.8176 Intermediate Similarity NPD7799 Discontinued
0.8099 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD7239 Suspended
0.7676 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD7058 Phase 2
0.761 Intermediate Similarity NPD7057 Phase 3
0.744 Intermediate Similarity NPD8368 Discontinued
0.7412 Intermediate Similarity NPD8407 Phase 2
0.7372 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6085 Phase 2
0.731 Intermediate Similarity NPD5740 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7961 Discontinued
0.7293 Intermediate Similarity NPD6685 Approved
0.7259 Intermediate Similarity NPD2067 Discontinued
0.7225 Intermediate Similarity NPD8434 Phase 2
0.7188 Intermediate Similarity NPD6599 Discontinued
0.7185 Intermediate Similarity NPD2182 Approved
0.7162 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD4628 Phase 3
0.716 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8435 Approved
0.7135 Intermediate Similarity NPD7685 Pre-registration
0.7134 Intermediate Similarity NPD7075 Discontinued
0.7122 Intermediate Similarity NPD2629 Approved
0.7071 Intermediate Similarity NPD4198 Discontinued
0.7068 Intermediate Similarity NPD5765 Approved
0.7055 Intermediate Similarity NPD5761 Phase 2
0.7055 Intermediate Similarity NPD5760 Phase 2
0.7045 Intermediate Similarity NPD8360 Approved
0.7045 Intermediate Similarity NPD8361 Approved
0.7042 Intermediate Similarity NPD7741 Discontinued
0.7035 Intermediate Similarity NPD6764 Approved
0.7035 Intermediate Similarity NPD6765 Approved
0.7029 Intermediate Similarity NPD6912 Phase 3
0.7029 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6799 Approved
0.7014 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6981 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6002 Phase 3
0.6968 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6005 Phase 3
0.6968 Remote Similarity NPD6004 Phase 3
0.6968 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5647 Approved
0.694 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6932 Remote Similarity NPD8150 Discontinued
0.6923 Remote Similarity NPD9545 Approved
0.6906 Remote Similarity NPD8485 Approved
0.6899 Remote Similarity NPD6190 Approved
0.689 Remote Similarity NPD6801 Discontinued
0.6889 Remote Similarity NPD164 Approved
0.6875 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6785 Approved
0.6875 Remote Similarity NPD6784 Approved
0.6863 Remote Similarity NPD6355 Discontinued
0.686 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7819 Suspended
0.6828 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6653 Approved
0.6815 Remote Similarity NPD6647 Phase 2
0.6812 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6807 Remote Similarity NPD5402 Approved
0.6807 Remote Similarity NPD3817 Phase 2
0.6795 Remote Similarity NPD7137 Phase 2
0.6793 Remote Similarity NPD8486 Clinical (unspecified phase)
0.679 Remote Similarity NPD5403 Approved
0.6778 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6776 Remote Similarity NPD3764 Approved
0.677 Remote Similarity NPD5401 Approved
0.6753 Remote Similarity NPD230 Phase 1
0.6752 Remote Similarity NPD5763 Approved
0.6752 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5762 Approved
0.6738 Remote Similarity NPD7094 Approved
0.6738 Remote Similarity NPD6858 Approved
0.6735 Remote Similarity NPD6287 Discontinued
0.6731 Remote Similarity NPD7305 Phase 1
0.6728 Remote Similarity NPD6273 Approved
0.6715 Remote Similarity NPD5048 Discontinued
0.6711 Remote Similarity NPD7008 Discontinued
0.6706 Remote Similarity NPD8127 Discontinued
0.6667 Remote Similarity NPD2532 Approved
0.6667 Remote Similarity NPD2533 Approved
0.6667 Remote Similarity NPD2534 Approved
0.6667 Remote Similarity NPD6362 Approved
0.6667 Remote Similarity NPD4380 Phase 2
0.6667 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3882 Suspended
0.6642 Remote Similarity NPD1237 Approved
0.6625 Remote Similarity NPD2575 Approved
0.6624 Remote Similarity NPD2799 Discontinued
0.6624 Remote Similarity NPD7033 Discontinued
0.6622 Remote Similarity NPD4807 Approved
0.6622 Remote Similarity NPD4806 Approved
0.6607 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6606 Remote Similarity NPD7458 Discontinued
0.6599 Remote Similarity NPD5306 Approved
0.6599 Remote Similarity NPD5305 Approved
0.6593 Remote Similarity NPD1238 Approved
0.6584 Remote Similarity NPD3887 Approved
0.658 Remote Similarity NPD8462 Phase 1
0.6579 Remote Similarity NPD3661 Approved
0.6579 Remote Similarity NPD3664 Approved
0.6579 Remote Similarity NPD3663 Approved
0.6579 Remote Similarity NPD3662 Phase 3
0.6573 Remote Similarity NPD2650 Approved
0.6573 Remote Similarity NPD2652 Approved
0.6569 Remote Similarity NPD1930 Approved
0.6569 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6569 Remote Similarity NPD1929 Approved
0.6564 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6564 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6558 Remote Similarity NPD2313 Discontinued
0.6552 Remote Similarity NPD9493 Approved
0.6552 Remote Similarity NPD7473 Discontinued
0.6549 Remote Similarity NPD969 Suspended
0.6541 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6536 Remote Similarity NPD6832 Phase 2
0.6529 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6528 Remote Similarity NPD5951 Approved
0.6527 Remote Similarity NPD7411 Suspended
0.6522 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6519 Remote Similarity NPD9495 Approved
0.6516 Remote Similarity NPD6663 Approved
0.6506 Remote Similarity NPD3226 Approved
0.65 Remote Similarity NPD970 Clinical (unspecified phase)
0.649 Remote Similarity NPD5667 Approved
0.6481 Remote Similarity NPD2354 Approved
0.648 Remote Similarity NPD8313 Approved
0.648 Remote Similarity NPD8312 Approved
0.6479 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6478 Remote Similarity NPD2796 Approved
0.6474 Remote Similarity NPD8320 Phase 1
0.6474 Remote Similarity NPD8319 Approved
0.6471 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5736 Approved
0.6471 Remote Similarity NPD2066 Phase 3
0.6467 Remote Similarity NPD1608 Approved
0.6463 Remote Similarity NPD7009 Phase 2
0.6463 Remote Similarity NPD6319 Approved
0.646 Remote Similarity NPD2800 Approved
0.6458 Remote Similarity NPD6010 Discontinued
0.6456 Remote Similarity NPD2569 Approved
0.6456 Remote Similarity NPD2567 Approved
0.6453 Remote Similarity NPD5494 Approved
0.645 Remote Similarity NPD7972 Discontinued
0.6443 Remote Similarity NPD4136 Approved
0.6443 Remote Similarity NPD4135 Approved
0.6443 Remote Similarity NPD4106 Approved
0.6438 Remote Similarity NPD2346 Discontinued
0.6437 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6434 Remote Similarity NPD8297 Approved
0.6433 Remote Similarity NPD447 Suspended
0.6425 Remote Similarity NPD7808 Phase 3
0.6425 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6421 Remote Similarity NPD7497 Discontinued
0.642 Remote Similarity NPD3818 Discontinued
0.642 Remote Similarity NPD6398 Clinical (unspecified phase)
0.642 Remote Similarity NPD8166 Discontinued
0.6418 Remote Similarity NPD1693 Approved
0.6415 Remote Similarity NPD1510 Phase 2
0.641 Remote Similarity NPD6233 Phase 2
0.6408 Remote Similarity NPD6371 Approved
0.6407 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6405 Remote Similarity NPD2798 Approved
0.6404 Remote Similarity NPD7993 Clinical (unspecified phase)
0.64 Remote Similarity NPD6168 Clinical (unspecified phase)
0.64 Remote Similarity NPD6166 Phase 2
0.64 Remote Similarity NPD7852 Clinical (unspecified phase)
0.64 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6398 Remote Similarity NPD1549 Phase 2
0.6395 Remote Similarity NPD919 Approved
0.6395 Remote Similarity NPD7610 Discontinued
0.6392 Remote Similarity NPD6651 Approved
0.6391 Remote Similarity NPD1934 Approved
0.6387 Remote Similarity NPD7095 Approved
0.6386 Remote Similarity NPD920 Approved
0.6386 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6382 Remote Similarity NPD1876 Approved
0.6379 Remote Similarity NPD6232 Discontinued
0.6376 Remote Similarity NPD5125 Phase 3
0.6376 Remote Similarity NPD5126 Approved
0.6375 Remote Similarity NPD2935 Discontinued
0.6374 Remote Similarity NPD7768 Phase 2
0.6369 Remote Similarity NPD1240 Approved
0.6369 Remote Similarity NPD7251 Discontinued
0.6364 Remote Similarity NPD5204 Approved
0.6364 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6358 Remote Similarity NPD3972 Approved
0.6358 Remote Similarity NPD9717 Approved
0.6358 Remote Similarity NPD6637 Approved
0.6353 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6798 Discontinued
0.6346 Remote Similarity NPD6859 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