Structure

Physi-Chem Properties

Molecular Weight:  480.25
Volume:  501.644
LogP:  4.986
LogD:  4.376
LogS:  -4.9
# Rotatable Bonds:  5
TPSA:  82.2
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.452
Synthetic Accessibility Score:  5.151
Fsp3:  0.621
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.932
MDCK Permeability:  3.273686161264777e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.086
30% Bioavailability (F30%):  0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  92.41211700439453%
Volume Distribution (VD):  2.644
Pgp-substrate:  7.351131916046143%

ADMET: Metabolism

CYP1A2-inhibitor:  0.057
CYP1A2-substrate:  0.129
CYP2C19-inhibitor:  0.392
CYP2C19-substrate:  0.2
CYP2C9-inhibitor:  0.672
CYP2C9-substrate:  0.065
CYP2D6-inhibitor:  0.077
CYP2D6-substrate:  0.118
CYP3A4-inhibitor:  0.886
CYP3A4-substrate:  0.529

ADMET: Excretion

Clearance (CL):  5.914
Half-life (T1/2):  0.227

ADMET: Toxicity

hERG Blockers:  0.793
Human Hepatotoxicity (H-HT):  0.926
Drug-inuced Liver Injury (DILI):  0.683
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.384
Maximum Recommended Daily Dose:  0.52
Skin Sensitization:  0.945
Carcinogencity:  0.091
Eye Corrosion:  0.004
Eye Irritation:  0.022
Respiratory Toxicity:  0.866

Download Data

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

  Natural Product: NPC477360

Natural Product ID:  NPC477360
Common Name*:   [(1R,2R,4R,7S,9S,10E,13R,15S,16S)-16-acetyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-13-yl] benzoate
IUPAC Name:   [(1R,2R,4R,7S,9S,10E,13R,15S,16S)-16-acetyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-13-yl] benzoate
Synonyms:  
Standard InCHIKey:  KXWUYCUPBXTAIE-AAEWGYDNSA-N
Standard InCHI:  InChI=1S/C29H36O6/c1-16-14-21-20(27(21,4)5)12-13-28(6)25(34-28)22-23(33-18(3)30)17(2)15-29(22,24(16)31)35-26(32)19-10-8-7-9-11-19/h7-11,14,17,20-23,25H,12-13,15H2,1-6H3/b16-14+/t17-,20-,21-,22+,23-,25+,28+,29+/m0/s1
SMILES:  C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@@H]3[C@](O3)(CC[C@H]4[C@@H](C4(C)C)/C=C(/C2=O)\C)C)OC(=O)C5=CC=CC=C5
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   56669870
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] 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
NPO28682 Jatropha multifida Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19036584]
NPO28682 Jatropha multifida Species Euphorbiaceae Eukaryota stems Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh 2006-AUG PMID[21534583]
NPO28682 Jatropha multifida 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
NPT177 Tissue Aorta Rattus norvegicus Activity = 41 % PMID[21534583]

☑ 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 NPC477360 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
0.9839 High Similarity NPC42234
0.9688 High Similarity NPC477358
0.9685 High Similarity NPC477359
0.9531 High Similarity NPC477368
0.9457 High Similarity NPC477367
0.9457 High Similarity NPC232888
0.9457 High Similarity NPC270364
0.9453 High Similarity NPC477364
0.9394 High Similarity NPC473654
0.9254 High Similarity NPC477096
0.9254 High Similarity NPC477094
0.9242 High Similarity NPC276652
0.9219 High Similarity NPC272946
0.92 High Similarity NPC8990
0.916 High Similarity NPC475262
0.916 High Similarity NPC290833
0.916 High Similarity NPC265459
0.9141 High Similarity NPC37968
0.9134 High Similarity NPC477357
0.9127 High Similarity NPC477369
0.9091 High Similarity NPC285221
0.9091 High Similarity NPC194769
0.9084 High Similarity NPC472250
0.907 High Similarity NPC475452
0.907 High Similarity NPC475671
0.9051 High Similarity NPC477095
0.9023 High Similarity NPC86772
0.8971 High Similarity NPC82467
0.8955 High Similarity NPC325805
0.8955 High Similarity NPC272523
0.8915 High Similarity NPC477370
0.8906 High Similarity NPC477366
0.8906 High Similarity NPC477363
0.8898 High Similarity NPC477362
0.8889 High Similarity NPC475660
0.8889 High Similarity NPC251294
0.8872 High Similarity NPC472247
0.8857 High Similarity NPC477101
0.8857 High Similarity NPC477099
0.8857 High Similarity NPC477097
0.8837 High Similarity NPC477365
0.8824 High Similarity NPC473497
0.8779 High Similarity NPC3450
0.8779 High Similarity NPC122504
0.8731 High Similarity NPC79699
0.8696 High Similarity NPC45307
0.8696 High Similarity NPC153214
0.8686 High Similarity NPC475413
0.8686 High Similarity NPC474303
0.8671 High Similarity NPC477100
0.8671 High Similarity NPC477098
0.8592 High Similarity NPC25484
0.8592 High Similarity NPC232583
0.8592 High Similarity NPC125033
0.8511 High Similarity NPC170668
0.8496 Intermediate Similarity NPC475508
0.8451 Intermediate Similarity NPC205389
0.8417 Intermediate Similarity NPC187566
0.8382 Intermediate Similarity NPC153617
0.837 Intermediate Similarity NPC233692
0.837 Intermediate Similarity NPC239358
0.837 Intermediate Similarity NPC233860
0.8333 Intermediate Similarity NPC476599
0.8309 Intermediate Similarity NPC472248
0.8295 Intermediate Similarity NPC473243
0.8248 Intermediate Similarity NPC311492
0.8248 Intermediate Similarity NPC28836
0.8248 Intermediate Similarity NPC134937
0.8248 Intermediate Similarity NPC324898
0.8248 Intermediate Similarity NPC298547
0.8188 Intermediate Similarity NPC279637
0.8188 Intermediate Similarity NPC200154
0.8188 Intermediate Similarity NPC149401
0.8156 Intermediate Similarity NPC242355
0.8134 Intermediate Similarity NPC472706
0.8129 Intermediate Similarity NPC217673
0.8129 Intermediate Similarity NPC52523
0.8129 Intermediate Similarity NPC202729
0.8099 Intermediate Similarity NPC183540
0.8074 Intermediate Similarity NPC472707
0.8071 Intermediate Similarity NPC327511
0.8071 Intermediate Similarity NPC27721
0.8071 Intermediate Similarity NPC205305
0.8065 Intermediate Similarity NPC469636
0.8045 Intermediate Similarity NPC472704
0.8042 Intermediate Similarity NPC191387
0.8042 Intermediate Similarity NPC131966
0.8031 Intermediate Similarity NPC307651
0.8029 Intermediate Similarity NPC470278
0.8014 Intermediate Similarity NPC121268
0.8014 Intermediate Similarity NPC53361
0.8014 Intermediate Similarity NPC473301
0.7986 Intermediate Similarity NPC329913
0.7972 Intermediate Similarity NPC475135
0.797 Intermediate Similarity NPC472703
0.7955 Intermediate Similarity NPC50872
0.7939 Intermediate Similarity NPC472708
0.7933 Intermediate Similarity NPC70344
0.7874 Intermediate Similarity NPC270699
0.7874 Intermediate Similarity NPC82899
0.7857 Intermediate Similarity NPC126516
0.7842 Intermediate Similarity NPC238370
0.7812 Intermediate Similarity NPC161611
0.7808 Intermediate Similarity NPC471100
0.7808 Intermediate Similarity NPC471162
0.7808 Intermediate Similarity NPC25043
0.7808 Intermediate Similarity NPC471107
0.7808 Intermediate Similarity NPC134131
0.7795 Intermediate Similarity NPC305912
0.7795 Intermediate Similarity NPC1082
0.7792 Intermediate Similarity NPC55744
0.7786 Intermediate Similarity NPC472656
0.7762 Intermediate Similarity NPC170718
0.7755 Intermediate Similarity NPC475552
0.7748 Intermediate Similarity NPC469456
0.7733 Intermediate Similarity NPC138641
0.7733 Intermediate Similarity NPC22571
0.7733 Intermediate Similarity NPC283875
0.7733 Intermediate Similarity NPC469648
0.7733 Intermediate Similarity NPC469647
0.773 Intermediate Similarity NPC203486
0.7724 Intermediate Similarity NPC51181
0.7717 Intermediate Similarity NPC214067
0.7717 Intermediate Similarity NPC93084
0.7717 Intermediate Similarity NPC251854
0.7717 Intermediate Similarity NPC196246
0.7698 Intermediate Similarity NPC82712
0.7698 Intermediate Similarity NPC147561
0.7674 Intermediate Similarity NPC128368
0.7671 Intermediate Similarity NPC95449
0.7667 Intermediate Similarity NPC472398
0.7661 Intermediate Similarity NPC474365
0.7661 Intermediate Similarity NPC301943
0.7651 Intermediate Similarity NPC473403
0.7643 Intermediate Similarity NPC72915
0.7638 Intermediate Similarity NPC265407
0.7638 Intermediate Similarity NPC83628
0.7638 Intermediate Similarity NPC17417
0.7638 Intermediate Similarity NPC10251
0.7634 Intermediate Similarity NPC149691
0.7616 Intermediate Similarity NPC233581
0.7616 Intermediate Similarity NPC145649
0.7609 Intermediate Similarity NPC169913
0.7603 Intermediate Similarity NPC182869
0.76 Intermediate Similarity NPC254558
0.7591 Intermediate Similarity NPC246166
0.7582 Intermediate Similarity NPC11410
0.7571 Intermediate Similarity NPC473247
0.7571 Intermediate Similarity NPC471832
0.7568 Intermediate Similarity NPC478264
0.7568 Intermediate Similarity NPC127857
0.7559 Intermediate Similarity NPC56493
0.7554 Intermediate Similarity NPC115797
0.7554 Intermediate Similarity NPC51448
0.7551 Intermediate Similarity NPC477894
0.755 Intermediate Similarity NPC471103
0.755 Intermediate Similarity NPC51602
0.755 Intermediate Similarity NPC161955
0.7536 Intermediate Similarity NPC121272
0.7536 Intermediate Similarity NPC275576
0.7534 Intermediate Similarity NPC282973
0.7519 Intermediate Similarity NPC94425
0.7518 Intermediate Similarity NPC469519
0.7517 Intermediate Similarity NPC9905
0.7517 Intermediate Similarity NPC478263
0.7516 Intermediate Similarity NPC251139
0.75 Intermediate Similarity NPC470231
0.75 Intermediate Similarity NPC226093
0.7484 Intermediate Similarity NPC161151
0.7484 Intermediate Similarity NPC159692
0.7483 Intermediate Similarity NPC48929
0.7483 Intermediate Similarity NPC471911
0.7483 Intermediate Similarity NPC4242
0.7483 Intermediate Similarity NPC474608
0.7482 Intermediate Similarity NPC51292
0.7481 Intermediate Similarity NPC153053
0.748 Intermediate Similarity NPC119271
0.7467 Intermediate Similarity NPC132652
0.7466 Intermediate Similarity NPC87934
0.7466 Intermediate Similarity NPC162613
0.7465 Intermediate Similarity NPC475569
0.7465 Intermediate Similarity NPC125153
0.7465 Intermediate Similarity NPC472394
0.7465 Intermediate Similarity NPC469499
0.7464 Intermediate Similarity NPC295664
0.7448 Intermediate Similarity NPC184109
0.7448 Intermediate Similarity NPC475373
0.7442 Intermediate Similarity NPC174099
0.7434 Intermediate Similarity NPC306799
0.7434 Intermediate Similarity NPC101043
0.7431 Intermediate Similarity NPC477893
0.7431 Intermediate Similarity NPC291638
0.7431 Intermediate Similarity NPC477896
0.7431 Intermediate Similarity NPC17877
0.7431 Intermediate Similarity NPC66761
0.7431 Intermediate Similarity NPC472577
0.7431 Intermediate Similarity NPC195647
0.7421 Intermediate Similarity NPC477491
0.7419 Intermediate Similarity NPC325497
0.7419 Intermediate Similarity NPC146351

  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 NPC477360 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
0.831 Intermediate Similarity NPD7236 Approved
0.8027 Intermediate Similarity NPD7239 Suspended
0.7795 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD2182 Approved
0.7548 Intermediate Similarity NPD7058 Phase 2
0.7548 Intermediate Similarity NPD7057 Phase 3
0.7442 Intermediate Similarity NPD2067 Discontinued
0.7426 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD164 Approved
0.7293 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7799 Discontinued
0.7226 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7961 Discontinued
0.7143 Intermediate Similarity NPD7094 Approved
0.7143 Intermediate Similarity NPD6858 Approved
0.7122 Intermediate Similarity NPD6287 Discontinued
0.7113 Intermediate Similarity NPD6085 Phase 2
0.7113 Intermediate Similarity NPD5740 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD6685 Approved
0.7068 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD1238 Approved
0.6977 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6966 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2629 Approved
0.6861 Remote Similarity NPD4198 Discontinued
0.6846 Remote Similarity NPD6647 Phase 2
0.6846 Remote Similarity NPD5765 Approved
0.6842 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6755 Remote Similarity NPD7305 Phase 1
0.6752 Remote Similarity NPD6273 Approved
0.6736 Remote Similarity NPD1876 Approved
0.6735 Remote Similarity NPD7008 Discontinued
0.6713 Remote Similarity NPD3972 Approved
0.671 Remote Similarity NPD3887 Approved
0.6691 Remote Similarity NPD6912 Phase 3
0.669 Remote Similarity NPD6362 Approved
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6002 Phase 3
0.6667 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6764 Approved
0.6667 Remote Similarity NPD1237 Approved
0.6667 Remote Similarity NPD7685 Pre-registration
0.6667 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6005 Phase 3
0.6667 Remote Similarity NPD6004 Phase 3
0.6667 Remote Similarity NPD6765 Approved
0.6645 Remote Similarity NPD4628 Phase 3
0.6623 Remote Similarity NPD6653 Approved
0.6621 Remote Similarity NPD5667 Approved
0.6596 Remote Similarity NPD7741 Discontinued
0.6596 Remote Similarity NPD9545 Approved
0.6591 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6591 Remote Similarity NPD1930 Approved
0.6591 Remote Similarity NPD1929 Approved
0.6584 Remote Similarity NPD6599 Discontinued
0.6579 Remote Similarity NPD2569 Approved
0.6579 Remote Similarity NPD2567 Approved
0.6571 Remote Similarity NPD8424 Clinical (unspecified phase)
0.657 Remote Similarity NPD8368 Discontinued
0.6564 Remote Similarity NPD5761 Phase 2
0.6564 Remote Similarity NPD5760 Phase 2
0.6558 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6554 Remote Similarity NPD6832 Phase 2
0.6554 Remote Similarity NPD7055 Discontinued
0.6552 Remote Similarity NPD8407 Phase 2
0.6549 Remote Similarity NPD5585 Approved
0.6547 Remote Similarity NPD4766 Approved
0.6547 Remote Similarity NPD5951 Approved
0.6533 Remote Similarity NPD6663 Approved
0.6533 Remote Similarity NPD7713 Phase 3
0.6531 Remote Similarity NPD5647 Approved
0.6514 Remote Similarity NPD6784 Approved
0.6514 Remote Similarity NPD6785 Approved
0.6506 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6494 Remote Similarity NPD7137 Phase 2
0.6489 Remote Similarity NPD2066 Phase 3
0.6486 Remote Similarity NPD5736 Approved
0.6484 Remote Similarity NPD1202 Approved
0.6483 Remote Similarity NPD6637 Approved
0.6479 Remote Similarity NPD7009 Phase 2
0.6467 Remote Similarity NPD3764 Approved
0.6463 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6452 Remote Similarity NPD9257 Approved
0.6452 Remote Similarity NPD9259 Approved
0.6452 Remote Similarity NPD2353 Approved
0.6452 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6434 Remote Similarity NPD1693 Approved
0.6429 Remote Similarity NPD2799 Discontinued
0.6424 Remote Similarity NPD8032 Phase 2
0.642 Remote Similarity NPD7458 Discontinued
0.6418 Remote Similarity NPD5909 Discontinued
0.6415 Remote Similarity NPD6799 Approved
0.6414 Remote Similarity NPD4806 Approved
0.6414 Remote Similarity NPD4807 Approved
0.6412 Remote Similarity NPD9495 Approved
0.6408 Remote Similarity NPD7610 Discontinued
0.64 Remote Similarity NPD6039 Approved
0.6395 Remote Similarity NPD2199 Approved
0.6395 Remote Similarity NPD2198 Approved
0.6389 Remote Similarity NPD5306 Approved
0.6389 Remote Similarity NPD5305 Approved
0.6385 Remote Similarity NPD1989 Approved
0.6384 Remote Similarity NPD8434 Phase 2
0.6378 Remote Similarity NPD3673 Approved
0.6378 Remote Similarity NPD3672 Approved
0.6377 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6376 Remote Similarity NPD3662 Phase 3
0.6376 Remote Similarity NPD3664 Approved
0.6376 Remote Similarity NPD3661 Approved
0.6376 Remote Similarity NPD3663 Approved
0.6358 Remote Similarity NPD2313 Discontinued
0.6357 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6357 Remote Similarity NPD2652 Approved
0.6357 Remote Similarity NPD2650 Approved
0.6351 Remote Similarity NPD3267 Approved
0.6351 Remote Similarity NPD3266 Approved
0.6347 Remote Similarity NPD7075 Discontinued
0.6346 Remote Similarity NPD1471 Phase 3
0.6346 Remote Similarity NPD5762 Approved
0.6346 Remote Similarity NPD5763 Approved
0.634 Remote Similarity NPD230 Phase 1
0.6338 Remote Similarity NPD9493 Approved
0.6338 Remote Similarity NPD4230 Clinical (unspecified phase)
0.6331 Remote Similarity NPD969 Suspended
0.6327 Remote Similarity NPD4359 Approved
0.6313 Remote Similarity NPD8435 Approved
0.6309 Remote Similarity NPD2798 Approved
0.6309 Remote Similarity NPD1019 Discontinued
0.6309 Remote Similarity NPD2788 Approved
0.6304 Remote Similarity NPD4234 Approved
0.6304 Remote Similarity NPD4233 Approved
0.6289 Remote Similarity NPD2354 Approved
0.6289 Remote Similarity NPD6190 Approved
0.6282 Remote Similarity NPD2796 Approved
0.6279 Remote Similarity NPD1088 Approved
0.6276 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6276 Remote Similarity NPD17 Approved
0.6275 Remote Similarity NPD4307 Phase 2
0.6273 Remote Similarity NPD7004 Clinical (unspecified phase)
0.627 Remote Similarity NPD1087 Approved
0.6269 Remote Similarity NPD1932 Approved
0.6266 Remote Similarity NPD7421 Clinical (unspecified phase)
0.625 Remote Similarity NPD9258 Approved
0.625 Remote Similarity NPD9256 Approved
0.625 Remote Similarity NPD3268 Approved
0.6242 Remote Similarity NPD2346 Discontinued
0.6241 Remote Similarity NPD6010 Discontinued
0.6241 Remote Similarity NPD7798 Approved
0.6241 Remote Similarity NPD1241 Discontinued
0.6236 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6234 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6233 Remote Similarity NPD4135 Approved
0.6233 Remote Similarity NPD4136 Approved
0.6233 Remote Similarity NPD4106 Approved
0.6232 Remote Similarity NPD2329 Discontinued
0.6226 Remote Similarity NPD8166 Discontinued
0.6222 Remote Similarity NPD8361 Approved
0.6222 Remote Similarity NPD8360 Approved
0.6209 Remote Similarity NPD4870 Approved
0.6209 Remote Similarity NPD6233 Phase 2
0.6207 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6205 Remote Similarity NPD6801 Discontinued
0.6204 Remote Similarity NPD3134 Approved
0.6196 Remote Similarity NPD7606 Phase 3
0.6196 Remote Similarity NPD920 Approved
0.6194 Remote Similarity NPD3528 Clinical (unspecified phase)
0.619 Remote Similarity NPD1547 Clinical (unspecified phase)
0.619 Remote Similarity NPD518 Clinical (unspecified phase)
0.6187 Remote Similarity NPD5237 Approved
0.6187 Remote Similarity NPD1317 Discontinued
0.6187 Remote Similarity NPD5235 Approved
0.6187 Remote Similarity NPD5236 Approved
0.6187 Remote Similarity NPD5240 Approved
0.6187 Remote Similarity NPD5239 Approved
0.6184 Remote Similarity NPD7095 Approved
0.6184 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6178 Remote Similarity NPD2935 Discontinued
0.6173 Remote Similarity NPD2534 Approved
0.6173 Remote Similarity NPD2533 Approved
0.6173 Remote Similarity NPD2532 Approved
0.6169 Remote Similarity NPD2979 Phase 3
0.6169 Remote Similarity NPD4140 Approved
0.6168 Remote Similarity NPD7819 Suspended
0.6159 Remote Similarity NPD7084 Phase 3
0.6159 Remote Similarity NPD6881 Approved
0.6159 Remote Similarity NPD5204 Approved
0.6159 Remote Similarity NPD6899 Approved
0.6149 Remote Similarity NPD9717 Approved
0.6149 Remote Similarity NPD1608 Approved
0.6144 Remote Similarity NPD6798 Discontinued
0.6143 Remote Similarity NPD2201 Approved
0.6143 Remote Similarity NPD6649 Approved
0.6143 Remote Similarity NPD6650 Approved
0.614 Remote Similarity NPD8127 Discontinued
0.6139 Remote Similarity NPD7611 Approved
0.6133 Remote Similarity NPD2797 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