Structure

Physi-Chem Properties

Molecular Weight:  762.3
Volume:  762.89
LogP:  2.687
LogD:  1.34
LogS:  -3.973
# Rotatable Bonds:  14
TPSA:  200.65
# H-Bond Aceptor:  15
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.207
Synthetic Accessibility Score:  5.8
Fsp3:  0.475
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:  -5.346
MDCK Permeability:  0.00011507223098305985
Pgp-inhibitor:  1.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.33
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.142
Plasma Protein Binding (PPB):  72.0644760131836%
Volume Distribution (VD):  1.815
Pgp-substrate:  19.32352638244629%

ADMET: Metabolism

CYP1A2-inhibitor:  0.039
CYP1A2-substrate:  0.035
CYP2C19-inhibitor:  0.268
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.89
CYP2C9-substrate:  0.039
CYP2D6-inhibitor:  0.031
CYP2D6-substrate:  0.024
CYP3A4-inhibitor:  0.938
CYP3A4-substrate:  0.424

ADMET: Excretion

Clearance (CL):  3.049
Half-life (T1/2):  0.857

ADMET: Toxicity

hERG Blockers:  0.183
Human Hepatotoxicity (H-HT):  0.985
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.44
Maximum Recommended Daily Dose:  0.043
Skin Sensitization:  0.202
Carcinogencity:  0.036
Eye Corrosion:  0.004
Eye Irritation:  0.125
Respiratory Toxicity:  0.039

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

  Natural Product: NPC319556

Natural Product ID:  NPC319556
Common Name*:   Esulatin K
IUPAC Name:   [(1R,2R,3aR,5R,6E,9R,11R,13R,13aS)-1,3a,11,13-tetraacetyloxy-2,5,8,8-tetramethyl-12-methylidene-4-oxo-2-(pyridine-3-carbonyloxy)-1,3,5,9,10,11,13,13a-octahydrocyclopenta[12]annulen-9-yl] pyridine-3-carboxylate
Synonyms:   Esulatin K
Standard InCHIKey:  JNESAYNUYICKCH-WVMGMPMTSA-N
Standard InCHI:  InChI=1S/C40H46N2O13/c1-22-14-15-38(7,8)31(53-36(48)28-12-10-16-41-19-28)18-30(50-24(3)43)23(2)33(51-25(4)44)32-35(52-26(5)45)39(9,21-40(32,34(22)47)54-27(6)46)55-37(49)29-13-11-17-42-20-29/h10-17,19-20,22,30-33,35H,2,18,21H2,1,3-9H3/b15-14+/t22-,30-,31-,32+,33+,35-,39-,40-/m1/s1
SMILES:  CC1C=CC(C(CC(C(=C)C(C2C(C(CC2(C1=O)OC(=O)C)(C)OC(=O)C3=CN=CC=C3)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C4=CN=CC=C4)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1811926
PubChem CID:   53359849
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
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21612217]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21612217]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[27447736]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[32233482]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3099 Euphorbia esula Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3099 Euphorbia esula 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
NPT165 Cell Line HeLa Homo sapiens GI = 0.5 % PMID[559315]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 7.5 % PMID[559315]
NPT83 Cell Line MCF7 Homo sapiens GI = 1.3 % PMID[559315]
NPT165 Cell Line HeLa Homo sapiens GI = 0.6 % PMID[559315]
NPT2738 Cell Line Ishikawa Homo sapiens GI = 0.1 % PMID[559315]
NPT83 Cell Line MCF7 Homo sapiens GI = 21.3 % PMID[559315]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 7.2 n.a. PMID[559315]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 19.8 n.a. PMID[559315]

☑ 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 NPC319556 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
0.9896 High Similarity NPC207531
0.9689 High Similarity NPC40919
0.9689 High Similarity NPC470189
0.9534 High Similarity NPC470190
0.9495 High Similarity NPC187494
0.9216 High Similarity NPC233727
0.92 High Similarity NPC193361
0.92 High Similarity NPC62844
0.9196 High Similarity NPC165837
0.9146 High Similarity NPC476467
0.91 High Similarity NPC41724
0.91 High Similarity NPC51008
0.905 High Similarity NPC280473
0.905 High Similarity NPC323551
0.8952 High Similarity NPC213143
0.89 High Similarity NPC311196
0.89 High Similarity NPC134384
0.8852 High Similarity NPC14116
0.8852 High Similarity NPC285411
0.8821 High Similarity NPC238278
0.8806 High Similarity NPC472752
0.8667 High Similarity NPC26881
0.8571 High Similarity NPC235364
0.8565 High Similarity NPC477901
0.8505 High Similarity NPC91125
0.8498 Intermediate Similarity NPC475601
0.8491 Intermediate Similarity NPC477900
0.8491 Intermediate Similarity NPC477899
0.8483 Intermediate Similarity NPC477911
0.8465 Intermediate Similarity NPC477906
0.8465 Intermediate Similarity NPC96801
0.8465 Intermediate Similarity NPC150698
0.8429 Intermediate Similarity NPC472555
0.8413 Intermediate Similarity NPC264674
0.8413 Intermediate Similarity NPC4421
0.8404 Intermediate Similarity NPC328154
0.8349 Intermediate Similarity NPC477903
0.8349 Intermediate Similarity NPC477912
0.8333 Intermediate Similarity NPC477908
0.8333 Intermediate Similarity NPC206343
0.8326 Intermediate Similarity NPC124029
0.8326 Intermediate Similarity NPC211920
0.8325 Intermediate Similarity NPC319128
0.8325 Intermediate Similarity NPC228331
0.8294 Intermediate Similarity NPC6576
0.8294 Intermediate Similarity NPC62367
0.8294 Intermediate Similarity NPC212768
0.8294 Intermediate Similarity NPC473115
0.8294 Intermediate Similarity NPC75600
0.8294 Intermediate Similarity NPC473089
0.8294 Intermediate Similarity NPC158020
0.8279 Intermediate Similarity NPC148860
0.8265 Intermediate Similarity NPC35208
0.8257 Intermediate Similarity NPC469748
0.8255 Intermediate Similarity NPC84815
0.8255 Intermediate Similarity NPC216428
0.8255 Intermediate Similarity NPC301368
0.8246 Intermediate Similarity NPC471016
0.8244 Intermediate Similarity NPC289086
0.8233 Intermediate Similarity NPC477902
0.823 Intermediate Similarity NPC472553
0.8199 Intermediate Similarity NPC470306
0.8199 Intermediate Similarity NPC477909
0.8199 Intermediate Similarity NPC477907
0.8199 Intermediate Similarity NPC42678
0.8199 Intermediate Similarity NPC477910
0.8198 Intermediate Similarity NPC253482
0.816 Intermediate Similarity NPC6981
0.816 Intermediate Similarity NPC471014
0.816 Intermediate Similarity NPC475408
0.814 Intermediate Similarity NPC127720
0.814 Intermediate Similarity NPC127026
0.814 Intermediate Similarity NPC477788
0.8122 Intermediate Similarity NPC144779
0.8122 Intermediate Similarity NPC294579
0.8102 Intermediate Similarity NPC471980
0.81 Intermediate Similarity NPC327769
0.8091 Intermediate Similarity NPC319880
0.8091 Intermediate Similarity NPC244839
0.8091 Intermediate Similarity NPC320324
0.8089 Intermediate Similarity NPC475648
0.8086 Intermediate Similarity NPC48042
0.8086 Intermediate Similarity NPC472550
0.8086 Intermediate Similarity NPC304179
0.8073 Intermediate Similarity NPC146824
0.8054 Intermediate Similarity NPC237702
0.8045 Intermediate Similarity NPC292416
0.8045 Intermediate Similarity NPC473689
0.8037 Intermediate Similarity NPC475362
0.8018 Intermediate Similarity NPC57797
0.8018 Intermediate Similarity NPC250807
0.8018 Intermediate Similarity NPC76565
0.7991 Intermediate Similarity NPC475600
0.7991 Intermediate Similarity NPC122968
0.7991 Intermediate Similarity NPC476110
0.7991 Intermediate Similarity NPC477787
0.7991 Intermediate Similarity NPC475631
0.7991 Intermediate Similarity NPC87152
0.7991 Intermediate Similarity NPC328186
0.7991 Intermediate Similarity NPC228377
0.7982 Intermediate Similarity NPC327904
0.7982 Intermediate Similarity NPC475137
0.7982 Intermediate Similarity NPC475498
0.7982 Intermediate Similarity NPC473850
0.7982 Intermediate Similarity NPC38959
0.7955 Intermediate Similarity NPC475644
0.7955 Intermediate Similarity NPC471190
0.7955 Intermediate Similarity NPC471977
0.7955 Intermediate Similarity NPC470486
0.7952 Intermediate Similarity NPC63041
0.7937 Intermediate Similarity NPC475426
0.7937 Intermediate Similarity NPC475406
0.7904 Intermediate Similarity NPC324619
0.7904 Intermediate Similarity NPC475315
0.7883 Intermediate Similarity NPC475303
0.7883 Intermediate Similarity NPC475596
0.7883 Intermediate Similarity NPC316841
0.7864 Intermediate Similarity NPC473506
0.786 Intermediate Similarity NPC475533
0.7848 Intermediate Similarity NPC30456
0.7804 Intermediate Similarity NPC292517
0.7788 Intermediate Similarity NPC470279
0.7778 Intermediate Similarity NPC170751
0.7778 Intermediate Similarity NPC30570
0.7773 Intermediate Similarity NPC309498
0.7731 Intermediate Similarity NPC328928
0.7722 Intermediate Similarity NPC473833
0.7702 Intermediate Similarity NPC53255
0.7702 Intermediate Similarity NPC326930
0.7702 Intermediate Similarity NPC475301
0.7702 Intermediate Similarity NPC85879
0.7669 Intermediate Similarity NPC13603
0.766 Intermediate Similarity NPC471015
0.7608 Intermediate Similarity NPC324245
0.7608 Intermediate Similarity NPC320748
0.7585 Intermediate Similarity NPC103230
0.7583 Intermediate Similarity NPC32451
0.7583 Intermediate Similarity NPC328559
0.758 Intermediate Similarity NPC162812
0.757 Intermediate Similarity NPC475835
0.7536 Intermediate Similarity NPC79223
0.7533 Intermediate Similarity NPC471004
0.7511 Intermediate Similarity NPC148896
0.7511 Intermediate Similarity NPC180668
0.7511 Intermediate Similarity NPC471013
0.7477 Intermediate Similarity NPC111732
0.7476 Intermediate Similarity NPC329024
0.7464 Intermediate Similarity NPC135950
0.7438 Intermediate Similarity NPC471978
0.7437 Intermediate Similarity NPC249614
0.7436 Intermediate Similarity NPC476090
0.7407 Intermediate Similarity NPC156044
0.7406 Intermediate Similarity NPC103361
0.7406 Intermediate Similarity NPC123395
0.7384 Intermediate Similarity NPC10904
0.7358 Intermediate Similarity NPC107287
0.7358 Intermediate Similarity NPC59033
0.7358 Intermediate Similarity NPC317672
0.7347 Intermediate Similarity NPC471979
0.7346 Intermediate Similarity NPC109922
0.7315 Intermediate Similarity NPC25442
0.7315 Intermediate Similarity NPC12944
0.7308 Intermediate Similarity NPC44354
0.7256 Intermediate Similarity NPC155792
0.7228 Intermediate Similarity NPC191310
0.7162 Intermediate Similarity NPC318299
0.7156 Intermediate Similarity NPC314270
0.715 Intermediate Similarity NPC112741
0.7136 Intermediate Similarity NPC317010
0.713 Intermediate Similarity NPC317752
0.7123 Intermediate Similarity NPC471546
0.7045 Intermediate Similarity NPC238457
0.7028 Intermediate Similarity NPC469489
0.7017 Intermediate Similarity NPC37473
0.7014 Intermediate Similarity NPC325775
0.7014 Intermediate Similarity NPC328798
0.7004 Intermediate Similarity NPC141385
0.7 Intermediate Similarity NPC282103
0.6995 Remote Similarity NPC114974
0.6986 Remote Similarity NPC327373
0.6971 Remote Similarity NPC471997
0.6952 Remote Similarity NPC207851
0.6927 Remote Similarity NPC50997
0.6927 Remote Similarity NPC160127
0.6923 Remote Similarity NPC164340
0.692 Remote Similarity NPC314834
0.6913 Remote Similarity NPC253314
0.6886 Remote Similarity NPC249428
0.6881 Remote Similarity NPC149708
0.6875 Remote Similarity NPC472070
0.6872 Remote Similarity NPC46895
0.6847 Remote Similarity NPC327592
0.6844 Remote Similarity NPC123839
0.6837 Remote Similarity NPC138370
0.6837 Remote Similarity NPC127647
0.6833 Remote Similarity NPC143977
0.6831 Remote Similarity NPC107123
0.683 Remote Similarity NPC470280
0.6828 Remote Similarity NPC234078
0.6828 Remote Similarity NPC221100

  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 NPC319556 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
0.8238 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7396 Approved
0.7513 Intermediate Similarity NPD820 Phase 3
0.7331 Intermediate Similarity NPD8468 Phase 2
0.7265 Intermediate Similarity NPD7885 Phase 2
0.7265 Intermediate Similarity NPD7886 Phase 2
0.722 Intermediate Similarity NPD3389 Approved
0.722 Intermediate Similarity NPD3394 Approved
0.722 Intermediate Similarity NPD3393 Approved
0.7188 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8326 Phase 3
0.7188 Intermediate Similarity NPD8325 Phase 3
0.7156 Intermediate Similarity NPD2831 Approved
0.7156 Intermediate Similarity NPD3947 Discontinued
0.715 Intermediate Similarity NPD9271 Approved
0.7136 Intermediate Similarity NPD2510 Approved
0.7136 Intermediate Similarity NPD2509 Approved
0.7104 Intermediate Similarity NPD4506 Discontinued
0.71 Intermediate Similarity NPD5088 Discontinued
0.7094 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD1270 Approved
0.7056 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD3794 Approved
0.7054 Intermediate Similarity NPD3795 Approved
0.704 Intermediate Similarity NPD4417 Approved
0.7032 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6529 Discontinued
0.692 Remote Similarity NPD5891 Approved
0.69 Remote Similarity NPD6770 Approved
0.6892 Remote Similarity NPD7010 Phase 3
0.6886 Remote Similarity NPD4989 Phase 2
0.687 Remote Similarity NPD8479 Phase 2
0.6858 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6847 Remote Similarity NPD6635 Approved
0.684 Remote Similarity NPD4301 Approved
0.6839 Remote Similarity NPD107 Approved
0.6804 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6797 Remote Similarity NPD3280 Approved
0.6791 Remote Similarity NPD8063 Discontinued
0.678 Remote Similarity NPD4952 Phase 3
0.6777 Remote Similarity NPD1483 Discontinued
0.6748 Remote Similarity NPD6525 Clinical (unspecified phase)
0.674 Remote Similarity NPD5475 Discontinued
0.674 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6725 Remote Similarity NPD7707 Approved
0.6723 Remote Similarity NPD5640 Discontinued
0.6714 Remote Similarity NPD6642 Approved
0.6714 Remote Similarity NPD6641 Approved
0.6712 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6711 Remote Similarity NPD3371 Approved
0.6709 Remote Similarity NPD8052 Clinical (unspecified phase)
0.6708 Remote Similarity NPD3006 Discontinued
0.6701 Remote Similarity NPD9075 Approved
0.6701 Remote Similarity NPD9074 Approved
0.6695 Remote Similarity NPD4373 Phase 2
0.6682 Remote Similarity NPD2336 Approved
0.668 Remote Similarity NPD8409 Suspended
0.6667 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6652 Remote Similarity NPD7777 Approved
0.6652 Remote Similarity NPD7778 Approved
0.6652 Remote Similarity NPD53 Approved
0.665 Remote Similarity NPD2581 Approved
0.665 Remote Similarity NPD2582 Approved
0.664 Remote Similarity NPD8350 Clinical (unspecified phase)
0.6638 Remote Similarity NPD7878 Phase 2
0.6635 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6622 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6622 Remote Similarity NPD6987 Phase 1
0.6618 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6614 Remote Similarity NPD8373 Clinical (unspecified phase)
0.6611 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6609 Remote Similarity NPD7404 Approved
0.6607 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6601 Remote Similarity NPD7708 Approved
0.66 Remote Similarity NPD8370 Discontinued
0.6592 Remote Similarity NPD4500 Approved
0.6592 Remote Similarity NPD4501 Approved
0.659 Remote Similarity NPD7233 Approved
0.659 Remote Similarity NPD7234 Approved
0.6585 Remote Similarity NPD2511 Approved
0.6582 Remote Similarity NPD8289 Discontinued
0.6575 Remote Similarity NPD4376 Phase 3
0.6562 Remote Similarity NPD7803 Approved
0.6561 Remote Similarity NPD2307 Discontinued
0.6552 Remote Similarity NPD8160 Phase 2
0.6546 Remote Similarity NPD5482 Discontinued
0.6545 Remote Similarity NPD4529 Approved
0.6545 Remote Similarity NPD4528 Approved
0.6545 Remote Similarity NPD4526 Approved
0.6544 Remote Similarity NPD8021 Approved
0.6544 Remote Similarity NPD8020 Approved
0.6525 Remote Similarity NPD8356 Approved
0.6518 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6516 Remote Similarity NPD4427 Phase 2
0.6511 Remote Similarity NPD1996 Discontinued
0.6506 Remote Similarity NPD4369 Phase 2
0.6504 Remote Similarity NPD6176 Phase 1
0.65 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6494 Remote Similarity NPD7069 Discontinued
0.6476 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6962 Phase 2
0.6468 Remote Similarity NPD6257 Clinical (unspecified phase)
0.646 Remote Similarity NPD6477 Clinical (unspecified phase)
0.6459 Remote Similarity NPD6446 Discontinued
0.6453 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6452 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4889 Approved
0.645 Remote Similarity NPD7470 Discontinued
0.6449 Remote Similarity NPD6825 Phase 1
0.6447 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6447 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6425 Remote Similarity NPD6665 Discontinued
0.6423 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6417 Remote Similarity NPD4086 Phase 1
0.6417 Remote Similarity NPD8430 Approved
0.6414 Remote Similarity NPD6298 Discontinued
0.6413 Remote Similarity NPD6226 Phase 3
0.6407 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6407 Remote Similarity NPD6262 Clinical (unspecified phase)
0.6405 Remote Similarity NPD7688 Phase 1
0.6402 Remote Similarity NPD3925 Approved
0.6402 Remote Similarity NPD1032 Phase 2
0.6402 Remote Similarity NPD3217 Phase 2
0.64 Remote Similarity NPD6276 Discontinued
0.64 Remote Similarity NPD751 Clinical (unspecified phase)
0.6398 Remote Similarity NPD6955 Clinical (unspecified phase)
0.6397 Remote Similarity NPD6790 Phase 1
0.6396 Remote Similarity NPD2896 Discontinued
0.6393 Remote Similarity NPD4948 Discontinued
0.6392 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6392 Remote Similarity NPD8091 Phase 3
0.6391 Remote Similarity NPD7467 Discontinued
0.6389 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6385 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6376 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6372 Remote Similarity NPD5228 Phase 3
0.6372 Remote Similarity NPD6479 Discontinued
0.6372 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6367 Remote Similarity NPD7955 Approved
0.6367 Remote Similarity NPD7956 Approved
0.6364 Remote Similarity NPD5022 Discontinued
0.6364 Remote Similarity NPD4804 Approved
0.636 Remote Similarity NPD5513 Phase 2
0.6356 Remote Similarity NPD1623 Approved
0.6356 Remote Similarity NPD1926 Approved
0.6356 Remote Similarity NPD4429 Discontinued
0.6352 Remote Similarity NPD5866 Approved
0.6348 Remote Similarity NPD7562 Approved
0.6341 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6341 Remote Similarity NPD180 Clinical (unspecified phase)
0.6332 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6332 Remote Similarity NPD5901 Discontinued
0.6325 Remote Similarity NPD5888 Phase 2
0.632 Remote Similarity NPD8423 Phase 2
0.632 Remote Similarity NPD8399 Phase 1
0.6313 Remote Similarity NPD3178 Discontinued
0.6308 Remote Similarity NPD5450 Discontinued
0.6304 Remote Similarity NPD7001 Phase 3
0.63 Remote Similarity NPD4805 Approved
0.6298 Remote Similarity NPD1630 Approved
0.6298 Remote Similarity NPD5293 Phase 2
0.6295 Remote Similarity NPD8375 Approved
0.629 Remote Similarity NPD6068 Discontinued
0.628 Remote Similarity NPD6026 Approved
0.6276 Remote Similarity NPD4923 Phase 1
0.6274 Remote Similarity NPD1343 Approved
0.6274 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6273 Remote Similarity NPD4375 Approved
0.6273 Remote Similarity NPD5444 Phase 1
0.6271 Remote Similarity NPD5490 Discontinued
0.6266 Remote Similarity NPD5072 Discontinued
0.6266 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6262 Remote Similarity NPD2077 Approved
0.6262 Remote Similarity NPD2076 Approved
0.6261 Remote Similarity NPD4499 Approved
0.626 Remote Similarity NPD8329 Phase 3
0.6256 Remote Similarity NPD1096 Discontinued
0.6255 Remote Similarity NPD7967 Discontinued
0.625 Remote Similarity NPD1173 Approved
0.625 Remote Similarity NPD6361 Phase 2
0.6245 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6244 Remote Similarity NPD6791 Phase 2
0.624 Remote Similarity NPD7426 Phase 1
0.6239 Remote Similarity NPD3386 Phase 2
0.6239 Remote Similarity NPD8485 Approved
0.6239 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6234 Remote Similarity NPD6242 Discontinued
0.6232 Remote Similarity NPD2809 Approved
0.6231 Remote Similarity NPD203 Clinical (unspecified phase)
0.623 Remote Similarity NPD8100 Phase 3
0.6229 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6227 Remote Similarity NPD6241 Phase 1
0.6223 Remote Similarity NPD5583 Clinical (unspecified phase)
0.622 Remote Similarity NPD6741 Clinical (unspecified phase)
0.622 Remote Similarity NPD5255 Approved
0.6218 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6215 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6213 Remote Similarity NPD8097 Phase 3
0.6213 Remote Similarity NPD8096 Phase 3
0.6211 Remote Similarity NPD4926 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