Structure

Physi-Chem Properties

Molecular Weight:  482.17
Volume:  456.6
LogP:  5.773
LogD:  5.43
LogS:  -6.669
# Rotatable Bonds:  10
TPSA:  61.83
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.421
Synthetic Accessibility Score:  3.919
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.761
MDCK Permeability:  2.340679020562675e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.3

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  100.297607421875%
Volume Distribution (VD):  1.28
Pgp-substrate:  2.160275459289551%

ADMET: Metabolism

CYP1A2-inhibitor:  0.218
CYP1A2-substrate:  0.831
CYP2C19-inhibitor:  0.866
CYP2C19-substrate:  0.757
CYP2C9-inhibitor:  0.951
CYP2C9-substrate:  0.552
CYP2D6-inhibitor:  0.427
CYP2D6-substrate:  0.287
CYP3A4-inhibitor:  0.608
CYP3A4-substrate:  0.759

ADMET: Excretion

Clearance (CL):  1.646
Half-life (T1/2):  0.029

ADMET: Toxicity

hERG Blockers:  0.066
Human Hepatotoxicity (H-HT):  0.027
Drug-inuced Liver Injury (DILI):  0.611
AMES Toxicity:  0.022
Rat Oral Acute Toxicity:  0.017
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.172
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.838
Respiratory Toxicity:  0.029

Download Data

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

  Natural Product: NPC474777

Natural Product ID:  NPC474777
Common Name*:   Tryethylhamigeran E
IUPAC Name:   ethyl 3-bromo-2-ethoxy-6-[(1R,2R,5R)-2-ethoxycarbonyl-2-methyl-5-propan-2-ylcyclopentyl]-4-methylbenzoate
Synonyms:   Tryethylhamigeran E
Standard InCHIKey:  RVBGQZLCMIXENV-SWWFSWNPSA-N
Standard InCHI:  InChI=1S/C24H35BrO5/c1-8-28-21-18(22(26)29-9-2)17(13-15(6)20(21)25)19-16(14(4)5)11-12-24(19,7)23(27)30-10-3/h13-14,16,19H,8-12H2,1-7H3/t16-,19-,24-/m1/s1
SMILES:  CCOC(=O)c1c(OCC)c(Br)c(cc1[C@H]1[C@H](CC[C@@]1(C)C(=O)OCC)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL482248
PubChem CID:   10457985
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO2050 Hamigera tarangaensis Species Hymedesmiidae Eukaryota n.a. n.a. n.a. PMID[10650083]
NPO2050 Hamigera tarangaensis Species Hymedesmiidae Eukaryota n.a. n.a. n.a. PMID[29373034]
NPO2050 Hamigera tarangaensis Species Hymedesmiidae 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
NPT168 Cell Line P388 Mus musculus IC50 = 54200.0 nM PMID[519500]

☑ 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 NPC474777 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
0.8323 Intermediate Similarity NPC475976
0.8293 Intermediate Similarity NPC200331
0.8153 Intermediate Similarity NPC160839
0.7929 Intermediate Similarity NPC90245
0.7882 Intermediate Similarity NPC293312
0.7738 Intermediate Similarity NPC471541
0.7667 Intermediate Similarity NPC470163
0.7667 Intermediate Similarity NPC470162
0.7593 Intermediate Similarity NPC84426
0.7529 Intermediate Similarity NPC470566
0.75 Intermediate Similarity NPC470160
0.7486 Intermediate Similarity NPC470567
0.747 Intermediate Similarity NPC472298
0.7468 Intermediate Similarity NPC217914
0.7396 Intermediate Similarity NPC472799
0.7396 Intermediate Similarity NPC477669
0.7394 Intermediate Similarity NPC211565
0.7394 Intermediate Similarity NPC60389
0.7394 Intermediate Similarity NPC471346
0.7394 Intermediate Similarity NPC473927
0.7375 Intermediate Similarity NPC471542
0.7365 Intermediate Similarity NPC228906
0.7365 Intermediate Similarity NPC469416
0.7365 Intermediate Similarity NPC471348
0.7355 Intermediate Similarity NPC281499
0.7321 Intermediate Similarity NPC477676
0.731 Intermediate Similarity NPC477674
0.7305 Intermediate Similarity NPC219560
0.7278 Intermediate Similarity NPC477673
0.7278 Intermediate Similarity NPC477672
0.7273 Intermediate Similarity NPC290038
0.7273 Intermediate Similarity NPC469385
0.7262 Intermediate Similarity NPC291049
0.7262 Intermediate Similarity NPC233267
0.725 Intermediate Similarity NPC470844
0.7235 Intermediate Similarity NPC273483
0.7229 Intermediate Similarity NPC75694
0.7226 Intermediate Similarity NPC475361
0.7219 Intermediate Similarity NPC150928
0.7219 Intermediate Similarity NPC144010
0.7219 Intermediate Similarity NPC158866
0.7219 Intermediate Similarity NPC474660
0.7215 Intermediate Similarity NPC279596
0.7215 Intermediate Similarity NPC196979
0.7215 Intermediate Similarity NPC470977
0.7215 Intermediate Similarity NPC470976
0.7215 Intermediate Similarity NPC15083
0.7212 Intermediate Similarity NPC471643
0.7212 Intermediate Similarity NPC471639
0.7209 Intermediate Similarity NPC4547
0.7202 Intermediate Similarity NPC37139
0.7202 Intermediate Similarity NPC95526
0.7202 Intermediate Similarity NPC105415
0.72 Intermediate Similarity NPC472206
0.7188 Intermediate Similarity NPC209858
0.7186 Intermediate Similarity NPC470357
0.7186 Intermediate Similarity NPC224418
0.7182 Intermediate Similarity NPC295914
0.7178 Intermediate Similarity NPC476191
0.7176 Intermediate Similarity NPC133856
0.7175 Intermediate Similarity NPC125465
0.7169 Intermediate Similarity NPC189650
0.7169 Intermediate Similarity NPC56731
0.7152 Intermediate Similarity NPC471640
0.7152 Intermediate Similarity NPC183348
0.7152 Intermediate Similarity NPC473271
0.7152 Intermediate Similarity NPC471644
0.7152 Intermediate Similarity NPC329493
0.7152 Intermediate Similarity NPC282230
0.7151 Intermediate Similarity NPC149618
0.7151 Intermediate Similarity NPC477687
0.7151 Intermediate Similarity NPC477671
0.7151 Intermediate Similarity NPC3898
0.7151 Intermediate Similarity NPC89625
0.7143 Intermediate Similarity NPC125801
0.7143 Intermediate Similarity NPC469425
0.7143 Intermediate Similarity NPC137296
0.7143 Intermediate Similarity NPC8817
0.7135 Intermediate Similarity NPC24232
0.7135 Intermediate Similarity NPC271681
0.7135 Intermediate Similarity NPC471347
0.7135 Intermediate Similarity NPC471349
0.7134 Intermediate Similarity NPC125861
0.7134 Intermediate Similarity NPC196034
0.7134 Intermediate Similarity NPC165172
0.7134 Intermediate Similarity NPC477535
0.7126 Intermediate Similarity NPC239118
0.7126 Intermediate Similarity NPC477692
0.7118 Intermediate Similarity NPC473466
0.711 Intermediate Similarity NPC477675
0.7108 Intermediate Similarity NPC163948
0.7107 Intermediate Similarity NPC7012
0.7107 Intermediate Similarity NPC164295
0.7107 Intermediate Similarity NPC239134
0.7107 Intermediate Similarity NPC477412
0.7105 Intermediate Similarity NPC230951
0.7093 Intermediate Similarity NPC470102
0.7093 Intermediate Similarity NPC477691
0.7091 Intermediate Similarity NPC149780
0.7091 Intermediate Similarity NPC1704
0.7091 Intermediate Similarity NPC149533
0.7091 Intermediate Similarity NPC67650
0.7089 Intermediate Similarity NPC170546
0.7089 Intermediate Similarity NPC66246
0.7089 Intermediate Similarity NPC57552
0.7086 Intermediate Similarity NPC47623
0.7083 Intermediate Similarity NPC225173
0.7083 Intermediate Similarity NPC163846
0.7083 Intermediate Similarity NPC237208
0.7083 Intermediate Similarity NPC286038
0.7081 Intermediate Similarity NPC27394
0.7081 Intermediate Similarity NPC324117
0.7079 Intermediate Similarity NPC165460
0.7076 Intermediate Similarity NPC175617
0.7076 Intermediate Similarity NPC478148
0.7069 Intermediate Similarity NPC67197
0.7069 Intermediate Similarity NPC158542
0.7069 Intermediate Similarity NPC272196
0.7066 Intermediate Similarity NPC470932
0.7063 Intermediate Similarity NPC293253
0.7059 Intermediate Similarity NPC474305
0.7059 Intermediate Similarity NPC322569
0.7048 Intermediate Similarity NPC469579
0.7048 Intermediate Similarity NPC24075
0.7048 Intermediate Similarity NPC96692
0.7048 Intermediate Similarity NPC470273
0.7041 Intermediate Similarity NPC93666
0.7041 Intermediate Similarity NPC66991
0.7037 Intermediate Similarity NPC298900
0.7035 Intermediate Similarity NPC87708
0.7035 Intermediate Similarity NPC44606
0.7035 Intermediate Similarity NPC477690
0.7035 Intermediate Similarity NPC217447
0.703 Intermediate Similarity NPC168471
0.703 Intermediate Similarity NPC477537
0.7029 Intermediate Similarity NPC4950
0.7029 Intermediate Similarity NPC474373
0.7029 Intermediate Similarity NPC218818
0.7024 Intermediate Similarity NPC62799
0.7024 Intermediate Similarity NPC134621
0.7024 Intermediate Similarity NPC29577
0.7022 Intermediate Similarity NPC316262
0.7022 Intermediate Similarity NPC314653
0.702 Intermediate Similarity NPC217423
0.7019 Intermediate Similarity NPC477536
0.7018 Intermediate Similarity NPC119929
0.7012 Intermediate Similarity NPC307883
0.7012 Intermediate Similarity NPC233707
0.7012 Intermediate Similarity NPC233780
0.7011 Intermediate Similarity NPC305490
0.7011 Intermediate Similarity NPC146211
0.7011 Intermediate Similarity NPC469507
0.7006 Intermediate Similarity NPC472006
0.7006 Intermediate Similarity NPC51106
0.7006 Intermediate Similarity NPC159721
0.7006 Intermediate Similarity NPC473022
0.7006 Intermediate Similarity NPC474737
0.7006 Intermediate Similarity NPC144843
0.7006 Intermediate Similarity NPC471731
0.7 Intermediate Similarity NPC475848
0.7 Intermediate Similarity NPC474306
0.6994 Remote Similarity NPC232996
0.6994 Remote Similarity NPC210942
0.6994 Remote Similarity NPC307401
0.6994 Remote Similarity NPC169990
0.6994 Remote Similarity NPC21797
0.6994 Remote Similarity NPC194847
0.6989 Remote Similarity NPC143050
0.6989 Remote Similarity NPC313368
0.6988 Remote Similarity NPC470856
0.6987 Remote Similarity NPC56332
0.6983 Remote Similarity NPC472621
0.6982 Remote Similarity NPC281398
0.6981 Remote Similarity NPC131684
0.6977 Remote Similarity NPC72958
0.6977 Remote Similarity NPC232645
0.6977 Remote Similarity NPC39819
0.6977 Remote Similarity NPC149526
0.6977 Remote Similarity NPC474417
0.6977 Remote Similarity NPC473732
0.6975 Remote Similarity NPC1249
0.6974 Remote Similarity NPC171023
0.697 Remote Similarity NPC36414
0.6966 Remote Similarity NPC100849
0.6966 Remote Similarity NPC17432
0.6964 Remote Similarity NPC260152
0.6964 Remote Similarity NPC42540
0.6964 Remote Similarity NPC66404
0.6964 Remote Similarity NPC95123
0.6964 Remote Similarity NPC151607
0.6964 Remote Similarity NPC184702
0.6964 Remote Similarity NPC89664
0.6964 Remote Similarity NPC274085
0.6962 Remote Similarity NPC293387
0.6959 Remote Similarity NPC97028
0.6959 Remote Similarity NPC100985
0.6959 Remote Similarity NPC288036
0.6959 Remote Similarity NPC70764
0.6959 Remote Similarity NPC65589
0.6959 Remote Similarity NPC97029

  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 NPC474777 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
0.7329 Intermediate Similarity NPD2346 Discontinued
0.7244 Intermediate Similarity NPD6832 Phase 2
0.7229 Intermediate Similarity NPD2533 Approved
0.7229 Intermediate Similarity NPD2534 Approved
0.7229 Intermediate Similarity NPD2532 Approved
0.7151 Intermediate Similarity NPD4288 Approved
0.7107 Intermediate Similarity NPD8032 Phase 2
0.7093 Intermediate Similarity NPD7819 Suspended
0.7083 Intermediate Similarity NPD6273 Approved
0.7059 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5691 Approved
0.7019 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.6994 Remote Similarity NPD2799 Discontinued
0.6988 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6951 Remote Similarity NPD2935 Discontinued
0.6937 Remote Similarity NPD411 Approved
0.6937 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6899 Remote Similarity NPD1019 Discontinued
0.6867 Remote Similarity NPD970 Clinical (unspecified phase)
0.686 Remote Similarity NPD3226 Approved
0.6859 Remote Similarity NPD9717 Approved
0.6857 Remote Similarity NPD2296 Approved
0.6852 Remote Similarity NPD2979 Phase 3
0.6832 Remote Similarity NPD2313 Discontinued
0.6824 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6821 Remote Similarity NPD6599 Discontinued
0.6795 Remote Similarity NPD1281 Approved
0.6786 Remote Similarity NPD7003 Approved
0.6774 Remote Similarity NPD4626 Approved
0.6748 Remote Similarity NPD4307 Phase 2
0.6747 Remote Similarity NPD2438 Suspended
0.672 Remote Similarity NPD4287 Approved
0.6707 Remote Similarity NPD6002 Phase 3
0.6707 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6707 Remote Similarity NPD5763 Approved
0.6707 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6004 Phase 3
0.6707 Remote Similarity NPD5762 Approved
0.6707 Remote Similarity NPD6005 Phase 3
0.6707 Remote Similarity NPD447 Suspended
0.6707 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1283 Approved
0.6667 Remote Similarity NPD1778 Approved
0.6667 Remote Similarity NPD1876 Approved
0.6647 Remote Similarity NPD1551 Phase 2
0.6647 Remote Similarity NPD2531 Phase 2
0.6646 Remote Similarity NPD4140 Approved
0.663 Remote Similarity NPD5710 Approved
0.663 Remote Similarity NPD5711 Approved
0.6629 Remote Similarity NPD7768 Phase 2
0.6627 Remote Similarity NPD1243 Approved
0.6625 Remote Similarity NPD3267 Approved
0.6625 Remote Similarity NPD2797 Approved
0.6625 Remote Similarity NPD3266 Approved
0.6625 Remote Similarity NPD1203 Approved
0.6612 Remote Similarity NPD7473 Discontinued
0.661 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6606 Remote Similarity NPD6355 Discontinued
0.6606 Remote Similarity NPD1933 Approved
0.6604 Remote Similarity NPD5327 Phase 3
0.6603 Remote Similarity NPD5585 Approved
0.6588 Remote Similarity NPD4628 Phase 3
0.6587 Remote Similarity NPD3748 Approved
0.6587 Remote Similarity NPD4308 Phase 3
0.6584 Remote Similarity NPD2798 Approved
0.6582 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6582 Remote Similarity NPD1611 Approved
0.6581 Remote Similarity NPD7644 Approved
0.6575 Remote Similarity NPD6959 Discontinued
0.6575 Remote Similarity NPD8127 Discontinued
0.6571 Remote Similarity NPD7458 Discontinued
0.6561 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6556 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6552 Remote Similarity NPD920 Approved
0.6548 Remote Similarity NPD6099 Approved
0.6548 Remote Similarity NPD6100 Approved
0.6548 Remote Similarity NPD2796 Approved
0.6543 Remote Similarity NPD8313 Approved
0.6543 Remote Similarity NPD8312 Approved
0.6538 Remote Similarity NPD6232 Discontinued
0.6529 Remote Similarity NPD2800 Approved
0.6524 Remote Similarity NPD3268 Approved
0.6524 Remote Similarity NPD7985 Registered
0.6519 Remote Similarity NPD5494 Approved
0.6519 Remote Similarity NPD3496 Discontinued
0.6512 Remote Similarity NPD643 Clinical (unspecified phase)
0.6509 Remote Similarity NPD1471 Phase 3
0.65 Remote Similarity NPD7075 Discontinued
0.6497 Remote Similarity NPD1651 Approved
0.6497 Remote Similarity NPD5889 Approved
0.6497 Remote Similarity NPD7411 Suspended
0.6497 Remote Similarity NPD5890 Approved
0.6495 Remote Similarity NPD7539 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4110 Phase 3
0.6491 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6485 Remote Similarity NPD4870 Approved
0.648 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6474 Remote Similarity NPD6799 Approved
0.6467 Remote Similarity NPD6653 Approved
0.6464 Remote Similarity NPD919 Approved
0.6457 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6456 Remote Similarity NPD17 Approved
0.6452 Remote Similarity NPD5844 Phase 1
0.645 Remote Similarity NPD5408 Approved
0.645 Remote Similarity NPD4477 Approved
0.645 Remote Similarity NPD5404 Approved
0.645 Remote Similarity NPD4476 Approved
0.645 Remote Similarity NPD5406 Approved
0.645 Remote Similarity NPD5405 Approved
0.6446 Remote Similarity NPD4060 Phase 1
0.6438 Remote Similarity NPD3972 Approved
0.6437 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6437 Remote Similarity NPD642 Clinical (unspecified phase)
0.6433 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6425 Remote Similarity NPD5761 Phase 2
0.6425 Remote Similarity NPD5760 Phase 2
0.6425 Remote Similarity NPD2393 Clinical (unspecified phase)
0.641 Remote Similarity NPD9493 Approved
0.6398 Remote Similarity NPD4359 Approved
0.6398 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6395 Remote Similarity NPD3750 Approved
0.6389 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6389 Remote Similarity NPD3817 Phase 2
0.6386 Remote Similarity NPD6663 Approved
0.638 Remote Similarity NPD5647 Approved
0.6369 Remote Similarity NPD6801 Discontinued
0.6369 Remote Similarity NPD6651 Approved
0.6364 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7315 Approved
0.6358 Remote Similarity NPD6696 Suspended
0.6349 Remote Similarity NPD1298 Discontinued
0.6349 Remote Similarity NPD6559 Discontinued
0.6348 Remote Similarity NPD6585 Discontinued
0.6341 Remote Similarity NPD5736 Approved
0.6341 Remote Similarity NPD2237 Approved
0.634 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6335 Remote Similarity NPD1608 Approved
0.6325 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6325 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6322 Remote Similarity NPD7236 Approved
0.6319 Remote Similarity NPD6362 Approved
0.631 Remote Similarity NPD7177 Discontinued
0.6304 Remote Similarity NPD7199 Phase 2
0.6301 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6301 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6298 Remote Similarity NPD5402 Approved
0.6294 Remote Similarity NPD7033 Discontinued
0.629 Remote Similarity NPD7852 Clinical (unspecified phase)
0.628 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6272 Remote Similarity NPD6353 Approved
0.6271 Remote Similarity NPD5403 Approved
0.627 Remote Similarity NPD7229 Phase 3
0.625 Remote Similarity NPD7410 Clinical (unspecified phase)
0.625 Remote Similarity NPD1578 Phase 2
0.625 Remote Similarity NPD5401 Approved
0.6237 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6236 Remote Similarity NPD7239 Suspended
0.623 Remote Similarity NPD3749 Approved
0.6224 Remote Similarity NPD3269 Clinical (unspecified phase)
0.6224 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4302 Clinical (unspecified phase)
0.6223 Remote Similarity NPD6620 Discovery
0.6222 Remote Similarity NPD6873 Phase 2
0.6221 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6221 Remote Similarity NPD2344 Approved
0.6221 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6218 Remote Similarity NPD1241 Discontinued
0.6213 Remote Similarity NPD5735 Approved
0.6213 Remote Similarity NPD4622 Approved
0.6213 Remote Similarity NPD4618 Approved
0.6209 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6209 Remote Similarity NPD2182 Approved
0.62 Remote Similarity NPD8285 Discontinued
0.6188 Remote Similarity NPD3025 Approved
0.6188 Remote Similarity NPD1934 Approved
0.6188 Remote Similarity NPD3024 Approved
0.6186 Remote Similarity NPD8434 Phase 2
0.6185 Remote Similarity NPD2897 Discontinued
0.6185 Remote Similarity NPD1549 Phase 2
0.6183 Remote Similarity NPD6808 Phase 2
0.6176 Remote Similarity NPD2157 Approved
0.6176 Remote Similarity NPD1607 Approved
0.6175 Remote Similarity NPD3882 Suspended
0.6168 Remote Similarity NPD7095 Approved
0.6167 Remote Similarity NPD7028 Phase 2
0.614 Remote Similarity NPD5689 Approved
0.614 Remote Similarity NPD5688 Approved
0.6131 Remote Similarity NPD6798 Discontinued
0.6129 Remote Similarity NPD1247 Approved
0.6122 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6114 Remote Similarity NPD8166 Discontinued
0.6111 Remote Similarity NPD3026 Approved
0.6111 Remote Similarity NPD3023 Approved
0.6111 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6105 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6105 Remote Similarity NPD1510 Phase 2
0.6103 Remote Similarity NPD8150 Discontinued
0.6102 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6101 Remote Similarity NPD7340 Approved
0.6099 Remote Similarity NPD37 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