Structure

Physi-Chem Properties

Molecular Weight:  891.52
Volume:  919.675
LogP:  3.414
LogD:  3.629
LogS:  -3.213
# Rotatable Bonds:  34
TPSA:  293.44
# H-Bond Aceptor:  18
# H-Bond Donor:  12
# Rings:  3
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.022
Synthetic Accessibility Score:  4.771
Fsp3:  0.543
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:  -6.123
MDCK Permeability:  6.787262009311235e-06
Pgp-inhibitor:  0.062
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.084
20% Bioavailability (F20%):  0.974
30% Bioavailability (F30%):  0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  76.92980194091797%
Volume Distribution (VD):  0.411
Pgp-substrate:  9.671506881713867%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.15
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.441
CYP2C9-substrate:  0.618
CYP2D6-inhibitor:  0.066
CYP2D6-substrate:  0.17
CYP3A4-inhibitor:  0.808
CYP3A4-substrate:  0.04

ADMET: Excretion

Clearance (CL):  4.61
Half-life (T1/2):  0.783

ADMET: Toxicity

hERG Blockers:  0.2
Human Hepatotoxicity (H-HT):  0.937
Drug-inuced Liver Injury (DILI):  0.3
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.457
Maximum Recommended Daily Dose:  0.905
Skin Sensitization:  0.172
Carcinogencity:  0.041
Eye Corrosion:  0.003
Eye Irritation:  0.004
Respiratory Toxicity:  0.294

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

  Natural Product: NPC125597

Natural Product ID:  NPC125597
Common Name*:   Tauramamide Ethyl Ester
IUPAC Name:   ethyl (2S)-5-(diaminomethylideneamino)-2-[[(2S)-2-[[(2R)-2-[[(2S)-3-hydroxy-2-[[(2R)-3-(4-hydroxyphenyl)-2-(7-methyloctanoylamino)propanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]pentanoate
Synonyms:   tauramamide ethyl ester
Standard InCHIKey:  PXRAOBALJVAXFC-SKPRLWQBSA-N
Standard InCHI:  InChI=1S/C46H69N9O9/c1-6-64-45(63)35(16-12-22-49-46(47)48)52-43(61)38(25-31-26-50-34-15-11-10-14-33(31)34)54-41(59)36(23-29(4)5)53-44(62)39(27-56)55-42(60)37(24-30-18-20-32(57)21-19-30)51-40(58)17-9-7-8-13-28(2)3/h10-11,14-15,18-21,26,28-29,35-39,50,56-57H,6-9,12-13,16-17,22-25,27H2,1-5H3,(H,51,58)(H,52,61)(H,53,62)(H,54,59)(H,55,60)(H4,47,48,49)/t35-,36+,37+,38-,39-/m0/s1
SMILES:  CCOC(=O)[C@H](CCCNC(=N)N)N=C([C@H](Cc1c[nH]c2ccccc12)N=C([C@@H](CC(C)C)N=C([C@H](CO)N=C([C@@H](Cc1ccc(cc1)O)N=C(CCCCCC(C)C)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL441010
PubChem CID:   24762733
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004831] Oligopeptides

*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
NPO4083 Brevibacillus laterosporus Species Paenibacillaceae Bacteria n.a. n.a. n.a. PMID[18044840]
NPO4083 Brevibacillus laterosporus Species Paenibacillaceae Bacteria 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
NPT5760 Organism Enterococcus sp. Enterococcus sp. MIC = 0.1 ug.mL-1 PMID[511952]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 9.4 ug.mL-1 PMID[511952]
NPT20 Organism Candida albicans Candida albicans MIC = 75.0 ug.mL-1 PMID[511952]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25.0 ug.mL-1 PMID[511952]
NPT20 Organism Candida albicans Candida albicans MIC = 200.0 ug.mL-1 PMID[511952]

☑ 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 NPC125597 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
0.9849 High Similarity NPC473317
0.8795 High Similarity NPC314882
0.8732 High Similarity NPC319232
0.8732 High Similarity NPC24370
0.8578 High Similarity NPC323752
0.8493 Intermediate Similarity NPC220852
0.8462 Intermediate Similarity NPC28945
0.8439 Intermediate Similarity NPC476874
0.8419 Intermediate Similarity NPC315467
0.8398 Intermediate Similarity NPC478006
0.8378 Intermediate Similarity NPC285343
0.8305 Intermediate Similarity NPC478009
0.8295 Intermediate Similarity NPC64216
0.8253 Intermediate Similarity NPC477630
0.8253 Intermediate Similarity NPC477635
0.8252 Intermediate Similarity NPC315491
0.8252 Intermediate Similarity NPC45459
0.8224 Intermediate Similarity NPC74969
0.822 Intermediate Similarity NPC314056
0.8216 Intermediate Similarity NPC54744
0.819 Intermediate Similarity NPC326363
0.8151 Intermediate Similarity NPC478010
0.8133 Intermediate Similarity NPC478011
0.8117 Intermediate Similarity NPC478013
0.8108 Intermediate Similarity NPC322135
0.8107 Intermediate Similarity NPC156704
0.8099 Intermediate Similarity NPC314176
0.8088 Intermediate Similarity NPC99666
0.8086 Intermediate Similarity NPC193761
0.8065 Intermediate Similarity NPC281049
0.8063 Intermediate Similarity NPC100547
0.8044 Intermediate Similarity NPC325976
0.8037 Intermediate Similarity NPC320968
0.8036 Intermediate Similarity NPC89987
0.8028 Intermediate Similarity NPC478158
0.8027 Intermediate Similarity NPC95240
0.8027 Intermediate Similarity NPC223409
0.8019 Intermediate Similarity NPC88008
0.8018 Intermediate Similarity NPC124920
0.8018 Intermediate Similarity NPC304307
0.8018 Intermediate Similarity NPC261251
0.8018 Intermediate Similarity NPC34580
0.8018 Intermediate Similarity NPC118559
0.8009 Intermediate Similarity NPC478157
0.7991 Intermediate Similarity NPC14288
0.7984 Intermediate Similarity NPC478012
0.7973 Intermediate Similarity NPC214142
0.7956 Intermediate Similarity NPC321592
0.7956 Intermediate Similarity NPC54803
0.7925 Intermediate Similarity NPC473376
0.792 Intermediate Similarity NPC323198
0.7913 Intermediate Similarity NPC171393
0.7913 Intermediate Similarity NPC295452
0.7905 Intermediate Similarity NPC213308
0.7895 Intermediate Similarity NPC306376
0.785 Intermediate Similarity NPC323927
0.7843 Intermediate Similarity NPC235684
0.7841 Intermediate Similarity NPC284888
0.7834 Intermediate Similarity NPC75634
0.7817 Intermediate Similarity NPC15801
0.7807 Intermediate Similarity NPC33064
0.7807 Intermediate Similarity NPC245055
0.7805 Intermediate Similarity NPC46580
0.7799 Intermediate Similarity NPC242209
0.7797 Intermediate Similarity NPC153400
0.7794 Intermediate Similarity NPC314002
0.7778 Intermediate Similarity NPC162860
0.7778 Intermediate Similarity NPC323244
0.7769 Intermediate Similarity NPC477633
0.7767 Intermediate Similarity NPC54420
0.7767 Intermediate Similarity NPC321708
0.7756 Intermediate Similarity NPC171171
0.7745 Intermediate Similarity NPC204717
0.7727 Intermediate Similarity NPC330009
0.7717 Intermediate Similarity NPC266931
0.7711 Intermediate Similarity NPC267885
0.771 Intermediate Similarity NPC476098
0.7706 Intermediate Similarity NPC82472
0.7703 Intermediate Similarity NPC315804
0.7703 Intermediate Similarity NPC313804
0.7696 Intermediate Similarity NPC220765
0.7682 Intermediate Similarity NPC313640
0.7678 Intermediate Similarity NPC77555
0.7674 Intermediate Similarity NPC470500
0.7671 Intermediate Similarity NPC207020
0.7662 Intermediate Similarity NPC149155
0.7662 Intermediate Similarity NPC203468
0.7662 Intermediate Similarity NPC110500
0.7658 Intermediate Similarity NPC264285
0.7656 Intermediate Similarity NPC324149
0.7647 Intermediate Similarity NPC71037
0.7642 Intermediate Similarity NPC328924
0.7636 Intermediate Similarity NPC229348
0.7635 Intermediate Similarity NPC283219
0.7635 Intermediate Similarity NPC126709
0.7635 Intermediate Similarity NPC248041
0.7634 Intermediate Similarity NPC60621
0.7619 Intermediate Similarity NPC272549
0.7617 Intermediate Similarity NPC475506
0.7612 Intermediate Similarity NPC314603
0.759 Intermediate Similarity NPC477634
0.7588 Intermediate Similarity NPC160105
0.7581 Intermediate Similarity NPC155143
0.758 Intermediate Similarity NPC5145
0.7569 Intermediate Similarity NPC476465
0.7568 Intermediate Similarity NPC469928
0.7559 Intermediate Similarity NPC473640
0.7547 Intermediate Similarity NPC251090
0.7536 Intermediate Similarity NPC307963
0.7523 Intermediate Similarity NPC183777
0.7523 Intermediate Similarity NPC100321
0.7522 Intermediate Similarity NPC16352
0.7512 Intermediate Similarity NPC475070
0.7511 Intermediate Similarity NPC276657
0.7511 Intermediate Similarity NPC184225
0.75 Intermediate Similarity NPC11464
0.75 Intermediate Similarity NPC84827
0.75 Intermediate Similarity NPC14113
0.75 Intermediate Similarity NPC94752
0.75 Intermediate Similarity NPC145885
0.75 Intermediate Similarity NPC315555
0.75 Intermediate Similarity NPC96890
0.75 Intermediate Similarity NPC184964
0.748 Intermediate Similarity NPC321939
0.7477 Intermediate Similarity NPC171317
0.7467 Intermediate Similarity NPC186351
0.7467 Intermediate Similarity NPC244536
0.7467 Intermediate Similarity NPC74360
0.7466 Intermediate Similarity NPC82370
0.7463 Intermediate Similarity NPC213468
0.7463 Intermediate Similarity NPC78020
0.7458 Intermediate Similarity NPC181081
0.7456 Intermediate Similarity NPC235885
0.7455 Intermediate Similarity NPC223791
0.7455 Intermediate Similarity NPC107077
0.7443 Intermediate Similarity NPC316403
0.744 Intermediate Similarity NPC469358
0.7432 Intermediate Similarity NPC219087
0.7429 Intermediate Similarity NPC213629
0.7418 Intermediate Similarity NPC74619
0.7418 Intermediate Similarity NPC276517
0.7413 Intermediate Similarity NPC54988
0.7413 Intermediate Similarity NPC49954
0.7413 Intermediate Similarity NPC474561
0.7412 Intermediate Similarity NPC130570
0.7411 Intermediate Similarity NPC36405
0.7409 Intermediate Similarity NPC39679
0.7409 Intermediate Similarity NPC171787
0.74 Intermediate Similarity NPC311276
0.7393 Intermediate Similarity NPC76748
0.7379 Intermediate Similarity NPC72980
0.7378 Intermediate Similarity NPC27041
0.7376 Intermediate Similarity NPC63751
0.7368 Intermediate Similarity NPC280290
0.7361 Intermediate Similarity NPC293917
0.7358 Intermediate Similarity NPC92111
0.7354 Intermediate Similarity NPC110182
0.7352 Intermediate Similarity NPC285558
0.7349 Intermediate Similarity NPC74153
0.7346 Intermediate Similarity NPC296527
0.7333 Intermediate Similarity NPC204491
0.7333 Intermediate Similarity NPC170114
0.7333 Intermediate Similarity NPC203614
0.7331 Intermediate Similarity NPC478029
0.733 Intermediate Similarity NPC258062
0.733 Intermediate Similarity NPC111275
0.733 Intermediate Similarity NPC127677
0.7327 Intermediate Similarity NPC249040
0.7325 Intermediate Similarity NPC2395
0.7321 Intermediate Similarity NPC477610
0.7318 Intermediate Similarity NPC175602
0.7317 Intermediate Similarity NPC469938
0.7313 Intermediate Similarity NPC213530
0.7313 Intermediate Similarity NPC102423
0.7313 Intermediate Similarity NPC193267
0.7306 Intermediate Similarity NPC98715
0.7301 Intermediate Similarity NPC304926
0.7301 Intermediate Similarity NPC477114
0.7301 Intermediate Similarity NPC472285
0.7301 Intermediate Similarity NPC476041
0.7297 Intermediate Similarity NPC61038
0.7297 Intermediate Similarity NPC271862
0.7296 Intermediate Similarity NPC260434
0.7295 Intermediate Similarity NPC55772
0.7294 Intermediate Similarity NPC300183
0.7291 Intermediate Similarity NPC201700
0.729 Intermediate Similarity NPC106937
0.7289 Intermediate Similarity NPC470549
0.7286 Intermediate Similarity NPC469762
0.7286 Intermediate Similarity NPC94943
0.7285 Intermediate Similarity NPC225821
0.7285 Intermediate Similarity NPC46225
0.7284 Intermediate Similarity NPC33949
0.7281 Intermediate Similarity NPC476167
0.7277 Intermediate Similarity NPC471603
0.7277 Intermediate Similarity NPC118940
0.7277 Intermediate Similarity NPC316981
0.7277 Intermediate Similarity NPC182222
0.7277 Intermediate Similarity NPC128084
0.7273 Intermediate Similarity NPC472762

  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 NPC125597 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
0.8491 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.8465 Intermediate Similarity NPD7948 Phase 1
0.8252 Intermediate Similarity NPD484 Approved
0.8122 Intermediate Similarity NPD7470 Discontinued
0.8057 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.8019 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7991 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7972 Intermediate Similarity NPD5612 Discontinued
0.7926 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7814 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7804 Intermediate Similarity NPD7957 Phase 1
0.7804 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD8072 Approved
0.7788 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7783 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7773 Intermediate Similarity NPD3814 Phase 1
0.7733 Intermediate Similarity NPD7603 Discontinued
0.7696 Intermediate Similarity NPD2092 Phase 2
0.7696 Intermediate Similarity NPD2094 Phase 2
0.7696 Intermediate Similarity NPD2095 Phase 2
0.7692 Intermediate Similarity NPD8406 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD8073 Approved
0.7662 Intermediate Similarity NPD482 Approved
0.7659 Intermediate Similarity NPD2091 Phase 2
0.7659 Intermediate Similarity NPD2096 Phase 2
0.7624 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD2189 Approved
0.7569 Intermediate Similarity NPD2187 Approved
0.7544 Intermediate Similarity NPD8292 Phase 2
0.7536 Intermediate Similarity NPD1038 Approved
0.7523 Intermediate Similarity NPD7971 Clinical (unspecified phase)
0.7523 Intermediate Similarity NPD7970 Approved
0.7512 Intermediate Similarity NPD6595 Phase 3
0.7512 Intermediate Similarity NPD5901 Discontinued
0.75 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7689 Approved
0.7467 Intermediate Similarity NPD8430 Approved
0.7467 Intermediate Similarity NPD4086 Phase 1
0.7465 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD7558 Phase 2
0.7455 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7454 Intermediate Similarity NPD4511 Phase 1
0.7445 Intermediate Similarity NPD8356 Approved
0.7438 Intermediate Similarity NPD750 Phase 2
0.7431 Intermediate Similarity NPD8272 Phase 2
0.743 Intermediate Similarity NPD5003 Discontinued
0.7429 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD5065 Approved
0.7399 Intermediate Similarity NPD8094 Discontinued
0.7393 Intermediate Similarity NPD4454 Phase 2
0.7387 Intermediate Similarity NPD5066 Phase 2
0.7387 Intermediate Similarity NPD5067 Phase 2
0.7381 Intermediate Similarity NPD8431 Approved
0.7379 Intermediate Similarity NPD8386 Phase 2
0.7373 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7371 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7336 Intermediate Similarity NPD7944 Discontinued
0.7322 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7980 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD8442 Discontinued
0.7293 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD802 Phase 2
0.7286 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD1392 Approved
0.7281 Intermediate Similarity NPD6242 Discontinued
0.7281 Intermediate Similarity NPD3825 Phase 3
0.7277 Intermediate Similarity NPD7069 Discontinued
0.7277 Intermediate Similarity NPD3330 Phase 1
0.7269 Intermediate Similarity NPD3354 Phase 2
0.7257 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7249 Intermediate Similarity NPD7726 Phase 1
0.724 Intermediate Similarity NPD3003 Approved
0.7238 Intermediate Similarity NPD6473 Phase 1
0.7227 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD5482 Discontinued
0.72 Intermediate Similarity NPD8093 Discontinued
0.72 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8321 Discontinued
0.7181 Intermediate Similarity NPD7112 Discontinued
0.7178 Intermediate Similarity NPD8026 Phase 1
0.7175 Intermediate Similarity NPD2509 Approved
0.7175 Intermediate Similarity NPD2510 Approved
0.7174 Intermediate Similarity NPD5147 Discontinued
0.7169 Intermediate Similarity NPD4600 Approved
0.7169 Intermediate Similarity NPD4601 Approved
0.7168 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD7777 Approved
0.7156 Intermediate Similarity NPD53 Approved
0.7156 Intermediate Similarity NPD7778 Approved
0.7143 Intermediate Similarity NPD5512 Phase 3
0.7137 Intermediate Similarity NPD5559 Phase 2
0.713 Intermediate Similarity NPD7453 Approved
0.713 Intermediate Similarity NPD7452 Approved
0.713 Intermediate Similarity NPD7222 Phase 2
0.7124 Intermediate Similarity NPD2794 Discontinued
0.7123 Intermediate Similarity NPD4889 Approved
0.7122 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD3960 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5632 Approved
0.7113 Intermediate Similarity NPD6154 Approved
0.7111 Intermediate Similarity NPD7465 Suspended
0.7105 Intermediate Similarity NPD3393 Approved
0.7105 Intermediate Similarity NPD3394 Approved
0.7105 Intermediate Similarity NPD3389 Approved
0.7104 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4418 Discontinued
0.7094 Intermediate Similarity NPD7994 Phase 2
0.7089 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD1325 Approved
0.7087 Intermediate Similarity NPD1326 Approved
0.7085 Intermediate Similarity NPD7001 Phase 3
0.7083 Intermediate Similarity NPD6665 Discontinued
0.7081 Intermediate Similarity NPD2144 Approved
0.707 Intermediate Similarity NPD2564 Approved
0.707 Intermediate Similarity NPD2565 Phase 2
0.7062 Intermediate Similarity NPD3178 Discontinued
0.7062 Intermediate Similarity NPD3038 Discontinued
0.7061 Intermediate Similarity NPD5902 Approved
0.7061 Intermediate Similarity NPD5903 Approved
0.7048 Intermediate Similarity NPD4076 Approved
0.7048 Intermediate Similarity NPD4079 Approved
0.7045 Intermediate Similarity NPD2175 Phase 3
0.7045 Intermediate Similarity NPD2176 Approved
0.7045 Intermediate Similarity NPD4548 Discontinued
0.7045 Intermediate Similarity NPD2177 Approved
0.7042 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6735 Approved
0.7027 Intermediate Similarity NPD6975 Discontinued
0.7022 Intermediate Similarity NPD2916 Discontinued
0.7021 Intermediate Similarity NPD4845 Discontinued
0.7021 Intermediate Similarity NPD7731 Approved
0.7021 Intermediate Similarity NPD6165 Phase 2
0.7021 Intermediate Similarity NPD7730 Approved
0.7021 Intermediate Similarity NPD6164 Phase 2
0.702 Intermediate Similarity NPD4558 Phase 2
0.7014 Intermediate Similarity NPD6452 Discontinued
0.7014 Intermediate Similarity NPD6479 Discontinued
0.7005 Intermediate Similarity NPD6569 Phase 2
0.7 Intermediate Similarity NPD3506 Approved
0.7 Intermediate Similarity NPD8271 Discontinued
0.7 Intermediate Similarity NPD3505 Approved
0.7 Intermediate Similarity NPD8421 Discontinued
0.6996 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6992 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6991 Remote Similarity NPD6529 Discontinued
0.6991 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6991 Remote Similarity NPD8063 Discontinued
0.6979 Remote Similarity NPD7051 Phase 3
0.6979 Remote Similarity NPD7050 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6290 Phase 2
0.6978 Remote Similarity NPD8524 Approved
0.6977 Remote Similarity NPD2383 Phase 1
0.6977 Remote Similarity NPD6141 Clinical (unspecified phase)
0.697 Remote Similarity NPD8109 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1768 Approved
0.6968 Remote Similarity NPD8395 Approved
0.6968 Remote Similarity NPD8396 Approved
0.6964 Remote Similarity NPD5426 Phase 3
0.6962 Remote Similarity NPD7824 Approved
0.6962 Remote Similarity NPD5801 Clinical (unspecified phase)
0.696 Remote Similarity NPD3014 Clinical (unspecified phase)
0.696 Remote Similarity NPD3013 Phase 3
0.6958 Remote Similarity NPD7853 Phase 2
0.6958 Remote Similarity NPD3006 Discontinued
0.6957 Remote Similarity NPD2844 Phase 3
0.6957 Remote Similarity NPD2781 Approved
0.6955 Remote Similarity NPD6664 Approved
0.6955 Remote Similarity NPD3914 Clinical (unspecified phase)
0.6949 Remote Similarity NPD7268 Clinical (unspecified phase)
0.6948 Remote Similarity NPD5596 Phase 2
0.6946 Remote Similarity NPD8019 Approved
0.6946 Remote Similarity NPD4080 Discontinued
0.6946 Remote Similarity NPD7791 Approved
0.6946 Remote Similarity NPD7790 Approved
0.6946 Remote Similarity NPD7952 Approved
0.6946 Remote Similarity NPD7950 Approved
0.6946 Remote Similarity NPD7953 Approved
0.6946 Remote Similarity NPD7789 Approved
0.6946 Remote Similarity NPD7951 Approved
0.6943 Remote Similarity NPD1322 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3243 Approved
0.6942 Remote Similarity NPD2780 Approved
0.6942 Remote Similarity NPD2782 Approved
0.6941 Remote Similarity NPD7618 Phase 3
0.6941 Remote Similarity NPD3324 Clinical (unspecified phase)
0.6941 Remote Similarity NPD7619 Phase 3
0.6941 Remote Similarity NPD8641 Approved
0.694 Remote Similarity NPD3514 Clinical (unspecified phase)
0.6936 Remote Similarity NPD7271 Approved
0.6934 Remote Similarity NPD8464 Clinical (unspecified phase)
0.6934 Remote Similarity NPD5897 Approved
0.6934 Remote Similarity NPD5898 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