Structure

Physi-Chem Properties

Molecular Weight:  879.47
Volume:  897.966
LogP:  2.905
LogD:  3.674
LogS:  -1.25
# Rotatable Bonds:  16
TPSA:  280.93
# H-Bond Aceptor:  18
# H-Bond Donor:  9
# Rings:  3
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.124
Synthetic Accessibility Score:  5.967
Fsp3:  0.556
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:  -5.84
MDCK Permeability:  2.220770693384111e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.272
20% Bioavailability (F20%):  0.877
30% Bioavailability (F30%):  0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.048
Plasma Protein Binding (PPB):  53.57619094848633%
Volume Distribution (VD):  0.434
Pgp-substrate:  39.82002258300781%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.001
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.046
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.127
CYP2D6-substrate:  0.04
CYP3A4-inhibitor:  0.108
CYP3A4-substrate:  0.028

ADMET: Excretion

Clearance (CL):  1.348
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  1.0
Drug-inuced Liver Injury (DILI):  0.868
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.011
Maximum Recommended Daily Dose:  0.008
Skin Sensitization:  0.044
Carcinogencity:  0.015
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.38

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

  Natural Product: NPC45777

Natural Product ID:  NPC45777
Common Name*:   (R)-N-((3S,6R,9R,12R,15R,18R,19S)-12-Benzyl-6-((S)-1-Hydroxyethyl)-3-(Hydroxymethyl)-9,15-Diisobutyl-19-Methyl-2,5,8,11,14,17-Hexaoxo-1-Oxa-4,7,10,13,16-Pentaazacyclononadecan-18-Yl)-2-Isobutyramido-3-Phenylpropanamide
IUPAC Name:   N-[(2R)-1-[[(3S,6R,9R,12R,15R,18R,19S)-12-benzyl-6-[(1S)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentazacyclononadec-18-yl]amino]-1-oxo-3-phenylpropan-2-yl]-2-methylpropanamide
Synonyms:  
Standard InCHIKey:  WQWACYPWBAFTDI-PIBGLXTRSA-N
Standard InCHI:  InChI=1S/C45H65N7O11/c1-24(2)19-31-39(56)48-33(21-29-15-11-9-12-16-29)40(57)47-32(20-25(3)4)41(58)51-36(27(7)54)43(60)50-35(23-53)45(62)63-28(8)37(44(61)49-31)52-42(59)34(46-38(55)26(5)6)22-30-17-13-10-14-18-30/h9-18,24-28,31-37,53-54H,19-23H2,1-8H3,(H,46,55)(H,47,57)(H,48,56)(H,49,61)(H,50,60)(H,51,58)(H,52,59)/t27-,28-,31+,32+,33+,34+,35-,36+,37+/m0/s1
SMILES:  CC(C)C[C@@H]1C(=N[C@H](Cc2ccccc2)C(=N[C@H](CC(C)C)C(=N[C@H]([C@H](C)O)C(=N[C@@H](CO)C(=O)O[C@@H](C)[C@H](C(=N1)O)N=C([C@@H](Cc1ccccc1)N=C(C(C)C)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2304288
PubChem CID:   44613908
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO17267 Synoicum adareanum Species Polyclinidae Eukaryota n.a. Antarctic n.a. PMID[18039009]
NPO13341 Bryopsis pennata Species Bryopsidaceae Eukaryota n.a. Hawaiian n.a. PMID[19916528]
NPO17267 Synoicum adareanum Species Polyclinidae Eukaryota n.a. n.a. n.a. PMID[21737286]
NPO17052 Podocarpus nivalis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO687 Monachosorum flagellare Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12759 Rheum australe Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO687 Monachosorum flagellare Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17052 Podocarpus nivalis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17052 Podocarpus nivalis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13544 Aparisthmium cordatum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15052 Stachys lanata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO687 Monachosorum flagellare Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8708 Vibrio cholerae Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12759 Rheum australe Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18232 Beauveria tenella Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22679 Vellozia pusilla Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16810 Drypetes laciniata Species Putranjivaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18370 Diazona chinensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17052 Podocarpus nivalis Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10689 Clostridium pasteurianum Species Clostridiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13341 Bryopsis pennata Species Bryopsidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17267 Synoicum adareanum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18932.1 Melia azedarach var. toosendan Varieties Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16440 Bidens aurea Species Asteraceae 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
NPT267 Individual Protein Neuropeptide Y receptor type 1 Homo sapiens Activity = 100.0 % PMID[470772]
NPT267 Individual Protein Neuropeptide Y receptor type 1 Homo sapiens Activity = 18.0 % PMID[470772]
NPT247 Individual Protein Endothelin receptor ET-A Homo sapiens Activity = 99.0 % PMID[470772]
NPT247 Individual Protein Endothelin receptor ET-A Homo sapiens Activity = 96.0 % PMID[470772]

☑ 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 NPC45777 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
1.0 High Similarity NPC477061
0.9052 High Similarity NPC169328
0.8974 High Similarity NPC310467
0.8824 High Similarity NPC478015
0.8824 High Similarity NPC478016
0.8824 High Similarity NPC478014
0.8814 High Similarity NPC237420
0.877 High Similarity NPC47667
0.8462 Intermediate Similarity NPC273814
0.8361 Intermediate Similarity NPC190663
0.8361 Intermediate Similarity NPC80150
0.8246 Intermediate Similarity NPC88267
0.8246 Intermediate Similarity NPC194390
0.8246 Intermediate Similarity NPC224610
0.8246 Intermediate Similarity NPC113326
0.8226 Intermediate Similarity NPC160493
0.816 Intermediate Similarity NPC35996
0.812 Intermediate Similarity NPC163392
0.812 Intermediate Similarity NPC239762
0.8106 Intermediate Similarity NPC127741
0.8049 Intermediate Similarity NPC314992
0.8047 Intermediate Similarity NPC319766
0.8036 Intermediate Similarity NPC475439
0.8036 Intermediate Similarity NPC473501
0.8033 Intermediate Similarity NPC2265
0.8 Intermediate Similarity NPC474584
0.8 Intermediate Similarity NPC161069
0.7985 Intermediate Similarity NPC307357
0.7985 Intermediate Similarity NPC268841
0.7985 Intermediate Similarity NPC46098
0.7953 Intermediate Similarity NPC476241
0.7953 Intermediate Similarity NPC476260
0.7946 Intermediate Similarity NPC25565
0.7926 Intermediate Similarity NPC469427
0.7926 Intermediate Similarity NPC197921
0.7926 Intermediate Similarity NPC469426
0.7891 Intermediate Similarity NPC476125
0.7891 Intermediate Similarity NPC476179
0.7891 Intermediate Similarity NPC4974
0.7868 Intermediate Similarity NPC91953
0.7868 Intermediate Similarity NPC469360
0.7836 Intermediate Similarity NPC68865
0.7833 Intermediate Similarity NPC319579
0.781 Intermediate Similarity NPC476978
0.7797 Intermediate Similarity NPC327481
0.7778 Intermediate Similarity NPC476183
0.777 Intermediate Similarity NPC138775
0.776 Intermediate Similarity NPC470546
0.7754 Intermediate Similarity NPC209509
0.7742 Intermediate Similarity NPC470544
0.7737 Intermediate Similarity NPC176226
0.7734 Intermediate Similarity NPC46427
0.7721 Intermediate Similarity NPC476259
0.7717 Intermediate Similarity NPC476184
0.7717 Intermediate Similarity NPC476281
0.7714 Intermediate Similarity NPC105717
0.7704 Intermediate Similarity NPC6570
0.7704 Intermediate Similarity NPC471264
0.7704 Intermediate Similarity NPC471265
0.7699 Intermediate Similarity NPC58674
0.768 Intermediate Similarity NPC470545
0.7669 Intermediate Similarity NPC246079
0.7669 Intermediate Similarity NPC246913
0.7661 Intermediate Similarity NPC197470
0.7656 Intermediate Similarity NPC252878
0.7634 Intermediate Similarity NPC199738
0.7634 Intermediate Similarity NPC210950
0.7626 Intermediate Similarity NPC5620
0.7622 Intermediate Similarity NPC122590
0.7612 Intermediate Similarity NPC287401
0.7609 Intermediate Similarity NPC139326
0.7597 Intermediate Similarity NPC476278
0.7586 Intermediate Similarity NPC12730
0.7578 Intermediate Similarity NPC202521
0.7571 Intermediate Similarity NPC314358
0.7565 Intermediate Similarity NPC311242
0.7557 Intermediate Similarity NPC477937
0.7544 Intermediate Similarity NPC303045
0.7544 Intermediate Similarity NPC161972
0.7536 Intermediate Similarity NPC263493
0.7536 Intermediate Similarity NPC168113
0.7536 Intermediate Similarity NPC269398
0.752 Intermediate Similarity NPC188010
0.7518 Intermediate Similarity NPC135121
0.7518 Intermediate Similarity NPC145113
0.75 Intermediate Similarity NPC477217
0.75 Intermediate Similarity NPC286551
0.75 Intermediate Similarity NPC105114
0.75 Intermediate Similarity NPC239990
0.75 Intermediate Similarity NPC89923
0.75 Intermediate Similarity NPC476990
0.75 Intermediate Similarity NPC71933
0.75 Intermediate Similarity NPC201244
0.75 Intermediate Similarity NPC152850
0.75 Intermediate Similarity NPC313867
0.75 Intermediate Similarity NPC473341
0.75 Intermediate Similarity NPC316008
0.7483 Intermediate Similarity NPC7817
0.7483 Intermediate Similarity NPC475168
0.7482 Intermediate Similarity NPC197682
0.7462 Intermediate Similarity NPC6975
0.7447 Intermediate Similarity NPC262077
0.7445 Intermediate Similarity NPC43755
0.7432 Intermediate Similarity NPC471527
0.7431 Intermediate Similarity NPC162104
0.7429 Intermediate Similarity NPC315283
0.7429 Intermediate Similarity NPC314388
0.7424 Intermediate Similarity NPC136453
0.7413 Intermediate Similarity NPC2501
0.7413 Intermediate Similarity NPC129666
0.7407 Intermediate Similarity NPC326966
0.7402 Intermediate Similarity NPC254088
0.7395 Intermediate Similarity NPC164859
0.7394 Intermediate Similarity NPC329761
0.7394 Intermediate Similarity NPC225648
0.7391 Intermediate Similarity NPC178662
0.7391 Intermediate Similarity NPC98424
0.7391 Intermediate Similarity NPC92784
0.7391 Intermediate Similarity NPC470884
0.7391 Intermediate Similarity NPC476133
0.736 Intermediate Similarity NPC1986
0.736 Intermediate Similarity NPC474544
0.7339 Intermediate Similarity NPC329011
0.7333 Intermediate Similarity NPC130309
0.7333 Intermediate Similarity NPC471053
0.7333 Intermediate Similarity NPC471051
0.7333 Intermediate Similarity NPC157311
0.7333 Intermediate Similarity NPC471052
0.7329 Intermediate Similarity NPC470902
0.7321 Intermediate Similarity NPC325441
0.7305 Intermediate Similarity NPC52748
0.7299 Intermediate Similarity NPC64897
0.7299 Intermediate Similarity NPC90693
0.7281 Intermediate Similarity NPC226438
0.7279 Intermediate Similarity NPC44805
0.7279 Intermediate Similarity NPC8761
0.7273 Intermediate Similarity NPC211551
0.7266 Intermediate Similarity NPC132636
0.7252 Intermediate Similarity NPC169485
0.7252 Intermediate Similarity NPC474862
0.7252 Intermediate Similarity NPC317474
0.7252 Intermediate Similarity NPC84281
0.7252 Intermediate Similarity NPC213126
0.7252 Intermediate Similarity NPC291027
0.7248 Intermediate Similarity NPC1390
0.7248 Intermediate Similarity NPC62104
0.7226 Intermediate Similarity NPC244866
0.7222 Intermediate Similarity NPC471820
0.7222 Intermediate Similarity NPC471821
0.7206 Intermediate Similarity NPC255447
0.7197 Intermediate Similarity NPC472415
0.7193 Intermediate Similarity NPC258627
0.7193 Intermediate Similarity NPC172128
0.719 Intermediate Similarity NPC294516
0.719 Intermediate Similarity NPC107938
0.7185 Intermediate Similarity NPC296712
0.7185 Intermediate Similarity NPC473322
0.7181 Intermediate Similarity NPC56635
0.7181 Intermediate Similarity NPC297145
0.7181 Intermediate Similarity NPC197743
0.7179 Intermediate Similarity NPC158277
0.7176 Intermediate Similarity NPC71684
0.7174 Intermediate Similarity NPC248283
0.7172 Intermediate Similarity NPC132771
0.7163 Intermediate Similarity NPC239770
0.7133 Intermediate Similarity NPC266741
0.7132 Intermediate Similarity NPC69496
0.713 Intermediate Similarity NPC245259
0.7123 Intermediate Similarity NPC473491
0.712 Intermediate Similarity NPC323007
0.7107 Intermediate Similarity NPC471317
0.7101 Intermediate Similarity NPC245836
0.7101 Intermediate Similarity NPC233910
0.7097 Intermediate Similarity NPC40234
0.709 Intermediate Similarity NPC472414
0.7083 Intermediate Similarity NPC81026
0.7075 Intermediate Similarity NPC470274
0.7067 Intermediate Similarity NPC207675
0.7067 Intermediate Similarity NPC212699
0.7059 Intermediate Similarity NPC22883
0.7059 Intermediate Similarity NPC5719
0.7059 Intermediate Similarity NPC210377
0.7059 Intermediate Similarity NPC111428
0.7059 Intermediate Similarity NPC217804
0.7051 Intermediate Similarity NPC230611
0.7043 Intermediate Similarity NPC159178
0.7043 Intermediate Similarity NPC121872
0.7043 Intermediate Similarity NPC471307
0.7043 Intermediate Similarity NPC141139
0.7043 Intermediate Similarity NPC209764
0.7043 Intermediate Similarity NPC78041
0.7043 Intermediate Similarity NPC74936
0.7031 Intermediate Similarity NPC33742
0.7014 Intermediate Similarity NPC315266
0.7007 Intermediate Similarity NPC325651
0.7006 Intermediate Similarity NPC248670
0.7006 Intermediate Similarity NPC137627
0.7006 Intermediate Similarity NPC273755
0.7006 Intermediate Similarity NPC306804
0.7 Intermediate Similarity NPC314835

  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 NPC45777 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
0.8049 Intermediate Similarity NPD2217 Approved
0.8049 Intermediate Similarity NPD2218 Phase 2
0.7955 Intermediate Similarity NPD8265 Approved
0.7863 Intermediate Similarity NPD4738 Phase 2
0.784 Intermediate Similarity NPD5981 Approved
0.7833 Intermediate Similarity NPD3644 Approved
0.7833 Intermediate Similarity NPD3642 Approved
0.7833 Intermediate Similarity NPD3643 Approved
0.7778 Intermediate Similarity NPD6852 Discontinued
0.7661 Intermediate Similarity NPD1348 Approved
0.7609 Intermediate Similarity NPD7978 Discontinued
0.7597 Intermediate Similarity NPD5108 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7828 Discontinued
0.7574 Intermediate Similarity NPD8172 Phase 2
0.7574 Intermediate Similarity NPD8173 Phase 2
0.7534 Intermediate Similarity NPD7749 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD7508 Discontinued
0.7518 Intermediate Similarity NPD8323 Discontinued
0.7422 Intermediate Similarity NPD4209 Clinical (unspecified phase)
0.7422 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD7522 Discontinued
0.7373 Intermediate Similarity NPD4760 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD8118 Discontinued
0.7353 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD4479 Discontinued
0.7338 Intermediate Similarity NPD6864 Phase 2
0.7338 Intermediate Similarity NPD6865 Phase 2
0.7333 Intermediate Similarity NPD3136 Phase 2
0.7328 Intermediate Similarity NPD2584 Suspended
0.7308 Intermediate Similarity NPD2956 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD1080 Approved
0.7273 Intermediate Similarity NPD1040 Phase 2
0.7259 Intermediate Similarity NPD6359 Clinical (unspecified phase)
0.7252 Intermediate Similarity NPD2611 Approved
0.7252 Intermediate Similarity NPD4216 Approved
0.7252 Intermediate Similarity NPD4218 Approved
0.7252 Intermediate Similarity NPD4215 Approved
0.7252 Intermediate Similarity NPD3132 Approved
0.7252 Intermediate Similarity NPD2610 Approved
0.7252 Intermediate Similarity NPD2612 Approved
0.7252 Intermediate Similarity NPD4480 Approved
0.7252 Intermediate Similarity NPD3131 Approved
0.7252 Intermediate Similarity NPD4217 Approved
0.7252 Intermediate Similarity NPD2609 Approved
0.7252 Intermediate Similarity NPD2608 Approved
0.7241 Intermediate Similarity NPD4814 Discontinued
0.7231 Intermediate Similarity NPD7342 Discontinued
0.7217 Intermediate Similarity NPD6690 Approved
0.7213 Intermediate Similarity NPD5705 Approved
0.7213 Intermediate Similarity NPD5706 Approved
0.7213 Intermediate Similarity NPD5704 Approved
0.7188 Intermediate Similarity NPD5292 Approved
0.7188 Intermediate Similarity NPD5291 Approved
0.7174 Intermediate Similarity NPD8416 Discontinued
0.7164 Intermediate Similarity NPD6302 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD2613 Approved
0.7122 Intermediate Similarity NPD8643 Discontinued
0.7122 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD5618 Discontinued
0.7101 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3089 Approved
0.7101 Intermediate Similarity NPD4745 Approved
0.7101 Intermediate Similarity NPD3087 Approved
0.7101 Intermediate Similarity NPD2574 Discontinued
0.7101 Intermediate Similarity NPD2571 Approved
0.7101 Intermediate Similarity NPD2570 Approved
0.7101 Intermediate Similarity NPD3088 Approved
0.7101 Intermediate Similarity NPD4746 Phase 3
0.7101 Intermediate Similarity NPD3614 Approved
0.7101 Intermediate Similarity NPD2573 Approved
0.7101 Intermediate Similarity NPD3090 Approved
0.7101 Intermediate Similarity NPD3616 Approved
0.7101 Intermediate Similarity NPD3615 Approved
0.7101 Intermediate Similarity NPD2566 Approved
0.709 Intermediate Similarity NPD5367 Discontinued
0.7087 Intermediate Similarity NPD2650 Approved
0.7087 Intermediate Similarity NPD2652 Approved
0.7069 Intermediate Similarity NPD1812 Approved
0.7069 Intermediate Similarity NPD1814 Approved
0.7068 Intermediate Similarity NPD6624 Discontinued
0.7016 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD6406 Approved
0.7009 Intermediate Similarity NPD1066 Discontinued
0.7 Intermediate Similarity NPD4686 Approved
0.7 Intermediate Similarity NPD6360 Discontinued
0.7 Intermediate Similarity NPD4684 Phase 3
0.7 Intermediate Similarity NPD4685 Phase 3
0.6972 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3400 Discontinued
0.6947 Remote Similarity NPD6093 Discontinued
0.6944 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6934 Remote Similarity NPD4006 Discontinued
0.6923 Remote Similarity NPD4574 Approved
0.6923 Remote Similarity NPD4576 Approved
0.6906 Remote Similarity NPD7908 Discontinued
0.6887 Remote Similarity NPD8417 Discontinued
0.6885 Remote Similarity NPD4719 Phase 2
0.686 Remote Similarity NPD1067 Discontinued
0.6855 Remote Similarity NPD999 Phase 2
0.6855 Remote Similarity NPD5048 Discontinued
0.6835 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6833 Remote Similarity NPD9566 Approved
0.6828 Remote Similarity NPD6681 Discovery
0.6815 Remote Similarity NPD7814 Approved
0.6809 Remote Similarity NPD6623 Phase 3
0.6803 Remote Similarity NPD7274 Clinical (unspecified phase)
0.68 Remote Similarity NPD467 Phase 1
0.6797 Remote Similarity NPD8019 Approved
0.6763 Remote Similarity NPD4125 Approved
0.6759 Remote Similarity NPD8076 Discontinued
0.6755 Remote Similarity NPD8315 Phase 1
0.6753 Remote Similarity NPD7972 Discontinued
0.6742 Remote Similarity NPD6065 Approved
0.6736 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6390 Discontinued
0.6733 Remote Similarity NPD7613 Discontinued
0.6721 Remote Similarity NPD7798 Approved
0.672 Remote Similarity NPD5717 Approved
0.6713 Remote Similarity NPD6073 Approved
0.6712 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6088 Approved
0.6694 Remote Similarity NPD6647 Phase 2
0.6694 Remote Similarity NPD2487 Clinical (unspecified phase)
0.6691 Remote Similarity NPD3626 Phase 3
0.669 Remote Similarity NPD6346 Approved
0.6667 Remote Similarity NPD7813 Approved
0.6667 Remote Similarity NPD3123 Discovery
0.6667 Remote Similarity NPD8154 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7130 Phase 3
0.6667 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1081 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7815 Approved
0.6667 Remote Similarity NPD6294 Approved
0.6667 Remote Similarity NPD2585 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6685 Approved
0.6667 Remote Similarity NPD6295 Approved
0.6644 Remote Similarity NPD4152 Approved
0.6643 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6641 Remote Similarity NPD5235 Approved
0.6641 Remote Similarity NPD5240 Approved
0.6641 Remote Similarity NPD5236 Approved
0.6641 Remote Similarity NPD5239 Approved
0.6641 Remote Similarity NPD5237 Approved
0.6623 Remote Similarity NPD7105 Phase 1
0.6621 Remote Similarity NPD3648 Clinical (unspecified phase)
0.6619 Remote Similarity NPD5339 Clinical (unspecified phase)
0.6619 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6619 Remote Similarity NPD7451 Discontinued
0.6618 Remote Similarity NPD4807 Approved
0.6618 Remote Similarity NPD3603 Phase 3
0.6618 Remote Similarity NPD4806 Approved
0.6615 Remote Similarity NPD2607 Approved
0.6614 Remote Similarity NPD5979 Clinical (unspecified phase)
0.6613 Remote Similarity NPD854 Approved
0.6613 Remote Similarity NPD855 Approved
0.6612 Remote Similarity NPD2895 Discontinued
0.6612 Remote Similarity NPD2507 Clinical (unspecified phase)
0.6594 Remote Similarity NPD6325 Discontinued
0.6593 Remote Similarity NPD5723 Approved
0.6583 Remote Similarity NPD3719 Approved
0.6583 Remote Similarity NPD3718 Approved
0.6581 Remote Similarity NPD7495 Discontinued
0.6579 Remote Similarity NPD5982 Phase 2
0.6577 Remote Similarity NPD2743 Approved
0.6575 Remote Similarity NPD7450 Phase 2
0.6573 Remote Similarity NPD5323 Approved
0.6571 Remote Similarity NPD4175 Approved
0.6571 Remote Similarity NPD4177 Approved
0.6567 Remote Similarity NPD2617 Discontinued
0.6562 Remote Similarity NPD7608 Discontinued
0.6556 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6549 Remote Similarity NPD4621 Approved
0.6549 Remote Similarity NPD4619 Approved
0.6547 Remote Similarity NPD2626 Approved
0.6547 Remote Similarity NPD2160 Approved
0.6547 Remote Similarity NPD2627 Approved
0.6547 Remote Similarity NPD2159 Approved
0.6547 Remote Similarity NPD2625 Approved
0.6547 Remote Similarity NPD2628 Approved
0.6544 Remote Similarity NPD4106 Approved
0.6544 Remote Similarity NPD4135 Approved
0.6544 Remote Similarity NPD4136 Approved
0.6538 Remote Similarity NPD6912 Phase 3
0.6536 Remote Similarity NPD7836 Clinical (unspecified phase)
0.6525 Remote Similarity NPD4617 Approved
0.6525 Remote Similarity NPD4620 Approved
0.6525 Remote Similarity NPD5201 Approved
0.6525 Remote Similarity NPD5203 Approved
0.6522 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4677 Discontinued
0.6516 Remote Similarity NPD6913 Approved
0.6515 Remote Similarity NPD1711 Phase 2
0.651 Remote Similarity NPD7488 Clinical (unspecified phase)
0.651 Remote Similarity NPD2575 Approved
0.6504 Remote Similarity NPD9609 Approved
0.6504 Remote Similarity NPD9611 Approved
0.6504 Remote Similarity NPD5926 Approved
0.6504 Remote Similarity NPD9612 Approved
0.6503 Remote Similarity NPD7715 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