Structure

Physi-Chem Properties

Molecular Weight:  724.49
Volume:  781.56
LogP:  3.285
LogD:  2.485
LogS:  -3.89
# Rotatable Bonds:  25
TPSA:  153.43
# H-Bond Aceptor:  12
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.156
Synthetic Accessibility Score:  4.74
Fsp3:  0.65
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:  -5.063
MDCK Permeability:  1.8568014638731256e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.224
Human Intestinal Absorption (HIA):  0.807
20% Bioavailability (F20%):  0.169
30% Bioavailability (F30%):  0.535

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.064
Plasma Protein Binding (PPB):  93.9564437866211%
Volume Distribution (VD):  0.768
Pgp-substrate:  3.2080512046813965%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.058
CYP2C19-inhibitor:  0.179
CYP2C19-substrate:  0.831
CYP2C9-inhibitor:  0.225
CYP2C9-substrate:  0.041
CYP2D6-inhibitor:  0.041
CYP2D6-substrate:  0.096
CYP3A4-inhibitor:  0.956
CYP3A4-substrate:  0.916

ADMET: Excretion

Clearance (CL):  6.774
Half-life (T1/2):  0.077

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.986
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.073
Maximum Recommended Daily Dose:  0.334
Skin Sensitization:  0.083
Carcinogencity:  0.009
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.705

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

  Natural Product: NPC101719

Natural Product ID:  NPC101719
Common Name*:   Almiramide B
IUPAC Name:   (2R)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]-methylamino]-1-oxopropan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-N,2-dimethyloct-7-ynamide
Synonyms:  
Standard InCHIKey:  VQNWOYVWHDVFJY-CWXFOQKSSA-N
Standard InCHI:  InChI=1S/C40H64N6O6/c1-14-15-16-18-21-28(8)37(49)46(13)34(27(6)7)40(52)45(12)33(26(4)5)36(48)42-32(25(2)3)39(51)43(10)29(9)38(50)44(11)31(35(41)47)24-30-22-19-17-20-23-30/h1,17,19-20,22-23,25-29,31-34H,15-16,18,21,24H2,2-13H3,(H2,41,47)(H,42,48)/t28-,29+,31+,32+,33+,34+/m1/s1
SMILES:  C#CCCCC[C@@H](C)C(=O)N(C)[C@@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=N[C@@H](C(C)C)C(=O)N(C)[C@@H](C)C(=O)N(C)[C@@H](Cc1ccccc1)C(=N)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1097666
PubChem CID:   46237303
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

*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
NPO29839 Oscillatoria nigroviridis Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18715036]
NPO29839 Oscillatoria nigroviridis Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[25468043]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 52300.0 nM PMID[487791]
NPT189 Cell Line Vero Chlorocebus aethiops LD50 = 52.3 uM PMID[487792]
NPT81 Cell Line A549 Homo sapiens IC50 = 76000.0 nM PMID[487793]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 100000.0 nM PMID[487793]
NPT165 Cell Line HeLa Homo sapiens IC50 = 53000.0 nM PMID[487793]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 13000.0 nM PMID[487793]
NPT2 Others Unspecified Ratio IC50 = 21.8 n.a. PMID[487791]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 2400.0 nM PMID[487791]
NPT2 Others Unspecified Ratio LD50/IC50 = 8.7 n.a. PMID[487792]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 = 6000.0 nM PMID[487792]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 2400.0 nM PMID[487792]
NPT27 Others Unspecified IC50 = 0.0000027 nM PMID[487793]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 107000.0 nM PMID[487793]

☑ 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 NPC101719 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
0.9915 High Similarity NPC222466
0.9256 High Similarity NPC22746
0.8917 High Similarity NPC470546
0.8833 High Similarity NPC470545
0.877 High Similarity NPC200964
0.875 High Similarity NPC470544
0.8699 High Similarity NPC71684
0.8661 High Similarity NPC473322
0.8661 High Similarity NPC111428
0.8647 High Similarity NPC139326
0.8595 High Similarity NPC239357
0.85 High Similarity NPC276949
0.85 High Similarity NPC35850
0.843 Intermediate Similarity NPC33742
0.8421 Intermediate Similarity NPC132636
0.8413 Intermediate Similarity NPC6975
0.8394 Intermediate Similarity NPC138775
0.8385 Intermediate Similarity NPC255447
0.8295 Intermediate Similarity NPC319766
0.8273 Intermediate Similarity NPC129666
0.8261 Intermediate Similarity NPC225648
0.8261 Intermediate Similarity NPC329761
0.8254 Intermediate Similarity NPC202521
0.8244 Intermediate Similarity NPC130309
0.8175 Intermediate Similarity NPC476990
0.8168 Intermediate Similarity NPC200589
0.8162 Intermediate Similarity NPC269398
0.8162 Intermediate Similarity NPC263493
0.8125 Intermediate Similarity NPC46427
0.8115 Intermediate Similarity NPC474584
0.8102 Intermediate Similarity NPC161069
0.8069 Intermediate Similarity NPC287757
0.8069 Intermediate Similarity NPC319320
0.8047 Intermediate Similarity NPC252878
0.803 Intermediate Similarity NPC300315
0.8014 Intermediate Similarity NPC2501
0.8 Intermediate Similarity NPC285926
0.8 Intermediate Similarity NPC315276
0.8 Intermediate Similarity NPC14672
0.7986 Intermediate Similarity NPC5620
0.7926 Intermediate Similarity NPC248283
0.7914 Intermediate Similarity NPC476978
0.7914 Intermediate Similarity NPC52748
0.7883 Intermediate Similarity NPC470884
0.7883 Intermediate Similarity NPC92784
0.7883 Intermediate Similarity NPC476133
0.7883 Intermediate Similarity NPC178662
0.7883 Intermediate Similarity NPC98424
0.7857 Intermediate Similarity NPC209509
0.7852 Intermediate Similarity NPC287401
0.7847 Intermediate Similarity NPC122590
0.7842 Intermediate Similarity NPC197682
0.7826 Intermediate Similarity NPC163392
0.7826 Intermediate Similarity NPC239762
0.7826 Intermediate Similarity NPC476259
0.781 Intermediate Similarity NPC471265
0.781 Intermediate Similarity NPC471264
0.781 Intermediate Similarity NPC68865
0.781 Intermediate Similarity NPC127741
0.7803 Intermediate Similarity NPC477937
0.777 Intermediate Similarity NPC168113
0.7746 Intermediate Similarity NPC135121
0.7734 Intermediate Similarity NPC310467
0.773 Intermediate Similarity NPC315266
0.7714 Intermediate Similarity NPC176226
0.7698 Intermediate Similarity NPC46098
0.7698 Intermediate Similarity NPC307357
0.7698 Intermediate Similarity NPC268841
0.7692 Intermediate Similarity NPC475439
0.7692 Intermediate Similarity NPC471821
0.7692 Intermediate Similarity NPC473501
0.7692 Intermediate Similarity NPC471820
0.7664 Intermediate Similarity NPC141050
0.7656 Intermediate Similarity NPC169328
0.7643 Intermediate Similarity NPC469426
0.7643 Intermediate Similarity NPC469427
0.7635 Intermediate Similarity NPC297145
0.7635 Intermediate Similarity NPC197743
0.7626 Intermediate Similarity NPC89489
0.7623 Intermediate Similarity NPC327481
0.7622 Intermediate Similarity NPC16188
0.7619 Intermediate Similarity NPC469903
0.7607 Intermediate Similarity NPC25565
0.7606 Intermediate Similarity NPC313867
0.7606 Intermediate Similarity NPC477217
0.7606 Intermediate Similarity NPC201244
0.7606 Intermediate Similarity NPC316008
0.7586 Intermediate Similarity NPC324081
0.7576 Intermediate Similarity NPC474082
0.7576 Intermediate Similarity NPC175726
0.7569 Intermediate Similarity NPC105717
0.7552 Intermediate Similarity NPC314358
0.7552 Intermediate Similarity NPC262077
0.7535 Intermediate Similarity NPC314388
0.7535 Intermediate Similarity NPC315283
0.7534 Intermediate Similarity NPC233702
0.7521 Intermediate Similarity NPC164859
0.752 Intermediate Similarity NPC319579
0.7518 Intermediate Similarity NPC246079
0.75 Intermediate Similarity NPC145113
0.75 Intermediate Similarity NPC473580
0.7483 Intermediate Similarity NPC473341
0.7483 Intermediate Similarity NPC322878
0.7481 Intermediate Similarity NPC478016
0.7481 Intermediate Similarity NPC478015
0.7481 Intermediate Similarity NPC478014
0.7462 Intermediate Similarity NPC220698
0.746 Intermediate Similarity NPC329011
0.7448 Intermediate Similarity NPC240848
0.7432 Intermediate Similarity NPC473002
0.7426 Intermediate Similarity NPC469666
0.7417 Intermediate Similarity NPC12730
0.7417 Intermediate Similarity NPC469902
0.7417 Intermediate Similarity NPC469243
0.7417 Intermediate Similarity NPC473003
0.7415 Intermediate Similarity NPC162104
0.7403 Intermediate Similarity NPC473502
0.7398 Intermediate Similarity NPC473418
0.7398 Intermediate Similarity NPC67043
0.7379 Intermediate Similarity NPC311658
0.7365 Intermediate Similarity NPC56685
0.7365 Intermediate Similarity NPC286551
0.7365 Intermediate Similarity NPC202198
0.7364 Intermediate Similarity NPC197470
0.7357 Intermediate Similarity NPC314835
0.7348 Intermediate Similarity NPC27833
0.7347 Intermediate Similarity NPC7817
0.7347 Intermediate Similarity NPC475168
0.7343 Intermediate Similarity NPC77905
0.7343 Intermediate Similarity NPC468984
0.7333 Intermediate Similarity NPC322598
0.7328 Intermediate Similarity NPC237420
0.7303 Intermediate Similarity NPC475544
0.7279 Intermediate Similarity NPC283783
0.7279 Intermediate Similarity NPC254798
0.7273 Intermediate Similarity NPC476989
0.7273 Intermediate Similarity NPC223207
0.7255 Intermediate Similarity NPC241794
0.7248 Intermediate Similarity NPC261934
0.7248 Intermediate Similarity NPC5194
0.7248 Intermediate Similarity NPC262166
0.7237 Intermediate Similarity NPC469898
0.7237 Intermediate Similarity NPC1390
0.7237 Intermediate Similarity NPC62104
0.7236 Intermediate Similarity NPC471317
0.7226 Intermediate Similarity NPC471771
0.7226 Intermediate Similarity NPC105114
0.7226 Intermediate Similarity NPC89923
0.7226 Intermediate Similarity NPC152850
0.7226 Intermediate Similarity NPC71933
0.7226 Intermediate Similarity NPC290755
0.7226 Intermediate Similarity NPC304074
0.7226 Intermediate Similarity NPC239990
0.7218 Intermediate Similarity NPC190663
0.7206 Intermediate Similarity NPC47667
0.72 Intermediate Similarity NPC45033
0.72 Intermediate Similarity NPC470902
0.7197 Intermediate Similarity NPC314992
0.719 Intermediate Similarity NPC469901
0.719 Intermediate Similarity NPC471527
0.7185 Intermediate Similarity NPC35996
0.7181 Intermediate Similarity NPC300443
0.7177 Intermediate Similarity NPC224610
0.7177 Intermediate Similarity NPC194390
0.7177 Intermediate Similarity NPC88267
0.7177 Intermediate Similarity NPC113326
0.7161 Intermediate Similarity NPC63931
0.7153 Intermediate Similarity NPC136453
0.7143 Intermediate Similarity NPC325479
0.7134 Intermediate Similarity NPC469904
0.7133 Intermediate Similarity NPC313694
0.7133 Intermediate Similarity NPC242159
0.7111 Intermediate Similarity NPC160493
0.7097 Intermediate Similarity NPC471051
0.7097 Intermediate Similarity NPC471052
0.7097 Intermediate Similarity NPC471053
0.7089 Intermediate Similarity NPC274198
0.7089 Intermediate Similarity NPC198254
0.7083 Intermediate Similarity NPC303045
0.7083 Intermediate Similarity NPC161972
0.7075 Intermediate Similarity NPC81026
0.7075 Intermediate Similarity NPC314114
0.7071 Intermediate Similarity NPC157311
0.707 Intermediate Similarity NPC328649
0.7063 Intermediate Similarity NPC477462
0.7059 Intermediate Similarity NPC324850
0.7051 Intermediate Similarity NPC22883
0.7051 Intermediate Similarity NPC210377
0.7051 Intermediate Similarity NPC5719
0.7051 Intermediate Similarity NPC217804
0.7051 Intermediate Similarity NPC189116
0.7045 Intermediate Similarity NPC2265
0.7039 Intermediate Similarity NPC244509
0.7032 Intermediate Similarity NPC73655
0.7025 Intermediate Similarity NPC129486
0.7021 Intermediate Similarity NPC257390
0.7021 Intermediate Similarity NPC8761
0.7021 Intermediate Similarity NPC44805
0.7007 Intermediate Similarity NPC471680
0.7007 Intermediate Similarity NPC266741

  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 NPC101719 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
0.8438 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD8172 Phase 2
0.8209 Intermediate Similarity NPD8173 Phase 2
0.8154 Intermediate Similarity NPD3608 Clinical (unspecified phase)
0.8106 Intermediate Similarity NPD6919 Clinical (unspecified phase)
0.8102 Intermediate Similarity NPD7720 Phase 2
0.803 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD7728 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD4791 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD4677 Discontinued
0.7883 Intermediate Similarity NPD6901 Phase 3
0.7868 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7846 Intermediate Similarity NPD3073 Approved
0.7846 Intermediate Similarity NPD3072 Approved
0.7846 Intermediate Similarity NPD3071 Approved
0.7842 Intermediate Similarity NPD8076 Discontinued
0.7812 Intermediate Similarity NPD4504 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD4782 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD4761 Approved
0.7769 Intermediate Similarity NPD4762 Approved
0.7769 Intermediate Similarity NPD4706 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD4125 Approved
0.7746 Intermediate Similarity NPD7602 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD8323 Discontinued
0.7737 Intermediate Similarity NPD8643 Discontinued
0.771 Intermediate Similarity NPD2584 Suspended
0.7664 Intermediate Similarity NPD8416 Discontinued
0.766 Intermediate Similarity NPD5341 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD4676 Approved
0.763 Intermediate Similarity NPD5263 Approved
0.7594 Intermediate Similarity NPD5367 Discontinued
0.7571 Intermediate Similarity NPD5301 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD4175 Approved
0.7556 Intermediate Similarity NPD3040 Approved
0.7556 Intermediate Similarity NPD3626 Phase 3
0.7556 Intermediate Similarity NPD4177 Approved
0.752 Intermediate Similarity NPD3644 Approved
0.752 Intermediate Similarity NPD3643 Approved
0.752 Intermediate Similarity NPD3642 Approved
0.7518 Intermediate Similarity NPD5581 Approved
0.7464 Intermediate Similarity NPD3561 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD8290 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6073 Approved
0.7429 Intermediate Similarity NPD5725 Approved
0.741 Intermediate Similarity NPD6623 Phase 3
0.741 Intermediate Similarity NPD5323 Approved
0.7397 Intermediate Similarity NPD7892 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD6088 Approved
0.7397 Intermediate Similarity NPD6631 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3632 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD6552 Clinical (unspecified phase)
0.7364 Intermediate Similarity NPD1348 Approved
0.7361 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD4151 Approved
0.7353 Intermediate Similarity NPD3604 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD2087 Approved
0.7343 Intermediate Similarity NPD2088 Approved
0.7339 Intermediate Similarity NPD7130 Phase 3
0.731 Intermediate Similarity NPD1968 Approved
0.731 Intermediate Similarity NPD1967 Approved
0.7292 Intermediate Similarity NPD2437 Approved
0.7292 Intermediate Similarity NPD6681 Discovery
0.7292 Intermediate Similarity NPD2436 Approved
0.7286 Intermediate Similarity NPD4153 Approved
0.7285 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD5299 Approved
0.7266 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD1330 Phase 2
0.7254 Intermediate Similarity NPD6295 Approved
0.7254 Intermediate Similarity NPD6294 Approved
0.7234 Intermediate Similarity NPD4757 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2022 Approved
0.7218 Intermediate Similarity NPD7342 Discontinued
0.7214 Intermediate Similarity NPD7634 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD4760 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD2031 Discontinued
0.7206 Intermediate Similarity NPD3125 Approved
0.7197 Intermediate Similarity NPD2217 Approved
0.7197 Intermediate Similarity NPD2218 Phase 2
0.7194 Intermediate Similarity NPD2047 Approved
0.7194 Intermediate Similarity NPD2045 Approved
0.7194 Intermediate Similarity NPD2051 Approved
0.7194 Intermediate Similarity NPD2043 Approved
0.7194 Intermediate Similarity NPD2044 Approved
0.7194 Intermediate Similarity NPD2050 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD2049 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD2048 Approved
0.7194 Intermediate Similarity NPD21 Approved
0.7194 Intermediate Similarity NPD2046 Approved
0.7176 Intermediate Similarity NPD3123 Discovery
0.7174 Intermediate Similarity NPD7828 Discontinued
0.7174 Intermediate Similarity NPD5759 Approved
0.7163 Intermediate Similarity NPD8265 Approved
0.7163 Intermediate Similarity NPD5296 Approved
0.7133 Intermediate Similarity NPD4126 Approved
0.7133 Intermediate Similarity NPD6852 Discontinued
0.7133 Intermediate Similarity NPD4214 Discontinued
0.7132 Intermediate Similarity NPD480 Approved
0.7122 Intermediate Similarity NPD6359 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD999 Phase 2
0.712 Intermediate Similarity NPD1040 Phase 2
0.7113 Intermediate Similarity NPD3908 Approved
0.7105 Intermediate Similarity NPD7267 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD5747 Discontinued
0.7086 Intermediate Similarity NPD6670 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD7613 Discontinued
0.7067 Intermediate Similarity NPD6078 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1814 Approved
0.7059 Intermediate Similarity NPD1812 Approved
0.7034 Intermediate Similarity NPD6897 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6302 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD747 Discontinued
0.7021 Intermediate Similarity NPD7908 Discontinued
0.7008 Intermediate Similarity NPD6038 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4432 Discontinued
0.6986 Remote Similarity NPD4152 Approved
0.6984 Remote Similarity NPD5717 Approved
0.6974 Remote Similarity NPD8315 Phase 1
0.6972 Remote Similarity NPD941 Approved
0.6968 Remote Similarity NPD7599 Phase 2
0.6967 Remote Similarity NPD9566 Approved
0.6966 Remote Similarity NPD4158 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5298 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6325 Discontinued
0.6957 Remote Similarity NPD6792 Phase 3
0.6957 Remote Similarity NPD5578 Approved
0.6957 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6954 Remote Similarity NPD5229 Approved
0.6954 Remote Similarity NPD5230 Approved
0.695 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6947 Remote Similarity NPD3598 Phase 3
0.6944 Remote Similarity NPD8125 Discontinued
0.694 Remote Similarity NPD998 Approved
0.6934 Remote Similarity NPD5335 Discontinued
0.6934 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6933 Remote Similarity NPD5614 Approved
0.6933 Remote Similarity NPD2013 Approved
0.6933 Remote Similarity NPD5613 Approved
0.6933 Remote Similarity NPD3987 Approved
0.6933 Remote Similarity NPD2014 Approved
0.6933 Remote Similarity NPD2016 Approved
0.6933 Remote Similarity NPD3988 Approved
0.6923 Remote Similarity NPD7600 Phase 2
0.6923 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7450 Phase 2
0.6917 Remote Similarity NPD6690 Approved
0.6912 Remote Similarity NPD2956 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6899 Remote Similarity NPD8303 Discontinued
0.6894 Remote Similarity NPD3551 Approved
0.6892 Remote Similarity NPD5024 Approved
0.6892 Remote Similarity NPD5265 Approved
0.6892 Remote Similarity NPD5264 Approved
0.6889 Remote Similarity NPD5981 Approved
0.6883 Remote Similarity NPD8417 Discontinued
0.688 Remote Similarity NPD4803 Discontinued
0.6866 Remote Similarity NPD3806 Clinical (unspecified phase)
0.6866 Remote Similarity NPD7522 Discontinued
0.6863 Remote Similarity NPD4648 Approved
0.6863 Remote Similarity NPD4646 Approved
0.6863 Remote Similarity NPD4647 Approved
0.6857 Remote Similarity NPD3588 Discontinued
0.685 Remote Similarity NPD1765 Approved
0.685 Remote Similarity NPD1018 Approved
0.685 Remote Similarity NPD1763 Approved
0.685 Remote Similarity NPD1766 Approved
0.685 Remote Similarity NPD1761 Approved
0.685 Remote Similarity NPD1767 Approved
0.6849 Remote Similarity NPD3480 Approved
0.6842 Remote Similarity NPD7303 Discontinued
0.6831 Remote Similarity NPD4794 Discontinued
0.6815 Remote Similarity NPD6093 Discontinued
0.6813 Remote Similarity NPD7485 Phase 3
0.6813 Remote Similarity NPD7484 Phase 3
0.6803 Remote Similarity NPD7511 Approved
0.6803 Remote Similarity NPD7512 Approved
0.6797 Remote Similarity NPD7131 Phase 3
0.6794 Remote Similarity NPD753 Approved
0.6791 Remote Similarity NPD7679 Phase 2
0.6786 Remote Similarity NPD3029 Clinical (unspecified phase)
0.6772 Remote Similarity NPD8351 Phase 2
0.6769 Remote Similarity NPD3581 Discontinued
0.6768 Remote Similarity NPD8362 Clinical (unspecified phase)
0.6755 Remote Similarity NPD3519 Discontinued
0.6746 Remote Similarity NPD5716 Approved
0.6746 Remote Similarity NPD4119 Approved
0.6733 Remote Similarity NPD6676 Phase 2
0.6732 Remote Similarity NPD5748 Phase 2
0.6716 Remote Similarity NPD7508 Discontinued
0.6715 Remote Similarity NPD6806 Phase 1
0.6714 Remote Similarity NPD2634 Clinical (unspecified phase)
0.6712 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6707 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6691 Remote Similarity NPD6343 Approved
0.6691 Remote Similarity NPD6345 Approved
0.6691 Remote Similarity NPD6408 Phase 1
0.6667 Remote Similarity NPD4077 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2846 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3606 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