Structure

Physi-Chem Properties

Molecular Weight:  960.5
Volume:  973.107
LogP:  2.189
LogD:  1.532
LogS:  -2.523
# Rotatable Bonds:  16
TPSA:  302.95
# H-Bond Aceptor:  20
# H-Bond Donor:  9
# Rings:  4
# Heavy Atoms:  20

MedChem Properties

QED Drug-Likeness Score:  0.072
Synthetic Accessibility Score:  7.083
Fsp3:  0.531
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:  -6.813
MDCK Permeability:  6.771637708880007e-05
Pgp-inhibitor:  0.161
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.346
20% Bioavailability (F20%):  0.494
30% Bioavailability (F30%):  0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.068
Plasma Protein Binding (PPB):  52.222434997558594%
Volume Distribution (VD):  0.567
Pgp-substrate:  37.10811996459961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.002
CYP2C19-inhibitor:  0.033
CYP2C19-substrate:  0.041
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.467
CYP2D6-inhibitor:  0.053
CYP2D6-substrate:  0.082
CYP3A4-inhibitor:  0.203
CYP3A4-substrate:  0.067

ADMET: Excretion

Clearance (CL):  2.395
Half-life (T1/2):  0.588

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.995
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.612
Maximum Recommended Daily Dose:  0.978
Skin Sensitization:  0.064
Carcinogencity:  0.191
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.905

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

  Natural Product: NPC248670

Natural Product ID:  NPC248670
Common Name*:   (S)-N1-((2S,5S,8S,11R,12S,15S,18S)-5-Benzyl-2,15-Diisobutyl-8-Isopropyl-4,11-Dimethyl-3,6,9,13,16,22-Hexaoxo-10-Oxa-1,4,7,14,17-Pentaazabicyclo[16.3.1]Docos-20-En-12-Yl)-2-((R)-2-Hydroxy-3-(4-Hydroxyphenyl)Propanamido)Succinamide
IUPAC Name:   (2S)-N-[(2S,5S,8S,11R,12S,15S,18S)-5-benzyl-4,11-dimethyl-2,15-bis(2-methylpropyl)-3,6,9,13,16,22-hexaoxo-8-propan-2-yl-10-oxa-1,4,7,14,17-pentazabicyclo[16.3.1]docos-20-en-12-yl]-2-[[(2R)-2-hydroxy-3-(4-hydroxyphenyl)propanoyl]amino]butanediamide
Synonyms:  
Standard InCHIKey:  DFOCHYXOOMGICE-QGHDNFDISA-N
Standard InCHI:  InChI=1S/C49H68N8O12/c1-26(2)21-34-42(61)51-33-15-12-20-57(47(33)66)37(22-27(3)4)48(67)56(8)36(23-30-13-10-9-11-14-30)44(63)54-40(28(5)6)49(68)69-29(7)41(46(65)53-34)55-43(62)35(25-39(50)60)52-45(64)38(59)24-31-16-18-32(58)19-17-31/h9-14,16-20,26-29,33-38,40-41,58-59H,15,21-25H2,1-8H3,(H2,50,60)(H,51,61)(H,52,64)(H,53,65)(H,54,63)(H,55,62)/t29-,33+,34+,35+,36+,37+,38-,40+,41+/m1/s1
SMILES:  CC(C[C@@H]1N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](Cc2ccc(cc2)O)O)O)CC(=N)O)O)[C@@H](C)OC(=O)[C@@H](N=C([C@@H](N(C(=O)[C@@H](N2C(=O)[C@@H](N=C1O)CC=C2)CC(C)C)C)Cc1ccccc1)O)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2385896
PubChem CID:   71725294
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
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11000050]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11374973]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Einan Reservoir in Israel n.a. PMID[12141855]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[12141855]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18163584]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18558743]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18973386]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria water bloom of the cyanobacterium Microcystis aeruginosa n.a. n.a. PMID[19650639]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria bloom material Lake Kinneret, Israel n.a. PMID[22280481]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Kibbutz Geva, Israel n.a. PMID[23153007]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Water Reservoir near Kibbutz Hafetz Haim, Israel n.a. PMID[23718637]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[24261937]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24642434]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24868986]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[29405714]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[29847132]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9249979]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9842728]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. Database[Title]
NPO3288 Microcystis aeruginosa Species Microcystaceae 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
NPT2 Others Unspecified IC50 = 55500.0 nM PMID[536209]
NPT2 Others Unspecified IC50 = 48500.0 nM PMID[536209]

☑ 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 NPC248670 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
0.9259 High Similarity NPC50016
0.908 High Similarity NPC471165
0.9018 High Similarity NPC273755
0.8963 High Similarity NPC158277
0.8916 High Similarity NPC45037
0.8802 High Similarity NPC269750
0.8802 High Similarity NPC194671
0.8788 High Similarity NPC306804
0.878 High Similarity NPC40234
0.8735 High Similarity NPC279871
0.8735 High Similarity NPC26108
0.8735 High Similarity NPC473354
0.8706 High Similarity NPC294951
0.8667 High Similarity NPC475204
0.8667 High Similarity NPC475123
0.8659 High Similarity NPC294516
0.8659 High Similarity NPC107938
0.865 High Similarity NPC63931
0.8614 High Similarity NPC230611
0.8614 High Similarity NPC89831
0.8563 High Similarity NPC137627
0.8554 High Similarity NPC46009
0.8512 High Similarity NPC476227
0.8512 High Similarity NPC473402
0.8488 Intermediate Similarity NPC471050
0.8488 Intermediate Similarity NPC471048
0.8488 Intermediate Similarity NPC471049
0.848 Intermediate Similarity NPC476321
0.8457 Intermediate Similarity NPC473305
0.8457 Intermediate Similarity NPC163961
0.843 Intermediate Similarity NPC471526
0.8402 Intermediate Similarity NPC159767
0.8402 Intermediate Similarity NPC155506
0.8352 Intermediate Similarity NPC240130
0.8352 Intermediate Similarity NPC61332
0.8315 Intermediate Similarity NPC302715
0.8291 Intermediate Similarity NPC81026
0.8228 Intermediate Similarity NPC266741
0.8221 Intermediate Similarity NPC476268
0.8212 Intermediate Similarity NPC65714
0.8192 Intermediate Similarity NPC102959
0.8166 Intermediate Similarity NPC186617
0.8161 Intermediate Similarity NPC473404
0.8155 Intermediate Similarity NPC61004
0.8146 Intermediate Similarity NPC60516
0.8136 Intermediate Similarity NPC94862
0.8133 Intermediate Similarity NPC469243
0.8132 Intermediate Similarity NPC323662
0.8122 Intermediate Similarity NPC473371
0.8118 Intermediate Similarity NPC196091
0.8118 Intermediate Similarity NPC473693
0.8118 Intermediate Similarity NPC471568
0.8107 Intermediate Similarity NPC209463
0.8101 Intermediate Similarity NPC473378
0.8101 Intermediate Similarity NPC91953
0.8101 Intermediate Similarity NPC473407
0.8095 Intermediate Similarity NPC223207
0.8086 Intermediate Similarity NPC473491
0.8077 Intermediate Similarity NPC127741
0.8077 Intermediate Similarity NPC471592
0.8077 Intermediate Similarity NPC6570
0.8072 Intermediate Similarity NPC244336
0.8049 Intermediate Similarity NPC39431
0.8047 Intermediate Similarity NPC254700
0.8047 Intermediate Similarity NPC304074
0.8047 Intermediate Similarity NPC290755
0.8047 Intermediate Similarity NPC471771
0.8038 Intermediate Similarity NPC197921
0.8037 Intermediate Similarity NPC233702
0.8033 Intermediate Similarity NPC477552
0.8033 Intermediate Similarity NPC477550
0.8032 Intermediate Similarity NPC478005
0.8024 Intermediate Similarity NPC475544
0.8011 Intermediate Similarity NPC328763
0.8 Intermediate Similarity NPC302597
0.7988 Intermediate Similarity NPC472923
0.7988 Intermediate Similarity NPC262166
0.7987 Intermediate Similarity NPC469360
0.7976 Intermediate Similarity NPC241794
0.7965 Intermediate Similarity NPC328494
0.7946 Intermediate Similarity NPC477551
0.7907 Intermediate Similarity NPC274198
0.7907 Intermediate Similarity NPC198254
0.7901 Intermediate Similarity NPC16188
0.7895 Intermediate Similarity NPC328649
0.7892 Intermediate Similarity NPC244509
0.7892 Intermediate Similarity NPC473580
0.7879 Intermediate Similarity NPC202198
0.7879 Intermediate Similarity NPC56685
0.7874 Intermediate Similarity NPC477462
0.7853 Intermediate Similarity NPC477637
0.7849 Intermediate Similarity NPC280022
0.7841 Intermediate Similarity NPC119652
0.7841 Intermediate Similarity NPC97526
0.7829 Intermediate Similarity NPC196243
0.7821 Intermediate Similarity NPC315542
0.7812 Intermediate Similarity NPC476989
0.7803 Intermediate Similarity NPC276506
0.7771 Intermediate Similarity NPC122590
0.7771 Intermediate Similarity NPC136797
0.7754 Intermediate Similarity NPC469443
0.7751 Intermediate Similarity NPC287757
0.7751 Intermediate Similarity NPC319320
0.774 Intermediate Similarity NPC475421
0.7722 Intermediate Similarity NPC299806
0.7719 Intermediate Similarity NPC191863
0.7719 Intermediate Similarity NPC471052
0.7719 Intermediate Similarity NPC471051
0.7719 Intermediate Similarity NPC471053
0.7719 Intermediate Similarity NPC289776
0.7719 Intermediate Similarity NPC133470
0.7707 Intermediate Similarity NPC326966
0.7706 Intermediate Similarity NPC471527
0.7692 Intermediate Similarity NPC56635
0.7688 Intermediate Similarity NPC473502
0.7683 Intermediate Similarity NPC135121
0.7676 Intermediate Similarity NPC477632
0.7676 Intermediate Similarity NPC477638
0.7669 Intermediate Similarity NPC477217
0.7669 Intermediate Similarity NPC201244
0.7665 Intermediate Similarity NPC473341
0.7665 Intermediate Similarity NPC5194
0.7665 Intermediate Similarity NPC261934
0.7651 Intermediate Similarity NPC7817
0.7651 Intermediate Similarity NPC475168
0.7641 Intermediate Similarity NPC326027
0.7629 Intermediate Similarity NPC326333
0.7625 Intermediate Similarity NPC68865
0.7611 Intermediate Similarity NPC167763
0.7611 Intermediate Similarity NPC470112
0.7611 Intermediate Similarity NPC470903
0.7609 Intermediate Similarity NPC248822
0.7598 Intermediate Similarity NPC170302
0.7598 Intermediate Similarity NPC475409
0.7598 Intermediate Similarity NPC475564
0.7593 Intermediate Similarity NPC168113
0.759 Intermediate Similarity NPC245974
0.759 Intermediate Similarity NPC2501
0.7588 Intermediate Similarity NPC297145
0.7588 Intermediate Similarity NPC197743
0.7588 Intermediate Similarity NPC323336
0.7588 Intermediate Similarity NPC326349
0.7588 Intermediate Similarity NPC478007
0.7586 Intermediate Similarity NPC141957
0.7582 Intermediate Similarity NPC276120
0.7546 Intermediate Similarity NPC176226
0.7546 Intermediate Similarity NPC197682
0.7531 Intermediate Similarity NPC476259
0.7531 Intermediate Similarity NPC239762
0.7531 Intermediate Similarity NPC163392
0.753 Intermediate Similarity NPC9373
0.7527 Intermediate Similarity NPC138083
0.7527 Intermediate Similarity NPC314083
0.7516 Intermediate Similarity NPC64205
0.7515 Intermediate Similarity NPC470902
0.7514 Intermediate Similarity NPC475532
0.7513 Intermediate Similarity NPC220060
0.7512 Intermediate Similarity NPC478008
0.75 Intermediate Similarity NPC153554
0.75 Intermediate Similarity NPC32064
0.7487 Intermediate Similarity NPC311357
0.7486 Intermediate Similarity NPC473546
0.7484 Intermediate Similarity NPC257390
0.7474 Intermediate Similarity NPC469444
0.7472 Intermediate Similarity NPC165285
0.7472 Intermediate Similarity NPC17698
0.747 Intermediate Similarity NPC247298
0.7469 Intermediate Similarity NPC242159
0.7469 Intermediate Similarity NPC313694
0.746 Intermediate Similarity NPC50548
0.7459 Intermediate Similarity NPC174122
0.7459 Intermediate Similarity NPC64140
0.7442 Intermediate Similarity NPC62104
0.7442 Intermediate Similarity NPC1390
0.744 Intermediate Similarity NPC324081
0.7439 Intermediate Similarity NPC212850
0.7439 Intermediate Similarity NPC161069
0.7439 Intermediate Similarity NPC189724
0.7439 Intermediate Similarity NPC83289
0.7438 Intermediate Similarity NPC244866
0.7423 Intermediate Similarity NPC307357
0.7423 Intermediate Similarity NPC46098
0.7423 Intermediate Similarity NPC268841
0.7407 Intermediate Similarity NPC144314
0.7405 Intermediate Similarity NPC234069
0.7396 Intermediate Similarity NPC476744
0.7394 Intermediate Similarity NPC52748
0.7384 Intermediate Similarity NPC212699
0.7384 Intermediate Similarity NPC207675
0.7382 Intermediate Similarity NPC242728
0.7381 Intermediate Similarity NPC132771
0.738 Intermediate Similarity NPC477631
0.7375 Intermediate Similarity NPC45191
0.7374 Intermediate Similarity NPC164608
0.7366 Intermediate Similarity NPC477636
0.736 Intermediate Similarity NPC469445
0.7358 Intermediate Similarity NPC325651
0.7354 Intermediate Similarity NPC149962
0.7349 Intermediate Similarity NPC209509
0.7345 Intermediate Similarity NPC129486

  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 NPC248670 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
0.8012 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7875 Intermediate Similarity NPD7978 Discontinued
0.7701 Intermediate Similarity NPD7608 Discontinued
0.7643 Intermediate Similarity NPD3136 Phase 2
0.763 Intermediate Similarity NPD8303 Discontinued
0.756 Intermediate Similarity NPD7131 Phase 3
0.7544 Intermediate Similarity NPD8019 Approved
0.7543 Intermediate Similarity NPD7484 Phase 3
0.7543 Intermediate Similarity NPD7485 Phase 3
0.7438 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7303 Discontinued
0.7378 Intermediate Similarity NPD7450 Phase 2
0.7341 Intermediate Similarity NPD7495 Discontinued
0.7337 Intermediate Similarity NPD5946 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD8031 Discontinued
0.7251 Intermediate Similarity NPD7523 Phase 3
0.7247 Intermediate Similarity NPD2017 Approved
0.7247 Intermediate Similarity NPD2890 Approved
0.7247 Intermediate Similarity NPD2888 Approved
0.7247 Intermediate Similarity NPD2889 Approved
0.7212 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD4652 Approved
0.7167 Intermediate Similarity NPD5137 Approved
0.716 Intermediate Similarity NPD8323 Discontinued
0.715 Intermediate Similarity NPD7810 Phase 3
0.715 Intermediate Similarity NPD7811 Phase 3
0.7093 Intermediate Similarity NPD7613 Discontinued
0.7083 Intermediate Similarity NPD6681 Discovery
0.7079 Intermediate Similarity NPD2098 Approved
0.7079 Intermediate Similarity NPD5219 Approved
0.7079 Intermediate Similarity NPD5218 Approved
0.7073 Intermediate Similarity NPD6346 Approved
0.7029 Intermediate Similarity NPD8417 Discontinued
0.7012 Intermediate Similarity NPD5745 Approved
0.7 Intermediate Similarity NPD3400 Discontinued
0.7 Intermediate Similarity NPD5481 Discontinued
0.6974 Remote Similarity NPD7565 Approved
0.6968 Remote Similarity NPD6853 Approved
0.6968 Remote Similarity NPD6851 Approved
0.6968 Remote Similarity NPD6237 Clinical (unspecified phase)
0.6966 Remote Similarity NPD2097 Approved
0.6946 Remote Similarity NPD6852 Discontinued
0.6941 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6937 Remote Similarity NPD4659 Approved
0.6936 Remote Similarity NPD3536 Discontinued
0.6914 Remote Similarity NPD7451 Discontinued
0.6901 Remote Similarity NPD6676 Phase 2
0.6895 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6893 Remote Similarity NPD2541 Clinical (unspecified phase)
0.689 Remote Similarity NPD5746 Approved
0.6889 Remote Similarity NPD4521 Clinical (unspecified phase)
0.6889 Remote Similarity NPD8070 Approved
0.6886 Remote Similarity NPD8172 Phase 2
0.6886 Remote Similarity NPD8173 Phase 2
0.6879 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2562 Approved
0.6875 Remote Similarity NPD2561 Approved
0.6862 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4103 Phase 2
0.6852 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6845 Remote Similarity NPD3552 Approved
0.6845 Remote Similarity NPD3555 Approved
0.6845 Remote Similarity NPD3554 Approved
0.6845 Remote Similarity NPD3553 Approved
0.6842 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6839 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6824 Remote Similarity NPD8076 Discontinued
0.6823 Remote Similarity NPD7617 Discontinued
0.6816 Remote Similarity NPD7972 Discontinued
0.6802 Remote Similarity NPD1968 Approved
0.6802 Remote Similarity NPD1967 Approved
0.6791 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6784 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6772 Remote Similarity NPD2217 Approved
0.6772 Remote Similarity NPD2218 Phase 2
0.6765 Remote Similarity NPD2240 Approved
0.6765 Remote Similarity NPD2239 Approved
0.6762 Remote Similarity NPD8356 Approved
0.6755 Remote Similarity NPD6297 Approved
0.6755 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6743 Remote Similarity NPD3985 Discontinued
0.6742 Remote Similarity NPD2891 Approved
0.6726 Remote Similarity NPD555 Phase 2
0.6723 Remote Similarity NPD6670 Clinical (unspecified phase)
0.672 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6716 Remote Similarity NPD3803 Clinical (unspecified phase)
0.6714 Remote Similarity NPD8430 Approved
0.6707 Remote Similarity NPD6407 Approved
0.6707 Remote Similarity NPD6405 Approved
0.6705 Remote Similarity NPD6390 Discontinued
0.6705 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6704 Remote Similarity NPD6677 Suspended
0.6703 Remote Similarity NPD2388 Discontinued
0.67 Remote Similarity NPD6863 Phase 2
0.67 Remote Similarity NPD8162 Phase 2
0.67 Remote Similarity NPD8163 Clinical (unspecified phase)
0.6687 Remote Similarity NPD4738 Phase 2
0.6687 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6686 Remote Similarity NPD3054 Approved
0.6686 Remote Similarity NPD3052 Approved
0.6686 Remote Similarity NPD5314 Approved
0.6686 Remote Similarity NPD2568 Approved
0.6685 Remote Similarity NPD3455 Phase 2
0.6685 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6684 Remote Similarity NPD8025 Phase 2
0.6667 Remote Similarity NPD4173 Approved
0.6667 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4172 Approved
0.6667 Remote Similarity NPD6623 Phase 3
0.6667 Remote Similarity NPD8416 Discontinued
0.665 Remote Similarity NPD3879 Approved
0.6647 Remote Similarity NPD6294 Approved
0.6647 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1330 Phase 2
0.6647 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6295 Approved
0.6632 Remote Similarity NPD8103 Clinical (unspecified phase)
0.663 Remote Similarity NPD5772 Approved
0.663 Remote Similarity NPD5773 Approved
0.6629 Remote Similarity NPD8315 Phase 1
0.6628 Remote Similarity NPD4152 Approved
0.6627 Remote Similarity NPD8643 Discontinued
0.6627 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6614 Remote Similarity NPD5485 Approved
0.6614 Remote Similarity NPD5484 Approved
0.6611 Remote Similarity NPD6072 Discontinued
0.661 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6607 Remote Similarity NPD259 Phase 1
0.6607 Remote Similarity NPD1423 Approved
0.6602 Remote Similarity NPD3878 Approved
0.6591 Remote Similarity NPD2013 Approved
0.6591 Remote Similarity NPD2016 Approved
0.6591 Remote Similarity NPD2014 Approved
0.6591 Remote Similarity NPD6088 Approved
0.659 Remote Similarity NPD6119 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6073 Approved
0.6585 Remote Similarity NPD3125 Approved
0.6584 Remote Similarity NPD5723 Approved
0.6579 Remote Similarity NPD5445 Approved
0.6575 Remote Similarity NPD7945 Clinical (unspecified phase)
0.657 Remote Similarity NPD6897 Clinical (unspecified phase)
0.657 Remote Similarity NPD9570 Approved
0.6568 Remote Similarity NPD3059 Approved
0.6568 Remote Similarity NPD3062 Approved
0.6568 Remote Similarity NPD825 Approved
0.6568 Remote Similarity NPD826 Approved
0.6568 Remote Similarity NPD8265 Approved
0.6568 Remote Similarity NPD3061 Approved
0.6567 Remote Similarity NPD6254 Approved
0.6567 Remote Similarity NPD6256 Approved
0.6567 Remote Similarity NPD6255 Approved
0.6566 Remote Similarity NPD4993 Discontinued
0.6564 Remote Similarity NPD2584 Suspended
0.6561 Remote Similarity NPD6042 Phase 2
0.6561 Remote Similarity NPD42 Phase 2
0.6557 Remote Similarity NPD6796 Discontinued
0.6554 Remote Similarity NPD6419 Discontinued
0.655 Remote Similarity NPD6901 Phase 3
0.6548 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6543 Remote Similarity NPD5200 Clinical (unspecified phase)
0.6541 Remote Similarity NPD9568 Approved
0.6541 Remote Similarity NPD2904 Discontinued
0.6538 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6538 Remote Similarity NPD4557 Approved
0.6537 Remote Similarity NPD7585 Approved
0.6534 Remote Similarity NPD7554 Discontinued
0.6534 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6532 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6528 Remote Similarity NPD6556 Clinical (unspecified phase)
0.6528 Remote Similarity NPD6557 Phase 2
0.6527 Remote Similarity NPD4617 Approved
0.6527 Remote Similarity NPD5201 Approved
0.6527 Remote Similarity NPD4620 Approved
0.6527 Remote Similarity NPD5203 Approved
0.6524 Remote Similarity NPD4677 Discontinued
0.6522 Remote Similarity NPD4504 Clinical (unspecified phase)
0.6519 Remote Similarity NPD7749 Clinical (unspecified phase)
0.6519 Remote Similarity NPD7105 Phase 1
0.6517 Remote Similarity NPD6253 Approved
0.6514 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6513 Remote Similarity NPD4435 Approved
0.6508 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6506 Remote Similarity NPD3604 Clinical (unspecified phase)
0.6506 Remote Similarity NPD5339 Clinical (unspecified phase)
0.65 Remote Similarity NPD318 Approved
0.65 Remote Similarity NPD16 Approved
0.65 Remote Similarity NPD317 Approved
0.65 Remote Similarity NPD856 Approved
0.6491 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6489 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6488 Remote Similarity NPD7583 Approved
0.6484 Remote Similarity NPD5356 Approved
0.6484 Remote Similarity NPD2515 Approved
0.6484 Remote Similarity NPD3007 Approved
0.6484 Remote Similarity NPD5355 Approved
0.6484 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6481 Remote Similarity NPD4086 Phase 1
0.6477 Remote Similarity NPD5035 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