Structure

Physi-Chem Properties

Molecular Weight:  703.43
Volume:  756.734
LogP:  3.802
LogD:  3.596
LogS:  -4.849
# Rotatable Bonds:  24
TPSA:  142.35
# H-Bond Aceptor:  11
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.159
Synthetic Accessibility Score:  4.525
Fsp3:  0.525
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:  -4.963
MDCK Permeability:  6.471985398093238e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.317
20% Bioavailability (F20%):  0.056
30% Bioavailability (F30%):  0.581

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.01
Plasma Protein Binding (PPB):  95.90479278564453%
Volume Distribution (VD):  0.691
Pgp-substrate:  1.8205431699752808%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.197
CYP2C19-inhibitor:  0.505
CYP2C19-substrate:  0.905
CYP2C9-inhibitor:  0.862
CYP2C9-substrate:  0.113
CYP2D6-inhibitor:  0.278
CYP2D6-substrate:  0.265
CYP3A4-inhibitor:  0.981
CYP3A4-substrate:  0.919

ADMET: Excretion

Clearance (CL):  6.716
Half-life (T1/2):  0.267

ADMET: Toxicity

hERG Blockers:  0.112
Human Hepatotoxicity (H-HT):  0.952
Drug-inuced Liver Injury (DILI):  0.931
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.766
Maximum Recommended Daily Dose:  0.734
Skin Sensitization:  0.04
Carcinogencity:  0.006
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.023

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

  Natural Product: NPC319320

Natural Product ID:  NPC319320
Common Name*:   Carmabin A
IUPAC Name:   N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-amino-3-(4-methoxyphenyl)-1-oxopropan-2-yl]-methylamino]-1-oxopropan-2-yl]-methylamino]-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]-N,2,4-trimethyldec-9-ynamide
Synonyms:  
Standard InCHIKey:  BRWIYXLUWTZWGU-PBQPNXEGSA-N
Standard InCHI:  InChI=1S/C40H57N5O6/c1-10-11-12-14-17-27(2)24-28(3)38(48)45(8)35(26-31-18-15-13-16-19-31)37(47)42-29(4)39(49)43(6)30(5)40(50)44(7)34(36(41)46)25-32-20-22-33(51-9)23-21-32/h1,13,15-16,18-23,27-30,34-35H,11-12,14,17,24-26H2,2-9H3,(H2,41,46)(H,42,47)/t27?,28?,29-,30-,34-,35-/m0/s1
SMILES:  C#CCCCCC(CC(C(=O)N([C@H](C(=N[C@H](C(=O)N([C@H](C(=O)N([C@H](C(=N)O)Cc1ccc(cc1)OC)C)C)C)C)O)Cc1ccccc1)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL228839
PubChem CID:   16757536
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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10514329]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10654420]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10691708]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. palauan n.a. PMID[10691729]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10843570]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10924172]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[10978206]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076571]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076573]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11076574]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11277744]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11389621]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11430000]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11473443]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[11922791]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762816]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[12828459]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14575437]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[1517734]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Papua New Guinea n.a. PMID[16643028]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17125217]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[17441769]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18444683]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Singapore n.a. PMID[19093843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19489598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. eastern Caribbean n.a. PMID[19739598]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[19839606]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20030365]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. panamanian n.a. PMID[20158242]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Floridian n.a. PMID[20166701]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[20936843]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21138309]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[2128518]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21341718]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21539315]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21806011]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[21999614]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[22035372]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[29792428]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[3924698]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[7623050]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. Caribbean n.a. PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9584405]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599278]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9599279]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[9784156]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 9800.0 nM PMID[539115]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1400.0 nM PMID[539115]

☑ 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 NPC319320 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 NPC287757
0.9122 High Similarity NPC324081
0.8854 High Similarity NPC473502
0.8421 Intermediate Similarity NPC16188
0.8366 Intermediate Similarity NPC9373
0.8354 Intermediate Similarity NPC164608
0.8323 Intermediate Similarity NPC254700
0.8323 Intermediate Similarity NPC233702
0.8261 Intermediate Similarity NPC472923
0.8187 Intermediate Similarity NPC469243
0.8176 Intermediate Similarity NPC138083
0.8171 Intermediate Similarity NPC196091
0.8155 Intermediate Similarity NPC32064
0.8153 Intermediate Similarity NPC202198
0.811 Intermediate Similarity NPC186617
0.8092 Intermediate Similarity NPC476989
0.8075 Intermediate Similarity NPC475544
0.8069 Intermediate Similarity NPC101719
0.8061 Intermediate Similarity NPC471568
0.8061 Intermediate Similarity NPC473693
0.8037 Intermediate Similarity NPC63931
0.8037 Intermediate Similarity NPC223207
0.8025 Intermediate Similarity NPC241794
0.8 Intermediate Similarity NPC222466
0.7988 Intermediate Similarity NPC290755
0.7988 Intermediate Similarity NPC475421
0.7988 Intermediate Similarity NPC304074
0.7988 Intermediate Similarity NPC471771
0.7965 Intermediate Similarity NPC315542
0.7965 Intermediate Similarity NPC299806
0.7964 Intermediate Similarity NPC306804
0.7937 Intermediate Similarity NPC473580
0.7919 Intermediate Similarity NPC276120
0.7911 Intermediate Similarity NPC473491
0.7867 Intermediate Similarity NPC257390
0.7849 Intermediate Similarity NPC470903
0.7849 Intermediate Similarity NPC470112
0.7849 Intermediate Similarity NPC167763
0.7844 Intermediate Similarity NPC198254
0.7844 Intermediate Similarity NPC274198
0.7831 Intermediate Similarity NPC328649
0.7812 Intermediate Similarity NPC56685
0.7812 Intermediate Similarity NPC262166
0.7811 Intermediate Similarity NPC26108
0.7806 Intermediate Similarity NPC189724
0.7806 Intermediate Similarity NPC212850
0.7806 Intermediate Similarity NPC83289
0.7791 Intermediate Similarity NPC244336
0.7784 Intermediate Similarity NPC174122
0.7784 Intermediate Similarity NPC64140
0.7784 Intermediate Similarity NPC29531
0.7778 Intermediate Similarity NPC269750
0.7778 Intermediate Similarity NPC194671
0.7771 Intermediate Similarity NPC4910
0.7771 Intermediate Similarity NPC81026
0.7751 Intermediate Similarity NPC273755
0.7751 Intermediate Similarity NPC248670
0.7751 Intermediate Similarity NPC137627
0.774 Intermediate Similarity NPC477526
0.7738 Intermediate Similarity NPC276506
0.7727 Intermediate Similarity NPC234069
0.7727 Intermediate Similarity NPC242159
0.7727 Intermediate Similarity NPC313694
0.7725 Intermediate Similarity NPC294516
0.7725 Intermediate Similarity NPC141957
0.7725 Intermediate Similarity NPC107938
0.7722 Intermediate Similarity NPC247298
0.7716 Intermediate Similarity NPC476268
0.7707 Intermediate Similarity NPC266741
0.7706 Intermediate Similarity NPC155506
0.7706 Intermediate Similarity NPC159767
0.7706 Intermediate Similarity NPC279871
0.7706 Intermediate Similarity NPC476227
0.7702 Intermediate Similarity NPC5194
0.7702 Intermediate Similarity NPC261934
0.7697 Intermediate Similarity NPC470392
0.7692 Intermediate Similarity NPC89831
0.7679 Intermediate Similarity NPC280022
0.767 Intermediate Similarity NPC329731
0.7665 Intermediate Similarity NPC61004
0.7661 Intermediate Similarity NPC50016
0.7661 Intermediate Similarity NPC196243
0.7654 Intermediate Similarity NPC39431
0.7647 Intermediate Similarity NPC475532
0.764 Intermediate Similarity NPC473407
0.764 Intermediate Similarity NPC248822
0.764 Intermediate Similarity NPC473378
0.7633 Intermediate Similarity NPC40234
0.7633 Intermediate Similarity NPC475123
0.7633 Intermediate Similarity NPC46009
0.7633 Intermediate Similarity NPC475204
0.7632 Intermediate Similarity NPC326966
0.7625 Intermediate Similarity NPC132771
0.7625 Intermediate Similarity NPC245974
0.7622 Intermediate Similarity NPC56635
0.7619 Intermediate Similarity NPC302597
0.7611 Intermediate Similarity NPC471563
0.761 Intermediate Similarity NPC138775
0.7607 Intermediate Similarity NPC244509
0.7602 Intermediate Similarity NPC471165
0.7602 Intermediate Similarity NPC165285
0.7596 Intermediate Similarity NPC242728
0.7588 Intermediate Similarity NPC230611
0.7586 Intermediate Similarity NPC470546
0.7572 Intermediate Similarity NPC45037
0.7569 Intermediate Similarity NPC149962
0.7545 Intermediate Similarity NPC289776
0.7545 Intermediate Similarity NPC133470
0.7545 Intermediate Similarity NPC191863
0.7527 Intermediate Similarity NPC144314
0.7517 Intermediate Similarity NPC470545
0.7517 Intermediate Similarity NPC22746
0.7514 Intermediate Similarity NPC59827
0.7514 Intermediate Similarity NPC184933
0.75 Intermediate Similarity NPC473402
0.75 Intermediate Similarity NPC17698
0.75 Intermediate Similarity NPC473354
0.75 Intermediate Similarity NPC136797
0.75 Intermediate Similarity NPC158277
0.75 Intermediate Similarity NPC325651
0.7486 Intermediate Similarity NPC50548
0.7483 Intermediate Similarity NPC218323
0.7473 Intermediate Similarity NPC473460
0.7471 Intermediate Similarity NPC119652
0.7471 Intermediate Similarity NPC129486
0.7471 Intermediate Similarity NPC97526
0.7468 Intermediate Similarity NPC139326
0.7468 Intermediate Similarity NPC244866
0.7453 Intermediate Similarity NPC189908
0.7448 Intermediate Similarity NPC470544
0.7446 Intermediate Similarity NPC123859
0.7434 Intermediate Similarity NPC111428
0.7434 Intermediate Similarity NPC473322
0.7434 Intermediate Similarity NPC296712
0.7433 Intermediate Similarity NPC473422
0.7432 Intermediate Similarity NPC71684
0.7429 Intermediate Similarity NPC153554
0.7419 Intermediate Similarity NPC266425
0.7412 Intermediate Similarity NPC209463
0.741 Intermediate Similarity NPC207675
0.741 Intermediate Similarity NPC326349
0.741 Intermediate Similarity NPC323336
0.741 Intermediate Similarity NPC212699
0.7401 Intermediate Similarity NPC471050
0.7401 Intermediate Similarity NPC471048
0.7401 Intermediate Similarity NPC294951
0.7401 Intermediate Similarity NPC471049
0.7391 Intermediate Similarity NPC477527
0.7391 Intermediate Similarity NPC329761
0.7391 Intermediate Similarity NPC225648
0.7389 Intermediate Similarity NPC283207
0.7389 Intermediate Similarity NPC240130
0.7389 Intermediate Similarity NPC61332
0.7374 Intermediate Similarity NPC94862
0.7363 Intermediate Similarity NPC328763
0.7358 Intermediate Similarity NPC91953
0.7358 Intermediate Similarity NPC161069
0.7355 Intermediate Similarity NPC274732
0.7325 Intermediate Similarity NPC138365
0.7325 Intermediate Similarity NPC127741
0.7312 Intermediate Similarity NPC473450
0.7303 Intermediate Similarity NPC124776
0.7297 Intermediate Similarity NPC477552
0.7297 Intermediate Similarity NPC477550
0.7297 Intermediate Similarity NPC43275
0.7296 Intermediate Similarity NPC197921
0.729 Intermediate Similarity NPC45191
0.7288 Intermediate Similarity NPC476321
0.7288 Intermediate Similarity NPC473404
0.7284 Intermediate Similarity NPC135121
0.7283 Intermediate Similarity NPC328494
0.7278 Intermediate Similarity NPC132636
0.7273 Intermediate Similarity NPC283079
0.7268 Intermediate Similarity NPC302715
0.7261 Intermediate Similarity NPC29650
0.7248 Intermediate Similarity NPC321133
0.7247 Intermediate Similarity NPC471526
0.7238 Intermediate Similarity NPC124626
0.7233 Intermediate Similarity NPC471316
0.7226 Intermediate Similarity NPC255447
0.7219 Intermediate Similarity NPC477551
0.7204 Intermediate Similarity NPC323662
0.7198 Intermediate Similarity NPC473305
0.7198 Intermediate Similarity NPC163961
0.7195 Intermediate Similarity NPC129666
0.7181 Intermediate Similarity NPC283760
0.7169 Intermediate Similarity NPC122590
0.7168 Intermediate Similarity NPC469505
0.716 Intermediate Similarity NPC201244
0.716 Intermediate Similarity NPC477217
0.716 Intermediate Similarity NPC209509
0.7152 Intermediate Similarity NPC27581
0.7143 Intermediate Similarity NPC317254
0.7143 Intermediate Similarity NPC469360
0.7143 Intermediate Similarity NPC311357
0.7134 Intermediate Similarity NPC471953
0.7133 Intermediate Similarity NPC200964
0.7124 Intermediate Similarity NPC62101
0.7124 Intermediate Similarity NPC95733
0.7113 Intermediate Similarity NPC326333

  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 NPC319320 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
0.8627 High Similarity NPD7131 Phase 3
0.8333 Intermediate Similarity NPD7485 Phase 3
0.8333 Intermediate Similarity NPD7484 Phase 3
0.8171 Intermediate Similarity NPD7608 Discontinued
0.784 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD7450 Phase 2
0.7697 Intermediate Similarity NPD5967 Approved
0.7643 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7303 Discontinued
0.7605 Intermediate Similarity NPD8031 Discontinued
0.7595 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD5745 Approved
0.7547 Intermediate Similarity NPD5481 Discontinued
0.7543 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD3655 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6297 Approved
0.7517 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD5484 Approved
0.7471 Intermediate Similarity NPD5485 Approved
0.7469 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD6851 Approved
0.7458 Intermediate Similarity NPD6853 Approved
0.7451 Intermediate Similarity NPD5746 Approved
0.7423 Intermediate Similarity NPD7613 Discontinued
0.7423 Intermediate Similarity NPD6390 Discontinued
0.7421 Intermediate Similarity NPD6681 Discovery
0.7375 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD7495 Discontinued
0.7353 Intermediate Similarity NPD8303 Discontinued
0.7321 Intermediate Similarity NPD7972 Discontinued
0.7303 Intermediate Similarity NPD7281 Phase 3
0.7303 Intermediate Similarity NPD7280 Phase 3
0.7288 Intermediate Similarity NPD5192 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2460 Phase 3
0.7267 Intermediate Similarity NPD2459 Approved
0.7267 Intermediate Similarity NPD2458 Approved
0.7262 Intermediate Similarity NPD5356 Approved
0.7262 Intermediate Similarity NPD8019 Approved
0.7262 Intermediate Similarity NPD5355 Approved
0.7258 Intermediate Similarity NPD7810 Phase 3
0.7258 Intermediate Similarity NPD7811 Phase 3
0.7253 Intermediate Similarity NPD6505 Approved
0.7253 Intermediate Similarity NPD6504 Approved
0.7248 Intermediate Similarity NPD2668 Approved
0.7248 Intermediate Similarity NPD2667 Approved
0.7237 Intermediate Similarity NPD196 Phase 1
0.7226 Intermediate Similarity NPD3136 Phase 2
0.7219 Intermediate Similarity NPD5108 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1725 Approved
0.7182 Intermediate Similarity NPD6089 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7080 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2874 Phase 2
0.7151 Intermediate Similarity NPD6862 Phase 2
0.7143 Intermediate Similarity NPD6875 Approved
0.7143 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6876 Approved
0.7134 Intermediate Similarity NPD2245 Discovery
0.7125 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD4186 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1975 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD8172 Phase 2
0.7107 Intermediate Similarity NPD3052 Approved
0.7107 Intermediate Similarity NPD8173 Phase 2
0.7107 Intermediate Similarity NPD3054 Approved
0.7101 Intermediate Similarity NPD7110 Phase 1
0.7101 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD6072 Discontinued
0.7081 Intermediate Similarity NPD2239 Approved
0.7081 Intermediate Similarity NPD2240 Approved
0.7076 Intermediate Similarity NPD2097 Approved
0.7076 Intermediate Similarity NPD7318 Phase 3
0.7073 Intermediate Similarity NPD8323 Discontinued
0.707 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1536 Approved
0.7051 Intermediate Similarity NPD2614 Approved
0.7045 Intermediate Similarity NPD6894 Phase 1
0.7037 Intermediate Similarity NPD7720 Phase 2
0.7032 Intermediate Similarity NPD7451 Discontinued
0.7025 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7477 Discontinued
0.7025 Intermediate Similarity NPD1423 Approved
0.7018 Intermediate Similarity NPD6060 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6677 Suspended
0.7 Intermediate Similarity NPD7438 Suspended
0.7 Intermediate Similarity NPD7193 Clinical (unspecified phase)
0.6995 Remote Similarity NPD4434 Approved
0.6994 Remote Similarity NPD2098 Approved
0.6994 Remote Similarity NPD8070 Approved
0.6989 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6983 Remote Similarity NPD5557 Phase 1
0.6978 Remote Similarity NPD6556 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1538 Phase 1
0.6975 Remote Similarity NPD1519 Approved
0.6975 Remote Similarity NPD1537 Approved
0.6973 Remote Similarity NPD5525 Clinical (unspecified phase)
0.697 Remote Similarity NPD7602 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7523 Phase 3
0.6964 Remote Similarity NPD1670 Discontinued
0.6962 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4227 Discontinued
0.6959 Remote Similarity NPD7317 Phase 3
0.6957 Remote Similarity NPD5688 Approved
0.6957 Remote Similarity NPD1521 Approved
0.6957 Remote Similarity NPD1520 Approved
0.6957 Remote Similarity NPD4435 Approved
0.6957 Remote Similarity NPD5689 Approved
0.6948 Remote Similarity NPD1669 Approved
0.6946 Remote Similarity NPD3536 Discontinued
0.6946 Remote Similarity NPD3985 Discontinued
0.6946 Remote Similarity NPD6419 Discontinued
0.6941 Remote Similarity NPD6502 Phase 2
0.6933 Remote Similarity NPD7978 Discontinued
0.6933 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4652 Approved
0.6928 Remote Similarity NPD6666 Approved
0.6928 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6928 Remote Similarity NPD6667 Approved
0.6928 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7861 Discontinued
0.6919 Remote Similarity NPD5773 Approved
0.6919 Remote Similarity NPD5772 Approved
0.6919 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6914 Remote Similarity NPD7728 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7258 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6899 Remote Similarity NPD5163 Phase 2
0.6899 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6893 Remote Similarity NPD5137 Approved
0.6875 Remote Similarity NPD2888 Approved
0.6875 Remote Similarity NPD2516 Approved
0.6875 Remote Similarity NPD2017 Approved
0.6875 Remote Similarity NPD6346 Approved
0.6875 Remote Similarity NPD2890 Approved
0.6875 Remote Similarity NPD2889 Approved
0.6872 Remote Similarity NPD3909 Discontinued
0.6871 Remote Similarity NPD1522 Approved
0.6871 Remote Similarity NPD4476 Approved
0.6871 Remote Similarity NPD1523 Approved
0.6871 Remote Similarity NPD4477 Approved
0.6867 Remote Similarity NPD2219 Phase 1
0.6867 Remote Similarity NPD3596 Phase 2
0.6863 Remote Similarity NPD3847 Discontinued
0.686 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6857 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6856 Remote Similarity NPD8161 Suspended
0.6855 Remote Similarity NPD5718 Phase 2
0.6847 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7020 Approved
0.6845 Remote Similarity NPD7019 Approved
0.6842 Remote Similarity NPD2592 Discontinued
0.6839 Remote Similarity NPD6582 Phase 2
0.6839 Remote Similarity NPD6583 Phase 3
0.6839 Remote Similarity NPD4659 Approved
0.6836 Remote Similarity NPD2517 Approved
0.6833 Remote Similarity NPD6042 Phase 2
0.6833 Remote Similarity NPD3965 Phase 1
0.6833 Remote Similarity NPD42 Phase 2
0.6832 Remote Similarity NPD4618 Approved
0.6832 Remote Similarity NPD4622 Approved
0.6832 Remote Similarity NPD7113 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7617 Discontinued
0.6828 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6825 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2904 Discontinued
0.6818 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6815 Remote Similarity NPD7905 Discontinued
0.6811 Remote Similarity NPD3863 Clinical (unspecified phase)
0.681 Remote Similarity NPD6380 Phase 1
0.6807 Remote Similarity NPD1662 Clinical (unspecified phase)
0.6805 Remote Similarity NPD7526 Approved
0.6805 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6805 Remote Similarity NPD52 Approved
0.6802 Remote Similarity NPD6873 Phase 2
0.6793 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6792 Remote Similarity NPD4497 Clinical (unspecified phase)
0.6788 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7045 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7598 Phase 2
0.6784 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6782 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6774 Remote Similarity NPD2233 Approved
0.6774 Remote Similarity NPD4157 Discontinued
0.6774 Remote Similarity NPD2561 Approved
0.6774 Remote Similarity NPD2232 Approved
0.6774 Remote Similarity NPD7291 Discontinued
0.6774 Remote Similarity NPD2230 Approved
0.6774 Remote Similarity NPD2562 Approved
0.6772 Remote Similarity NPD4993 Discontinued
0.6772 Remote Similarity NPD2040 Clinical (unspecified phase)
0.6771 Remote Similarity NPD6519 Phase 2
0.677 Remote Similarity NPD3142 Approved
0.677 Remote Similarity NPD3140 Approved
0.6768 Remote Similarity NPD3175 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