Structure

Physi-Chem Properties

Molecular Weight:  640.38
Volume:  675.957
LogP:  3.483
LogD:  3.052
LogS:  -4.333
# Rotatable Bonds:  9
TPSA:  134.35
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.241
Synthetic Accessibility Score:  5.253
Fsp3:  0.629
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:  -5.039
MDCK Permeability:  1.7928003217093647e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.018
Human Intestinal Absorption (HIA):  0.715
20% Bioavailability (F20%):  0.078
30% Bioavailability (F30%):  0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  94.0389633178711%
Volume Distribution (VD):  0.682
Pgp-substrate:  1.1061315536499023%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.203
CYP2C19-inhibitor:  0.258
CYP2C19-substrate:  0.87
CYP2C9-inhibitor:  0.366
CYP2C9-substrate:  0.102
CYP2D6-inhibitor:  0.055
CYP2D6-substrate:  0.177
CYP3A4-inhibitor:  0.96
CYP3A4-substrate:  0.914

ADMET: Excretion

Clearance (CL):  4.938
Half-life (T1/2):  0.334

ADMET: Toxicity

hERG Blockers:  0.021
Human Hepatotoxicity (H-HT):  0.937
Drug-inuced Liver Injury (DILI):  0.893
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.774
Maximum Recommended Daily Dose:  0.291
Skin Sensitization:  0.022
Carcinogencity:  0.012
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.022

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

  Natural Product: NPC473502

Natural Product ID:  NPC473502
Common Name*:   Guineamide C
IUPAC Name:   (5S,8S,11S)-2-butan-2-yl-5-[(4-methoxyphenyl)methyl]-4,10,11,15-tetramethyl-14-pent-4-ynyl-8-propan-2-yl-1-oxa-4,7,10,13-tetrazacyclohexadecane-3,6,9,12,16-pentone
Synonyms:   Guineamide C
Standard InCHIKey:  LTQSSFDXKQDYDB-RGHLRUQMSA-N
Standard InCHI:  InChI=1S/C35H52N4O7/c1-11-13-14-15-27-23(6)35(44)46-30(22(5)12-2)34(43)39(9)28(20-25-16-18-26(45-10)19-17-25)32(41)37-29(21(3)4)33(42)38(8)24(7)31(40)36-27/h1,16-19,21-24,27-30H,12-15,20H2,2-10H3,(H,36,40)(H,37,41)/t22?,23?,24-,27?,28-,29-,30?/m0/s1
SMILES:  CCC(C)C1C(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(C(=O)O1)C)CCCC#C)C)C)C(C)C)CC2=CC=C(C=C2)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443937
PubChem CID:   10054915
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
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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 16000.0 nM PMID[514883]

☑ 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 NPC473502 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
0.9 High Similarity NPC196091
0.8854 High Similarity NPC319320
0.8854 High Similarity NPC287757
0.8675 High Similarity NPC475421
0.8634 High Similarity NPC472923
0.8589 High Similarity NPC186617
0.8537 High Similarity NPC471568
0.8537 High Similarity NPC473693
0.8526 High Similarity NPC324081
0.8521 High Similarity NPC470903
0.8521 High Similarity NPC167763
0.8521 High Similarity NPC470112
0.8431 Intermediate Similarity NPC139326
0.8421 Intermediate Similarity NPC299806
0.8269 Intermediate Similarity NPC81026
0.8242 Intermediate Similarity NPC254700
0.8228 Intermediate Similarity NPC132771
0.8205 Intermediate Similarity NPC266741
0.8137 Intermediate Similarity NPC39431
0.8114 Intermediate Similarity NPC4910
0.8103 Intermediate Similarity NPC315542
0.8101 Intermediate Similarity NPC329761
0.8101 Intermediate Similarity NPC225648
0.8013 Intermediate Similarity NPC269398
0.8013 Intermediate Similarity NPC263493
0.8011 Intermediate Similarity NPC329731
0.7988 Intermediate Similarity NPC212699
0.7988 Intermediate Similarity NPC207675
0.7978 Intermediate Similarity NPC477526
0.7974 Intermediate Similarity NPC470392
0.7953 Intermediate Similarity NPC476227
0.7888 Intermediate Similarity NPC129666
0.7882 Intermediate Similarity NPC40234
0.7849 Intermediate Similarity NPC26108
0.7845 Intermediate Similarity NPC184933
0.7845 Intermediate Similarity NPC59827
0.7821 Intermediate Similarity NPC471265
0.7821 Intermediate Similarity NPC471264
0.7791 Intermediate Similarity NPC306804
0.7791 Intermediate Similarity NPC137627
0.7778 Intermediate Similarity NPC475123
0.7778 Intermediate Similarity NPC475204
0.7771 Intermediate Similarity NPC98424
0.7771 Intermediate Similarity NPC470884
0.7771 Intermediate Similarity NPC476133
0.7771 Intermediate Similarity NPC178662
0.7771 Intermediate Similarity NPC92784
0.7771 Intermediate Similarity NPC56635
0.7765 Intermediate Similarity NPC294516
0.7765 Intermediate Similarity NPC107938
0.7764 Intermediate Similarity NPC16188
0.775 Intermediate Similarity NPC209509
0.7746 Intermediate Similarity NPC164608
0.7746 Intermediate Similarity NPC159767
0.7746 Intermediate Similarity NPC155506
0.7746 Intermediate Similarity NPC279871
0.7717 Intermediate Similarity NPC477527
0.7716 Intermediate Similarity NPC9373
0.7688 Intermediate Similarity NPC248670
0.768 Intermediate Similarity NPC473407
0.768 Intermediate Similarity NPC248822
0.768 Intermediate Similarity NPC473378
0.7674 Intermediate Similarity NPC46009
0.7654 Intermediate Similarity NPC135121
0.7654 Intermediate Similarity NPC138775
0.7651 Intermediate Similarity NPC473580
0.7647 Intermediate Similarity NPC63931
0.7644 Intermediate Similarity NPC471165
0.764 Intermediate Similarity NPC5620
0.763 Intermediate Similarity NPC230611
0.763 Intermediate Similarity NPC89831
0.7625 Intermediate Similarity NPC212850
0.7625 Intermediate Similarity NPC83289
0.7625 Intermediate Similarity NPC189724
0.7625 Intermediate Similarity NPC91953
0.7614 Intermediate Similarity NPC269750
0.7614 Intermediate Similarity NPC194671
0.7607 Intermediate Similarity NPC105717
0.76 Intermediate Similarity NPC50016
0.7597 Intermediate Similarity NPC296712
0.7595 Intermediate Similarity NPC6570
0.7586 Intermediate Similarity NPC273755
0.7576 Intermediate Similarity NPC162104
0.7576 Intermediate Similarity NPC233702
0.7574 Intermediate Similarity NPC469243
0.7571 Intermediate Similarity NPC32064
0.7564 Intermediate Similarity NPC246079
0.7562 Intermediate Similarity NPC197921
0.7558 Intermediate Similarity NPC209463
0.7556 Intermediate Similarity NPC276120
0.7546 Intermediate Similarity NPC247298
0.7543 Intermediate Similarity NPC473354
0.7543 Intermediate Similarity NPC473402
0.7543 Intermediate Similarity NPC158277
0.7531 Intermediate Similarity NPC201244
0.7531 Intermediate Similarity NPC477217
0.753 Intermediate Similarity NPC202198
0.753 Intermediate Similarity NPC262166
0.7527 Intermediate Similarity NPC174122
0.7527 Intermediate Similarity NPC64140
0.7516 Intermediate Similarity NPC274732
0.7515 Intermediate Similarity NPC473491
0.7514 Intermediate Similarity NPC469505
0.75 Intermediate Similarity NPC268841
0.75 Intermediate Similarity NPC328763
0.75 Intermediate Similarity NPC307357
0.75 Intermediate Similarity NPC46098
0.7484 Intermediate Similarity NPC68865
0.7473 Intermediate Similarity NPC234069
0.7471 Intermediate Similarity NPC151030
0.7471 Intermediate Similarity NPC475544
0.7471 Intermediate Similarity NPC269383
0.7455 Intermediate Similarity NPC245974
0.7453 Intermediate Similarity NPC476989
0.7444 Intermediate Similarity NPC471050
0.7444 Intermediate Similarity NPC471048
0.7444 Intermediate Similarity NPC471049
0.7444 Intermediate Similarity NPC294951
0.7442 Intermediate Similarity NPC223207
0.7439 Intermediate Similarity NPC145113
0.7433 Intermediate Similarity NPC477550
0.7433 Intermediate Similarity NPC477552
0.7432 Intermediate Similarity NPC240130
0.7432 Intermediate Similarity NPC61332
0.7425 Intermediate Similarity NPC286551
0.7425 Intermediate Similarity NPC56685
0.7416 Intermediate Similarity NPC45037
0.7407 Intermediate Similarity NPC161069
0.7407 Intermediate Similarity NPC469360
0.7403 Intermediate Similarity NPC101719
0.7403 Intermediate Similarity NPC138083
0.7399 Intermediate Similarity NPC469479
0.7399 Intermediate Similarity NPC61004
0.7399 Intermediate Similarity NPC304074
0.7399 Intermediate Similarity NPC471771
0.7399 Intermediate Similarity NPC290755
0.7394 Intermediate Similarity NPC240848
0.7375 Intermediate Similarity NPC127741
0.7362 Intermediate Similarity NPC476978
0.7354 Intermediate Similarity NPC477551
0.7354 Intermediate Similarity NPC473450
0.734 Intermediate Similarity NPC323662
0.7338 Intermediate Similarity NPC222466
0.7337 Intermediate Similarity NPC476268
0.7337 Intermediate Similarity NPC244509
0.7333 Intermediate Similarity NPC476321
0.7333 Intermediate Similarity NPC473404
0.7329 Intermediate Similarity NPC313694
0.7329 Intermediate Similarity NPC242159
0.7326 Intermediate Similarity NPC149962
0.7326 Intermediate Similarity NPC241794
0.7322 Intermediate Similarity NPC94862
0.7321 Intermediate Similarity NPC261934
0.7321 Intermediate Similarity NPC5194
0.7302 Intermediate Similarity NPC123859
0.7301 Intermediate Similarity NPC197682
0.7293 Intermediate Similarity NPC471526
0.7288 Intermediate Similarity NPC49315
0.7287 Intermediate Similarity NPC144314
0.7278 Intermediate Similarity NPC45112
0.7278 Intermediate Similarity NPC271958
0.7278 Intermediate Similarity NPC134413
0.7278 Intermediate Similarity NPC263507
0.7273 Intermediate Similarity NPC198254
0.7273 Intermediate Similarity NPC274198
0.7256 Intermediate Similarity NPC204546
0.7251 Intermediate Similarity NPC297145
0.7251 Intermediate Similarity NPC197743
0.7249 Intermediate Similarity NPC50548
0.7247 Intermediate Similarity NPC136797
0.7245 Intermediate Similarity NPC326333
0.7244 Intermediate Similarity NPC124776
0.7243 Intermediate Similarity NPC163961
0.7243 Intermediate Similarity NPC473305
0.7243 Intermediate Similarity NPC29531
0.7239 Intermediate Similarity NPC168113
0.7209 Intermediate Similarity NPC244336
0.7208 Intermediate Similarity NPC160493
0.7195 Intermediate Similarity NPC176226
0.7195 Intermediate Similarity NPC251439
0.7188 Intermediate Similarity NPC244866
0.7186 Intermediate Similarity NPC189908
0.7186 Intermediate Similarity NPC471821
0.7186 Intermediate Similarity NPC471820
0.7178 Intermediate Similarity NPC239762
0.7178 Intermediate Similarity NPC163392
0.7175 Intermediate Similarity NPC276506
0.7173 Intermediate Similarity NPC242728
0.7172 Intermediate Similarity NPC326027
0.7171 Intermediate Similarity NPC310467
0.716 Intermediate Similarity NPC109580
0.7159 Intermediate Similarity NPC328649
0.7159 Intermediate Similarity NPC302597
0.7143 Intermediate Similarity NPC248283
0.7135 Intermediate Similarity NPC328494
0.7134 Intermediate Similarity NPC469427
0.7134 Intermediate Similarity NPC469426
0.7128 Intermediate Similarity NPC302715
0.7128 Intermediate Similarity NPC219350
0.7128 Intermediate Similarity NPC65714

  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 NPC473502 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
0.8302 Intermediate Similarity NPD7131 Phase 3
0.7882 Intermediate Similarity NPD7608 Discontinued
0.7824 Intermediate Similarity NPD7484 Phase 3
0.7824 Intermediate Similarity NPD7485 Phase 3
0.7791 Intermediate Similarity NPD6390 Discontinued
0.7784 Intermediate Similarity NPD7972 Discontinued
0.7742 Intermediate Similarity NPD5745 Approved
0.7647 Intermediate Similarity NPD8031 Discontinued
0.7613 Intermediate Similarity NPD5746 Approved
0.7578 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5348 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1725 Approved
0.7405 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7811 Phase 3
0.7394 Intermediate Similarity NPD7810 Phase 3
0.7365 Intermediate Similarity NPD7613 Discontinued
0.7365 Intermediate Similarity NPD4186 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2240 Approved
0.7346 Intermediate Similarity NPD2239 Approved
0.7322 Intermediate Similarity NPD6089 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD5484 Approved
0.7318 Intermediate Similarity NPD5485 Approved
0.7317 Intermediate Similarity NPD2976 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7959 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD8173 Phase 2
0.7267 Intermediate Similarity NPD8172 Phase 2
0.7256 Intermediate Similarity NPD6681 Discovery
0.7238 Intermediate Similarity NPD8014 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD7318 Phase 3
0.7213 Intermediate Similarity NPD6851 Approved
0.7213 Intermediate Similarity NPD6853 Approved
0.7212 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD5355 Approved
0.7209 Intermediate Similarity NPD5356 Approved
0.7202 Intermediate Similarity NPD3146 Approved
0.7202 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD8303 Discontinued
0.717 Intermediate Similarity NPD3136 Phase 2
0.7158 Intermediate Similarity NPD7280 Phase 3
0.7158 Intermediate Similarity NPD7281 Phase 3
0.7152 Intermediate Similarity NPD3655 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5967 Approved
0.7112 Intermediate Similarity NPD6504 Approved
0.7112 Intermediate Similarity NPD6505 Approved
0.711 Intermediate Similarity NPD7317 Phase 3
0.7101 Intermediate Similarity NPD3536 Discontinued
0.7099 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7978 Discontinued
0.707 Intermediate Similarity NPD196 Phase 1
0.7052 Intermediate Similarity NPD6677 Suspended
0.7052 Intermediate Similarity NPD2513 Approved
0.7052 Intermediate Similarity NPD2541 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6556 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD8323 Discontinued
0.7019 Intermediate Similarity NPD3374 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD1670 Discontinued
0.7018 Intermediate Similarity NPD7523 Phase 3
0.7012 Intermediate Similarity NPD5689 Approved
0.7012 Intermediate Similarity NPD5688 Approved
0.7011 Intermediate Similarity NPD3007 Approved
0.7011 Intermediate Similarity NPD2515 Approved
0.7 Intermediate Similarity NPD3451 Clinical (unspecified phase)
0.6995 Remote Similarity NPD6297 Approved
0.6988 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6978 Remote Similarity NPD5312 Approved
0.6978 Remote Similarity NPD5313 Approved
0.6975 Remote Similarity NPD1423 Approved
0.6971 Remote Similarity NPD5773 Approved
0.6971 Remote Similarity NPD5772 Approved
0.6964 Remote Similarity NPD5481 Discontinued
0.6957 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6952 Remote Similarity NPD4434 Approved
0.6943 Remote Similarity NPD2584 Suspended
0.6936 Remote Similarity NPD2052 Approved
0.6935 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6932 Remote Similarity NPD2097 Approved
0.6932 Remote Similarity NPD7080 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5994 Discontinued
0.6928 Remote Similarity NPD6032 Approved
0.6928 Remote Similarity NPD7450 Phase 2
0.6927 Remote Similarity NPD2516 Approved
0.6915 Remote Similarity NPD4435 Approved
0.6914 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1048 Approved
0.6914 Remote Similarity NPD7495 Discontinued
0.6914 Remote Similarity NPD8019 Approved
0.6907 Remote Similarity NPD6519 Phase 2
0.6899 Remote Similarity NPD3685 Discontinued
0.6897 Remote Similarity NPD8417 Discontinued
0.6897 Remote Similarity NPD22 Approved
0.6897 Remote Similarity NPD2053 Approved
0.689 Remote Similarity NPD4618 Approved
0.689 Remote Similarity NPD4622 Approved
0.6889 Remote Similarity NPD4652 Approved
0.6889 Remote Similarity NPD2517 Approved
0.6882 Remote Similarity NPD6667 Approved
0.6882 Remote Similarity NPD6666 Approved
0.6878 Remote Similarity NPD5114 Approved
0.6878 Remote Similarity NPD5113 Approved
0.6878 Remote Similarity NPD5112 Approved
0.6875 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6872 Remote Similarity NPD2904 Discontinued
0.6872 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6872 Remote Similarity NPD2042 Clinical (unspecified phase)
0.686 Remote Similarity NPD1975 Clinical (unspecified phase)
0.686 Remote Similarity NPD7303 Discontinued
0.6859 Remote Similarity NPD2667 Approved
0.6859 Remote Similarity NPD2668 Approved
0.6856 Remote Similarity NPD7565 Approved
0.6854 Remote Similarity NPD2098 Approved
0.6854 Remote Similarity NPD8070 Approved
0.6852 Remote Similarity NPD5163 Phase 2
0.6848 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6848 Remote Similarity NPD5557 Phase 1
0.6845 Remote Similarity NPD2897 Discontinued
0.6842 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6835 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6829 Remote Similarity NPD8416 Discontinued
0.6826 Remote Similarity NPD4476 Approved
0.6826 Remote Similarity NPD4477 Approved
0.6818 Remote Similarity NPD4018 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6862 Phase 2
0.6811 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6802 Remote Similarity NPD6419 Discontinued
0.68 Remote Similarity NPD6502 Phase 2
0.6793 Remote Similarity NPD3965 Phase 1
0.6793 Remote Similarity NPD6042 Phase 2
0.6793 Remote Similarity NPD42 Phase 2
0.679 Remote Similarity NPD2614 Approved
0.6788 Remote Similarity NPD6355 Discontinued
0.6786 Remote Similarity NPD6238 Discontinued
0.6786 Remote Similarity NPD3656 Approved
0.6784 Remote Similarity NPD5295 Discontinued
0.6782 Remote Similarity NPD4210 Discontinued
0.678 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6768 Remote Similarity NPD2245 Discovery
0.6763 Remote Similarity NPD7526 Approved
0.6763 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6763 Remote Similarity NPD52 Approved
0.6748 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6747 Remote Similarity NPD3052 Approved
0.6747 Remote Similarity NPD3054 Approved
0.674 Remote Similarity NPD6107 Approved
0.6739 Remote Similarity NPD3909 Discontinued
0.6734 Remote Similarity NPD8161 Suspended
0.6727 Remote Similarity NPD6346 Approved
0.6727 Remote Similarity NPD8265 Approved
0.6727 Remote Similarity NPD3142 Approved
0.6727 Remote Similarity NPD3140 Approved
0.6726 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6725 Remote Similarity NPD3692 Discontinued
0.6724 Remote Similarity NPD7427 Discontinued
0.6722 Remote Similarity NPD6315 Phase 2
0.6722 Remote Similarity NPD5709 Phase 3
0.6722 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6707 Remote Similarity NPD1536 Approved
0.6707 Remote Similarity NPD6798 Discontinued
0.6706 Remote Similarity NPD2459 Approved
0.6706 Remote Similarity NPD4237 Approved
0.6706 Remote Similarity NPD4236 Phase 3
0.6706 Remote Similarity NPD2458 Approved
0.6706 Remote Similarity NPD2460 Phase 3
0.6703 Remote Similarity NPD7315 Approved
0.6702 Remote Similarity NPD7861 Discontinued
0.6701 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6687 Remote Similarity NPD8643 Discontinued
0.6686 Remote Similarity NPD5756 Phase 2
0.6685 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6685 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6685 Remote Similarity NPD6746 Phase 2
0.6685 Remote Similarity NPD4666 Phase 3
0.6667 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6386 Approved
0.6667 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6385 Approved
0.6667 Remote Similarity NPD6863 Phase 2
0.6667 Remote Similarity NPD7477 Discontinued
0.6667 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5338 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3274 Phase 2
0.6667 Remote Similarity NPD6866 Clinical (unspecified phase)
0.665 Remote Similarity NPD3878 Approved
0.6649 Remote Similarity NPD7693 Approved
0.6649 Remote Similarity NPD6312 Discontinued
0.6649 Remote Similarity NPD6620 Discovery
0.6649 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6648 Remote Similarity NPD2890 Approved
0.6648 Remote Similarity NPD2017 Approved
0.6648 Remote Similarity NPD2889 Approved
0.6648 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6648 Remote Similarity NPD2888 Approved
0.6646 Remote Similarity NPD3164 Approved
0.6646 Remote Similarity NPD3165 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