Structure

Physi-Chem Properties

Molecular Weight:  643.3
Volume:  645.018
LogP:  3.892
LogD:  3.046
LogS:  -4.153
# Rotatable Bonds:  5
TPSA:  158.24
# H-Bond Aceptor:  12
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.42
Synthetic Accessibility Score:  5.834
Fsp3:  0.562
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:  -4.965
MDCK Permeability:  1.3547683010983746e-05
Pgp-inhibitor:  0.986
Pgp-substrate:  0.979
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.051
Plasma Protein Binding (PPB):  70.05831146240234%
Volume Distribution (VD):  0.315
Pgp-substrate:  23.93137550354004%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.093
CYP2C19-inhibitor:  0.398
CYP2C19-substrate:  0.256
CYP2C9-inhibitor:  0.643
CYP2C9-substrate:  0.108
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.908
CYP3A4-substrate:  0.749

ADMET: Excretion

Clearance (CL):  5.36
Half-life (T1/2):  0.134

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.964
Drug-inuced Liver Injury (DILI):  0.977
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.066
Maximum Recommended Daily Dose:  0.553
Skin Sensitization:  0.029
Carcinogencity:  0.022
Eye Corrosion:  0.003
Eye Irritation:  0.006
Respiratory Toxicity:  0.111

Download Data

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

  Natural Product: NPC14877

Natural Product ID:  NPC14877
Common Name*:   Ulongamide B
IUPAC Name:   (4R,5R,8S,11S,14S,17S)-11-[(4-hydroxyphenyl)methyl]-5,8,10,13,17-pentamethyl-14-propan-2-yl-4-propyl-7-oxa-19-thia-3,10,13,16,21-pentazabicyclo[16.2.1]henicosa-1(20),18(21)-diene-2,6,9,12,15-pentone
Synonyms:  
Standard InCHIKey:  GGYQVLOCMGQKAQ-DUUHMJOYSA-N
Standard InCHI:  InChI=1S/C32H45N5O7S/c1-9-10-23-18(4)32(43)44-20(6)30(41)36(7)25(15-21-11-13-22(38)14-12-21)31(42)37(8)26(17(2)3)28(40)33-19(5)29-35-24(16-45-29)27(39)34-23/h11-14,16-20,23,25-26,38H,9-10,15H2,1-8H3,(H,33,40)(H,34,39)/t18-,19+,20+,23-,25+,26+/m1/s1
SMILES:  CCC[C@@H]1[C@@H](C)C(=O)O[C@@H](C)C(=O)N(C)[C@@H](Cc2ccc(cc2)O)C(=O)N(C)[C@@H](C(C)C)C(=N[C@@H](C)c2nc(cs2)C(=N1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503941
PubChem CID:   11093484
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
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. Palauan n.a. PMID[12141859]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12502348]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[12762789]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. Palauan n.a. PMID[12762800]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[14695793]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. Florida Everglades n.a. PMID[17432902]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. n.a. n.a. PMID[18693761]
NPO32881 Lyngbya sp. Species Oscillatoriaceae Bacteria n.a. Florida Keys n.a. PMID[21705224]

☑ 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
NPT91 Cell Line KB Homo sapiens IC50 = 1000.0 nM PMID[556246]
NPT114 Cell Line LoVo Homo sapiens IC50 = 5000.0 nM PMID[556246]

☑ 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 NPC14877 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 NPC145178
1.0 High Similarity NPC475350
0.984 High Similarity NPC251036
0.9189 High Similarity NPC165538
0.9081 High Similarity NPC122427
0.9081 High Similarity NPC329961
0.8224 Intermediate Similarity NPC475196
0.8159 Intermediate Similarity NPC75498
0.7681 Intermediate Similarity NPC257511
0.7626 Intermediate Similarity NPC96016
0.7525 Intermediate Similarity NPC161143
0.7461 Intermediate Similarity NPC24990
0.7415 Intermediate Similarity NPC239660
0.7415 Intermediate Similarity NPC106235
0.7411 Intermediate Similarity NPC161242
0.7376 Intermediate Similarity NPC329731
0.7376 Intermediate Similarity NPC4910
0.7337 Intermediate Similarity NPC229160
0.7337 Intermediate Similarity NPC263485
0.7337 Intermediate Similarity NPC25316
0.7323 Intermediate Similarity NPC475534
0.7323 Intermediate Similarity NPC476080
0.7286 Intermediate Similarity NPC475330
0.725 Intermediate Similarity NPC174652
0.7246 Intermediate Similarity NPC184933
0.7246 Intermediate Similarity NPC59827
0.7245 Intermediate Similarity NPC476103
0.7227 Intermediate Similarity NPC315804
0.7227 Intermediate Similarity NPC313804
0.7184 Intermediate Similarity NPC477526
0.7149 Intermediate Similarity NPC323198
0.7149 Intermediate Similarity NPC323752
0.7143 Intermediate Similarity NPC477527
0.7136 Intermediate Similarity NPC26108
0.7136 Intermediate Similarity NPC279871
0.7085 Intermediate Similarity NPC137627
0.7074 Intermediate Similarity NPC105717
0.7056 Intermediate Similarity NPC473502
0.7054 Intermediate Similarity NPC478141
0.705 Intermediate Similarity NPC326407
0.705 Intermediate Similarity NPC318930
0.705 Intermediate Similarity NPC317362
0.705 Intermediate Similarity NPC317725
0.7041 Intermediate Similarity NPC63931
0.7035 Intermediate Similarity NPC319232
0.7035 Intermediate Similarity NPC24370
0.703 Intermediate Similarity NPC269750
0.703 Intermediate Similarity NPC194671
0.7004 Intermediate Similarity NPC304307
0.7004 Intermediate Similarity NPC118559
0.7004 Intermediate Similarity NPC34580
0.7004 Intermediate Similarity NPC124920
0.7 Intermediate Similarity NPC248670
0.6985 Remote Similarity NPC475204
0.6985 Remote Similarity NPC475123
0.6976 Remote Similarity NPC471050
0.6976 Remote Similarity NPC471048
0.6976 Remote Similarity NPC294951
0.6976 Remote Similarity NPC471049
0.6974 Remote Similarity NPC100547
0.6968 Remote Similarity NPC81026
0.6965 Remote Similarity NPC471165
0.695 Remote Similarity NPC89831
0.6946 Remote Similarity NPC475421
0.6943 Remote Similarity NPC95240
0.6943 Remote Similarity NPC322135
0.6943 Remote Similarity NPC223409
0.6931 Remote Similarity NPC16188
0.693 Remote Similarity NPC186351
0.693 Remote Similarity NPC261251
0.6927 Remote Similarity NPC286551
0.6915 Remote Similarity NPC266741
0.6913 Remote Similarity NPC469858
0.6913 Remote Similarity NPC14288
0.6912 Remote Similarity NPC249662
0.69 Remote Similarity NPC196091
0.69 Remote Similarity NPC40234
0.689 Remote Similarity NPC473305
0.689 Remote Similarity NPC163961
0.6886 Remote Similarity NPC214142
0.6883 Remote Similarity NPC54803
0.6883 Remote Similarity NPC321592
0.6881 Remote Similarity NPC158277
0.6881 Remote Similarity NPC316403
0.6881 Remote Similarity NPC476227
0.6875 Remote Similarity NPC233702
0.6869 Remote Similarity NPC472923
0.6853 Remote Similarity NPC284888
0.6849 Remote Similarity NPC478005
0.6845 Remote Similarity NPC167763
0.6845 Remote Similarity NPC470112
0.6845 Remote Similarity NPC470903
0.6845 Remote Similarity NPC263493
0.6845 Remote Similarity NPC269398
0.6832 Remote Similarity NPC306804
0.6825 Remote Similarity NPC209509
0.6824 Remote Similarity NPC33064
0.6824 Remote Similarity NPC245055
0.6805 Remote Similarity NPC316110
0.6805 Remote Similarity NPC313587
0.6805 Remote Similarity NPC315893
0.6804 Remote Similarity NPC39431
0.68 Remote Similarity NPC294516
0.68 Remote Similarity NPC107938
0.6798 Remote Similarity NPC159767
0.6798 Remote Similarity NPC155506
0.6794 Remote Similarity NPC238242
0.6779 Remote Similarity NPC299806
0.6766 Remote Similarity NPC315388
0.6765 Remote Similarity NPC50016
0.6753 Remote Similarity NPC262166
0.6753 Remote Similarity NPC202198
0.675 Remote Similarity NPC254700
0.6749 Remote Similarity NPC273755
0.6748 Remote Similarity NPC153554
0.6738 Remote Similarity NPC470884
0.6738 Remote Similarity NPC178662
0.6738 Remote Similarity NPC476133
0.6738 Remote Similarity NPC92784
0.6738 Remote Similarity NPC98424
0.6737 Remote Similarity NPC82472
0.6736 Remote Similarity NPC473491
0.6734 Remote Similarity NPC133470
0.6734 Remote Similarity NPC191863
0.6734 Remote Similarity NPC289776
0.6716 Remote Similarity NPC473354
0.6714 Remote Similarity NPC94862
0.6701 Remote Similarity NPC323336
0.6701 Remote Similarity NPC326349
0.67 Remote Similarity NPC230611
0.6684 Remote Similarity NPC471265
0.6684 Remote Similarity NPC471264
0.6683 Remote Similarity NPC186617
0.6667 Remote Similarity NPC83790
0.6667 Remote Similarity NPC319751
0.6667 Remote Similarity NPC128237
0.6667 Remote Similarity NPC61004
0.6667 Remote Similarity NPC476989
0.665 Remote Similarity NPC471568
0.665 Remote Similarity NPC46009
0.665 Remote Similarity NPC473693
0.6639 Remote Similarity NPC477590
0.6639 Remote Similarity NPC477585
0.6639 Remote Similarity NPC477586
0.6639 Remote Similarity NPC477588
0.6638 Remote Similarity NPC220852
0.6636 Remote Similarity NPC328763
0.6635 Remote Similarity NPC477637
0.6635 Remote Similarity NPC476321
0.6634 Remote Similarity NPC473402
0.6633 Remote Similarity NPC469243
0.6618 Remote Similarity NPC45037
0.6604 Remote Similarity NPC188104
0.6603 Remote Similarity NPC471526
0.66 Remote Similarity NPC241794
0.6599 Remote Similarity NPC476268
0.6599 Remote Similarity NPC473580
0.6598 Remote Similarity NPC283783
0.6596 Remote Similarity NPC477516
0.659 Remote Similarity NPC323662
0.6582 Remote Similarity NPC5194
0.6582 Remote Similarity NPC56685
0.6582 Remote Similarity NPC261934
0.658 Remote Similarity NPC329761
0.658 Remote Similarity NPC225648
0.6573 Remote Similarity NPC240130
0.6573 Remote Similarity NPC61332
0.6564 Remote Similarity NPC119481
0.6564 Remote Similarity NPC74969
0.6562 Remote Similarity NPC5620
0.656 Remote Similarity NPC140284
0.656 Remote Similarity NPC75609
0.6555 Remote Similarity NPC477589
0.6555 Remote Similarity NPC477587
0.6555 Remote Similarity NPC285343
0.6553 Remote Similarity NPC136797
0.6552 Remote Similarity NPC302597
0.6552 Remote Similarity NPC209463
0.655 Remote Similarity NPC475544
0.6545 Remote Similarity NPC139326
0.6535 Remote Similarity NPC223207
0.6532 Remote Similarity NPC472286
0.6532 Remote Similarity NPC472287
0.6528 Remote Similarity NPC477632
0.6528 Remote Similarity NPC477638
0.6522 Remote Similarity NPC478007
0.652 Remote Similarity NPC280022
0.6515 Remote Similarity NPC244509
0.6514 Remote Similarity NPC472284
0.6513 Remote Similarity NPC473398
0.6508 Remote Similarity NPC6570
0.6508 Remote Similarity NPC314056
0.6504 Remote Similarity NPC153400
0.6502 Remote Similarity NPC304074
0.6502 Remote Similarity NPC290755
0.6502 Remote Similarity NPC471771
0.65 Remote Similarity NPC244336
0.6495 Remote Similarity NPC145113
0.6481 Remote Similarity NPC302715
0.6477 Remote Similarity NPC322878

  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 NPC14877 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
0.7415 Intermediate Similarity NPD8339 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD4652 Approved
0.7054 Intermediate Similarity NPD8356 Approved
0.7053 Intermediate Similarity NPD6348 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD2098 Approved
0.7039 Intermediate Similarity NPD6632 Clinical (unspecified phase)
0.6955 Remote Similarity NPD3879 Approved
0.6939 Remote Similarity NPD2097 Approved
0.693 Remote Similarity NPD8430 Approved
0.6923 Remote Similarity NPD6349 Phase 1
0.6909 Remote Similarity NPD3878 Approved
0.6891 Remote Similarity NPD3328 Phase 2
0.6863 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5994 Discontinued
0.6835 Remote Similarity NPD6495 Clinical (unspecified phase)
0.681 Remote Similarity NPD5114 Approved
0.681 Remote Similarity NPD5112 Approved
0.681 Remote Similarity NPD5113 Approved
0.6802 Remote Similarity NPD5452 Phase 2
0.6786 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6766 Remote Similarity NPD2888 Approved
0.6766 Remote Similarity NPD2890 Approved
0.6766 Remote Similarity NPD2017 Approved
0.6766 Remote Similarity NPD2889 Approved
0.6763 Remote Similarity NPD7977 Clinical (unspecified phase)
0.6762 Remote Similarity NPD8255 Phase 2
0.6729 Remote Similarity NPD3127 Clinical (unspecified phase)
0.6712 Remote Similarity NPD4742 Phase 3
0.6712 Remote Similarity NPD2853 Approved
0.6712 Remote Similarity NPD4741 Phase 3
0.6701 Remote Similarity NPD6390 Discontinued
0.6699 Remote Similarity NPD5484 Approved
0.6699 Remote Similarity NPD5485 Approved
0.6695 Remote Similarity NPD7806 Phase 2
0.6681 Remote Similarity NPD1976 Approved
0.668 Remote Similarity NPD8107 Approved
0.6667 Remote Similarity NPD8108 Approved
0.6637 Remote Similarity NPD5191 Clinical (unspecified phase)
0.6622 Remote Similarity NPD3351 Approved
0.6615 Remote Similarity NPD7303 Discontinued
0.6612 Remote Similarity NPD6205 Discontinued
0.661 Remote Similarity NPD7807 Clinical (unspecified phase)
0.6608 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6607 Remote Similarity NPD7703 Clinical (unspecified phase)
0.6582 Remote Similarity NPD7131 Phase 3
0.6577 Remote Similarity NPD3350 Approved
0.6576 Remote Similarity NPD6627 Discontinued
0.6575 Remote Similarity NPD6256 Approved
0.6575 Remote Similarity NPD6254 Approved
0.6575 Remote Similarity NPD6255 Approved
0.6571 Remote Similarity NPD5857 Phase 3
0.6562 Remote Similarity NPD3803 Clinical (unspecified phase)
0.6557 Remote Similarity NPD6475 Phase 2
0.6542 Remote Similarity NPD6505 Approved
0.6542 Remote Similarity NPD6504 Approved
0.654 Remote Similarity NPD3074 Discontinued
0.6538 Remote Similarity NPD2957 Phase 2
0.6534 Remote Similarity NPD4884 Discovery
0.6533 Remote Similarity NPD2513 Approved
0.653 Remote Similarity NPD6253 Approved
0.6526 Remote Similarity NPD4435 Approved
0.6515 Remote Similarity NPD5189 Clinical (unspecified phase)
0.6508 Remote Similarity NPD8284 Discontinued
0.6507 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6502 Remote Similarity NPD8071 Approved
0.65 Remote Similarity NPD3007 Approved
0.65 Remote Similarity NPD2515 Approved
0.6498 Remote Similarity NPD6347 Phase 2
0.6488 Remote Similarity NPD2517 Approved
0.6479 Remote Similarity NPD4434 Approved
0.6468 Remote Similarity NPD8253 Phase 3
0.6466 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6459 Remote Similarity NPD7655 Discontinued
0.645 Remote Similarity NPD5634 Approved
0.6441 Remote Similarity NPD4898 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6888 Discontinued
0.644 Remote Similarity NPD6866 Clinical (unspecified phase)
0.644 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6439 Remote Similarity NPD2516 Approved
0.6435 Remote Similarity NPD3479 Discontinued
0.6432 Remote Similarity NPD2052 Approved
0.6426 Remote Similarity NPD8292 Phase 2
0.6422 Remote Similarity NPD8303 Discontinued
0.6419 Remote Similarity NPD7496 Phase 2
0.6413 Remote Similarity NPD5055 Clinical (unspecified phase)
0.6413 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6406 Remote Similarity NPD6751 Clinical (unspecified phase)
0.6404 Remote Similarity NPD4331 Approved
0.6404 Remote Similarity NPD6188 Approved
0.6404 Remote Similarity NPD6189 Approved
0.6402 Remote Similarity NPD6089 Clinical (unspecified phase)
0.64 Remote Similarity NPD22 Approved
0.64 Remote Similarity NPD2053 Approved
0.6398 Remote Similarity NPD2852 Approved
0.6395 Remote Similarity NPD8061 Clinical (unspecified phase)
0.6393 Remote Similarity NPD7490 Discontinued
0.639 Remote Similarity NPD7133 Discontinued
0.6389 Remote Similarity NPD4949 Discontinued
0.6386 Remote Similarity NPD4557 Approved
0.6384 Remote Similarity NPD6551 Clinical (unspecified phase)
0.6382 Remote Similarity NPD4646 Approved
0.6382 Remote Similarity NPD4648 Approved
0.6382 Remote Similarity NPD4647 Approved
0.638 Remote Similarity NPD6389 Clinical (unspecified phase)
0.6376 Remote Similarity NPD4897 Phase 2
0.6373 Remote Similarity NPD2022 Approved
0.6368 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6367 Remote Similarity NPD5817 Discontinued
0.6364 Remote Similarity NPD4125 Approved
0.6364 Remote Similarity NPD5638 Approved
0.636 Remote Similarity NPD6187 Approved
0.6354 Remote Similarity NPD3480 Approved
0.6345 Remote Similarity NPD7284 Clinical (unspecified phase)
0.634 Remote Similarity NPD2436 Approved
0.634 Remote Similarity NPD2437 Approved
0.633 Remote Similarity NPD2046 Approved
0.633 Remote Similarity NPD2048 Approved
0.633 Remote Similarity NPD2045 Approved
0.633 Remote Similarity NPD2049 Clinical (unspecified phase)
0.633 Remote Similarity NPD2047 Approved
0.633 Remote Similarity NPD2043 Approved
0.633 Remote Similarity NPD2044 Approved
0.633 Remote Similarity NPD2050 Clinical (unspecified phase)
0.633 Remote Similarity NPD2051 Approved
0.633 Remote Similarity NPD21 Approved
0.6327 Remote Similarity NPD8260 Approved
0.632 Remote Similarity NPD5453 Phase 2
0.6318 Remote Similarity NPD2891 Approved
0.6316 Remote Similarity NPD5323 Approved
0.6314 Remote Similarity NPD7711 Discontinued
0.6313 Remote Similarity NPD5076 Approved
0.6313 Remote Similarity NPD5077 Approved
0.6309 Remote Similarity NPD7180 Phase 3
0.6309 Remote Similarity NPD3308 Approved
0.6308 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6307 Remote Similarity NPD7853 Phase 2
0.6301 Remote Similarity NPD3396 Approved
0.6301 Remote Similarity NPD3395 Approved
0.6296 Remote Similarity NPD3335 Approved
0.629 Remote Similarity NPD7873 Clinical (unspecified phase)
0.6289 Remote Similarity NPD2087 Approved
0.6289 Remote Similarity NPD2088 Approved
0.6282 Remote Similarity NPD6796 Discontinued
0.6281 Remote Similarity NPD5230 Approved
0.6281 Remote Similarity NPD5229 Approved
0.6279 Remote Similarity NPD3334 Approved
0.6275 Remote Similarity NPD7494 Clinical (unspecified phase)
0.6275 Remote Similarity NPD6276 Discontinued
0.6272 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6267 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6266 Remote Similarity NPD3307 Approved
0.6263 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6261 Remote Similarity NPD6857 Phase 3
0.626 Remote Similarity NPD7967 Discontinued
0.6255 Remote Similarity NPD4394 Clinical (unspecified phase)
0.6255 Remote Similarity NPD8247 Approved
0.6255 Remote Similarity NPD8246 Approved
0.6245 Remote Similarity NPD8116 Phase 3
0.6245 Remote Similarity NPD8117 Approved
0.6245 Remote Similarity NPD5640 Discontinued
0.6239 Remote Similarity NPD6659 Phase 2
0.6238 Remote Similarity NPD6915 Approved
0.6238 Remote Similarity NPD2020 Approved
0.6235 Remote Similarity NPD8359 Phase 2
0.6225 Remote Similarity NPD8101 Phase 3
0.6224 Remote Similarity NPD4460 Clinical (unspecified phase)
0.6223 Remote Similarity NPD7692 Discontinued
0.6222 Remote Similarity NPD6324 Phase 1
0.6221 Remote Similarity NPD5852 Approved
0.6221 Remote Similarity NPD5851 Approved
0.6215 Remote Similarity NPD8370 Discontinued
0.6213 Remote Similarity NPD5506 Approved
0.6213 Remote Similarity NPD5507 Approved
0.6212 Remote Similarity NPD1979 Approved
0.6211 Remote Similarity NPD5299 Approved
0.621 Remote Similarity NPD7868 Clinical (unspecified phase)
0.62 Remote Similarity NPD7613 Discontinued
0.6195 Remote Similarity NPD4903 Approved
0.6195 Remote Similarity NPD4905 Approved
0.6195 Remote Similarity NPD8272 Phase 2
0.6195 Remote Similarity NPD7737 Approved
0.6195 Remote Similarity NPD4906 Approved
0.6195 Remote Similarity NPD7738 Approved
0.6188 Remote Similarity NPD2019 Approved
0.6188 Remote Similarity NPD2018 Approved
0.6186 Remote Similarity NPD3275 Approved
0.6186 Remote Similarity NPD3271 Approved
0.6183 Remote Similarity NPD7796 Approved
0.6183 Remote Similarity NPD7797 Approved
0.6181 Remote Similarity NPD5613 Approved
0.6181 Remote Similarity NPD2016 Approved
0.6181 Remote Similarity NPD2014 Approved
0.6181 Remote Similarity NPD5614 Approved
0.6181 Remote Similarity NPD3988 Approved
0.6181 Remote Similarity NPD2013 Approved
0.6181 Remote Similarity NPD3987 Approved
0.6181 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6176 Remote Similarity NPD7603 Discontinued
0.6175 Remote Similarity NPD6891 Phase 2
0.6174 Remote Similarity NPD7468 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