Structure

Physi-Chem Properties

Molecular Weight:  702.48
Volume:  751.223
LogP:  4.053
LogD:  3.777
LogS:  -4.641
# Rotatable Bonds:  20
TPSA:  140.26
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.088
Synthetic Accessibility Score:  5.885
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
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:  -4.816
MDCK Permeability:  2.7570609745453112e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.622
30% Bioavailability (F30%):  0.789

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.039
Plasma Protein Binding (PPB):  96.90691375732422%
Volume Distribution (VD):  1.366
Pgp-substrate:  3.0401341915130615%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.108
CYP2C19-substrate:  0.866
CYP2C9-inhibitor:  0.112
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.113
CYP3A4-inhibitor:  0.947
CYP3A4-substrate:  0.73

ADMET: Excretion

Clearance (CL):  12.857
Half-life (T1/2):  0.161

ADMET: Toxicity

hERG Blockers:  0.119
Human Hepatotoxicity (H-HT):  0.978
Drug-inuced Liver Injury (DILI):  0.483
AMES Toxicity:  0.941
Rat Oral Acute Toxicity:  0.704
Maximum Recommended Daily Dose:  0.946
Skin Sensitization:  0.957
Carcinogencity:  0.941
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.674

Download Data

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

  Natural Product: NPC473578

Natural Product ID:  NPC473578
Common Name*:   Bistramide C
IUPAC Name:   (2S,3R)-N-[3-[(2R,3S,6S,8S)-8-[(E,3S)-3,5-dimethyl-6-oxohept-4-enyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl]-3-hydroxy-2-methyl-4-[[2-[(2S,3S,6R)-3-methyl-6-[(E)-2-oxopent-3-enyl]oxan-2-yl]acetyl]amino]butanamide
Synonyms:   Bistramide C
Standard InCHIKey:  WFVNZHRELNLEFI-ZMEWJFTKSA-N
Standard InCHI:  InChI=1S/C40H66N2O8/c1-8-11-32(44)23-34-17-15-27(3)37(48-34)24-38(46)42-25-35(45)30(6)39(47)41-21-10-13-36-28(4)18-20-40(50-36)19-9-12-33(49-40)16-14-26(2)22-29(5)31(7)43/h8,11,22,26-28,30,33-37,45H,9-10,12-21,23-25H2,1-7H3,(H,41,47)(H,42,46)/b11-8+,29-22+/t26-,27-,28-,30-,33-,34+,35-,36+,37-,40-/m0/s1
SMILES:  CC=CC(=O)CC1CCC(C(O1)CC(=O)NCC(C(C)C(=O)NCCCC2C(CCC3(O2)CCCC(O3)CCC(C)C=C(C)C(=O)C)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL446267
PubChem CID:   11366040
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:0000347] Amino acids and derivatives
            • [CHEMONTID:0001880] Gamma amino acids and derivatives

*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
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[12608858]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota n.a. n.a. n.a. PMID[7807120]
NPO22842 Lissoclinum bistratum Species Didemnidae Eukaryota 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
NPT91 Cell Line KB Homo sapiens IC50 = 0.65 ug.mL-1 PMID[545973]
NPT168 Cell Line P388 Mus musculus IC50 = 0.02 ug.mL-1 PMID[545973]
NPT168 Cell Line P388 Mus musculus IC50 = 0.05 ug.mL-1 PMID[545973]
NPT319 Cell Line B16 Mus musculus IC50 = 0.06 ug.mL-1 PMID[545973]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 0.5 ug.mL-1 PMID[545973]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 0.05 ug.mL-1 PMID[545973]

☑ 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 NPC473578 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
0.9709 High Similarity NPC469865
0.932 High Similarity NPC475150
0.8447 Intermediate Similarity NPC475646
0.8173 Intermediate Similarity NPC475503
0.7317 Intermediate Similarity NPC314629
0.7302 Intermediate Similarity NPC315387
0.7302 Intermediate Similarity NPC316205
0.7281 Intermediate Similarity NPC201128
0.7258 Intermediate Similarity NPC469494
0.7203 Intermediate Similarity NPC261750
0.7203 Intermediate Similarity NPC1111
0.7197 Intermediate Similarity NPC180770
0.7154 Intermediate Similarity NPC469515
0.7143 Intermediate Similarity NPC225978
0.7143 Intermediate Similarity NPC271207
0.7143 Intermediate Similarity NPC206711
0.7143 Intermediate Similarity NPC255175
0.7132 Intermediate Similarity NPC314361
0.713 Intermediate Similarity NPC475918
0.7117 Intermediate Similarity NPC278506
0.7107 Intermediate Similarity NPC316325
0.709 Intermediate Similarity NPC162910
0.7083 Intermediate Similarity NPC471645
0.7068 Intermediate Similarity NPC302276
0.7064 Intermediate Similarity NPC478037
0.7064 Intermediate Similarity NPC478036
0.7059 Intermediate Similarity NPC60432
0.7054 Intermediate Similarity NPC139585
0.7027 Intermediate Similarity NPC189629
0.7023 Intermediate Similarity NPC75318
0.7018 Intermediate Similarity NPC477198
0.6992 Remote Similarity NPC200788
0.6992 Remote Similarity NPC243680
0.6985 Remote Similarity NPC298469
0.6985 Remote Similarity NPC284625
0.6985 Remote Similarity NPC193579
0.6985 Remote Similarity NPC69176
0.6985 Remote Similarity NPC141669
0.6983 Remote Similarity NPC271269
0.6983 Remote Similarity NPC476738
0.6983 Remote Similarity NPC476740
0.6972 Remote Similarity NPC314500
0.697 Remote Similarity NPC145899
0.6967 Remote Similarity NPC6531
0.6957 Remote Similarity NPC474581
0.6957 Remote Similarity NPC475367
0.6957 Remote Similarity NPC309398
0.6957 Remote Similarity NPC473816
0.6947 Remote Similarity NPC78189
0.6947 Remote Similarity NPC76999
0.6934 Remote Similarity NPC298067
0.6934 Remote Similarity NPC214821
0.693 Remote Similarity NPC476611
0.693 Remote Similarity NPC316250
0.6923 Remote Similarity NPC251330
0.6905 Remote Similarity NPC315783
0.6903 Remote Similarity NPC70733
0.6903 Remote Similarity NPC234542
0.6903 Remote Similarity NPC56071
0.6897 Remote Similarity NPC14537
0.6894 Remote Similarity NPC235772
0.6894 Remote Similarity NPC280941
0.6889 Remote Similarity NPC172365
0.6889 Remote Similarity NPC82931
0.6889 Remote Similarity NPC210729
0.6885 Remote Similarity NPC30196
0.6875 Remote Similarity NPC180722
0.6875 Remote Similarity NPC195645
0.6875 Remote Similarity NPC165332
0.687 Remote Similarity NPC119794
0.687 Remote Similarity NPC73829
0.6864 Remote Similarity NPC193765
0.6857 Remote Similarity NPC185949
0.6857 Remote Similarity NPC107498
0.6842 Remote Similarity NPC473224
0.6838 Remote Similarity NPC473252
0.6838 Remote Similarity NPC154601
0.6835 Remote Similarity NPC61717
0.6835 Remote Similarity NPC244380
0.6833 Remote Similarity NPC21713
0.6833 Remote Similarity NPC475608
0.6831 Remote Similarity NPC475527
0.6831 Remote Similarity NPC265699
0.6822 Remote Similarity NPC477793
0.6822 Remote Similarity NPC329919
0.6815 Remote Similarity NPC265908
0.6814 Remote Similarity NPC476613
0.6814 Remote Similarity NPC476612
0.681 Remote Similarity NPC474563
0.6807 Remote Similarity NPC24389
0.6794 Remote Similarity NPC475472
0.6794 Remote Similarity NPC316401
0.6789 Remote Similarity NPC159369
0.6789 Remote Similarity NPC39290
0.6788 Remote Similarity NPC475394
0.6788 Remote Similarity NPC475584
0.6788 Remote Similarity NPC475152
0.6783 Remote Similarity NPC475599
0.6783 Remote Similarity NPC187497
0.6783 Remote Similarity NPC175531
0.6783 Remote Similarity NPC100612
0.6783 Remote Similarity NPC174336
0.6783 Remote Similarity NPC113620
0.6752 Remote Similarity NPC74035
0.6752 Remote Similarity NPC231271
0.6752 Remote Similarity NPC470519
0.6739 Remote Similarity NPC475892
0.6738 Remote Similarity NPC298005
0.6738 Remote Similarity NPC36463
0.6729 Remote Similarity NPC92633
0.6724 Remote Similarity NPC128501
0.6723 Remote Similarity NPC140251
0.6723 Remote Similarity NPC307903
0.672 Remote Similarity NPC314268
0.672 Remote Similarity NPC67917
0.672 Remote Similarity NPC313802
0.672 Remote Similarity NPC477515
0.6696 Remote Similarity NPC5418
0.6695 Remote Similarity NPC472615
0.6694 Remote Similarity NPC29501
0.6694 Remote Similarity NPC201968
0.6667 Remote Similarity NPC50694
0.6667 Remote Similarity NPC61894
0.6667 Remote Similarity NPC266842
0.6667 Remote Similarity NPC474725
0.6667 Remote Similarity NPC230889
0.6667 Remote Similarity NPC313668
0.6667 Remote Similarity NPC475603
0.6667 Remote Similarity NPC315836
0.6641 Remote Similarity NPC318445
0.6641 Remote Similarity NPC316133
0.6639 Remote Similarity NPC315531
0.6639 Remote Similarity NPC475800
0.6637 Remote Similarity NPC108141
0.6612 Remote Similarity NPC127578
0.6612 Remote Similarity NPC477997
0.661 Remote Similarity NPC472616
0.6609 Remote Similarity NPC255592
0.6609 Remote Similarity NPC261377
0.6609 Remote Similarity NPC308567
0.6589 Remote Similarity NPC314512
0.6589 Remote Similarity NPC204639
0.6589 Remote Similarity NPC313342
0.6589 Remote Similarity NPC314451
0.6589 Remote Similarity NPC313333
0.6583 Remote Similarity NPC473807
0.6581 Remote Similarity NPC313569
0.656 Remote Similarity NPC475642
0.6552 Remote Similarity NPC469871
0.6552 Remote Similarity NPC469870
0.6549 Remote Similarity NPC192066
0.6549 Remote Similarity NPC256570
0.6549 Remote Similarity NPC17290
0.6549 Remote Similarity NPC3568
0.6547 Remote Similarity NPC803
0.6542 Remote Similarity NPC69469
0.6535 Remote Similarity NPC473808
0.6532 Remote Similarity NPC165439
0.6529 Remote Similarity NPC133729
0.6525 Remote Similarity NPC316249
0.6518 Remote Similarity NPC476084
0.6518 Remote Similarity NPC476075
0.6518 Remote Similarity NPC472199
0.6512 Remote Similarity NPC16709
0.6508 Remote Similarity NPC296361
0.6489 Remote Similarity NPC314282
0.6484 Remote Similarity NPC315915
0.648 Remote Similarity NPC7905
0.648 Remote Similarity NPC315652
0.6466 Remote Similarity NPC40182
0.6466 Remote Similarity NPC187761
0.6466 Remote Similarity NPC198422
0.6466 Remote Similarity NPC83895
0.646 Remote Similarity NPC159092
0.6457 Remote Similarity NPC241050
0.6455 Remote Similarity NPC313658
0.6455 Remote Similarity NPC86005
0.6455 Remote Similarity NPC316138
0.6455 Remote Similarity NPC477959
0.6452 Remote Similarity NPC5485
0.6449 Remote Similarity NPC474312
0.6446 Remote Similarity NPC207820
0.6446 Remote Similarity NPC70235
0.6446 Remote Similarity NPC476034
0.6446 Remote Similarity NPC474969
0.6444 Remote Similarity NPC477072
0.6441 Remote Similarity NPC473596
0.6435 Remote Similarity NPC475375
0.6435 Remote Similarity NPC475164
0.6435 Remote Similarity NPC183449
0.6435 Remote Similarity NPC175614
0.6435 Remote Similarity NPC473765
0.6435 Remote Similarity NPC475241
0.6435 Remote Similarity NPC473605
0.6435 Remote Similarity NPC475525
0.6435 Remote Similarity NPC123141
0.6435 Remote Similarity NPC197294
0.6435 Remote Similarity NPC475540
0.6435 Remote Similarity NPC476066
0.6435 Remote Similarity NPC475593

  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 NPC473578 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
0.7107 Intermediate Similarity NPD7500 Approved
0.6977 Remote Similarity NPD6914 Discontinued
0.6911 Remote Similarity NPD7641 Discontinued
0.6905 Remote Similarity NPD7829 Approved
0.6905 Remote Similarity NPD7830 Approved
0.6891 Remote Similarity NPD6421 Discontinued
0.6875 Remote Similarity NPD7839 Suspended
0.6846 Remote Similarity NPD8392 Approved
0.6846 Remote Similarity NPD8391 Approved
0.6846 Remote Similarity NPD8390 Approved
0.6746 Remote Similarity NPD8269 Approved
0.6746 Remote Similarity NPD8268 Approved
0.6746 Remote Similarity NPD8266 Approved
0.6746 Remote Similarity NPD8267 Approved
0.6694 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6693 Remote Similarity NPD8080 Discontinued
0.6692 Remote Similarity NPD8336 Approved
0.6692 Remote Similarity NPD8337 Approved
0.6641 Remote Similarity NPD7642 Approved
0.6615 Remote Similarity NPD8074 Phase 3
0.6607 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6589 Remote Similarity NPD8342 Approved
0.6589 Remote Similarity NPD8340 Approved
0.6589 Remote Similarity NPD8299 Approved
0.6589 Remote Similarity NPD8341 Approved
0.656 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6538 Remote Similarity NPD8451 Approved
0.6493 Remote Similarity NPD8338 Approved
0.6489 Remote Similarity NPD8448 Approved
0.6484 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6484 Remote Similarity NPD8444 Approved
0.6466 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6434 Remote Similarity NPD7623 Phase 3
0.6434 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6429 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6423 Remote Similarity NPD1719 Phase 1
0.6397 Remote Similarity NPD8415 Approved
0.6393 Remote Similarity NPD8306 Approved
0.6393 Remote Similarity NPD8305 Approved
0.6364 Remote Similarity NPD7746 Phase 1
0.6364 Remote Similarity NPD7747 Phase 1
0.6357 Remote Similarity NPD7739 Clinical (unspecified phase)
0.635 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6311 Remote Similarity NPD6686 Approved
0.6293 Remote Similarity NPD4228 Discovery
0.629 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6283 Remote Similarity NPD6698 Approved
0.6283 Remote Similarity NPD46 Approved
0.6281 Remote Similarity NPD4211 Phase 1
0.623 Remote Similarity NPD8307 Discontinued
0.623 Remote Similarity NPD8140 Approved
0.623 Remote Similarity NPD6412 Phase 2
0.6228 Remote Similarity NPD7983 Approved
0.6226 Remote Similarity NPD7917 Clinical (unspecified phase)
0.6226 Remote Similarity NPD7918 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6195 Remote Similarity NPD6101 Approved
0.6167 Remote Similarity NPD8086 Approved
0.6167 Remote Similarity NPD8082 Approved
0.6167 Remote Similarity NPD8139 Approved
0.6167 Remote Similarity NPD8085 Approved
0.6167 Remote Similarity NPD8138 Approved
0.6167 Remote Similarity NPD8084 Approved
0.6167 Remote Similarity NPD8083 Approved
0.6165 Remote Similarity NPD8273 Phase 1
0.6143 Remote Similarity NPD6333 Approved
0.6143 Remote Similarity NPD6334 Approved
0.6136 Remote Similarity NPD8328 Phase 3
0.6121 Remote Similarity NPD5282 Discontinued
0.6116 Remote Similarity NPD8276 Approved
0.6116 Remote Similarity NPD8275 Approved
0.6107 Remote Similarity NPD8513 Phase 3
0.6107 Remote Similarity NPD8515 Approved
0.6107 Remote Similarity NPD8516 Approved
0.6107 Remote Similarity NPD8517 Approved
0.6087 Remote Similarity NPD6411 Approved
0.608 Remote Similarity NPD6420 Discontinued
0.608 Remote Similarity NPD8087 Discontinued
0.6066 Remote Similarity NPD8081 Approved
0.6034 Remote Similarity NPD5778 Approved
0.6034 Remote Similarity NPD5779 Approved
0.6031 Remote Similarity NPD6054 Approved
0.6016 Remote Similarity NPD5357 Phase 1
0.6016 Remote Similarity NPD8393 Approved
0.6014 Remote Similarity NPD8384 Approved
0.6 Remote Similarity NPD6413 Approved
0.594 Remote Similarity NPD6370 Approved
0.5926 Remote Similarity NPD3732 Approved
0.5909 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5909 Remote Similarity NPD8345 Approved
0.5909 Remote Similarity NPD8346 Approved
0.5909 Remote Similarity NPD8347 Approved
0.5865 Remote Similarity NPD6016 Approved
0.5865 Remote Similarity NPD6015 Approved
0.5862 Remote Similarity NPD7838 Discovery
0.5859 Remote Similarity NPD6882 Approved
0.5856 Remote Similarity NPD7345 Approved
0.5854 Remote Similarity NPD2258 Approved
0.5854 Remote Similarity NPD2259 Approved
0.5852 Remote Similarity NPD7492 Approved
0.5841 Remote Similarity NPD5363 Approved
0.5839 Remote Similarity NPD7736 Approved
0.5821 Remote Similarity NPD5988 Approved
0.5809 Remote Similarity NPD6616 Approved
0.5789 Remote Similarity NPD6059 Approved
0.5781 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5772 Remote Similarity NPD7141 Clinical (unspecified phase)
0.5772 Remote Similarity NPD7140 Approved
0.5772 Remote Similarity NPD7139 Approved
0.5766 Remote Similarity NPD5369 Approved
0.5766 Remote Similarity NPD7078 Approved
0.5762 Remote Similarity NPD8389 Clinical (unspecified phase)
0.576 Remote Similarity NPD7333 Discontinued
0.575 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5748 Remote Similarity NPD6941 Approved
0.5748 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5734 Remote Similarity NPD8265 Approved
0.5726 Remote Similarity NPD1407 Approved
0.5726 Remote Similarity NPD5785 Approved
0.5714 Remote Similarity NPD7748 Approved
0.5714 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6435 Approved
0.5714 Remote Similarity NPD8414 Discontinued
0.5714 Remote Similarity NPD7260 Phase 2
0.5682 Remote Similarity NPD6936 Clinical (unspecified phase)
0.5682 Remote Similarity NPD6935 Phase 3
0.5682 Remote Similarity NPD7505 Discontinued
0.5682 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5677 Remote Similarity NPD8417 Discontinued
0.5674 Remote Similarity NPD2613 Approved
0.5672 Remote Similarity NPD6319 Approved
0.5669 Remote Similarity NPD8174 Phase 2
0.5667 Remote Similarity NPD8323 Discontinued
0.5667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7154 Phase 3
0.5652 Remote Similarity NPD8293 Discontinued
0.5648 Remote Similarity NPD2257 Approved
0.5645 Remote Similarity NPD8301 Approved
0.5645 Remote Similarity NPD8300 Approved
0.5641 Remote Similarity NPD7749 Clinical (unspecified phase)
0.563 Remote Similarity NPD6908 Approved
0.563 Remote Similarity NPD6909 Approved
0.563 Remote Similarity NPD6921 Approved
0.5615 Remote Similarity NPD8297 Approved
0.5615 Remote Similarity NPD6429 Approved
0.5615 Remote Similarity NPD6430 Approved
0.561 Remote Similarity NPD6404 Discontinued

  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