Structure

Physi-Chem Properties

Molecular Weight:  878.47
Volume:  889.498
LogP:  4.991
LogD:  3.309
LogS:  -5.273
# Rotatable Bonds:  14
TPSA:  219.88
# H-Bond Aceptor:  16
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  16

MedChem Properties

QED Drug-Likeness Score:  0.154
Synthetic Accessibility Score:  7.887
Fsp3:  0.761
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:  -5.008
MDCK Permeability:  0.0001477774349041283
Pgp-inhibitor:  0.992
Pgp-substrate:  0.997
Human Intestinal Absorption (HIA):  0.157
20% Bioavailability (F20%):  0.05
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  75.12831115722656%
Volume Distribution (VD):  0.996
Pgp-substrate:  10.765009880065918%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.056
CYP2C19-inhibitor:  0.207
CYP2C19-substrate:  0.21
CYP2C9-inhibitor:  0.828
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.038
CYP3A4-inhibitor:  0.946
CYP3A4-substrate:  0.922

ADMET: Excretion

Clearance (CL):  5.071
Half-life (T1/2):  0.242

ADMET: Toxicity

hERG Blockers:  0.162
Human Hepatotoxicity (H-HT):  0.942
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.556
Rat Oral Acute Toxicity:  0.671
Maximum Recommended Daily Dose:  1.0
Skin Sensitization:  0.374
Carcinogencity:  0.371
Eye Corrosion:  0.003
Eye Irritation:  0.019
Respiratory Toxicity:  0.97

Download Data

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

  Natural Product: NPC474581

Natural Product ID:  NPC474581
Common Name*:   VOVMVLHYONASNA-BIAGIDITSA-N
IUPAC Name:   n.a.
Synonyms:   Bryostatin 10 26-N-Butyrate
Standard InCHIKey:  VOVMVLHYONASNA-BIAGIDITSA-N
Standard InCHI:  InChI=1S/C46H70O16/c1-12-13-37(48)57-27(2)35-23-32-18-29(20-39(50)56-11)25-45(53,61-32)43(6,7)15-14-31-16-28(19-38(49)55-10)17-34(58-31)26-46(54)44(8,9)36(60-41(52)42(3,4)5)24-33(62-46)21-30(47)22-40(51)59-35/h14-15,19-20,27,30-36,47,53-54H,12-13,16-18,21-26H2,1-11H3/b15-14+,28-19+,29-20-/t27-,30-,31+,32+,33-,34+,35-,36+,45-,46+/m1/s1
SMILES:  CCCC(=O)OC(C)C1CC2CC(=CC(=O)OC)CC(O2)(C(C=CC3CC(=CC(=O)OC)CC(O3)CC4(C(C(CC(O4)CC(CC(=O)O1)O)OC(=O)C(C)(C)C)(C)C)O)(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL474869
PubChem CID:   44559900
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0002995] Pentacarboxylic 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
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. DOI[10.1021/ja00388a092]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. South China Sea n.a. PMID[25932671]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. Gulf of Aomori, Japan n.a. PMID[8691208]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. PMID[8882431]
NPO11979 Bugula neritina Species Bugulidae 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
NPT168 Cell Line P388 Mus musculus ED50 = 0.32 ug ml-1 PMID[547813]
NPT2 Others Unspecified Inhibition = 80.0 % PMID[547813]

☑ 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 NPC474581 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 NPC473816
1.0 High Similarity NPC475367
0.9794 High Similarity NPC476740
0.9794 High Similarity NPC476738
0.9792 High Similarity NPC309398
0.9596 High Similarity NPC193765
0.9208 High Similarity NPC473807
0.8416 Intermediate Similarity NPC308567
0.8416 Intermediate Similarity NPC255592
0.8416 Intermediate Similarity NPC261377
0.8396 Intermediate Similarity NPC313668
0.8396 Intermediate Similarity NPC315836
0.8235 Intermediate Similarity NPC187761
0.8235 Intermediate Similarity NPC83895
0.8218 Intermediate Similarity NPC143446
0.819 Intermediate Similarity NPC472748
0.819 Intermediate Similarity NPC469869
0.8173 Intermediate Similarity NPC473596
0.8137 Intermediate Similarity NPC40812
0.8113 Intermediate Similarity NPC472749
0.8113 Intermediate Similarity NPC472751
0.81 Intermediate Similarity NPC320089
0.8095 Intermediate Similarity NPC472747
0.8095 Intermediate Similarity NPC472750
0.8039 Intermediate Similarity NPC255410
0.802 Intermediate Similarity NPC71589
0.8 Intermediate Similarity NPC470379
0.8 Intermediate Similarity NPC313569
0.8 Intermediate Similarity NPC472754
0.8 Intermediate Similarity NPC470373
0.7982 Intermediate Similarity NPC83005
0.7965 Intermediate Similarity NPC13710
0.7961 Intermediate Similarity NPC120299
0.7941 Intermediate Similarity NPC300710
0.7913 Intermediate Similarity NPC473228
0.7913 Intermediate Similarity NPC470829
0.7905 Intermediate Similarity NPC154132
0.7905 Intermediate Similarity NPC475655
0.7905 Intermediate Similarity NPC57586
0.7905 Intermediate Similarity NPC472753
0.7905 Intermediate Similarity NPC2313
0.7905 Intermediate Similarity NPC471637
0.7905 Intermediate Similarity NPC475157
0.79 Intermediate Similarity NPC313670
0.7885 Intermediate Similarity NPC475653
0.7864 Intermediate Similarity NPC473605
0.7864 Intermediate Similarity NPC475525
0.7864 Intermediate Similarity NPC475540
0.7864 Intermediate Similarity NPC475375
0.7864 Intermediate Similarity NPC473765
0.7864 Intermediate Similarity NPC475593
0.7864 Intermediate Similarity NPC476066
0.7864 Intermediate Similarity NPC475164
0.7864 Intermediate Similarity NPC475241
0.785 Intermediate Similarity NPC470519
0.785 Intermediate Similarity NPC231271
0.7843 Intermediate Similarity NPC294293
0.7843 Intermediate Similarity NPC472198
0.7843 Intermediate Similarity NPC159698
0.7826 Intermediate Similarity NPC48692
0.7826 Intermediate Similarity NPC476127
0.7826 Intermediate Similarity NPC476150
0.7822 Intermediate Similarity NPC476075
0.7822 Intermediate Similarity NPC476084
0.7822 Intermediate Similarity NPC472199
0.7798 Intermediate Similarity NPC392
0.7798 Intermediate Similarity NPC219900
0.7798 Intermediate Similarity NPC177524
0.7788 Intermediate Similarity NPC266842
0.7788 Intermediate Similarity NPC475332
0.7778 Intermediate Similarity NPC86005
0.7778 Intermediate Similarity NPC199382
0.7778 Intermediate Similarity NPC477959
0.7768 Intermediate Similarity NPC311592
0.7768 Intermediate Similarity NPC75167
0.7759 Intermediate Similarity NPC183353
0.7759 Intermediate Similarity NPC469812
0.7759 Intermediate Similarity NPC170880
0.7759 Intermediate Similarity NPC476204
0.7759 Intermediate Similarity NPC170084
0.7757 Intermediate Similarity NPC472755
0.7757 Intermediate Similarity NPC197736
0.775 Intermediate Similarity NPC470912
0.7748 Intermediate Similarity NPC126897
0.7748 Intermediate Similarity NPC297945
0.7745 Intermediate Similarity NPC478037
0.7745 Intermediate Similarity NPC238090
0.7745 Intermediate Similarity NPC472195
0.7745 Intermediate Similarity NPC472196
0.7745 Intermediate Similarity NPC159092
0.7745 Intermediate Similarity NPC478036
0.7739 Intermediate Similarity NPC77689
0.7739 Intermediate Similarity NPC473839
0.7739 Intermediate Similarity NPC473636
0.7739 Intermediate Similarity NPC211093
0.7719 Intermediate Similarity NPC474483
0.7719 Intermediate Similarity NPC473968
0.7714 Intermediate Similarity NPC40182
0.7714 Intermediate Similarity NPC161855
0.7714 Intermediate Similarity NPC198422
0.7712 Intermediate Similarity NPC318135
0.7705 Intermediate Similarity NPC225791
0.7699 Intermediate Similarity NPC181145
0.7692 Intermediate Similarity NPC165332
0.7692 Intermediate Similarity NPC195645
0.7692 Intermediate Similarity NPC180722
0.7686 Intermediate Similarity NPC477197
0.7685 Intermediate Similarity NPC203659
0.7685 Intermediate Similarity NPC472756
0.767 Intermediate Similarity NPC477348
0.767 Intermediate Similarity NPC477345
0.767 Intermediate Similarity NPC238264
0.7667 Intermediate Similarity NPC112492
0.7667 Intermediate Similarity NPC472269
0.7667 Intermediate Similarity NPC477075
0.7667 Intermediate Similarity NPC477078
0.7667 Intermediate Similarity NPC329923
0.7667 Intermediate Similarity NPC472270
0.7667 Intermediate Similarity NPC23020
0.7667 Intermediate Similarity NPC245094
0.7667 Intermediate Similarity NPC472268
0.7667 Intermediate Similarity NPC475281
0.7664 Intermediate Similarity NPC201191
0.7652 Intermediate Similarity NPC109603
0.7652 Intermediate Similarity NPC93688
0.7652 Intermediate Similarity NPC475309
0.7647 Intermediate Similarity NPC114172
0.7647 Intermediate Similarity NPC206679
0.7647 Intermediate Similarity NPC477349
0.7647 Intermediate Similarity NPC471324
0.7647 Intermediate Similarity NPC472197
0.7642 Intermediate Similarity NPC469870
0.7642 Intermediate Similarity NPC469871
0.7636 Intermediate Similarity NPC475960
0.7632 Intermediate Similarity NPC44170
0.7623 Intermediate Similarity NPC277212
0.7623 Intermediate Similarity NPC30279
0.7623 Intermediate Similarity NPC473918
0.7623 Intermediate Similarity NPC312650
0.7623 Intermediate Similarity NPC476776
0.7623 Intermediate Similarity NPC46823
0.7623 Intermediate Similarity NPC178264
0.7623 Intermediate Similarity NPC192765
0.7623 Intermediate Similarity NPC71391
0.7619 Intermediate Similarity NPC278506
0.7615 Intermediate Similarity NPC315070
0.7603 Intermediate Similarity NPC141600
0.7603 Intermediate Similarity NPC280029
0.7603 Intermediate Similarity NPC470518
0.7603 Intermediate Similarity NPC47995
0.7603 Intermediate Similarity NPC115656
0.7603 Intermediate Similarity NPC269484
0.7603 Intermediate Similarity NPC477079
0.7603 Intermediate Similarity NPC477196
0.7603 Intermediate Similarity NPC252289
0.7603 Intermediate Similarity NPC244296
0.7603 Intermediate Similarity NPC107536
0.7603 Intermediate Similarity NPC305793
0.7603 Intermediate Similarity NPC82380
0.7603 Intermediate Similarity NPC472267
0.7603 Intermediate Similarity NPC470913
0.7603 Intermediate Similarity NPC477076
0.7603 Intermediate Similarity NPC88311
0.7603 Intermediate Similarity NPC265841
0.7603 Intermediate Similarity NPC97918
0.7603 Intermediate Similarity NPC9470
0.7603 Intermediate Similarity NPC477077
0.7603 Intermediate Similarity NPC1314
0.7603 Intermediate Similarity NPC252657
0.7603 Intermediate Similarity NPC11577
0.7603 Intermediate Similarity NPC273878
0.7596 Intermediate Similarity NPC36954
0.7596 Intermediate Similarity NPC471142
0.7593 Intermediate Similarity NPC4620
0.7593 Intermediate Similarity NPC110989
0.7586 Intermediate Similarity NPC477515
0.7586 Intermediate Similarity NPC67917
0.7586 Intermediate Similarity NPC475775
0.7586 Intermediate Similarity NPC476529
0.7586 Intermediate Similarity NPC314268
0.7586 Intermediate Similarity NPC313802
0.7583 Intermediate Similarity NPC470516
0.7581 Intermediate Similarity NPC110700
0.7581 Intermediate Similarity NPC279915
0.7576 Intermediate Similarity NPC471494
0.7573 Intermediate Similarity NPC476300
0.7573 Intermediate Similarity NPC109406
0.757 Intermediate Similarity NPC476611
0.7565 Intermediate Similarity NPC475809
0.7565 Intermediate Similarity NPC134430
0.7563 Intermediate Similarity NPC470922
0.7561 Intermediate Similarity NPC476779
0.7551 Intermediate Similarity NPC69469
0.7547 Intermediate Similarity NPC203627
0.7547 Intermediate Similarity NPC70733
0.7547 Intermediate Similarity NPC56071
0.7545 Intermediate Similarity NPC475570
0.7544 Intermediate Similarity NPC110861
0.7541 Intermediate Similarity NPC329993
0.7541 Intermediate Similarity NPC476074

  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 NPC474581 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
0.8081 Intermediate Similarity NPD46 Approved
0.8081 Intermediate Similarity NPD6698 Approved
0.8 Intermediate Similarity NPD7983 Approved
0.7885 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD6686 Approved
0.7759 Intermediate Similarity NPD8513 Phase 3
0.7759 Intermediate Similarity NPD8516 Approved
0.7759 Intermediate Similarity NPD8517 Approved
0.7759 Intermediate Similarity NPD8515 Approved
0.7748 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7839 Suspended
0.7479 Intermediate Similarity NPD7829 Approved
0.7479 Intermediate Similarity NPD7830 Approved
0.7379 Intermediate Similarity NPD7838 Discovery
0.7333 Intermediate Similarity NPD8328 Phase 3
0.7308 Intermediate Similarity NPD6411 Approved
0.7295 Intermediate Similarity NPD8074 Phase 3
0.7238 Intermediate Similarity NPD5778 Approved
0.7238 Intermediate Similarity NPD5779 Approved
0.7177 Intermediate Similarity NPD7319 Approved
0.7167 Intermediate Similarity NPD8444 Approved
0.7154 Intermediate Similarity NPD8448 Approved
0.712 Intermediate Similarity NPD8392 Approved
0.712 Intermediate Similarity NPD8391 Approved
0.712 Intermediate Similarity NPD8390 Approved
0.7115 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD6101 Approved
0.7103 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD8451 Approved
0.7073 Intermediate Similarity NPD7507 Approved
0.7043 Intermediate Similarity NPD6371 Approved
0.7009 Intermediate Similarity NPD8133 Approved
0.6975 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6911 Remote Similarity NPD7642 Approved
0.6887 Remote Similarity NPD5785 Approved
0.687 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6855 Remote Similarity NPD8342 Approved
0.6855 Remote Similarity NPD8341 Approved
0.6855 Remote Similarity NPD8340 Approved
0.6855 Remote Similarity NPD8299 Approved
0.6803 Remote Similarity NPD8377 Approved
0.6803 Remote Similarity NPD8294 Approved
0.6796 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6412 Phase 2
0.678 Remote Similarity NPD6053 Discontinued
0.6757 Remote Similarity NPD4225 Approved
0.6757 Remote Similarity NPD7638 Approved
0.6748 Remote Similarity NPD8033 Approved
0.6748 Remote Similarity NPD8296 Approved
0.6748 Remote Similarity NPD8335 Approved
0.6748 Remote Similarity NPD8379 Approved
0.6748 Remote Similarity NPD8380 Approved
0.6748 Remote Similarity NPD8378 Approved
0.672 Remote Similarity NPD7492 Approved
0.6697 Remote Similarity NPD5282 Discontinued
0.6696 Remote Similarity NPD7640 Approved
0.6696 Remote Similarity NPD7639 Approved
0.6694 Remote Similarity NPD7115 Discovery
0.6693 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6616 Approved
0.6667 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD7637 Suspended
0.6641 Remote Similarity NPD8415 Approved
0.6639 Remote Similarity NPD7641 Discontinued
0.6639 Remote Similarity NPD8297 Approved
0.6614 Remote Similarity NPD7078 Approved
0.6614 Remote Similarity NPD8293 Discontinued
0.6613 Remote Similarity NPD8269 Approved
0.6613 Remote Similarity NPD8268 Approved
0.6613 Remote Similarity NPD8266 Approved
0.6613 Remote Similarity NPD8267 Approved
0.6591 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6571 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6566 Remote Similarity NPD8039 Approved
0.656 Remote Similarity NPD6370 Approved
0.656 Remote Similarity NPD8080 Discontinued
0.6557 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7260 Phase 2
0.6538 Remote Similarity NPD7154 Phase 3
0.6532 Remote Similarity NPD6059 Approved
0.6525 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6525 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6509 Remote Similarity NPD5786 Approved
0.6504 Remote Similarity NPD7327 Approved
0.6504 Remote Similarity NPD7328 Approved
0.65 Remote Similarity NPD6882 Approved
0.6491 Remote Similarity NPD5344 Discontinued
0.648 Remote Similarity NPD7503 Approved
0.648 Remote Similarity NPD6015 Approved
0.648 Remote Similarity NPD6016 Approved
0.6471 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7516 Approved
0.6442 Remote Similarity NPD6435 Approved
0.6429 Remote Similarity NPD5988 Approved
0.6423 Remote Similarity NPD7500 Approved
0.6423 Remote Similarity NPD6009 Approved
0.6415 Remote Similarity NPD5363 Approved
0.6406 Remote Similarity NPD8273 Phase 1
0.6349 Remote Similarity NPD6921 Approved
0.6349 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6311 Remote Similarity NPD4632 Approved
0.6303 Remote Similarity NPD6899 Approved
0.6303 Remote Similarity NPD6881 Approved
0.6296 Remote Similarity NPD4251 Approved
0.6296 Remote Similarity NPD4250 Approved
0.6286 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6286 Remote Similarity NPD4269 Approved
0.6286 Remote Similarity NPD4270 Approved
0.6281 Remote Similarity NPD6649 Approved
0.6281 Remote Similarity NPD6650 Approved
0.6281 Remote Similarity NPD8130 Phase 1
0.6271 Remote Similarity NPD5739 Approved
0.6271 Remote Similarity NPD7128 Approved
0.6271 Remote Similarity NPD6402 Approved
0.6271 Remote Similarity NPD6675 Approved
0.6261 Remote Similarity NPD6648 Approved
0.625 Remote Similarity NPD6373 Approved
0.625 Remote Similarity NPD5790 Clinical (unspecified phase)
0.625 Remote Similarity NPD7748 Approved
0.625 Remote Similarity NPD5368 Approved
0.625 Remote Similarity NPD6372 Approved
0.6232 Remote Similarity NPD8384 Approved
0.6228 Remote Similarity NPD7902 Approved
0.6226 Remote Similarity NPD5362 Discontinued
0.6218 Remote Similarity NPD5697 Approved
0.6218 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6204 Remote Similarity NPD4249 Approved
0.6198 Remote Similarity NPD6883 Approved
0.6198 Remote Similarity NPD7290 Approved
0.6198 Remote Similarity NPD7102 Approved
0.619 Remote Similarity NPD5369 Approved
0.6181 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7320 Approved
0.6161 Remote Similarity NPD6399 Phase 3
0.6154 Remote Similarity NPD7632 Discontinued
0.6148 Remote Similarity NPD6617 Approved
0.6148 Remote Similarity NPD6869 Approved
0.6148 Remote Similarity NPD6847 Approved
0.6132 Remote Similarity NPD5209 Approved
0.6124 Remote Similarity NPD7604 Phase 2
0.6119 Remote Similarity NPD6845 Suspended
0.6116 Remote Similarity NPD6014 Approved
0.6116 Remote Similarity NPD6013 Approved
0.6116 Remote Similarity NPD6012 Approved
0.6111 Remote Similarity NPD1694 Approved
0.6095 Remote Similarity NPD4252 Approved
0.6095 Remote Similarity NPD4820 Approved
0.6095 Remote Similarity NPD4822 Approved
0.6095 Remote Similarity NPD4819 Approved
0.6095 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6095 Remote Similarity NPD4821 Approved
0.6094 Remote Similarity NPD5983 Phase 2
0.6087 Remote Similarity NPD6084 Phase 2
0.6087 Remote Similarity NPD6083 Phase 2
0.6083 Remote Similarity NPD5701 Approved
0.6071 Remote Similarity NPD7515 Phase 2
0.6066 Remote Similarity NPD4634 Approved
0.6066 Remote Similarity NPD6421 Discontinued
0.6061 Remote Similarity NPD8337 Approved
0.6061 Remote Similarity NPD8336 Approved
0.6061 Remote Similarity NPD6033 Approved
0.6058 Remote Similarity NPD4268 Approved
0.6058 Remote Similarity NPD4271 Approved
0.6055 Remote Similarity NPD6422 Discontinued
0.6033 Remote Similarity NPD6011 Approved
0.6031 Remote Similarity NPD6336 Discontinued
0.602 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6016 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6 Remote Similarity NPD5048 Discontinued
0.6 Remote Similarity NPD6010 Discontinued
0.6 Remote Similarity NPD6008 Approved
0.6 Remote Similarity NPD7329 Approved
0.5965 Remote Similarity NPD7900 Approved
0.5965 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5963 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5929 Remote Similarity NPD6079 Approved
0.5926 Remote Similarity NPD6110 Phase 1
0.5918 Remote Similarity NPD7331 Phase 2
0.5913 Remote Similarity NPD5695 Phase 3
0.5909 Remote Similarity NPD6684 Approved
0.5909 Remote Similarity NPD5330 Approved
0.5909 Remote Similarity NPD7521 Approved
0.5909 Remote Similarity NPD6409 Approved
0.5909 Remote Similarity NPD7146 Approved
0.5909 Remote Similarity NPD7334 Approved
0.5893 Remote Similarity NPD5328 Approved
0.5893 Remote Similarity NPD1695 Approved
0.5887 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8139 Approved
0.5882 Remote Similarity NPD5211 Phase 2
0.5882 Remote Similarity NPD8086 Approved
0.5882 Remote Similarity NPD8084 Approved
0.5882 Remote Similarity NPD8082 Approved
0.5882 Remote Similarity NPD8085 Approved
0.5882 Remote Similarity NPD8338 Approved
0.5882 Remote Similarity NPD8083 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