Structure

Physi-Chem Properties

Molecular Weight:  422.33
Volume:  464.51
LogP:  4.0
LogD:  5.273
LogS:  -3.094
# Rotatable Bonds:  5
TPSA:  61.34
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.505
Synthetic Accessibility Score:  4.814
Fsp3:  0.654
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.443
MDCK Permeability:  2.9810485102643725e-06
Pgp-inhibitor:  0.003
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.487
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.209
Plasma Protein Binding (PPB):  66.41240692138672%
Volume Distribution (VD):  1.095
Pgp-substrate:  40.528804779052734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.114
CYP2C19-inhibitor:  0.076
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.028
CYP2C9-substrate:  0.216
CYP2D6-inhibitor:  0.962
CYP2D6-substrate:  0.365
CYP3A4-inhibitor:  0.149
CYP3A4-substrate:  0.24

ADMET: Excretion

Clearance (CL):  5.636
Half-life (T1/2):  0.819

ADMET: Toxicity

hERG Blockers:  0.138
Human Hepatotoxicity (H-HT):  0.843
Drug-inuced Liver Injury (DILI):  0.119
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.669
Maximum Recommended Daily Dose:  0.941
Skin Sensitization:  0.059
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.05
Respiratory Toxicity:  0.773

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

  Natural Product: NPC476433

Natural Product ID:  NPC476433
Common Name*:   Agelasine D
IUPAC Name:   7-[(E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enyl]-9-methylpurin-9-ium-6-amine;chloride
Synonyms:   Agelasine D
Standard InCHIKey:  VKMLEXNPDUMVEC-ZHZNLTMTSA-M
Standard InCHI:  InChI=1S/C26H40N5.ClH/c1-18(12-15-31-17-30(6)24-22(31)23(27)28-16-29-24)8-10-20-19(2)9-11-21-25(3,4)13-7-14-26(20,21)5;/h12,16-17,20-21H,2,7-11,13-15H2,1,3-6H3,(H2,27,28,29);1H/q+1;/p-1/b18-12+;/t20-,21-,26+;/m1./s1
SMILES:  CC(=CCN1C=[N+](C2=NC=NC(=C21)N)C)CCC3C(=C)CCC4C3(CCCC4(C)C)C.[Cl-]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL604730
PubChem CID:   46231918
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia 1997-AUG PMID[10514317]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. n.a. n.a. PMID[14677933]
NPO33334 agelas sponges Species Agelasidae Eukaryota n.a. Indonesian n.a. PMID[20061160]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. Okinawan n.a. PMID[26083682]
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota n.a. papua new guinean n.a. PMID[9784179]
NPO11199 Agelas nakamurai Species Agelasidae 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
NPT1864 Cell Line L5178Y Mus musculus GI = 1.9 % PMID[531475]
NPT1864 Cell Line L5178Y Mus musculus IC50 = 4030.0 nM PMID[531475]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 > 24000.0 nM PMID[531477]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC < 87.7 nM PMID[531475]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei MIC = 14800.0 nM PMID[531476]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IZ = 18.0 mm PMID[531477]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IZ = 14.0 mm PMID[531477]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 36000.0 nM PMID[531477]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 19000.0 nM PMID[531477]

☑ 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 NPC476433 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 NPC476528
0.9773 High Similarity NPC476522
0.9773 High Similarity NPC476013
0.9773 High Similarity NPC474986
0.9769 High Similarity NPC296437
0.9701 High Similarity NPC476408
0.9699 High Similarity NPC476521
0.9695 High Similarity NPC470266
0.9624 High Similarity NPC476520
0.9065 High Similarity NPC244700
0.8836 High Similarity NPC18308
0.8836 High Similarity NPC472832
0.8819 High Similarity NPC472834
0.8759 High Similarity NPC472833
0.8511 High Similarity NPC217656
0.8194 Intermediate Similarity NPC89139
0.8012 Intermediate Similarity NPC473585
0.7818 Intermediate Similarity NPC265111
0.7154 Intermediate Similarity NPC174114
0.7154 Intermediate Similarity NPC87981
0.6974 Remote Similarity NPC167285
0.6923 Remote Similarity NPC317054
0.6863 Remote Similarity NPC226184
0.6863 Remote Similarity NPC76544
0.6846 Remote Similarity NPC57279
0.6686 Remote Similarity NPC164845
0.6618 Remote Similarity NPC476564
0.6618 Remote Similarity NPC18335
0.649 Remote Similarity NPC104011
0.6458 Remote Similarity NPC68938
0.641 Remote Similarity NPC33996
0.6383 Remote Similarity NPC4837
0.6383 Remote Similarity NPC312187
0.6369 Remote Similarity NPC129756
0.6347 Remote Similarity NPC239737
0.6226 Remote Similarity NPC317821
0.6182 Remote Similarity NPC150853
0.6175 Remote Similarity NPC313514
0.6169 Remote Similarity NPC246193
0.6158 Remote Similarity NPC313897
0.6154 Remote Similarity NPC93365
0.6154 Remote Similarity NPC476219
0.6126 Remote Similarity NPC469308
0.6125 Remote Similarity NPC209525
0.6125 Remote Similarity NPC161659
0.6122 Remote Similarity NPC189314
0.6089 Remote Similarity NPC477119
0.6059 Remote Similarity NPC476297
0.6049 Remote Similarity NPC314152
0.6049 Remote Similarity NPC229974
0.6047 Remote Similarity NPC300238
0.6037 Remote Similarity NPC189068
0.6036 Remote Similarity NPC469975
0.6 Remote Similarity NPC219313
0.6 Remote Similarity NPC309832
0.5977 Remote Similarity NPC470203
0.5976 Remote Similarity NPC107374
0.5976 Remote Similarity NPC156461
0.5976 Remote Similarity NPC21448
0.5952 Remote Similarity NPC114209
0.5948 Remote Similarity NPC248007
0.5939 Remote Similarity NPC164665
0.5928 Remote Similarity NPC136349
0.592 Remote Similarity NPC470204
0.5904 Remote Similarity NPC269827
0.5892 Remote Similarity NPC477118
0.5872 Remote Similarity NPC120070
0.5868 Remote Similarity NPC121222
0.586 Remote Similarity NPC477120
0.5858 Remote Similarity NPC161224
0.5856 Remote Similarity NPC189261
0.5838 Remote Similarity NPC195140
0.5824 Remote Similarity NPC328479
0.5822 Remote Similarity NPC158055
0.5804 Remote Similarity NPC476099
0.5789 Remote Similarity NPC302778
0.5789 Remote Similarity NPC212551
0.5765 Remote Similarity NPC185991
0.5765 Remote Similarity NPC85689
0.5765 Remote Similarity NPC211025
0.5758 Remote Similarity NPC8590
0.5756 Remote Similarity NPC174802
0.5752 Remote Similarity NPC139776
0.5739 Remote Similarity NPC122141
0.5731 Remote Similarity NPC472816
0.5731 Remote Similarity NPC321814
0.5728 Remote Similarity NPC250178
0.5723 Remote Similarity NPC224076
0.5714 Remote Similarity NPC276373
0.5706 Remote Similarity NPC225018
0.5698 Remote Similarity NPC130586
0.5698 Remote Similarity NPC164952
0.5696 Remote Similarity NPC14330
0.569 Remote Similarity NPC226245
0.5685 Remote Similarity NPC5802
0.5674 Remote Similarity NPC317105
0.5668 Remote Similarity NPC24589
0.5667 Remote Similarity NPC290959
0.5665 Remote Similarity NPC471603
0.5664 Remote Similarity NPC476561
0.566 Remote Similarity NPC287876
0.5657 Remote Similarity NPC157821
0.564 Remote Similarity NPC207633
0.5634 Remote Similarity NPC115595
0.5632 Remote Similarity NPC325903
0.5607 Remote Similarity NPC40070
0.5607 Remote Similarity NPC160666
0.56 Remote Similarity NPC316618

  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 NPC476433 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
0.7379 Intermediate Similarity NPD1058 Discontinued
0.7073 Intermediate Similarity NPD1313 Approved
0.6788 Remote Similarity NPD6074 Clinical (unspecified phase)
0.6766 Remote Similarity NPD1333 Phase 3
0.6706 Remote Similarity NPD1567 Clinical (unspecified phase)
0.6705 Remote Similarity NPD2930 Clinical (unspecified phase)
0.6689 Remote Similarity NPD870 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7158 Phase 1
0.6687 Remote Similarity NPD2593 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5962 Phase 2
0.6667 Remote Similarity NPD3378 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7023 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1015 Phase 2
0.6647 Remote Similarity NPD2875 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1016 Phase 2
0.6627 Remote Similarity NPD516 Clinical (unspecified phase)
0.6618 Remote Similarity NPD8836 Approved
0.6609 Remote Similarity NPD3341 Clinical (unspecified phase)
0.6606 Remote Similarity NPD2927 Phase 3
0.6554 Remote Similarity NPD9408 Phase 3
0.6538 Remote Similarity NPD3485 Clinical (unspecified phase)
0.6534 Remote Similarity NPD4649 Clinical (unspecified phase)
0.6533 Remote Similarity NPD9633 Phase 3
0.6529 Remote Similarity NPD1215 Discontinued
0.6524 Remote Similarity NPD6129 Phase 2
0.6519 Remote Similarity NPD4240 Approved
0.6519 Remote Similarity NPD3419 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6816 Phase 3
0.6491 Remote Similarity NPD2333 Discontinued
0.649 Remote Similarity NPD248 Discontinued
0.6471 Remote Similarity NPD5269 Clinical (unspecified phase)
0.6461 Remote Similarity NPD2457 Phase 2
0.6461 Remote Similarity NPD2456 Phase 2
0.6457 Remote Similarity NPD7111 Discontinued
0.6455 Remote Similarity NPD2965 Clinical (unspecified phase)
0.6437 Remote Similarity NPD3799 Suspended
0.6433 Remote Similarity NPD6794 Approved
0.6429 Remote Similarity NPD6761 Discontinued
0.642 Remote Similarity NPD5730 Phase 2
0.642 Remote Similarity NPD40 Phase 2
0.641 Remote Similarity NPD799 Phase 1
0.6393 Remote Similarity NPD7722 Suspended
0.6392 Remote Similarity NPD4352 Phase 1
0.6389 Remote Similarity NPD2793 Discontinued
0.6389 Remote Similarity NPD4902 Discontinued
0.6384 Remote Similarity NPD5508 Phase 1
0.638 Remote Similarity NPD4568 Phase 2
0.6374 Remote Similarity NPD8120 Approved
0.6374 Remote Similarity NPD8121 Phase 3
0.6369 Remote Similarity NPD5463 Clinical (unspecified phase)
0.6344 Remote Similarity NPD5462 Discontinued
0.6343 Remote Similarity NPD7006 Approved
0.6337 Remote Similarity NPD2647 Phase 3
0.6335 Remote Similarity NPD7323 Phase 2
0.6329 Remote Similarity NPD3696 Approved
0.6329 Remote Similarity NPD3695 Approved
0.6325 Remote Similarity NPD2524 Discontinued
0.6323 Remote Similarity NPD4763 Clinical (unspecified phase)
0.6304 Remote Similarity NPD3431 Approved
0.6304 Remote Similarity NPD6619 Phase 3
0.6304 Remote Similarity NPD3430 Approved
0.6298 Remote Similarity NPD2591 Phase 2
0.6298 Remote Similarity NPD6721 Phase 1
0.6286 Remote Similarity NPD5324 Clinical (unspecified phase)
0.6273 Remote Similarity NPD171 Discontinued
0.6272 Remote Similarity NPD5300 Clinical (unspecified phase)
0.6271 Remote Similarity NPD3041 Approved
0.6257 Remote Similarity NPD2526 Phase 2
0.6257 Remote Similarity NPD1637 Clinical (unspecified phase)
0.6257 Remote Similarity NPD2523 Phase 2
0.6257 Remote Similarity NPD5806 Clinical (unspecified phase)
0.625 Remote Similarity NPD5969 Clinical (unspecified phase)
0.6243 Remote Similarity NPD2478 Clinical (unspecified phase)
0.6236 Remote Similarity NPD1892 Phase 2
0.6236 Remote Similarity NPD3409 Phase 1
0.6236 Remote Similarity NPD1893 Phase 2
0.6229 Remote Similarity NPD6828 Phase 2
0.6229 Remote Similarity NPD6827 Clinical (unspecified phase)
0.6223 Remote Similarity NPD6468 Clinical (unspecified phase)
0.6223 Remote Similarity NPD6469 Phase 3
0.6218 Remote Similarity NPD7445 Phase 1
0.6218 Remote Similarity NPD2450 Phase 2
0.6218 Remote Similarity NPD2452 Phase 2
0.6218 Remote Similarity NPD2453 Phase 2
0.6218 Remote Similarity NPD2451 Phase 2
0.6216 Remote Similarity NPD6577 Clinical (unspecified phase)
0.6216 Remote Similarity NPD4615 Phase 2
0.6216 Remote Similarity NPD2839 Phase 2
0.6215 Remote Similarity NPD5843 Discontinued
0.6215 Remote Similarity NPD2406 Clinical (unspecified phase)
0.6205 Remote Similarity NPD6192 Phase 3
0.6198 Remote Similarity NPD5012 Phase 2
0.6186 Remote Similarity NPD4612 Discontinued
0.6185 Remote Similarity NPD3889 Approved
0.6175 Remote Similarity NPD7138 Phase 2
0.6168 Remote Similarity NPD3107 Discontinued
0.6166 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6166 Remote Similarity NPD2876 Phase 3
0.6159 Remote Similarity NPD4183 Phase 3
0.6159 Remote Similarity NPD4182 Phase 3
0.6158 Remote Similarity NPD7297 Phase 2
0.6158 Remote Similarity NPD6849 Phase 2
0.6158 Remote Similarity NPD6850 Phase 2
0.6154 Remote Similarity NPD2646 Discontinued
0.6154 Remote Similarity NPD546 Clinical (unspecified phase)
0.6133 Remote Similarity NPD306 Approved
0.6133 Remote Similarity NPD4441 Phase 2
0.6131 Remote Similarity NPD1257 Approved
0.6126 Remote Similarity NPD6151 Phase 2
0.6126 Remote Similarity NPD4318 Clinical (unspecified phase)
0.6125 Remote Similarity NPD193 Suspended
0.6122 Remote Similarity NPD8831 Approved
0.6122 Remote Similarity NPD8833 Approved
0.612 Remote Similarity NPD5642 Approved
0.612 Remote Similarity NPD5682 Phase 3
0.612 Remote Similarity NPD5683 Clinical (unspecified phase)
0.612 Remote Similarity NPD5684 Clinical (unspecified phase)
0.6117 Remote Similarity NPD3362 Clinical (unspecified phase)
0.6111 Remote Similarity NPD174 Discontinued
0.6108 Remote Similarity NPD2818 Discontinued
0.6108 Remote Similarity NPD5145 Clinical (unspecified phase)
0.6105 Remote Similarity NPD1288 Clinical (unspecified phase)
0.6103 Remote Similarity NPD2824 Phase 2
0.6103 Remote Similarity NPD6520 Phase 3
0.6103 Remote Similarity NPD6521 Phase 3
0.6102 Remote Similarity NPD5996 Clinical (unspecified phase)
0.6092 Remote Similarity NPD509 Phase 3
0.6091 Remote Similarity NPD4863 Approved
0.6087 Remote Similarity NPD6418 Phase 1
0.6084 Remote Similarity NPD3708 Phase 2
0.6071 Remote Similarity NPD3860 Discontinued
0.6071 Remote Similarity NPD1029 Clinical (unspecified phase)
0.6071 Remote Similarity NPD1030 Approved
0.6071 Remote Similarity NPD1027 Approved
0.6062 Remote Similarity NPD2364 Suspended
0.6059 Remote Similarity NPD4854 Phase 3
0.6054 Remote Similarity NPD7504 Discontinued
0.6053 Remote Similarity NPD5885 Approved
0.6051 Remote Similarity NPD3905 Phase 3
0.6049 Remote Similarity NPD185 Approved
0.6042 Remote Similarity NPD4142 Discontinued
0.6036 Remote Similarity NPD3612 Phase 2
0.6033 Remote Similarity NPD2963 Phase 1
0.6032 Remote Similarity NPD2960 Clinical (unspecified phase)
0.6024 Remote Similarity NPD1690 Clinical (unspecified phase)
0.6022 Remote Similarity NPD4716 Approved
0.6022 Remote Similarity NPD1873 Clinical (unspecified phase)
0.6022 Remote Similarity NPD702 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6352 Phase 2
0.601 Remote Similarity NPD5486 Discontinued
0.6 Remote Similarity NPD2880 Discontinued
0.6 Remote Similarity NPD1303 Phase 1
0.6 Remote Similarity NPD4023 Clinical (unspecified phase)
0.6 Remote Similarity NPD3002 Clinical (unspecified phase)
0.6 Remote Similarity NPD1272 Clinical (unspecified phase)
0.6 Remote Similarity NPD2731 Phase 2
0.6 Remote Similarity NPD7988 Suspended
0.6 Remote Similarity NPD1807 Clinical (unspecified phase)
0.6 Remote Similarity NPD6271 Approved
0.599 Remote Similarity NPD6470 Phase 3
0.5989 Remote Similarity NPD1895 Discontinued
0.5989 Remote Similarity NPD7709 Discontinued
0.5989 Remote Similarity NPD4744 Clinical (unspecified phase)
0.5989 Remote Similarity NPD1674 Clinical (unspecified phase)
0.5989 Remote Similarity NPD1675 Phase 1
0.598 Remote Similarity NPD2903 Clinical (unspecified phase)
0.598 Remote Similarity NPD7164 Discontinued
0.598 Remote Similarity NPD2902 Phase 2
0.5978 Remote Similarity NPD2868 Clinical (unspecified phase)
0.5978 Remote Similarity NPD4298 Clinical (unspecified phase)
0.5976 Remote Similarity NPD250 Approved
0.5976 Remote Similarity NPD166 Approved
0.5976 Remote Similarity NPD249 Approved
0.5972 Remote Similarity NPD7502 Clinical (unspecified phase)
0.5968 Remote Similarity NPD2728 Approved
0.5968 Remote Similarity NPD2729 Approved
0.5968 Remote Similarity NPD2730 Approved
0.5967 Remote Similarity NPD3432 Approved
0.5966 Remote Similarity NPD4213 Clinical (unspecified phase)
0.5966 Remote Similarity NPD3361 Phase 1
0.5965 Remote Similarity NPD3405 Phase 3
0.596 Remote Similarity NPD4990 Clinical (unspecified phase)
0.5949 Remote Similarity NPD7103 Approved
0.5948 Remote Similarity NPD9084 Phase 2
0.5947 Remote Similarity NPD7935 Phase 2
0.5946 Remote Similarity NPD5757 Discontinued
0.5944 Remote Similarity NPD5943 Clinical (unspecified phase)
0.5941 Remote Similarity NPD2128 Phase 1
0.593 Remote Similarity NPD2150 Discontinued
0.593 Remote Similarity NPD3265 Phase 1
0.5928 Remote Similarity NPD2881 Approved
0.5928 Remote Similarity NPD2807 Discontinued
0.5928 Remote Similarity NPD548 Clinical (unspecified phase)
0.5928 Remote Similarity NPD2879 Approved
0.5918 Remote Similarity NPD5458 Discontinued
0.5916 Remote Similarity NPD3830 Phase 1
0.5915 Remote Similarity NPD3706 Clinical (unspecified phase)
0.5914 Remote Similarity NPD7394 Phase 2
0.5912 Remote Similarity NPD4155 Approved
0.5912 Remote Similarity NPD9484 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