Structure

Physi-Chem Properties

Molecular Weight:  659.44
Volume:  687.874
LogP:  5.122
LogD:  4.12
LogS:  -3.639
# Rotatable Bonds:  6
TPSA:  145.55
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.2
Synthetic Accessibility Score:  5.256
Fsp3:  0.895
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:  -5.466
MDCK Permeability:  5.881548531760927e-06
Pgp-inhibitor:  0.477
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  0.548
30% Bioavailability (F30%):  0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  86.35618591308594%
Volume Distribution (VD):  0.69
Pgp-substrate:  5.987848281860352%

ADMET: Metabolism

CYP1A2-inhibitor:  0.001
CYP1A2-substrate:  0.236
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.517
CYP2C9-inhibitor:  0.065
CYP2C9-substrate:  0.063
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.102
CYP3A4-inhibitor:  0.28
CYP3A4-substrate:  0.195

ADMET: Excretion

Clearance (CL):  1.285
Half-life (T1/2):  0.357

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.251
Drug-inuced Liver Injury (DILI):  0.023
AMES Toxicity:  0.064
Rat Oral Acute Toxicity:  0.11
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.033
Carcinogencity:  0.02
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.816

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

  Natural Product: NPC475472

Natural Product ID:  NPC475472
Common Name*:   Aridanin
IUPAC Name:   (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:   Aridanin
Standard InCHIKey:  VRFWJSCLROXBBW-XLUVLVBOSA-N
Standard InCHI:  InChI=1S/C38H61NO8/c1-21(41)39-28-30(43)29(42)24(20-40)46-31(28)47-27-12-13-35(6)25(34(27,4)5)11-14-37(8)26(35)10-9-22-23-19-33(2,3)15-17-38(23,32(44)45)18-16-36(22,37)7/h9,23-31,40,42-43H,10-20H2,1-8H3,(H,39,41)(H,44,45)/t23-,24-,25+,26-,27+,28-,29-,30-,31+,35+,36-,37-,38+/m1/s1
SMILES:  CC(=O)NC1C(C(C(OC1OC2CCC3(C(C2(C)C)CCC4(C3CC=C5C4(CCC6(C5CC(CC6)(C)C)C(=O)O)C)C)C)CO)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506209
PubChem CID:   44584412
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*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
NPO2634 Tetrapleura tetraptera Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[8289059]
NPO2634 Tetrapleura tetraptera Species Fabaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[527335]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 28.3 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 28.2 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 19.8 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 19.9 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 24.2 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 22.2 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 26.5 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 28.9 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 19.0 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 18.7 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 52.5 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 51.1 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 73.0 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 68.7 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 47.7 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 49.8 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 70.8 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 69.6 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 90.4 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 89.0 ppm PMID[527334]
NPT3469 Organism Biomphalaria glabrata Biomphalaria glabrata Activity = 100.0 % PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 4.5 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 2.5 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 5.6 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 2.9 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 4.1 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 3.2 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 3.3 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 2.8 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 4.2 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 4.0 n.a. PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 89.0 % PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 100.0 % PMID[527336]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium Activity = 98.0 % PMID[527336]

☑ 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 NPC475472 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
0.9917 High Similarity NPC119794
0.9917 High Similarity NPC73829
0.9836 High Similarity NPC76999
0.9756 High Similarity NPC280941
0.9756 High Similarity NPC235772
0.9756 High Similarity NPC75318
0.9677 High Similarity NPC145899
0.9524 High Similarity NPC200788
0.9524 High Similarity NPC243680
0.9375 High Similarity NPC210729
0.9375 High Similarity NPC172365
0.9375 High Similarity NPC82931
0.9231 High Similarity NPC475584
0.9231 High Similarity NPC475394
0.9231 High Similarity NPC475152
0.916 High Similarity NPC475892
0.8906 High Similarity NPC477072
0.8712 High Similarity NPC180770
0.8712 High Similarity NPC302276
0.8633 High Similarity NPC475527
0.8633 High Similarity NPC265699
0.8605 High Similarity NPC139585
0.8593 High Similarity NPC141669
0.8582 High Similarity NPC162910
0.8571 High Similarity NPC475599
0.8571 High Similarity NPC174336
0.8571 High Similarity NPC100612
0.8571 High Similarity NPC187497
0.8571 High Similarity NPC113620
0.8456 Intermediate Similarity NPC298469
0.8456 Intermediate Similarity NPC193579
0.8394 Intermediate Similarity NPC298067
0.8394 Intermediate Similarity NPC214821
0.8333 Intermediate Similarity NPC237503
0.8333 Intermediate Similarity NPC204407
0.8333 Intermediate Similarity NPC306746
0.8333 Intermediate Similarity NPC57362
0.8333 Intermediate Similarity NPC167383
0.8296 Intermediate Similarity NPC265908
0.8286 Intermediate Similarity NPC298005
0.8286 Intermediate Similarity NPC36463
0.8273 Intermediate Similarity NPC244380
0.8273 Intermediate Similarity NPC61717
0.8264 Intermediate Similarity NPC274507
0.8264 Intermediate Similarity NPC199457
0.8264 Intermediate Similarity NPC90856
0.8264 Intermediate Similarity NPC127056
0.8264 Intermediate Similarity NPC476885
0.8264 Intermediate Similarity NPC174679
0.8264 Intermediate Similarity NPC59804
0.8264 Intermediate Similarity NPC476883
0.8264 Intermediate Similarity NPC108709
0.8264 Intermediate Similarity NPC476887
0.8264 Intermediate Similarity NPC474589
0.8264 Intermediate Similarity NPC164194
0.8264 Intermediate Similarity NPC68419
0.8264 Intermediate Similarity NPC476881
0.8264 Intermediate Similarity NPC270667
0.8264 Intermediate Similarity NPC56713
0.8264 Intermediate Similarity NPC136877
0.8264 Intermediate Similarity NPC476882
0.8264 Intermediate Similarity NPC110139
0.8264 Intermediate Similarity NPC476880
0.8264 Intermediate Similarity NPC29069
0.8264 Intermediate Similarity NPC476884
0.8264 Intermediate Similarity NPC475296
0.8264 Intermediate Similarity NPC279554
0.8264 Intermediate Similarity NPC75747
0.8264 Intermediate Similarity NPC102914
0.8264 Intermediate Similarity NPC7870
0.8264 Intermediate Similarity NPC476886
0.825 Intermediate Similarity NPC28198
0.825 Intermediate Similarity NPC284807
0.825 Intermediate Similarity NPC177246
0.825 Intermediate Similarity NPC476123
0.8197 Intermediate Similarity NPC30397
0.8197 Intermediate Similarity NPC164419
0.8197 Intermediate Similarity NPC297208
0.8197 Intermediate Similarity NPC179434
0.8197 Intermediate Similarity NPC108748
0.8197 Intermediate Similarity NPC191763
0.8197 Intermediate Similarity NPC211798
0.8197 Intermediate Similarity NPC473481
0.8197 Intermediate Similarity NPC235841
0.8197 Intermediate Similarity NPC31839
0.8188 Intermediate Similarity NPC284625
0.8188 Intermediate Similarity NPC69176
0.8182 Intermediate Similarity NPC127853
0.8182 Intermediate Similarity NPC137917
0.8167 Intermediate Similarity NPC283849
0.8167 Intermediate Similarity NPC473538
0.813 Intermediate Similarity NPC471383
0.813 Intermediate Similarity NPC292677
0.813 Intermediate Similarity NPC104071
0.813 Intermediate Similarity NPC104400
0.813 Intermediate Similarity NPC475504
0.813 Intermediate Similarity NPC10320
0.813 Intermediate Similarity NPC80843
0.813 Intermediate Similarity NPC46388
0.813 Intermediate Similarity NPC475516
0.813 Intermediate Similarity NPC473373
0.813 Intermediate Similarity NPC471967
0.813 Intermediate Similarity NPC324875
0.813 Intermediate Similarity NPC102439
0.813 Intermediate Similarity NPC101744
0.813 Intermediate Similarity NPC109079
0.813 Intermediate Similarity NPC128925
0.813 Intermediate Similarity NPC48249
0.813 Intermediate Similarity NPC139894
0.813 Intermediate Similarity NPC257468
0.813 Intermediate Similarity NPC256798
0.813 Intermediate Similarity NPC276093
0.813 Intermediate Similarity NPC139044
0.813 Intermediate Similarity NPC469946
0.813 Intermediate Similarity NPC79718
0.813 Intermediate Similarity NPC116794
0.813 Intermediate Similarity NPC37739
0.813 Intermediate Similarity NPC473383
0.813 Intermediate Similarity NPC1046
0.8125 Intermediate Similarity NPC469943
0.8115 Intermediate Similarity NPC242611
0.8115 Intermediate Similarity NPC220984
0.8115 Intermediate Similarity NPC269095
0.8115 Intermediate Similarity NPC78046
0.8083 Intermediate Similarity NPC475611
0.8065 Intermediate Similarity NPC309714
0.8065 Intermediate Similarity NPC114287
0.8065 Intermediate Similarity NPC96641
0.8065 Intermediate Similarity NPC174720
0.8065 Intermediate Similarity NPC155410
0.8065 Intermediate Similarity NPC150400
0.8065 Intermediate Similarity NPC134835
0.8065 Intermediate Similarity NPC73318
0.8065 Intermediate Similarity NPC475467
0.8065 Intermediate Similarity NPC473343
0.8065 Intermediate Similarity NPC163183
0.8065 Intermediate Similarity NPC138334
0.8065 Intermediate Similarity NPC204458
0.8065 Intermediate Similarity NPC189884
0.8065 Intermediate Similarity NPC238935
0.8065 Intermediate Similarity NPC475287
0.8065 Intermediate Similarity NPC124296
0.8065 Intermediate Similarity NPC114304
0.8065 Intermediate Similarity NPC269315
0.8065 Intermediate Similarity NPC475208
0.8065 Intermediate Similarity NPC219180
0.8065 Intermediate Similarity NPC133818
0.8065 Intermediate Similarity NPC151543
0.8065 Intermediate Similarity NPC192600
0.8065 Intermediate Similarity NPC258885
0.8065 Intermediate Similarity NPC47063
0.8065 Intermediate Similarity NPC251263
0.8065 Intermediate Similarity NPC166422
0.8065 Intermediate Similarity NPC241909
0.8065 Intermediate Similarity NPC46665
0.8065 Intermediate Similarity NPC323341
0.8065 Intermediate Similarity NPC271138
0.8065 Intermediate Similarity NPC473826
0.8065 Intermediate Similarity NPC295823
0.8 Intermediate Similarity NPC119592
0.8 Intermediate Similarity NPC305981
0.8 Intermediate Similarity NPC473714
0.8 Intermediate Similarity NPC79643
0.8 Intermediate Similarity NPC471385
0.8 Intermediate Similarity NPC204414
0.8 Intermediate Similarity NPC43550
0.8 Intermediate Similarity NPC60557
0.8 Intermediate Similarity NPC54636
0.8 Intermediate Similarity NPC309907
0.8 Intermediate Similarity NPC224381
0.8 Intermediate Similarity NPC236638
0.8 Intermediate Similarity NPC202828
0.8 Intermediate Similarity NPC71065
0.8 Intermediate Similarity NPC227551
0.8 Intermediate Similarity NPC475160
0.8 Intermediate Similarity NPC293330
0.8 Intermediate Similarity NPC67857
0.8 Intermediate Similarity NPC65105
0.8 Intermediate Similarity NPC475486
0.8 Intermediate Similarity NPC100639
0.8 Intermediate Similarity NPC161717
0.8 Intermediate Similarity NPC4328
0.8 Intermediate Similarity NPC476068
0.8 Intermediate Similarity NPC469782
0.8 Intermediate Similarity NPC294453
0.8 Intermediate Similarity NPC475140
0.8 Intermediate Similarity NPC261506
0.8 Intermediate Similarity NPC298034
0.8 Intermediate Similarity NPC57484
0.8 Intermediate Similarity NPC471550
0.8 Intermediate Similarity NPC475633
0.8 Intermediate Similarity NPC41061
0.8 Intermediate Similarity NPC164389
0.8 Intermediate Similarity NPC76972
0.8 Intermediate Similarity NPC70809
0.8 Intermediate Similarity NPC123199
0.8 Intermediate Similarity NPC250247
0.7984 Intermediate Similarity NPC100383
0.7951 Intermediate Similarity NPC285576
0.7937 Intermediate Similarity NPC75287

  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 NPC475472 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
0.76 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD8328 Phase 3
0.7462 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD8133 Approved
0.7031 Intermediate Similarity NPD6412 Phase 2
0.6977 Remote Similarity NPD8174 Phase 2
0.6977 Remote Similarity NPD6686 Approved
0.6933 Remote Similarity NPD7625 Phase 1
0.6906 Remote Similarity NPD7507 Approved
0.687 Remote Similarity NPD6421 Discontinued
0.6853 Remote Similarity NPD8449 Approved
0.6849 Remote Similarity NPD6334 Approved
0.6849 Remote Similarity NPD6333 Approved
0.6831 Remote Similarity NPD6914 Discontinued
0.6829 Remote Similarity NPD7748 Approved
0.6809 Remote Similarity NPD8336 Approved
0.6809 Remote Similarity NPD8337 Approved
0.6806 Remote Similarity NPD8450 Suspended
0.68 Remote Similarity NPD7902 Approved
0.6788 Remote Similarity NPD8294 Approved
0.6788 Remote Similarity NPD8377 Approved
0.6761 Remote Similarity NPD7319 Approved
0.6741 Remote Similarity NPD6940 Discontinued
0.6739 Remote Similarity NPD8378 Approved
0.6739 Remote Similarity NPD8033 Approved
0.6739 Remote Similarity NPD8296 Approved
0.6739 Remote Similarity NPD8380 Approved
0.6739 Remote Similarity NPD8335 Approved
0.6739 Remote Similarity NPD8379 Approved
0.6736 Remote Similarity NPD8338 Approved
0.6714 Remote Similarity NPD8341 Approved
0.6714 Remote Similarity NPD8340 Approved
0.6714 Remote Similarity NPD8342 Approved
0.6714 Remote Similarity NPD8299 Approved
0.6713 Remote Similarity NPD8392 Approved
0.6713 Remote Similarity NPD8391 Approved
0.6713 Remote Similarity NPD8390 Approved
0.6693 Remote Similarity NPD8418 Phase 2
0.6691 Remote Similarity NPD8137 Clinical (unspecified phase)
0.669 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD8451 Approved
0.6642 Remote Similarity NPD7327 Approved
0.6642 Remote Similarity NPD7641 Discontinued
0.6642 Remote Similarity NPD7328 Approved
0.662 Remote Similarity NPD8074 Phase 3
0.662 Remote Similarity NPD8448 Approved
0.6599 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6594 Remote Similarity NPD7516 Approved
0.656 Remote Similarity NPD7901 Clinical (unspecified phase)
0.656 Remote Similarity NPD7900 Approved
0.6548 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6531 Remote Similarity NPD8415 Approved
0.6515 Remote Similarity NPD8307 Discontinued
0.6503 Remote Similarity NPD8293 Discontinued
0.65 Remote Similarity NPD7503 Approved
0.65 Remote Similarity NPD8515 Approved
0.65 Remote Similarity NPD6921 Approved
0.65 Remote Similarity NPD8516 Approved
0.65 Remote Similarity NPD8517 Approved
0.65 Remote Similarity NPD8513 Phase 3
0.65 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6454 Remote Similarity NPD8080 Discontinued
0.6408 Remote Similarity NPD7830 Approved
0.6408 Remote Similarity NPD7829 Approved
0.6391 Remote Similarity NPD8140 Approved
0.6383 Remote Similarity NPD6908 Approved
0.6383 Remote Similarity NPD8444 Approved
0.6383 Remote Similarity NPD6909 Approved
0.637 Remote Similarity NPD8087 Discontinued
0.6338 Remote Similarity NPD6370 Approved
0.632 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5357 Phase 1
0.6296 Remote Similarity NPD8306 Approved
0.6296 Remote Similarity NPD8305 Approved
0.6288 Remote Similarity NPD8276 Approved
0.6288 Remote Similarity NPD8275 Approved
0.6277 Remote Similarity NPD8297 Approved
0.6277 Remote Similarity NPD6429 Approved
0.6277 Remote Similarity NPD6882 Approved
0.6277 Remote Similarity NPD6430 Approved
0.627 Remote Similarity NPD8035 Phase 2
0.627 Remote Similarity NPD8034 Phase 2
0.625 Remote Similarity NPD7492 Approved
0.6241 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6231 Remote Similarity NPD7638 Approved
0.622 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6214 Remote Similarity NPD6009 Approved
0.6212 Remote Similarity NPD8139 Approved
0.6212 Remote Similarity NPD8085 Approved
0.6212 Remote Similarity NPD8086 Approved
0.6212 Remote Similarity NPD8084 Approved
0.6212 Remote Similarity NPD8138 Approved
0.6212 Remote Similarity NPD8082 Approved
0.6212 Remote Similarity NPD8083 Approved
0.6207 Remote Similarity NPD6616 Approved
0.6197 Remote Similarity NPD6059 Approved
0.6197 Remote Similarity NPD8347 Approved
0.6197 Remote Similarity NPD8346 Approved
0.6197 Remote Similarity NPD6054 Approved
0.6197 Remote Similarity NPD8345 Approved
0.6197 Remote Similarity NPD6319 Approved
0.6194 Remote Similarity NPD8393 Approved
0.6183 Remote Similarity NPD7639 Approved
0.6183 Remote Similarity NPD7640 Approved
0.6181 Remote Similarity NPD6067 Discontinued
0.6181 Remote Similarity NPD7642 Approved
0.6181 Remote Similarity NPD7604 Phase 2
0.6176 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6165 Remote Similarity NPD1407 Approved
0.6164 Remote Similarity NPD7078 Approved
0.6119 Remote Similarity NPD8081 Approved
0.6115 Remote Similarity NPD4632 Approved
0.6115 Remote Similarity NPD8298 Phase 2
0.6103 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6094 Remote Similarity NPD6399 Phase 3
0.609 Remote Similarity NPD7140 Approved
0.609 Remote Similarity NPD7139 Approved
0.609 Remote Similarity NPD7141 Clinical (unspecified phase)
0.6087 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6083 Remote Similarity NPD7645 Phase 2
0.6077 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6074 Remote Similarity NPD7128 Approved
0.6074 Remote Similarity NPD5739 Approved
0.6074 Remote Similarity NPD6675 Approved
0.6074 Remote Similarity NPD6402 Approved
0.6069 Remote Similarity NPD7122 Discontinued
0.6067 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6065 Remote Similarity NPD8384 Approved
0.6058 Remote Similarity NPD6372 Approved
0.6058 Remote Similarity NPD6941 Approved
0.6058 Remote Similarity NPD6373 Approved
0.6054 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6048 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6016 Approved
0.6042 Remote Similarity NPD6015 Approved
0.6038 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6037 Remote Similarity NPD8417 Discontinued
0.6032 Remote Similarity NPD618 Clinical (unspecified phase)
0.6014 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6014 Remote Similarity NPD6420 Discontinued
0.6 Remote Similarity NPD8361 Approved
0.6 Remote Similarity NPD8360 Approved
0.6 Remote Similarity NPD6436 Phase 3
0.6 Remote Similarity NPD8435 Approved
0.6 Remote Similarity NPD5988 Approved
0.5986 Remote Similarity NPD7115 Discovery
0.5985 Remote Similarity NPD6899 Approved
0.5985 Remote Similarity NPD6881 Approved
0.5985 Remote Similarity NPD7320 Approved
0.5971 Remote Similarity NPD8130 Phase 1
0.5971 Remote Similarity NPD6650 Approved
0.5971 Remote Similarity NPD6649 Approved
0.5969 Remote Similarity NPD1447 Phase 3
0.5969 Remote Similarity NPD1446 Phase 3
0.5966 Remote Similarity NPD8368 Discontinued
0.5955 Remote Similarity NPD8407 Phase 2
0.5954 Remote Similarity NPD6428 Approved
0.5926 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5914 Remote Similarity NPD7237 Clinical (unspecified phase)
0.5912 Remote Similarity NPD5697 Approved
0.5912 Remote Similarity NPD5701 Approved
0.5899 Remote Similarity NPD6883 Approved
0.5899 Remote Similarity NPD7102 Approved
0.5899 Remote Similarity NPD7290 Approved
0.5894 Remote Similarity NPD7260 Phase 2
0.5892 Remote Similarity NPD8485 Approved
0.5891 Remote Similarity NPD6411 Approved
0.5878 Remote Similarity NPD8273 Phase 1
0.5865 Remote Similarity NPD2255 Approved
0.5859 Remote Similarity NPD3716 Discontinued
0.5857 Remote Similarity NPD6869 Approved
0.5857 Remote Similarity NPD6617 Approved
0.5857 Remote Similarity NPD6847 Approved
0.5846 Remote Similarity NPD8171 Discontinued
0.5827 Remote Similarity NPD6013 Approved
0.5827 Remote Similarity NPD6012 Approved
0.5827 Remote Similarity NPD6014 Approved
0.5822 Remote Similarity NPD5983 Phase 2
0.5822 Remote Similarity NPD8266 Approved
0.5822 Remote Similarity NPD8268 Approved
0.5822 Remote Similarity NPD8267 Approved
0.5822 Remote Similarity NPD8269 Approved
0.5814 Remote Similarity NPD6698 Approved
0.5814 Remote Similarity NPD46 Approved
0.5814 Remote Similarity NPD3168 Discontinued
0.5804 Remote Similarity NPD7754 Approved
0.5804 Remote Similarity NPD7755 Approved
0.58 Remote Similarity NPD6033 Approved
0.5797 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6083 Phase 2
0.5789 Remote Similarity NPD6084 Phase 2
0.5781 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5775 Remote Similarity NPD3731 Phase 3
0.5772 Remote Similarity NPD6336 Discontinued
0.5755 Remote Similarity NPD6011 Approved
0.5752 Remote Similarity NPD6845 Suspended
0.5748 Remote Similarity NPD3618 Phase 1
0.5746 Remote Similarity NPD4225 Approved
0.5745 Remote Similarity NPD1719 Phase 1

  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