Structure

Physi-Chem Properties

Molecular Weight:  821.4
Volume:  786.959
LogP:  1.434
LogD:  1.246
LogS:  -2.837
# Rotatable Bonds:  13
TPSA:  254.19
# H-Bond Aceptor:  16
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.077
Synthetic Accessibility Score:  6.353
Fsp3:  0.949
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.699
MDCK Permeability:  2.9649168936884962e-05
Pgp-inhibitor:  0.036
Pgp-substrate:  0.514
Human Intestinal Absorption (HIA):  0.053
20% Bioavailability (F20%):  0.018
30% Bioavailability (F30%):  0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.071
Plasma Protein Binding (PPB):  82.71880340576172%
Volume Distribution (VD):  0.46
Pgp-substrate:  9.560481071472168%

ADMET: Metabolism

CYP1A2-inhibitor:  0.0
CYP1A2-substrate:  0.951
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.113
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.005
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.079
CYP3A4-inhibitor:  0.036
CYP3A4-substrate:  0.032

ADMET: Excretion

Clearance (CL):  0.995
Half-life (T1/2):  0.201

ADMET: Toxicity

hERG Blockers:  0.767
Human Hepatotoxicity (H-HT):  0.401
Drug-inuced Liver Injury (DILI):  0.032
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.223
Maximum Recommended Daily Dose:  0.92
Skin Sensitization:  0.554
Carcinogencity:  0.326
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.986

Download Data

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

  Natural Product: NPC475634

Natural Product ID:  NPC475634
Common Name*:   Certonardoside C
IUPAC Name:   sodium;[(2R,3R,4S,5R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy-5-hydroxy-2-[(6R)-2-methyl-3-methylidene-6-[(3S,5S,6S,8S,9R,10S,13R,14S,15R,17R)-3,6,8,15-tetrahydroxy-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]heptoxy]oxan-4-yl] sulfate
Synonyms:   Certonardoside C
Standard InCHIKey:  BFELZYPVGWVVKJ-ZYUGDXNYSA-M
Standard InCHI:  InChI=1S/C39H66O16S.Na/c1-19(21(3)16-51-35-33(31(28(44)18-52-35)55-56(47,48)49)54-36-32(50-6)30(45)27(43)17-53-36)7-8-20(2)23-14-25(41)34-38(23,5)12-10-29-37(4)11-9-22(40)13-24(37)26(42)15-39(29,34)46;/h20-36,40-46H,1,7-18H2,2-6H3,(H,47,48,49);/q;+1/p-1/t20-,21?,22+,23-,24-,25-,26+,27-,28-,29-,30+,31+,32-,33-,34-,35-,36+,37+,38-,39+;/m1./s1
SMILES:  CO[C@H]1[C@@H](OC[C@H]([C@@H]1O)O)O[C@H]1[C@@H](OC[C@H]([C@@H]1OS(=O)(=O)[O-])O)OCC(C(=C)CC[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)O)O)O)C)C.[Na+]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL509875
PubChem CID:   23675027
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001013] Steroidal glycosides

*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
NPO7293 Certonardoa semiregularis Species Ophidiasteridae Eukaryota n.a. n.a. n.a. PMID[12444692]
NPO7293 Certonardoa semiregularis Species Ophidiasteridae Eukaryota n.a. n.a. n.a. PMID[12662097]
NPO7293 Certonardoa semiregularis Species Ophidiasteridae Eukaryota n.a. n.a. n.a. PMID[15104487]
NPO7293 Certonardoa semiregularis Species Ophidiasteridae Eukaryota n.a. n.a. n.a. PMID[15497935]

☑ 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
NPT165 Cell Line HeLa Homo sapiens CC50 > 100.0 ug.mL-1 PMID[524179]
NPT25 Cell Line MT4 Homo sapiens CC50 = 1.4 ug.mL-1 PMID[524179]
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 97.5 ug.mL-1 PMID[524179]
NPT190 Organism Human herpesvirus 1 Human herpesvirus 1 EC50 > 97.5 ug.mL-1 PMID[524179]
NPT1141 Organism Human herpesvirus 2 Human herpesvirus 2 EC50 > 97.5 ug.mL-1 PMID[524179]
NPT3119 Organism Human coxsackievirus B3 Human coxsackievirus B3 EC50 > 100.0 ug.mL-1 PMID[524179]
NPT4337 Organism Encephalomyocarditis virus Encephalomyocarditis virus EC50 > 100.0 ug.mL-1 PMID[524179]
NPT2516 Organism Vesicular stomatitis Indiana virus Vesicular stomatitis Indiana virus EC50 > 100.0 ug.mL-1 PMID[524179]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 > 1.4 ug.mL-1 PMID[524179]
NPT3795 Organism Human immunodeficiency virus 2 Human immunodeficiency virus 2 EC50 > 1.4 ug.mL-1 PMID[524179]

☑ 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 NPC475634 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
0.99 High Similarity NPC474573
0.95 High Similarity NPC475521
0.9238 High Similarity NPC475312
0.9126 High Similarity NPC473469
0.9091 High Similarity NPC76486
0.8991 High Similarity NPC476692
0.8991 High Similarity NPC476691
0.899 High Similarity NPC472989
0.8932 High Similarity NPC476361
0.8932 High Similarity NPC476360
0.8911 High Similarity NPC91497
0.8857 High Similarity NPC7213
0.8846 High Similarity NPC208594
0.8846 High Similarity NPC160816
0.8846 High Similarity NPC242748
0.8846 High Similarity NPC269627
0.8846 High Similarity NPC127801
0.8846 High Similarity NPC473476
0.8846 High Similarity NPC194842
0.8846 High Similarity NPC473923
0.8846 High Similarity NPC69737
0.8846 High Similarity NPC208477
0.8846 High Similarity NPC152584
0.8835 High Similarity NPC131479
0.8835 High Similarity NPC31907
0.8835 High Similarity NPC245280
0.8835 High Similarity NPC120123
0.8835 High Similarity NPC472252
0.8835 High Similarity NPC114874
0.8835 High Similarity NPC473020
0.8835 High Similarity NPC189852
0.8835 High Similarity NPC8039
0.8835 High Similarity NPC211879
0.8835 High Similarity NPC286969
0.8835 High Similarity NPC157659
0.8835 High Similarity NPC155010
0.8835 High Similarity NPC16520
0.8824 High Similarity NPC31346
0.8796 High Similarity NPC476693
0.8788 High Similarity NPC473503
0.8762 High Similarity NPC190395
0.8762 High Similarity NPC14946
0.8762 High Similarity NPC208650
0.8762 High Similarity NPC63368
0.8762 High Similarity NPC181467
0.875 High Similarity NPC273879
0.875 High Similarity NPC221562
0.875 High Similarity NPC165033
0.875 High Similarity NPC187400
0.875 High Similarity NPC470885
0.8738 High Similarity NPC159036
0.8738 High Similarity NPC312553
0.8738 High Similarity NPC288694
0.8738 High Similarity NPC136816
0.8704 High Similarity NPC475354
0.87 High Similarity NPC469710
0.8679 High Similarity NPC49032
0.8679 High Similarity NPC159005
0.8679 High Similarity NPC476541
0.8679 High Similarity NPC51172
0.8679 High Similarity NPC220427
0.8679 High Similarity NPC246124
0.8679 High Similarity NPC476513
0.8679 High Similarity NPC476540
0.8679 High Similarity NPC6931
0.8679 High Similarity NPC125324
0.8679 High Similarity NPC476538
0.8679 High Similarity NPC476539
0.8679 High Similarity NPC180183
0.8667 High Similarity NPC309448
0.8667 High Similarity NPC474569
0.8654 High Similarity NPC16573
0.8641 High Similarity NPC129372
0.8641 High Similarity NPC160734
0.8641 High Similarity NPC472023
0.8641 High Similarity NPC47566
0.8641 High Similarity NPC4831
0.8641 High Similarity NPC309425
0.8641 High Similarity NPC88000
0.8627 High Similarity NPC473616
0.8627 High Similarity NPC473638
0.8624 High Similarity NPC476671
0.8614 High Similarity NPC473287
0.8611 High Similarity NPC294129
0.8611 High Similarity NPC475247
0.8611 High Similarity NPC114188
0.8611 High Similarity NPC197231
0.86 High Similarity NPC309866
0.8598 High Similarity NPC475670
0.8598 High Similarity NPC151134
0.8598 High Similarity NPC477026
0.8598 High Similarity NPC477027
0.8598 High Similarity NPC302057
0.8598 High Similarity NPC70204
0.8598 High Similarity NPC306131
0.8586 High Similarity NPC473637
0.8586 High Similarity NPC204881
0.8586 High Similarity NPC473830
0.8586 High Similarity NPC476668
0.8585 High Similarity NPC231340
0.8585 High Similarity NPC94272
0.8585 High Similarity NPC54619
0.8585 High Similarity NPC226642
0.8545 High Similarity NPC477810
0.8544 High Similarity NPC7341
0.8544 High Similarity NPC473200
0.8544 High Similarity NPC471247
0.8532 High Similarity NPC19888
0.8532 High Similarity NPC477050
0.8529 High Similarity NPC477222
0.8529 High Similarity NPC477223
0.8519 High Similarity NPC472717
0.8519 High Similarity NPC470867
0.8515 High Similarity NPC92196
0.8505 High Similarity NPC472897
0.8505 High Similarity NPC98696
0.8505 High Similarity NPC472988
0.8505 High Similarity NPC38217
0.8505 High Similarity NPC128123
0.8505 High Similarity NPC472896
0.85 High Similarity NPC476669
0.85 High Similarity NPC137004
0.85 High Similarity NPC172838
0.8491 Intermediate Similarity NPC181845
0.8491 Intermediate Similarity NPC472899
0.8491 Intermediate Similarity NPC472898
0.8491 Intermediate Similarity NPC472900
0.8485 Intermediate Similarity NPC279329
0.8485 Intermediate Similarity NPC65550
0.8476 Intermediate Similarity NPC213190
0.8476 Intermediate Similarity NPC473198
0.8462 Intermediate Similarity NPC477225
0.8462 Intermediate Similarity NPC470168
0.8447 Intermediate Similarity NPC280825
0.8447 Intermediate Similarity NPC234287
0.844 Intermediate Similarity NPC65167
0.844 Intermediate Similarity NPC473021
0.844 Intermediate Similarity NPC477028
0.844 Intermediate Similarity NPC124677
0.844 Intermediate Similarity NPC13190
0.844 Intermediate Similarity NPC472987
0.844 Intermediate Similarity NPC472715
0.844 Intermediate Similarity NPC476547
0.844 Intermediate Similarity NPC477032
0.8431 Intermediate Similarity NPC304011
0.8431 Intermediate Similarity NPC139271
0.8426 Intermediate Similarity NPC6806
0.8426 Intermediate Similarity NPC22779
0.8426 Intermediate Similarity NPC300557
0.8426 Intermediate Similarity NPC470433
0.8426 Intermediate Similarity NPC95051
0.8426 Intermediate Similarity NPC249265
0.8426 Intermediate Similarity NPC42482
0.8426 Intermediate Similarity NPC154085
0.8426 Intermediate Similarity NPC475550
0.8426 Intermediate Similarity NPC309278
0.8426 Intermediate Similarity NPC224098
0.8426 Intermediate Similarity NPC51925
0.8426 Intermediate Similarity NPC208383
0.8426 Intermediate Similarity NPC218571
0.8426 Intermediate Similarity NPC84956
0.8426 Intermediate Similarity NPC43976
0.8426 Intermediate Similarity NPC102016
0.8426 Intermediate Similarity NPC296761
0.8426 Intermediate Similarity NPC125361
0.8426 Intermediate Similarity NPC248746
0.8426 Intermediate Similarity NPC150372
0.8426 Intermediate Similarity NPC476835
0.8426 Intermediate Similarity NPC475333
0.8426 Intermediate Similarity NPC73243
0.8426 Intermediate Similarity NPC46190
0.8426 Intermediate Similarity NPC244086
0.8426 Intermediate Similarity NPC232054
0.8426 Intermediate Similarity NPC171073
0.8426 Intermediate Similarity NPC40440
0.8426 Intermediate Similarity NPC477809
0.8426 Intermediate Similarity NPC194207
0.8416 Intermediate Similarity NPC24960
0.8416 Intermediate Similarity NPC475325
0.8416 Intermediate Similarity NPC252253
0.8416 Intermediate Similarity NPC45959
0.8416 Intermediate Similarity NPC473774
0.8411 Intermediate Similarity NPC161676
0.8411 Intermediate Similarity NPC305423
0.8411 Intermediate Similarity NPC283829
0.8411 Intermediate Similarity NPC234160
0.8411 Intermediate Similarity NPC230507
0.8411 Intermediate Similarity NPC14704
0.8411 Intermediate Similarity NPC113044
0.8411 Intermediate Similarity NPC470432
0.84 Intermediate Similarity NPC36372
0.84 Intermediate Similarity NPC293609
0.8396 Intermediate Similarity NPC312774
0.8396 Intermediate Similarity NPC475365
0.8393 Intermediate Similarity NPC100048
0.8393 Intermediate Similarity NPC476690
0.8393 Intermediate Similarity NPC20979
0.8384 Intermediate Similarity NPC131466
0.8381 Intermediate Similarity NPC272015
0.8378 Intermediate Similarity NPC11548

  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 NPC475634 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
0.8137 Intermediate Similarity NPD8171 Discontinued
0.8125 Intermediate Similarity NPD8133 Approved
0.8103 Intermediate Similarity NPD8378 Approved
0.8103 Intermediate Similarity NPD8033 Approved
0.8103 Intermediate Similarity NPD8296 Approved
0.8103 Intermediate Similarity NPD8379 Approved
0.8103 Intermediate Similarity NPD8380 Approved
0.8103 Intermediate Similarity NPD8335 Approved
0.8017 Intermediate Similarity NPD8377 Approved
0.8017 Intermediate Similarity NPD8294 Approved
0.7845 Intermediate Similarity NPD7327 Approved
0.7845 Intermediate Similarity NPD7328 Approved
0.7778 Intermediate Similarity NPD7516 Approved
0.7411 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD7503 Approved
0.7281 Intermediate Similarity NPD6412 Phase 2
0.7258 Intermediate Similarity NPD7507 Approved
0.7222 Intermediate Similarity NPD7319 Approved
0.7129 Intermediate Similarity NPD6928 Phase 2
0.7025 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8450 Suspended
0.696 Remote Similarity NPD8328 Phase 3
0.6923 Remote Similarity NPD8449 Approved
0.6875 Remote Similarity NPD7736 Approved
0.6796 Remote Similarity NPD7525 Registered
0.6746 Remote Similarity NPD6370 Approved
0.6667 Remote Similarity NPD8293 Discontinued
0.6667 Remote Similarity NPD7524 Approved
0.6587 Remote Similarity NPD6059 Approved
0.6587 Remote Similarity NPD6054 Approved
0.6577 Remote Similarity NPD8034 Phase 2
0.6577 Remote Similarity NPD8035 Phase 2
0.6542 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6525 Remote Similarity NPD7625 Phase 1
0.65 Remote Similarity NPD6686 Approved
0.6465 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6695 Phase 3
0.6434 Remote Similarity NPD6067 Discontinued
0.6423 Remote Similarity NPD8297 Approved
0.6423 Remote Similarity NPD6882 Approved
0.6406 Remote Similarity NPD6015 Approved
0.6406 Remote Similarity NPD6016 Approved
0.6404 Remote Similarity NPD7991 Discontinued
0.6385 Remote Similarity NPD7492 Approved
0.6381 Remote Similarity NPD7645 Phase 2
0.6379 Remote Similarity NPD7638 Approved
0.6373 Remote Similarity NPD1811 Approved
0.6373 Remote Similarity NPD1810 Approved
0.6364 Remote Similarity NPD7750 Discontinued
0.6357 Remote Similarity NPD5988 Approved
0.6349 Remote Similarity NPD6009 Approved
0.6336 Remote Similarity NPD6616 Approved
0.633 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6319 Approved
0.6325 Remote Similarity NPD7640 Approved
0.6325 Remote Similarity NPD7639 Approved
0.6288 Remote Similarity NPD7078 Approved
0.6279 Remote Similarity NPD8513 Phase 3
0.6279 Remote Similarity NPD8517 Approved
0.6279 Remote Similarity NPD8516 Approved
0.6279 Remote Similarity NPD8515 Approved
0.625 Remote Similarity NPD3701 Clinical (unspecified phase)
0.624 Remote Similarity NPD4632 Approved
0.6216 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6198 Remote Similarity NPD6675 Approved
0.6198 Remote Similarity NPD5739 Approved
0.6198 Remote Similarity NPD6402 Approved
0.6198 Remote Similarity NPD7128 Approved
0.6179 Remote Similarity NPD6373 Approved
0.6179 Remote Similarity NPD6372 Approved
0.6168 Remote Similarity NPD6931 Approved
0.6168 Remote Similarity NPD6930 Phase 2
0.6154 Remote Similarity NPD6942 Approved
0.6154 Remote Similarity NPD7339 Approved
0.6134 Remote Similarity NPD4159 Approved
0.6119 Remote Similarity NPD6033 Approved
0.6098 Remote Similarity NPD7320 Approved
0.6098 Remote Similarity NPD6881 Approved
0.6098 Remote Similarity NPD6899 Approved
0.6098 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6095 Remote Similarity NPD6933 Approved
0.608 Remote Similarity NPD6650 Approved
0.608 Remote Similarity NPD8130 Phase 1
0.608 Remote Similarity NPD6649 Approved
0.6078 Remote Similarity NPD2686 Approved
0.6078 Remote Similarity NPD2687 Approved
0.6078 Remote Similarity NPD2254 Approved
0.6075 Remote Similarity NPD6929 Approved
0.6038 Remote Similarity NPD6932 Approved
0.6019 Remote Similarity NPD4748 Discontinued
0.6017 Remote Similarity NPD4755 Approved
0.6016 Remote Similarity NPD5701 Approved
0.6016 Remote Similarity NPD6940 Discontinued
0.6016 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD4634 Approved
0.6 Remote Similarity NPD7102 Approved
0.6 Remote Similarity NPD7290 Approved
0.6 Remote Similarity NPD4788 Approved
0.6 Remote Similarity NPD3669 Approved
0.6 Remote Similarity NPD7087 Discontinued
0.6 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6 Remote Similarity NPD6883 Approved
0.5969 Remote Similarity NPD7115 Discovery
0.5968 Remote Similarity NPD8174 Phase 2
0.5952 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5952 Remote Similarity NPD6847 Approved
0.5952 Remote Similarity NPD6869 Approved
0.5952 Remote Similarity NPD6617 Approved
0.5952 Remote Similarity NPD6401 Clinical (unspecified phase)
0.595 Remote Similarity NPD7632 Discontinued
0.5948 Remote Similarity NPD6399 Phase 3
0.5948 Remote Similarity NPD4202 Approved
0.594 Remote Similarity NPD7604 Phase 2
0.5935 Remote Similarity NPD6008 Approved
0.5926 Remote Similarity NPD6683 Phase 2
0.5922 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4787 Phase 1
0.592 Remote Similarity NPD6012 Approved
0.592 Remote Similarity NPD6014 Approved
0.592 Remote Similarity NPD4061 Clinical (unspecified phase)
0.592 Remote Similarity NPD6013 Approved
0.5917 Remote Similarity NPD5286 Approved
0.5917 Remote Similarity NPD4696 Approved
0.5917 Remote Similarity NPD5285 Approved
0.5917 Remote Similarity NPD4700 Approved
0.5913 Remote Similarity NPD3168 Discontinued
0.5909 Remote Similarity NPD5983 Phase 2
0.5905 Remote Similarity NPD4784 Approved
0.5905 Remote Similarity NPD4785 Approved
0.5905 Remote Similarity NPD6924 Approved
0.5905 Remote Similarity NPD6926 Approved
0.5897 Remote Similarity NPD7748 Approved
0.5893 Remote Similarity NPD6893 Approved
0.5888 Remote Similarity NPD6925 Approved
0.5888 Remote Similarity NPD5776 Phase 2
0.5882 Remote Similarity NPD6084 Phase 2
0.5882 Remote Similarity NPD7902 Approved
0.5882 Remote Similarity NPD6083 Phase 2
0.5872 Remote Similarity NPD7514 Phase 3
0.5865 Remote Similarity NPD4243 Approved
0.5852 Remote Similarity NPD6336 Discontinued
0.584 Remote Similarity NPD6011 Approved
0.5833 Remote Similarity NPD6115 Approved
0.5833 Remote Similarity NPD7145 Approved
0.5833 Remote Similarity NPD6118 Approved
0.5833 Remote Similarity NPD6697 Approved
0.5833 Remote Similarity NPD6114 Approved
0.582 Remote Similarity NPD5211 Phase 2
0.582 Remote Similarity NPD5225 Approved
0.582 Remote Similarity NPD5224 Approved
0.582 Remote Similarity NPD4633 Approved
0.582 Remote Similarity NPD5226 Approved
0.5806 Remote Similarity NPD4768 Approved
0.5806 Remote Similarity NPD4767 Approved
0.5804 Remote Similarity NPD4786 Approved
0.58 Remote Similarity NPD371 Approved
0.5772 Remote Similarity NPD4754 Approved
0.5772 Remote Similarity NPD5174 Approved
0.5772 Remote Similarity NPD5175 Approved
0.5748 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5741 Remote Similarity NPD6116 Phase 1
0.5738 Remote Similarity NPD5223 Approved
0.5738 Remote Similarity NPD5344 Discontinued
0.5727 Remote Similarity NPD7332 Phase 2
0.5727 Remote Similarity NPD7509 Discontinued
0.5726 Remote Similarity NPD7515 Phase 2
0.5726 Remote Similarity NPD7637 Suspended
0.5726 Remote Similarity NPD5141 Approved
0.5714 Remote Similarity NPD4729 Approved
0.5714 Remote Similarity NPD4730 Approved
0.5702 Remote Similarity NPD4225 Approved
0.569 Remote Similarity NPD6051 Approved
0.569 Remote Similarity NPD5328 Approved
0.569 Remote Similarity NPD4753 Phase 2
0.5683 Remote Similarity NPD5956 Approved
0.5676 Remote Similarity NPD6902 Approved
0.5676 Remote Similarity NPD6898 Phase 1
0.5672 Remote Similarity NPD6921 Approved
0.5664 Remote Similarity NPD3668 Phase 3
0.5649 Remote Similarity NPD6274 Approved
0.5648 Remote Similarity NPD6117 Approved
0.5639 Remote Similarity NPD7101 Approved
0.5639 Remote Similarity NPD7100 Approved
0.563 Remote Similarity NPD7901 Clinical (unspecified phase)
0.563 Remote Similarity NPD7900 Approved
0.5625 Remote Similarity NPD5247 Approved
0.5625 Remote Similarity NPD5248 Approved
0.5625 Remote Similarity NPD5251 Approved
0.5625 Remote Similarity NPD5250 Approved
0.5625 Remote Similarity NPD5249 Phase 3
0.5625 Remote Similarity NPD3667 Approved
0.5606 Remote Similarity NPD6317 Approved
0.5603 Remote Similarity NPD7513 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