Structure

Physi-Chem Properties

Molecular Weight:  297.14
Volume:  313.127
LogP:  1.368
LogD:  1.367
LogS:  -2.149
# Rotatable Bonds:  3
TPSA:  60.77
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.906
Synthetic Accessibility Score:  3.47
Fsp3:  0.278
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.071
MDCK Permeability:  4.1450144635746256e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.267
20% Bioavailability (F20%):  0.376
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.957
Plasma Protein Binding (PPB):  82.58916473388672%
Volume Distribution (VD):  1.538
Pgp-substrate:  20.710594177246094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.045
CYP1A2-substrate:  0.132
CYP2C19-inhibitor:  0.112
CYP2C19-substrate:  0.688
CYP2C9-inhibitor:  0.085
CYP2C9-substrate:  0.106
CYP2D6-inhibitor:  0.059
CYP2D6-substrate:  0.401
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.622

ADMET: Excretion

Clearance (CL):  0.954
Half-life (T1/2):  0.577

ADMET: Toxicity

hERG Blockers:  0.03
Human Hepatotoxicity (H-HT):  0.138
Drug-inuced Liver Injury (DILI):  0.926
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.142
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.055
Carcinogencity:  0.13
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.048

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

  Natural Product: NPC475598

Natural Product ID:  NPC475598
Common Name*:   (+)Clausenamide
IUPAC Name:   (3R,4S,5S)-3-hydroxy-5-[(R)-hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
Synonyms:   (+)-Clausenamide
Standard InCHIKey:  WGYGSZOQGYRGIP-MWDXBVQZSA-N
Standard InCHI:  InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3/t14-,15-,16+,17+/m0/s1
SMILES:  CN1C(C(C(C1=O)O)C2=CC=CC=C2)C(C3=CC=CC=C3)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL508970
PubChem CID:   128412
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000218] Pyrrolidines
        • [CHEMONTID:0002336] Phenylpyrrolidines

*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
NPO23546 Clausena lansium Species Rutaceae Eukaryota leaves n.a. n.a. PMID[19327990]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Stems n.a. n.a. PMID[22372931]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Roots n.a. n.a. PMID[24798144]
NPO23546 Clausena lansium Species Rutaceae Eukaryota Leaves n.a. n.a. PMID[26523463]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23546 Clausena lansium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23546 Clausena lansium Species Rutaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = -9.4 % PMID[545522]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 10.1 % PMID[545522]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 6.4 % PMID[545522]

☑ 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 NPC475598 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 NPC474811
1.0 High Similarity NPC90194
1.0 High Similarity NPC49577
1.0 High Similarity NPC474787
1.0 High Similarity NPC118099
1.0 High Similarity NPC9687
1.0 High Similarity NPC76785
1.0 High Similarity NPC273907
1.0 High Similarity NPC151706
1.0 High Similarity NPC474855
1.0 High Similarity NPC476102
1.0 High Similarity NPC475318
1.0 High Similarity NPC260045
1.0 High Similarity NPC293377
1.0 High Similarity NPC79465
0.8099 Intermediate Similarity NPC251439
0.781 Intermediate Similarity NPC65310
0.7692 Intermediate Similarity NPC109580
0.7664 Intermediate Similarity NPC285394
0.7597 Intermediate Similarity NPC65855
0.7597 Intermediate Similarity NPC292758
0.7591 Intermediate Similarity NPC474082
0.7591 Intermediate Similarity NPC175726
0.7578 Intermediate Similarity NPC129624
0.7571 Intermediate Similarity NPC469666
0.7534 Intermediate Similarity NPC150712
0.7518 Intermediate Similarity NPC84281
0.7518 Intermediate Similarity NPC69496
0.7518 Intermediate Similarity NPC317474
0.7518 Intermediate Similarity NPC291027
0.7518 Intermediate Similarity NPC213126
0.7518 Intermediate Similarity NPC169485
0.7517 Intermediate Similarity NPC16188
0.75 Intermediate Similarity NPC209509
0.7383 Intermediate Similarity NPC471680
0.7381 Intermediate Similarity NPC228400
0.7381 Intermediate Similarity NPC214200
0.7368 Intermediate Similarity NPC473491
0.7361 Intermediate Similarity NPC233910
0.7361 Intermediate Similarity NPC245836
0.7357 Intermediate Similarity NPC474847
0.7357 Intermediate Similarity NPC477248
0.7357 Intermediate Similarity NPC477249
0.7338 Intermediate Similarity NPC6975
0.731 Intermediate Similarity NPC248283
0.729 Intermediate Similarity NPC476268
0.7279 Intermediate Similarity NPC313694
0.7279 Intermediate Similarity NPC242159
0.7273 Intermediate Similarity NPC202198
0.7266 Intermediate Similarity NPC252878
0.7241 Intermediate Similarity NPC313663
0.7222 Intermediate Similarity NPC255447
0.7214 Intermediate Similarity NPC46427
0.7211 Intermediate Similarity NPC471264
0.7211 Intermediate Similarity NPC471265
0.7208 Intermediate Similarity NPC162104
0.7194 Intermediate Similarity NPC202521
0.7185 Intermediate Similarity NPC33742
0.7181 Intermediate Similarity NPC263493
0.7181 Intermediate Similarity NPC476989
0.7181 Intermediate Similarity NPC269398
0.7178 Intermediate Similarity NPC89831
0.7172 Intermediate Similarity NPC257390
0.717 Intermediate Similarity NPC241794
0.7163 Intermediate Similarity NPC307020
0.7162 Intermediate Similarity NPC476133
0.7162 Intermediate Similarity NPC178662
0.7162 Intermediate Similarity NPC92784
0.7162 Intermediate Similarity NPC98424
0.7162 Intermediate Similarity NPC470884
0.7152 Intermediate Similarity NPC5620
0.7143 Intermediate Similarity NPC473360
0.7143 Intermediate Similarity NPC469479
0.7134 Intermediate Similarity NPC137627
0.7133 Intermediate Similarity NPC161069
0.7133 Intermediate Similarity NPC239990
0.7133 Intermediate Similarity NPC152850
0.7133 Intermediate Similarity NPC71933
0.7133 Intermediate Similarity NPC89923
0.7133 Intermediate Similarity NPC105114
0.7123 Intermediate Similarity NPC287401
0.7122 Intermediate Similarity NPC476990
0.7122 Intermediate Similarity NPC200964
0.7115 Intermediate Similarity NPC68967
0.7113 Intermediate Similarity NPC171372
0.7097 Intermediate Similarity NPC233702
0.7091 Intermediate Similarity NPC136797
0.7091 Intermediate Similarity NPC26108
0.709 Intermediate Similarity NPC269340
0.7086 Intermediate Similarity NPC476978
0.7083 Intermediate Similarity NPC473322
0.708 Intermediate Similarity NPC285926
0.708 Intermediate Similarity NPC14672
0.708 Intermediate Similarity NPC315276
0.7063 Intermediate Similarity NPC136453
0.7055 Intermediate Similarity NPC280022
0.7051 Intermediate Similarity NPC262166
0.7051 Intermediate Similarity NPC122590
0.7047 Intermediate Similarity NPC316906
0.7044 Intermediate Similarity NPC244336
0.7037 Intermediate Similarity NPC61004
0.7034 Intermediate Similarity NPC200589
0.7029 Intermediate Similarity NPC470545
0.6994 Remote Similarity NPC302597
0.6994 Remote Similarity NPC328649
0.6988 Remote Similarity NPC476227
0.6988 Remote Similarity NPC471165
0.6986 Remote Similarity NPC183722
0.6986 Remote Similarity NPC157311
0.6986 Remote Similarity NPC130309
0.6985 Remote Similarity NPC35850
0.6985 Remote Similarity NPC276949
0.6981 Remote Similarity NPC297145
0.6981 Remote Similarity NPC197743
0.6978 Remote Similarity NPC470546
0.6975 Remote Similarity NPC63931
0.697 Remote Similarity NPC328494
0.6968 Remote Similarity NPC129666
0.6966 Remote Similarity NPC111428
0.6957 Remote Similarity NPC470544
0.6951 Remote Similarity NPC469505
0.6948 Remote Similarity NPC329761
0.6948 Remote Similarity NPC125852
0.6948 Remote Similarity NPC138775
0.6948 Remote Similarity NPC225648
0.6947 Remote Similarity NPC150254
0.6947 Remote Similarity NPC147000
0.6947 Remote Similarity NPC304761
0.6947 Remote Similarity NPC226778
0.6939 Remote Similarity NPC8761
0.6939 Remote Similarity NPC42423
0.6939 Remote Similarity NPC44805
0.6933 Remote Similarity NPC281104
0.6928 Remote Similarity NPC315266
0.6914 Remote Similarity NPC472117
0.6913 Remote Similarity NPC113325
0.6913 Remote Similarity NPC279045
0.6909 Remote Similarity NPC475204
0.6909 Remote Similarity NPC40234
0.6909 Remote Similarity NPC475123
0.6908 Remote Similarity NPC57976
0.6901 Remote Similarity NPC26285
0.6894 Remote Similarity NPC211551
0.689 Remote Similarity NPC294516
0.689 Remote Similarity NPC107938
0.6886 Remote Similarity NPC477462
0.6886 Remote Similarity NPC155506
0.6886 Remote Similarity NPC159767
0.6883 Remote Similarity NPC314358
0.6883 Remote Similarity NPC262077
0.6879 Remote Similarity NPC190663
0.6875 Remote Similarity NPC474479
0.6875 Remote Similarity NPC47667
0.6871 Remote Similarity NPC120251
0.6867 Remote Similarity NPC208725
0.6864 Remote Similarity NPC119652
0.6864 Remote Similarity NPC97526
0.6859 Remote Similarity NPC2501
0.6857 Remote Similarity NPC220698
0.6855 Remote Similarity NPC244509
0.6849 Remote Similarity NPC116057
0.6849 Remote Similarity NPC81092
0.6849 Remote Similarity NPC103605
0.6849 Remote Similarity NPC71271
0.6849 Remote Similarity NPC17374
0.6846 Remote Similarity NPC228511
0.6842 Remote Similarity NPC45033
0.6839 Remote Similarity NPC145113
0.6838 Remote Similarity NPC314550
0.6835 Remote Similarity NPC56685
0.6831 Remote Similarity NPC71684
0.6829 Remote Similarity NPC254700
0.6826 Remote Similarity NPC306804
0.6818 Remote Similarity NPC313867
0.6818 Remote Similarity NPC316008
0.6815 Remote Similarity NPC475168
0.6815 Remote Similarity NPC7817
0.6797 Remote Similarity NPC139326
0.6795 Remote Similarity NPC471821
0.6795 Remote Similarity NPC246412
0.6795 Remote Similarity NPC105717
0.6795 Remote Similarity NPC471820
0.6795 Remote Similarity NPC240848
0.6794 Remote Similarity NPC327226
0.6788 Remote Similarity NPC141957
0.6786 Remote Similarity NPC279871
0.6783 Remote Similarity NPC160493
0.6781 Remote Similarity NPC319766
0.6781 Remote Similarity NPC305717
0.6776 Remote Similarity NPC239762
0.6776 Remote Similarity NPC163392
0.6774 Remote Similarity NPC297322
0.6765 Remote Similarity NPC475421
0.6763 Remote Similarity NPC188010
0.6761 Remote Similarity NPC80150
0.6759 Remote Similarity NPC472414
0.6759 Remote Similarity NPC4974
0.6755 Remote Similarity NPC175870
0.6755 Remote Similarity NPC127741
0.6753 Remote Similarity NPC52748

  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 NPC475598 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
0.8235 Intermediate Similarity NPD4497 Clinical (unspecified phase)
0.8175 Intermediate Similarity NPD4619 Approved
0.8175 Intermediate Similarity NPD4621 Approved
0.8027 Intermediate Similarity NPD7613 Discontinued
0.7986 Intermediate Similarity NPD7086 Phase 2
0.7956 Intermediate Similarity NPD5204 Approved
0.781 Intermediate Similarity NPD2160 Approved
0.781 Intermediate Similarity NPD2628 Approved
0.781 Intermediate Similarity NPD2626 Approved
0.781 Intermediate Similarity NPD2159 Approved
0.781 Intermediate Similarity NPD2625 Approved
0.781 Intermediate Similarity NPD2627 Approved
0.7737 Intermediate Similarity NPD6792 Phase 3
0.7698 Intermediate Similarity NPD3664 Approved
0.7698 Intermediate Similarity NPD3662 Phase 3
0.7698 Intermediate Similarity NPD3663 Approved
0.7698 Intermediate Similarity NPD3661 Approved
0.7687 Intermediate Similarity NPD6676 Phase 2
0.7676 Intermediate Similarity NPD6309 Approved
0.7676 Intermediate Similarity NPD6311 Approved
0.7676 Intermediate Similarity NPD6310 Approved
0.7664 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD5159 Phase 2
0.7664 Intermediate Similarity NPD5157 Phase 1
0.7643 Intermediate Similarity NPD5202 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD7011 Discontinued
0.7569 Intermediate Similarity NPD6817 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD2575 Approved
0.7518 Intermediate Similarity NPD2611 Approved
0.7518 Intermediate Similarity NPD2608 Approved
0.7518 Intermediate Similarity NPD2610 Approved
0.7518 Intermediate Similarity NPD5203 Approved
0.7518 Intermediate Similarity NPD4218 Approved
0.7518 Intermediate Similarity NPD4620 Approved
0.7518 Intermediate Similarity NPD4215 Approved
0.7518 Intermediate Similarity NPD4217 Approved
0.7518 Intermediate Similarity NPD2613 Approved
0.7518 Intermediate Similarity NPD3132 Approved
0.7518 Intermediate Similarity NPD2609 Approved
0.7518 Intermediate Similarity NPD2612 Approved
0.7518 Intermediate Similarity NPD3131 Approved
0.7518 Intermediate Similarity NPD4617 Approved
0.7518 Intermediate Similarity NPD5201 Approved
0.7518 Intermediate Similarity NPD4216 Approved
0.75 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD6775 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD854 Approved
0.746 Intermediate Similarity NPD855 Approved
0.7448 Intermediate Similarity NPD8172 Phase 2
0.7448 Intermediate Similarity NPD8173 Phase 2
0.7445 Intermediate Similarity NPD4136 Approved
0.7445 Intermediate Similarity NPD4106 Approved
0.7445 Intermediate Similarity NPD4135 Approved
0.7431 Intermediate Similarity NPD5121 Approved
0.7431 Intermediate Similarity NPD5120 Approved
0.7431 Intermediate Similarity NPD5119 Approved
0.7417 Intermediate Similarity NPD8165 Discontinued
0.7402 Intermediate Similarity NPD3680 Approved
0.7402 Intermediate Similarity NPD3682 Approved
0.7391 Intermediate Similarity NPD4806 Approved
0.7391 Intermediate Similarity NPD4807 Approved
0.7368 Intermediate Similarity NPD3598 Phase 3
0.7361 Intermediate Similarity NPD3615 Approved
0.7361 Intermediate Similarity NPD3614 Approved
0.7361 Intermediate Similarity NPD3088 Approved
0.7361 Intermediate Similarity NPD3087 Approved
0.7361 Intermediate Similarity NPD3090 Approved
0.7361 Intermediate Similarity NPD4746 Phase 3
0.7361 Intermediate Similarity NPD2570 Approved
0.7361 Intermediate Similarity NPD2574 Discontinued
0.7361 Intermediate Similarity NPD4745 Approved
0.7361 Intermediate Similarity NPD2566 Approved
0.7361 Intermediate Similarity NPD2572 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD2573 Approved
0.7361 Intermediate Similarity NPD2571 Approved
0.7361 Intermediate Similarity NPD3089 Approved
0.7361 Intermediate Similarity NPD3616 Approved
0.7333 Intermediate Similarity NPD3123 Discovery
0.7329 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD5759 Approved
0.7313 Intermediate Similarity NPD1711 Phase 2
0.7308 Intermediate Similarity NPD7118 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4102 Approved
0.7299 Intermediate Similarity NPD4105 Approved
0.726 Intermediate Similarity NPD4685 Phase 3
0.726 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4684 Phase 3
0.726 Intermediate Similarity NPD4686 Approved
0.7246 Intermediate Similarity NPD5305 Approved
0.7246 Intermediate Similarity NPD5306 Approved
0.7241 Intermediate Similarity NPD7714 Approved
0.7241 Intermediate Similarity NPD7715 Approved
0.7226 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6345 Approved
0.7226 Intermediate Similarity NPD6343 Approved
0.7219 Intermediate Similarity NPD7488 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD4817 Approved
0.7188 Intermediate Similarity NPD4818 Approved
0.7183 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD4103 Phase 2
0.7181 Intermediate Similarity NPD7511 Approved
0.7181 Intermediate Similarity NPD7512 Approved
0.7178 Intermediate Similarity NPD5137 Approved
0.7174 Intermediate Similarity NPD1710 Approved
0.7171 Intermediate Similarity NPD7910 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD4659 Approved
0.7153 Intermediate Similarity NPD5991 Approved
0.7153 Intermediate Similarity NPD5990 Approved
0.7153 Intermediate Similarity NPD5263 Approved
0.7143 Intermediate Similarity NPD4025 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5338 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5667 Approved
0.7095 Intermediate Similarity NPD6073 Approved
0.7092 Intermediate Similarity NPD3072 Approved
0.7092 Intermediate Similarity NPD3073 Approved
0.7092 Intermediate Similarity NPD2584 Suspended
0.7092 Intermediate Similarity NPD3071 Approved
0.709 Intermediate Similarity NPD4572 Approved
0.709 Intermediate Similarity NPD4573 Approved
0.709 Intermediate Similarity NPD4571 Approved
0.7083 Intermediate Similarity NPD4175 Approved
0.7083 Intermediate Similarity NPD4177 Approved
0.708 Intermediate Similarity NPD4574 Approved
0.708 Intermediate Similarity NPD4576 Approved
0.7066 Intermediate Similarity NPD7695 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD8323 Discontinued
0.7054 Intermediate Similarity NPD4719 Phase 2
0.7047 Intermediate Similarity NPD7231 Approved
0.7047 Intermediate Similarity NPD7230 Approved
0.7042 Intermediate Similarity NPD1755 Approved
0.7027 Intermediate Similarity NPD8643 Discontinued
0.7025 Intermediate Similarity NPD8417 Discontinued
0.7021 Intermediate Similarity NPD4761 Approved
0.7021 Intermediate Similarity NPD4762 Approved
0.7015 Intermediate Similarity NPD4254 Approved
0.7015 Intermediate Similarity NPD4253 Approved
0.7014 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4229 Approved
0.7 Intermediate Similarity NPD7725 Approved
0.7 Intermediate Similarity NPD3681 Approved
0.7 Intermediate Similarity NPD3683 Approved
0.7 Intermediate Similarity NPD4231 Approved
0.6993 Remote Similarity NPD3125 Approved
0.698 Remote Similarity NPD7510 Approved
0.6959 Remote Similarity NPD8416 Discontinued
0.6954 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7939 Discontinued
0.6947 Remote Similarity NPD311 Approved
0.6947 Remote Similarity NPD310 Approved
0.6947 Remote Similarity NPD10 Approved
0.6947 Remote Similarity NPD309 Approved
0.6947 Remote Similarity NPD315 Approved
0.6947 Remote Similarity NPD314 Approved
0.6939 Remote Similarity NPD1330 Phase 2
0.6939 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6933 Remote Similarity NPD2567 Approved
0.6933 Remote Similarity NPD2569 Approved
0.6923 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4125 Approved
0.6918 Remote Similarity NPD4676 Approved
0.6906 Remote Similarity NPD2117 Pre-registration
0.6906 Remote Similarity NPD2116 Approved
0.6906 Remote Similarity NPD6065 Approved
0.6906 Remote Similarity NPD2115 Approved
0.6901 Remote Similarity NPD3529 Phase 2
0.6901 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6901 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2173 Clinical (unspecified phase)
0.6897 Remote Similarity NPD4980 Approved
0.689 Remote Similarity NPD5823 Approved
0.6879 Remote Similarity NPD5723 Approved
0.6879 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6871 Remote Similarity NPD6039 Approved
0.6871 Remote Similarity NPD4794 Discontinued
0.687 Remote Similarity NPD4658 Approved
0.687 Remote Similarity NPD4656 Approved
0.6867 Remote Similarity NPD5725 Approved
0.6866 Remote Similarity NPD4720 Approved
0.6866 Remote Similarity NPD4718 Approved
0.6866 Remote Similarity NPD4717 Approved
0.6861 Remote Similarity NPD2229 Approved
0.6861 Remote Similarity NPD2234 Approved
0.6861 Remote Similarity NPD2228 Approved
0.6857 Remote Similarity NPD2994 Approved
0.6857 Remote Similarity NPD5303 Approved
0.6857 Remote Similarity NPD5304 Approved
0.6855 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6853 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6853 Remote Similarity NPD2562 Approved
0.6853 Remote Similarity NPD2561 Approved
0.6846 Remote Similarity NPD6623 Phase 3
0.6842 Remote Similarity NPD7130 Phase 3
0.6835 Remote Similarity NPD7131 Phase 3
0.6832 Remote Similarity NPD3589 Clinical (unspecified phase)
0.6822 Remote Similarity NPD466 Approved
0.6815 Remote Similarity NPD5235 Approved
0.6815 Remote Similarity NPD5239 Approved
0.6815 Remote Similarity NPD5240 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