Structure

Physi-Chem Properties

Molecular Weight:  606.39
Volume:  651.388
LogP:  6.086
LogD:  4.585
LogS:  -4.487
# Rotatable Bonds:  5
TPSA:  107.22
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.171
Synthetic Accessibility Score:  5.613
Fsp3:  0.711
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:  -5.341
MDCK Permeability:  2.757306174316909e-05
Pgp-inhibitor:  0.342
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.277
30% Bioavailability (F30%):  0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.182
Plasma Protein Binding (PPB):  99.59297943115234%
Volume Distribution (VD):  1.102
Pgp-substrate:  2.938033103942871%

ADMET: Metabolism

CYP1A2-inhibitor:  0.046
CYP1A2-substrate:  0.153
CYP2C19-inhibitor:  0.056
CYP2C19-substrate:  0.609
CYP2C9-inhibitor:  0.243
CYP2C9-substrate:  0.763
CYP2D6-inhibitor:  0.59
CYP2D6-substrate:  0.201
CYP3A4-inhibitor:  0.78
CYP3A4-substrate:  0.474

ADMET: Excretion

Clearance (CL):  3.26
Half-life (T1/2):  0.362

ADMET: Toxicity

hERG Blockers:  0.571
Human Hepatotoxicity (H-HT):  0.127
Drug-inuced Liver Injury (DILI):  0.036
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.376
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.906
Carcinogencity:  0.056
Eye Corrosion:  0.003
Eye Irritation:  0.04
Respiratory Toxicity:  0.959

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

  Natural Product: NPC116742

Natural Product ID:  NPC116742
Common Name*:   (2Alpha,3Beta,17R*,18Beta)-23-O-(Cis-P-Coumaroyl)-19(18->17)-Abeo-28-Norolean-12-Ene-2,3,18-Triol
IUPAC Name:   [(1R,2R,3R,4aR,4bR,7S,8R,10aS,10bR,12aR)-2,3,7-trihydroxy-1,1',1',4a,10a,10b-hexamethylspiro[3,4,4b,5,7,9,10,11,12,12a-decahydro-2H-chrysene-8,3'-cyclopentane]-1-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  SHTKYNKUOCCDOU-CRKCRZQWSA-N
Standard InCHI:  InChI=1S/C38H54O6/c1-33(2)17-19-38(22-33)20-18-36(5)26(31(38)42)12-13-29-34(3)21-27(40)32(43)35(4,28(34)15-16-37(29,36)6)23-44-30(41)14-9-24-7-10-25(39)11-8-24/h7-12,14,27-29,31-32,39-40,42-43H,13,15-23H2,1-6H3/b14-9-/t27-,28-,29-,31-,32+,34+,35+,36-,37-,38-/m1/s1
SMILES:  CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(COC(=O)/C=Cc6ccc(cc6)O)[C@@H]5CC[C@@]34C)O)O)[C@H]2O)C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3104848
PubChem CID:   76313874
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001295] Hydroxysteroids
          • [CHEMONTID:0003241] 12-hydroxysteroids
            • [CHEMONTID:0003243] 12-beta-hydroxysteroids

*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
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[22703163]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota Fruits n.a. n.a. PMID[24328283]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[24704554]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[32935986]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23548 Leonurus heterophyllus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23548 Leonurus heterophyllus Species Lamiaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[535801]
NPT15 Cell Line Jurkat Homo sapiens IC50 > 10000.0 nM PMID[535801]
NPT1229 Cell Line Huh-7 Homo sapiens IC50 > 10000.0 nM PMID[535801]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 10000.0 nM PMID[535801]

☑ 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 NPC116742 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 NPC139243
0.9924 High Similarity NPC470616
0.9924 High Similarity NPC470617
0.9704 High Similarity NPC235557
0.9632 High Similarity NPC26045
0.9416 High Similarity NPC310621
0.9398 High Similarity NPC11266
0.9343 High Similarity NPC35212
0.9338 High Similarity NPC473591
0.9338 High Similarity NPC271494
0.9338 High Similarity NPC155192
0.9275 High Similarity NPC252133
0.927 High Similarity NPC473612
0.9265 High Similarity NPC182249
0.9225 High Similarity NPC470618
0.9225 High Similarity NPC208785
0.9225 High Similarity NPC470619
0.9225 High Similarity NPC145527
0.9167 High Similarity NPC86257
0.913 High Similarity NPC304110
0.913 High Similarity NPC27518
0.9071 High Similarity NPC25491
0.9051 High Similarity NPC475482
0.9051 High Similarity NPC216940
0.9051 High Similarity NPC198621
0.9051 High Similarity NPC22676
0.8986 High Similarity NPC234548
0.8986 High Similarity NPC248287
0.8978 High Similarity NPC249817
0.8944 High Similarity NPC8102
0.8944 High Similarity NPC66894
0.8931 High Similarity NPC474532
0.8905 High Similarity NPC173569
0.8905 High Similarity NPC477874
0.8865 High Similarity NPC469447
0.8865 High Similarity NPC477873
0.8857 High Similarity NPC472801
0.8788 High Similarity NPC10154
0.8788 High Similarity NPC265413
0.8759 High Similarity NPC298647
0.8759 High Similarity NPC273358
0.8741 High Similarity NPC235195
0.8741 High Similarity NPC53520
0.8741 High Similarity NPC280717
0.8741 High Similarity NPC307205
0.8741 High Similarity NPC271607
0.8741 High Similarity NPC19862
0.869 High Similarity NPC32017
0.869 High Similarity NPC96930
0.8681 High Similarity NPC320734
0.8652 High Similarity NPC471875
0.863 High Similarity NPC292206
0.8623 High Similarity NPC18982
0.8623 High Similarity NPC475627
0.8623 High Similarity NPC475457
0.8623 High Similarity NPC475346
0.8621 High Similarity NPC472937
0.8621 High Similarity NPC472938
0.8621 High Similarity NPC472936
0.8603 High Similarity NPC288290
0.8603 High Similarity NPC30174
0.8601 High Similarity NPC204644
0.8592 High Similarity NPC172311
0.8581 High Similarity NPC473773
0.8581 High Similarity NPC475579
0.8571 High Similarity NPC476699
0.8542 High Similarity NPC96447
0.8523 High Similarity NPC105942
0.8523 High Similarity NPC205392
0.8514 High Similarity NPC118033
0.8514 High Similarity NPC77310
0.8511 High Similarity NPC471152
0.8503 High Similarity NPC279442
0.85 High Similarity NPC472804
0.8446 Intermediate Similarity NPC472939
0.8435 Intermediate Similarity NPC477483
0.8435 Intermediate Similarity NPC325032
0.8431 Intermediate Similarity NPC269668
0.8392 Intermediate Similarity NPC164743
0.8389 Intermediate Similarity NPC475454
0.8389 Intermediate Similarity NPC473680
0.8389 Intermediate Similarity NPC473579
0.8389 Intermediate Similarity NPC475311
0.8358 Intermediate Similarity NPC478058
0.8322 Intermediate Similarity NPC76032
0.8322 Intermediate Similarity NPC132723
0.8322 Intermediate Similarity NPC327962
0.831 Intermediate Similarity NPC471872
0.831 Intermediate Similarity NPC154485
0.8309 Intermediate Similarity NPC137416
0.8289 Intermediate Similarity NPC472807
0.8288 Intermediate Similarity NPC477207
0.8239 Intermediate Similarity NPC43353
0.8228 Intermediate Similarity NPC286809
0.8201 Intermediate Similarity NPC475138
0.8169 Intermediate Similarity NPC194970
0.8165 Intermediate Similarity NPC200726
0.8163 Intermediate Similarity NPC471876
0.8153 Intermediate Similarity NPC161151
0.8141 Intermediate Similarity NPC266365
0.8133 Intermediate Similarity NPC473719
0.8133 Intermediate Similarity NPC477206
0.8116 Intermediate Similarity NPC190849
0.8116 Intermediate Similarity NPC171007
0.8113 Intermediate Similarity NPC177362
0.8063 Intermediate Similarity NPC202428
0.8063 Intermediate Similarity NPC266545
0.8056 Intermediate Similarity NPC470733
0.8039 Intermediate Similarity NPC471874
0.8014 Intermediate Similarity NPC106055
0.8014 Intermediate Similarity NPC110699
0.7973 Intermediate Similarity NPC477209
0.7972 Intermediate Similarity NPC48929
0.7972 Intermediate Similarity NPC203486
0.7972 Intermediate Similarity NPC126516
0.7972 Intermediate Similarity NPC476282
0.7961 Intermediate Similarity NPC116292
0.7961 Intermediate Similarity NPC267469
0.7961 Intermediate Similarity NPC35160
0.7961 Intermediate Similarity NPC87630
0.7961 Intermediate Similarity NPC179128
0.7961 Intermediate Similarity NPC162569
0.7947 Intermediate Similarity NPC95990
0.7945 Intermediate Similarity NPC475757
0.7945 Intermediate Similarity NPC474640
0.7941 Intermediate Similarity NPC470848
0.7941 Intermediate Similarity NPC470849
0.7931 Intermediate Similarity NPC120852
0.7927 Intermediate Similarity NPC475613
0.7925 Intermediate Similarity NPC471861
0.7922 Intermediate Similarity NPC115203
0.7919 Intermediate Similarity NPC472556
0.7917 Intermediate Similarity NPC471913
0.7914 Intermediate Similarity NPC45821
0.7914 Intermediate Similarity NPC475933
0.7914 Intermediate Similarity NPC470158
0.7908 Intermediate Similarity NPC261659
0.7905 Intermediate Similarity NPC477468
0.7905 Intermediate Similarity NPC20631
0.7905 Intermediate Similarity NPC93640
0.7899 Intermediate Similarity NPC472373
0.7895 Intermediate Similarity NPC253591
0.7883 Intermediate Similarity NPC475328
0.7881 Intermediate Similarity NPC470330
0.7877 Intermediate Similarity NPC477592
0.7872 Intermediate Similarity NPC93632
0.7868 Intermediate Similarity NPC260832
0.7868 Intermediate Similarity NPC135467
0.7863 Intermediate Similarity NPC139946
0.7862 Intermediate Similarity NPC279463
0.7857 Intermediate Similarity NPC471930
0.7857 Intermediate Similarity NPC476971
0.7857 Intermediate Similarity NPC471929
0.7857 Intermediate Similarity NPC471935
0.7857 Intermediate Similarity NPC476972
0.7853 Intermediate Similarity NPC469778
0.7853 Intermediate Similarity NPC469774
0.7853 Intermediate Similarity NPC295941
0.7853 Intermediate Similarity NPC469777
0.7853 Intermediate Similarity NPC135334
0.7853 Intermediate Similarity NPC469773
0.7853 Intermediate Similarity NPC32723
0.7853 Intermediate Similarity NPC469776
0.7853 Intermediate Similarity NPC469775
0.7853 Intermediate Similarity NPC469772
0.7853 Intermediate Similarity NPC100925
0.7852 Intermediate Similarity NPC203124
0.7852 Intermediate Similarity NPC309434
0.7852 Intermediate Similarity NPC475122
0.7847 Intermediate Similarity NPC329913
0.7842 Intermediate Similarity NPC471758
0.784 Intermediate Similarity NPC471870
0.7838 Intermediate Similarity NPC475513
0.7838 Intermediate Similarity NPC473755
0.7838 Intermediate Similarity NPC138149
0.7836 Intermediate Similarity NPC257540
0.7836 Intermediate Similarity NPC247858
0.7836 Intermediate Similarity NPC474358
0.7836 Intermediate Similarity NPC474387
0.7836 Intermediate Similarity NPC137496
0.7836 Intermediate Similarity NPC154511
0.7836 Intermediate Similarity NPC470820
0.7832 Intermediate Similarity NPC243305
0.7826 Intermediate Similarity NPC12016
0.7826 Intermediate Similarity NPC327070
0.7817 Intermediate Similarity NPC470747
0.7817 Intermediate Similarity NPC131684
0.7806 Intermediate Similarity NPC475595
0.7806 Intermediate Similarity NPC475216
0.7806 Intermediate Similarity NPC83663
0.7806 Intermediate Similarity NPC475145
0.7806 Intermediate Similarity NPC475162
0.7806 Intermediate Similarity NPC266084
0.7806 Intermediate Similarity NPC473544
0.7801 Intermediate Similarity NPC230331
0.7801 Intermediate Similarity NPC471077
0.78 Intermediate Similarity NPC29704
0.78 Intermediate Similarity NPC200471
0.78 Intermediate Similarity NPC96903
0.78 Intermediate Similarity NPC471104

  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 NPC116742 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
0.8662 High Similarity NPD8166 Discontinued
0.8058 Intermediate Similarity NPD5736 Approved
0.7914 Intermediate Similarity NPD3094 Phase 2
0.7911 Intermediate Similarity NPD8127 Discontinued
0.7832 Intermediate Similarity NPD6663 Approved
0.7778 Intermediate Similarity NPD4140 Approved
0.7754 Intermediate Similarity NPD3092 Approved
0.7721 Intermediate Similarity NPD3091 Approved
0.7703 Intermediate Similarity NPD7266 Discontinued
0.7647 Intermediate Similarity NPD6273 Approved
0.7566 Intermediate Similarity NPD7236 Approved
0.7534 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD3620 Phase 2
0.7483 Intermediate Similarity NPD5735 Approved
0.7482 Intermediate Similarity NPD3095 Discontinued
0.7467 Intermediate Similarity NPD5762 Approved
0.7467 Intermediate Similarity NPD5763 Approved
0.7434 Intermediate Similarity NPD7003 Approved
0.7415 Intermediate Similarity NPD4060 Phase 1
0.7389 Intermediate Similarity NPD7458 Discontinued
0.7383 Intermediate Similarity NPD7097 Phase 1
0.7357 Intermediate Similarity NPD2932 Approved
0.7357 Intermediate Similarity NPD3019 Approved
0.7338 Intermediate Similarity NPD7741 Discontinued
0.7325 Intermediate Similarity NPD7239 Suspended
0.7273 Intermediate Similarity NPD5327 Phase 3
0.7248 Intermediate Similarity NPD6355 Discontinued
0.7234 Intermediate Similarity NPD4059 Approved
0.7234 Intermediate Similarity NPD4626 Approved
0.723 Intermediate Similarity NPD8032 Phase 2
0.7226 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7095 Approved
0.7209 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4628 Phase 3
0.72 Intermediate Similarity NPD6353 Approved
0.7163 Intermediate Similarity NPD5691 Approved
0.7161 Intermediate Similarity NPD6190 Approved
0.7143 Intermediate Similarity NPD7228 Approved
0.7134 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD4624 Approved
0.7122 Intermediate Similarity NPD4198 Discontinued
0.7097 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4110 Phase 3
0.7086 Intermediate Similarity NPD6653 Approved
0.7069 Intermediate Similarity NPD8150 Discontinued
0.7063 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3021 Approved
0.7059 Intermediate Similarity NPD3022 Approved
0.7047 Intermediate Similarity NPD3764 Approved
0.7037 Intermediate Similarity NPD37 Approved
0.7032 Intermediate Similarity NPD6674 Discontinued
0.703 Intermediate Similarity NPD6234 Discontinued
0.7025 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7028 Phase 2
0.7012 Intermediate Similarity NPD4967 Phase 2
0.7012 Intermediate Similarity NPD4966 Approved
0.7012 Intermediate Similarity NPD4965 Approved
0.7 Intermediate Similarity NPD7157 Approved
0.6994 Remote Similarity NPD8455 Phase 2
0.6994 Remote Similarity NPD8313 Approved
0.6994 Remote Similarity NPD8312 Approved
0.6993 Remote Similarity NPD7743 Approved
0.6993 Remote Similarity NPD7742 Approved
0.6989 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6986 Remote Similarity NPD8651 Approved
0.698 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6971 Remote Similarity NPD8434 Phase 2
0.6959 Remote Similarity NPD2861 Phase 2
0.6951 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2935 Discontinued
0.6948 Remote Similarity NPD5404 Approved
0.6948 Remote Similarity NPD5406 Approved
0.6948 Remote Similarity NPD5405 Approved
0.6948 Remote Similarity NPD5408 Approved
0.6944 Remote Similarity NPD3023 Approved
0.6944 Remote Similarity NPD3496 Discontinued
0.6944 Remote Similarity NPD3026 Approved
0.6943 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6943 Remote Similarity NPD8131 Suspended
0.6933 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6798 Discontinued
0.6929 Remote Similarity NPD2629 Approved
0.6923 Remote Similarity NPD3025 Approved
0.6923 Remote Similarity NPD3024 Approved
0.6913 Remote Similarity NPD4908 Phase 1
0.6909 Remote Similarity NPD7057 Phase 3
0.6909 Remote Similarity NPD7768 Phase 2
0.6909 Remote Similarity NPD7058 Phase 2
0.6908 Remote Similarity NPD5124 Phase 1
0.6908 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6901 Remote Similarity NPD5844 Phase 1
0.6894 Remote Similarity NPD3020 Approved
0.6892 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6233 Phase 2
0.6887 Remote Similarity NPD7961 Discontinued
0.6879 Remote Similarity NPD7685 Pre-registration
0.6875 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6867 Remote Similarity NPD3027 Phase 3
0.6867 Remote Similarity NPD7833 Phase 2
0.6867 Remote Similarity NPD7831 Phase 2
0.6867 Remote Similarity NPD7008 Discontinued
0.6867 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6863 Remote Similarity NPD4097 Suspended
0.6842 Remote Similarity NPD7799 Discontinued
0.6838 Remote Similarity NPD3134 Approved
0.6824 Remote Similarity NPD2797 Approved
0.6816 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6811 Remote Similarity NPD7497 Discontinued
0.6807 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6803 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6803 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6797 Remote Similarity NPD3657 Discovery
0.6788 Remote Similarity NPD1358 Approved
0.6786 Remote Similarity NPD7094 Approved
0.6786 Remote Similarity NPD6858 Approved
0.6786 Remote Similarity NPD7635 Approved
0.6786 Remote Similarity NPD7843 Approved
0.6786 Remote Similarity NPD5535 Approved
0.6782 Remote Similarity NPD7240 Approved
0.6772 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3750 Approved
0.6768 Remote Similarity NPD6677 Suspended
0.6759 Remote Similarity NPD5126 Approved
0.6759 Remote Similarity NPD5125 Phase 3
0.6757 Remote Similarity NPD1283 Approved
0.6752 Remote Similarity NPD2424 Discontinued
0.6746 Remote Similarity NPD7199 Phase 2
0.6732 Remote Similarity NPD2979 Phase 3
0.6732 Remote Similarity NPD1613 Approved
0.6732 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6731 Remote Similarity NPD2438 Suspended
0.673 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6728 Remote Similarity NPD5699 Approved
0.6724 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6718 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6711 Remote Similarity NPD6362 Approved
0.6711 Remote Similarity NPD3268 Approved
0.6709 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6707 Remote Similarity NPD4380 Phase 2
0.669 Remote Similarity NPD5585 Approved
0.6688 Remote Similarity NPD6002 Phase 3
0.6688 Remote Similarity NPD230 Phase 1
0.6688 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6688 Remote Similarity NPD6004 Phase 3
0.6688 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6688 Remote Similarity NPD6005 Phase 3
0.6687 Remote Similarity NPD5761 Phase 2
0.6687 Remote Similarity NPD7819 Suspended
0.6687 Remote Similarity NPD1653 Approved
0.6687 Remote Similarity NPD5760 Phase 2
0.6686 Remote Similarity NPD7473 Discontinued
0.6667 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2859 Approved
0.6667 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7033 Discontinued
0.6667 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2799 Discontinued
0.6667 Remote Similarity NPD2860 Approved
0.6667 Remote Similarity NPD7075 Discontinued
0.6647 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7041 Phase 2
0.6646 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7037 Approved
0.6646 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6645 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6628 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6621 Remote Similarity NPD9545 Approved
0.662 Remote Similarity NPD7159 Clinical (unspecified phase)
0.662 Remote Similarity NPD5283 Phase 1
0.6619 Remote Similarity NPD2684 Approved
0.6618 Remote Similarity NPD6647 Phase 2
0.6609 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6608 Remote Similarity NPD6232 Discontinued
0.6605 Remote Similarity NPD3645 Discontinued
0.6604 Remote Similarity NPD3638 Discontinued
0.6604 Remote Similarity NPD1652 Phase 2
0.6601 Remote Similarity NPD7985 Registered
0.6596 Remote Similarity NPD6124 Clinical (unspecified phase)
0.6593 Remote Similarity NPD289 Clinical (unspecified phase)
0.6591 Remote Similarity NPD2933 Approved
0.6591 Remote Similarity NPD6765 Approved
0.6591 Remote Similarity NPD6764 Approved
0.6591 Remote Similarity NPD2934 Approved
0.6587 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6587 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6582 Remote Similarity NPD2346 Discontinued
0.6582 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6575 Remote Similarity NPD1357 Approved
0.6573 Remote Similarity NPD5951 Approved
0.6571 Remote Similarity NPD4750 Phase 3
0.657 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6558 Remote Similarity NPD4248 Discontinued
0.6556 Remote Similarity NPD5647 Approved
0.6554 Remote Similarity NPD422 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