Structure

Physi-Chem Properties

Molecular Weight:  542.12
Volume:  521.169
LogP:  4.585
LogD:  3.429
LogS:  -3.794
# Rotatable Bonds:  2
TPSA:  166.14
# H-Bond Aceptor:  10
# H-Bond Donor:  6
# Rings:  7
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.218
Synthetic Accessibility Score:  4.387
Fsp3:  0.167
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.84
MDCK Permeability:  7.315242328331806e-06
Pgp-inhibitor:  0.031
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.336
20% Bioavailability (F20%):  0.983
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  95.83697509765625%
Volume Distribution (VD):  0.512
Pgp-substrate:  1.5783839225769043%

ADMET: Metabolism

CYP1A2-inhibitor:  0.351
CYP1A2-substrate:  0.119
CYP2C19-inhibitor:  0.75
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.778
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.112
CYP2D6-substrate:  0.29
CYP3A4-inhibitor:  0.792
CYP3A4-substrate:  0.649

ADMET: Excretion

Clearance (CL):  3.896
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.12
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.96
AMES Toxicity:  0.855
Rat Oral Acute Toxicity:  0.689
Maximum Recommended Daily Dose:  0.503
Skin Sensitization:  0.932
Carcinogencity:  0.934
Eye Corrosion:  0.003
Eye Irritation:  0.886
Respiratory Toxicity:  0.04

Download Data

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

  Natural Product: NPC287884

Natural Product ID:  NPC287884
Common Name*:   KVPJDVHJFGPPAB-AXRGIPJOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  KVPJDVHJFGPPAB-AXRGIPJOSA-N
Standard InCHI:  InChI=1S/C30H22O10/c31-16-5-1-14(2-6-16)22-10-9-19-20(34)13-24-26(27(19)38-22)29(37)28(36)25-21(35)11-18(33)12-23(25)39-30(29,40-24)15-3-7-17(32)8-4-15/h1-8,11-13,22,31-35,37H,9-10H2/t22-,29-,30-/m0/s1
SMILES:  Oc1ccc(cc1)[C@@H]1CCc2c(O1)c1c(cc2O)O[C@]2([C@@]1(O)C(=O)c1c(O)cc(cc1O2)O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3121245
PubChem CID:   76317993
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22494026]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24156713]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32997496]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14015 Salacia cordata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10705 Marshallia graminifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15287 Vernonia megapotamica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12376 Baccharis macraei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10882 Acer caudatifolium Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17558 Cynoglossum formosanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7037 Rumohra adiantiformis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18247 Globicephala melas Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19406 Chrysanthemum leptophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13505 Grateloupia livida Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19479 Trametes feei Species Coriolaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 66680.0 nM PMID[554365]
NPT757 Organism Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 IC50 = 60580.0 nM PMID[554365]
NPT2 Others Unspecified IC50 = 5230.0 nM PMID[554365]

☑ 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 NPC287884 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 NPC8704
0.9444 High Similarity NPC82330
0.9441 High Similarity NPC63438
0.9313 High Similarity NPC123544
0.9277 High Similarity NPC168789
0.9268 High Similarity NPC292233
0.9193 High Similarity NPC295090
0.9187 High Similarity NPC69531
0.9162 High Similarity NPC17105
0.9162 High Similarity NPC474276
0.9162 High Similarity NPC147363
0.9162 High Similarity NPC73899
0.9141 High Similarity NPC259834
0.9136 High Similarity NPC306978
0.9125 High Similarity NPC134171
0.9125 High Similarity NPC300668
0.9102 High Similarity NPC257667
0.9102 High Similarity NPC472454
0.9102 High Similarity NPC186847
0.9102 High Similarity NPC477529
0.9096 High Similarity NPC53252
0.9085 High Similarity NPC183672
0.908 High Similarity NPC47923
0.9074 High Similarity NPC264932
0.9074 High Similarity NPC311574
0.9068 High Similarity NPC32867
0.9068 High Similarity NPC146636
0.9062 High Similarity NPC20907
0.9062 High Similarity NPC244250
0.903 High Similarity NPC473010
0.9024 High Similarity NPC93215
0.9024 High Similarity NPC44947
0.9024 High Similarity NPC131745
0.9018 High Similarity NPC472320
0.9018 High Similarity NPC172687
0.9018 High Similarity NPC200708
0.9012 High Similarity NPC75574
0.9012 High Similarity NPC475184
0.9012 High Similarity NPC161650
0.9012 High Similarity NPC106700
0.9012 High Similarity NPC210048
0.9006 High Similarity NPC66441
0.9006 High Similarity NPC201227
0.9006 High Similarity NPC476169
0.9006 High Similarity NPC258474
0.9006 High Similarity NPC182555
0.9 High Similarity NPC174086
0.9 High Similarity NPC210597
0.8994 High Similarity NPC108202
0.8982 High Similarity NPC107627
0.8982 High Similarity NPC5319
0.8976 High Similarity NPC224851
0.897 High Similarity NPC257566
0.897 High Similarity NPC278419
0.897 High Similarity NPC38591
0.897 High Similarity NPC66087
0.897 High Similarity NPC124155
0.897 High Similarity NPC179198
0.897 High Similarity NPC473009
0.8963 High Similarity NPC312273
0.8963 High Similarity NPC92589
0.8963 High Similarity NPC301256
0.8963 High Similarity NPC470125
0.8957 High Similarity NPC308265
0.8957 High Similarity NPC51760
0.8953 High Similarity NPC132111
0.8951 High Similarity NPC198489
0.8951 High Similarity NPC61112
0.8951 High Similarity NPC309648
0.8944 High Similarity NPC109594
0.8944 High Similarity NPC326592
0.8944 High Similarity NPC112701
0.8944 High Similarity NPC268193
0.8944 High Similarity NPC203080
0.8944 High Similarity NPC209760
0.8944 High Similarity NPC100134
0.8941 High Similarity NPC156635
0.8938 High Similarity NPC472636
0.8909 High Similarity NPC473012
0.8909 High Similarity NPC310603
0.8909 High Similarity NPC472876
0.8909 High Similarity NPC150164
0.8909 High Similarity NPC190450
0.8909 High Similarity NPC473011
0.8908 High Similarity NPC282636
0.8908 High Similarity NPC294863
0.8902 High Similarity NPC470405
0.8902 High Similarity NPC153342
0.8902 High Similarity NPC304741
0.8902 High Similarity NPC136761
0.8902 High Similarity NPC271479
0.8902 High Similarity NPC471079
0.8902 High Similarity NPC187379
0.8896 High Similarity NPC6985
0.8896 High Similarity NPC287789
0.8896 High Similarity NPC1796
0.8896 High Similarity NPC122809
0.8896 High Similarity NPC271741
0.8889 High Similarity NPC48579
0.8889 High Similarity NPC304745
0.8889 High Similarity NPC26195
0.8889 High Similarity NPC217706
0.8889 High Similarity NPC207809
0.8889 High Similarity NPC169248
0.8889 High Similarity NPC471116
0.8889 High Similarity NPC304207
0.8889 High Similarity NPC72649
0.8889 High Similarity NPC97052
0.8889 High Similarity NPC111341
0.8889 High Similarity NPC67302
0.8889 High Similarity NPC259710
0.8889 High Similarity NPC39351
0.8882 High Similarity NPC473996
0.8882 High Similarity NPC475790
0.8882 High Similarity NPC3718
0.8868 High Similarity NPC122894
0.8862 High Similarity NPC171985
0.8862 High Similarity NPC320741
0.8855 High Similarity NPC80068
0.8855 High Similarity NPC472581
0.8848 High Similarity NPC215710
0.8848 High Similarity NPC170052
0.8848 High Similarity NPC175513
0.8848 High Similarity NPC173582
0.8848 High Similarity NPC476215
0.8848 High Similarity NPC64305
0.8848 High Similarity NPC139320
0.8848 High Similarity NPC297987
0.8848 High Similarity NPC249281
0.8848 High Similarity NPC276377
0.8848 High Similarity NPC135846
0.8848 High Similarity NPC246943
0.8848 High Similarity NPC473438
0.8848 High Similarity NPC265885
0.8848 High Similarity NPC163242
0.8848 High Similarity NPC253788
0.8848 High Similarity NPC116458
0.8848 High Similarity NPC97812
0.8848 High Similarity NPC303913
0.8848 High Similarity NPC181465
0.8844 High Similarity NPC321916
0.8841 High Similarity NPC51247
0.8841 High Similarity NPC470607
0.8837 High Similarity NPC153578
0.8837 High Similarity NPC299149
0.8837 High Similarity NPC277710
0.8837 High Similarity NPC114257
0.8834 High Similarity NPC265480
0.8834 High Similarity NPC307938
0.8834 High Similarity NPC170475
0.8834 High Similarity NPC10754
0.8834 High Similarity NPC206378
0.8834 High Similarity NPC215917
0.8834 High Similarity NPC203500
0.8834 High Similarity NPC20530
0.8834 High Similarity NPC149368
0.8834 High Similarity NPC323593
0.883 High Similarity NPC475246
0.883 High Similarity NPC475233
0.8827 High Similarity NPC311579
0.8827 High Similarity NPC180301
0.8827 High Similarity NPC248793
0.8827 High Similarity NPC236756
0.8827 High Similarity NPC121568
0.8824 High Similarity NPC470336
0.8824 High Similarity NPC470335
0.882 High Similarity NPC472580
0.882 High Similarity NPC278476
0.882 High Similarity NPC289774
0.882 High Similarity NPC328740
0.882 High Similarity NPC254412
0.882 High Similarity NPC477897
0.882 High Similarity NPC474023
0.882 High Similarity NPC319910
0.882 High Similarity NPC209846
0.882 High Similarity NPC474021
0.882 High Similarity NPC471675
0.882 High Similarity NPC471229
0.882 High Similarity NPC262038
0.882 High Similarity NPC325429
0.882 High Similarity NPC262039
0.8817 High Similarity NPC188815
0.8817 High Similarity NPC280642
0.8817 High Similarity NPC469344
0.8817 High Similarity NPC218161
0.8817 High Similarity NPC96605
0.8817 High Similarity NPC279209
0.8817 High Similarity NPC76047
0.8817 High Similarity NPC102277
0.8812 High Similarity NPC3642
0.8812 High Similarity NPC277032
0.881 High Similarity NPC476459
0.881 High Similarity NPC260266
0.8802 High Similarity NPC85751
0.8802 High Similarity NPC139060
0.8802 High Similarity NPC205824
0.8802 High Similarity NPC62261
0.8802 High Similarity NPC19240
0.8802 High Similarity NPC72016
0.8802 High Similarity NPC129264

  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 NPC287884 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
0.8982 High Similarity NPD7804 Clinical (unspecified phase)
0.878 High Similarity NPD4381 Clinical (unspecified phase)
0.869 High Similarity NPD6167 Clinical (unspecified phase)
0.869 High Similarity NPD6166 Phase 2
0.869 High Similarity NPD6168 Clinical (unspecified phase)
0.8667 High Similarity NPD7075 Discontinued
0.8642 High Similarity NPD4380 Phase 2
0.8623 High Similarity NPD6959 Discontinued
0.8547 High Similarity NPD6797 Phase 2
0.8545 High Similarity NPD8443 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD7251 Discontinued
0.8488 Intermediate Similarity NPD7074 Phase 3
0.8485 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD3818 Discontinued
0.8471 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8448 Intermediate Similarity NPD7808 Phase 3
0.8447 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8439 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7054 Approved
0.8391 Intermediate Similarity NPD6559 Discontinued
0.8382 Intermediate Similarity NPD7472 Approved
0.8373 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD7411 Suspended
0.8343 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD3749 Approved
0.8333 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD6801 Discontinued
0.8295 Intermediate Similarity NPD8312 Approved
0.8295 Intermediate Similarity NPD8313 Approved
0.8278 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD5494 Approved
0.8204 Intermediate Similarity NPD1934 Approved
0.8187 Intermediate Similarity NPD1549 Phase 2
0.8166 Intermediate Similarity NPD3882 Suspended
0.8166 Intermediate Similarity NPD7768 Phase 2
0.8155 Intermediate Similarity NPD8455 Phase 2
0.814 Intermediate Similarity NPD3787 Discontinued
0.8057 Intermediate Similarity NPD3751 Discontinued
0.8049 Intermediate Similarity NPD6799 Approved
0.8047 Intermediate Similarity NPD7819 Suspended
0.8012 Intermediate Similarity NPD5403 Approved
0.8 Intermediate Similarity NPD5402 Approved
0.8 Intermediate Similarity NPD3817 Phase 2
0.7976 Intermediate Similarity NPD6599 Discontinued
0.7968 Intermediate Similarity NPD6777 Approved
0.7968 Intermediate Similarity NPD6782 Approved
0.7968 Intermediate Similarity NPD6776 Approved
0.7968 Intermediate Similarity NPD6780 Approved
0.7968 Intermediate Similarity NPD6778 Approved
0.7968 Intermediate Similarity NPD6781 Approved
0.7968 Intermediate Similarity NPD6779 Approved
0.7952 Intermediate Similarity NPD1512 Approved
0.7941 Intermediate Similarity NPD2801 Approved
0.7931 Intermediate Similarity NPD6232 Discontinued
0.7898 Intermediate Similarity NPD7473 Discontinued
0.7892 Intermediate Similarity NPD5401 Approved
0.7888 Intermediate Similarity NPD1510 Phase 2
0.7869 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7842 Intermediate Similarity NPD7698 Approved
0.7842 Intermediate Similarity NPD7697 Approved
0.7842 Intermediate Similarity NPD7435 Discontinued
0.7842 Intermediate Similarity NPD7696 Phase 3
0.784 Intermediate Similarity NPD2796 Approved
0.7831 Intermediate Similarity NPD1511 Approved
0.7809 Intermediate Similarity NPD5844 Phase 1
0.7805 Intermediate Similarity NPD2800 Approved
0.7802 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD7871 Phase 2
0.7801 Intermediate Similarity NPD7870 Phase 2
0.7772 Intermediate Similarity NPD7701 Phase 2
0.7732 Intermediate Similarity NPD8151 Discontinued
0.7701 Intermediate Similarity NPD6534 Approved
0.7701 Intermediate Similarity NPD6535 Approved
0.7697 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD2533 Approved
0.7679 Intermediate Similarity NPD2534 Approved
0.7679 Intermediate Similarity NPD2532 Approved
0.7672 Intermediate Similarity NPD7699 Phase 2
0.7672 Intermediate Similarity NPD7700 Phase 2
0.7654 Intermediate Similarity NPD7228 Approved
0.7653 Intermediate Similarity NPD7783 Phase 2
0.7653 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD3750 Approved
0.764 Intermediate Similarity NPD1240 Approved
0.763 Intermediate Similarity NPD1465 Phase 2
0.7619 Intermediate Similarity NPD7390 Discontinued
0.7619 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7458 Discontinued
0.7602 Intermediate Similarity NPD7874 Approved
0.7602 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD920 Approved
0.7584 Intermediate Similarity NPD3926 Phase 2
0.7574 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7199 Phase 2
0.7563 Intermediate Similarity NPD7801 Approved
0.7557 Intermediate Similarity NPD6234 Discontinued
0.7546 Intermediate Similarity NPD1607 Approved
0.7538 Intermediate Similarity NPD7584 Approved
0.7526 Intermediate Similarity NPD8320 Phase 1
0.7526 Intermediate Similarity NPD8319 Approved
0.7516 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD6823 Phase 2
0.7473 Intermediate Similarity NPD8150 Discontinued
0.7473 Intermediate Similarity NPD8434 Phase 2
0.7472 Intermediate Similarity NPD1247 Approved
0.7471 Intermediate Similarity NPD37 Approved
0.747 Intermediate Similarity NPD2344 Approved
0.7458 Intermediate Similarity NPD919 Approved
0.7456 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4965 Approved
0.7443 Intermediate Similarity NPD4967 Phase 2
0.7443 Intermediate Similarity NPD4966 Approved
0.744 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD4628 Phase 3
0.7432 Intermediate Similarity NPD5953 Discontinued
0.741 Intermediate Similarity NPD1551 Phase 2
0.7399 Intermediate Similarity NPD3226 Approved
0.7394 Intermediate Similarity NPD4287 Approved
0.7391 Intermediate Similarity NPD4908 Phase 1
0.7381 Intermediate Similarity NPD1243 Approved
0.7368 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD3748 Approved
0.7349 Intermediate Similarity NPD2799 Discontinued
0.7322 Intermediate Similarity NPD7286 Phase 2
0.7321 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD2935 Discontinued
0.7301 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD6798 Discontinued
0.7301 Intermediate Similarity NPD2313 Discontinued
0.7297 Intermediate Similarity NPD7240 Approved
0.7294 Intermediate Similarity NPD2309 Approved
0.7289 Intermediate Similarity NPD7097 Phase 1
0.724 Intermediate Similarity NPD4363 Phase 3
0.724 Intermediate Similarity NPD4360 Phase 2
0.7238 Intermediate Similarity NPD7229 Phase 3
0.7238 Intermediate Similarity NPD5710 Approved
0.7238 Intermediate Similarity NPD5711 Approved
0.7229 Intermediate Similarity NPD6651 Approved
0.7222 Intermediate Similarity NPD7211 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7685 Pre-registration
0.72 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD3764 Approved
0.7193 Intermediate Similarity NPD6190 Approved
0.7188 Intermediate Similarity NPD6212 Phase 3
0.7188 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6213 Phase 3
0.7169 Intermediate Similarity NPD6355 Discontinued
0.716 Intermediate Similarity NPD2346 Discontinued
0.7158 Intermediate Similarity NPD2403 Approved
0.7152 Intermediate Similarity NPD6233 Phase 2
0.715 Intermediate Similarity NPD7585 Approved
0.7143 Intermediate Similarity NPD7033 Discontinued
0.7143 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD2424 Discontinued
0.7108 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD1613 Approved
0.7108 Intermediate Similarity NPD943 Approved
0.7101 Intermediate Similarity NPD6100 Approved
0.7101 Intermediate Similarity NPD5408 Approved
0.7101 Intermediate Similarity NPD5405 Approved
0.7101 Intermediate Similarity NPD5404 Approved
0.7101 Intermediate Similarity NPD6099 Approved
0.7101 Intermediate Similarity NPD5406 Approved
0.71 Intermediate Similarity NPD7583 Approved
0.7069 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD5124 Phase 1
0.7066 Intermediate Similarity NPD1933 Approved
0.7066 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1610 Phase 2
0.7059 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD2798 Approved
0.7045 Intermediate Similarity NPD1653 Approved
0.7035 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7003 Approved
0.7026 Intermediate Similarity NPD4361 Phase 2
0.7026 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.6994 Remote Similarity NPD1203 Approved
0.6989 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6981 Remote Similarity NPD8059 Phase 3
0.6981 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6973 Remote Similarity NPD7784 Clinical (unspecified phase)
0.697 Remote Similarity NPD1529 Clinical (unspecified phase)
0.697 Remote Similarity NPD6832 Phase 2
0.6954 Remote Similarity NPD5058 Phase 3
0.695 Remote Similarity NPD7680 Approved
0.6944 Remote Similarity NPD5761 Phase 2
0.6944 Remote Similarity NPD5760 Phase 2
0.6942 Remote Similarity NPD7930 Approved
0.6941 Remote Similarity NPD651 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