Structure

Physi-Chem Properties

Molecular Weight:  692.23
Volume:  700.93
LogP:  6.782
LogD:  3.384
LogS:  -3.397
# Rotatable Bonds:  7
TPSA:  209.12
# H-Bond Aceptor:  11
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.063
Synthetic Accessibility Score:  4.616
Fsp3:  0.2
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:  -5.775
MDCK Permeability:  5.521363618754549e-06
Pgp-inhibitor:  0.076
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.191
20% Bioavailability (F20%):  0.916
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  95.76212310791016%
Volume Distribution (VD):  0.394
Pgp-substrate:  2.8968005180358887%

ADMET: Metabolism

CYP1A2-inhibitor:  0.641
CYP1A2-substrate:  0.162
CYP2C19-inhibitor:  0.941
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.883
CYP2C9-substrate:  0.97
CYP2D6-inhibitor:  0.442
CYP2D6-substrate:  0.241
CYP3A4-inhibitor:  0.261
CYP3A4-substrate:  0.077

ADMET: Excretion

Clearance (CL):  6.948
Half-life (T1/2):  0.485

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.823
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.601
Rat Oral Acute Toxicity:  0.699
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.945
Carcinogencity:  0.058
Eye Corrosion:  0.003
Eye Irritation:  0.88
Respiratory Toxicity:  0.066

Download Data

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

  Natural Product: NPC54830

Natural Product ID:  NPC54830
Common Name*:   Kumanon G
IUPAC Name:   8-[(1S,5R,6S)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3-methylbut-2-enyl)chromen-4-one
Synonyms:   Kumanon G
Standard InCHIKey:  APPXYONGBIXGRO-AIQWNVMPSA-N
Standard InCHI:  InChI=1S/C40H36O11/c1-18(2)4-8-26-38(50)36-33(48)17-32(47)35(40(36)51-39(26)25-11-7-22(43)16-31(25)46)28-13-19(3)12-27(23-9-5-20(41)14-29(23)44)34(28)37(49)24-10-6-21(42)15-30(24)45/h4-7,9-11,13-17,27-28,34,41-48H,8,12H2,1-3H3/t27-,28-,34-/m0/s1
SMILES:  CC(=CCc1c(=O)c2c(cc(c([C@H]3C=C(C)C[C@@H](c4ccc(cc4O)O)[C@@H]3C(=O)c3ccc(cc3O)O)c2oc1c1ccc(cc1O)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL444942
PubChem CID:   5281667
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae 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
NPT1600 Individual Protein Beta-glucuronidase Homo sapiens IC50 = 7400.0 nM PMID[490278]
NPT1600 Individual Protein Beta-glucuronidase Homo sapiens Inhibition > 70.0 % PMID[490278]
NPT20967 CELL-LINE Platelet n.a. IC50 = 89300.0 nM PMID[490277]
NPT20967 CELL-LINE Platelet n.a. IC50 = 132000.0 nM PMID[490277]
NPT25169 SINGLE PROTEIN Beta-glucuronidase Escherichia coli (strain K12) IC50 = 1600.0 nM PMID[490278]
NPT2 Others Unspecified IC50 = 980.0 nM PMID[490278]

☑ 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 NPC54830 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 NPC56049
0.9671 High Similarity NPC195136
0.9605 High Similarity NPC105584
0.9542 High Similarity NPC121647
0.9477 High Similarity NPC15815
0.9477 High Similarity NPC90497
0.947 High Similarity NPC324447
0.9416 High Similarity NPC98023
0.9416 High Similarity NPC226462
0.9412 High Similarity NPC1796
0.9412 High Similarity NPC257166
0.9408 High Similarity NPC265624
0.9408 High Similarity NPC186227
0.9408 High Similarity NPC159707
0.9408 High Similarity NPC215203
0.9408 High Similarity NPC150908
0.9408 High Similarity NPC100049
0.9408 High Similarity NPC37253
0.9408 High Similarity NPC79375
0.9408 High Similarity NPC121649
0.9408 High Similarity NPC158027
0.9408 High Similarity NPC248739
0.9408 High Similarity NPC52611
0.9408 High Similarity NPC205026
0.9408 High Similarity NPC14606
0.9396 High Similarity NPC152233
0.9363 High Similarity NPC251336
0.9351 High Similarity NPC51247
0.9342 High Similarity NPC290830
0.9342 High Similarity NPC303485
0.9342 High Similarity NPC121568
0.9342 High Similarity NPC194593
0.9342 High Similarity NPC72425
0.9342 High Similarity NPC71061
0.9338 High Similarity NPC111112
0.9338 High Similarity NPC67322
0.9338 High Similarity NPC222713
0.9338 High Similarity NPC138299
0.9333 High Similarity NPC288840
0.9333 High Similarity NPC291746
0.9329 High Similarity NPC475348
0.9329 High Similarity NPC261271
0.9304 High Similarity NPC286230
0.9304 High Similarity NPC253730
0.929 High Similarity NPC42965
0.9286 High Similarity NPC208258
0.9276 High Similarity NPC43345
0.9226 High Similarity NPC18699
0.9226 High Similarity NPC55443
0.9221 High Similarity NPC192587
0.9221 High Similarity NPC32867
0.9211 High Similarity NPC178484
0.9211 High Similarity NPC476551
0.9211 High Similarity NPC476552
0.9211 High Similarity NPC476553
0.9195 High Similarity NPC278175
0.9195 High Similarity NPC257236
0.9195 High Similarity NPC282957
0.9195 High Similarity NPC471523
0.9195 High Similarity NPC471473
0.9195 High Similarity NPC194949
0.9195 High Similarity NPC471524
0.9177 High Similarity NPC169471
0.9172 High Similarity NPC473012
0.9167 High Similarity NPC312993
0.9161 High Similarity NPC324358
0.9161 High Similarity NPC323627
0.9161 High Similarity NPC318527
0.9161 High Similarity NPC475184
0.9161 High Similarity NPC322459
0.9156 High Similarity NPC66441
0.9156 High Similarity NPC182555
0.9156 High Similarity NPC254351
0.915 High Similarity NPC39154
0.915 High Similarity NPC174086
0.915 High Similarity NPC115601
0.915 High Similarity NPC78324
0.915 High Similarity NPC208011
0.913 High Similarity NPC477529
0.9122 High Similarity NPC14871
0.9114 High Similarity NPC473009
0.9108 High Similarity NPC189552
0.9108 High Similarity NPC273467
0.9108 High Similarity NPC301256
0.9108 High Similarity NPC312273
0.9103 High Similarity NPC177650
0.9103 High Similarity NPC51760
0.9103 High Similarity NPC295090
0.9097 High Similarity NPC69531
0.9079 High Similarity NPC3642
0.9074 High Similarity NPC73899
0.9074 High Similarity NPC17105
0.9074 High Similarity NPC474276
0.9074 High Similarity NPC147363
0.906 High Similarity NPC297600
0.9057 High Similarity NPC473010
0.9054 High Similarity NPC261227
0.9054 High Similarity NPC172986
0.9054 High Similarity NPC270883
0.9045 High Similarity NPC186325
0.9038 High Similarity NPC287789
0.9038 High Similarity NPC271741
0.9032 High Similarity NPC300668
0.9032 High Similarity NPC134171
0.9013 High Similarity NPC122894
0.9007 High Similarity NPC477955
0.9 High Similarity NPC219915
0.9 High Similarity NPC38219
0.9 High Similarity NPC11700
0.8993 High Similarity NPC64908
0.8993 High Similarity NPC156590
0.8993 High Similarity NPC118840
0.8993 High Similarity NPC147688
0.8993 High Similarity NPC110969
0.8993 High Similarity NPC26238
0.8993 High Similarity NPC282300
0.8993 High Similarity NPC205006
0.8987 High Similarity NPC103816
0.8987 High Similarity NPC61382
0.8986 High Similarity NPC301217
0.8986 High Similarity NPC216978
0.8986 High Similarity NPC55018
0.8986 High Similarity NPC303633
0.8986 High Similarity NPC96565
0.8986 High Similarity NPC220062
0.8974 High Similarity NPC198489
0.8974 High Similarity NPC61112
0.8974 High Similarity NPC309648
0.897 High Similarity NPC121888
0.8963 High Similarity NPC101991
0.8961 High Similarity NPC305965
0.8954 High Similarity NPC132345
0.8947 High Similarity NPC79469
0.8947 High Similarity NPC24673
0.8947 High Similarity NPC201731
0.8947 High Similarity NPC97716
0.8947 High Similarity NPC237635
0.8947 High Similarity NPC104406
0.894 High Similarity NPC326500
0.894 High Similarity NPC271288
0.894 High Similarity NPC311741
0.894 High Similarity NPC234629
0.8938 High Similarity NPC469664
0.8933 High Similarity NPC299080
0.8933 High Similarity NPC293852
0.8933 High Similarity NPC78803
0.8933 High Similarity NPC217083
0.8933 High Similarity NPC214236
0.8933 High Similarity NPC226636
0.8933 High Similarity NPC144499
0.8933 High Similarity NPC62840
0.8933 High Similarity NPC11561
0.8933 High Similarity NPC59739
0.8926 High Similarity NPC475680
0.8926 High Similarity NPC69769
0.8926 High Similarity NPC241100
0.8926 High Similarity NPC235239
0.8926 High Similarity NPC305355
0.8926 High Similarity NPC265178
0.8926 High Similarity NPC159275
0.8919 High Similarity NPC201395
0.891 High Similarity NPC258474
0.891 High Similarity NPC201227
0.8896 High Similarity NPC29777
0.8896 High Similarity NPC151973
0.8896 High Similarity NPC188403
0.8896 High Similarity NPC471115
0.8889 High Similarity NPC6511
0.8889 High Similarity NPC132592
0.8889 High Similarity NPC160821
0.8889 High Similarity NPC145467
0.8889 High Similarity NPC39195
0.8889 High Similarity NPC266572
0.8882 High Similarity NPC109183
0.8882 High Similarity NPC473078
0.8882 High Similarity NPC110882
0.8882 High Similarity NPC271944
0.8882 High Similarity NPC470132
0.8882 High Similarity NPC228779
0.8882 High Similarity NPC154217
0.8882 High Similarity NPC181388
0.8882 High Similarity NPC85393
0.8882 High Similarity NPC470131
0.8882 High Similarity NPC470134
0.8882 High Similarity NPC470133
0.8882 High Similarity NPC476088
0.8882 High Similarity NPC25844
0.8882 High Similarity NPC474161
0.8875 High Similarity NPC159508
0.8875 High Similarity NPC469395
0.8874 High Similarity NPC212932
0.8874 High Similarity NPC9117
0.8874 High Similarity NPC106985
0.8874 High Similarity NPC190637
0.8874 High Similarity NPC166138
0.8874 High Similarity NPC24821
0.8874 High Similarity NPC293053
0.8874 High Similarity NPC18585
0.8868 High Similarity NPC175513
0.8868 High Similarity NPC18380

  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 NPC54830 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
0.9195 High Similarity NPD7410 Clinical (unspecified phase)
0.9156 High Similarity NPD8443 Clinical (unspecified phase)
0.8938 High Similarity NPD7852 Clinical (unspecified phase)
0.8854 High Similarity NPD7768 Phase 2
0.8816 High Similarity NPD4378 Clinical (unspecified phase)
0.875 High Similarity NPD6959 Discontinued
0.8718 High Similarity NPD7411 Suspended
0.8608 High Similarity NPD7819 Suspended
0.8535 High Similarity NPD4380 Phase 2
0.8467 Intermediate Similarity NPD1510 Phase 2
0.8447 Intermediate Similarity NPD7075 Discontinued
0.8431 Intermediate Similarity NPD3750 Approved
0.8421 Intermediate Similarity NPD1549 Phase 2
0.8411 Intermediate Similarity NPD2796 Approved
0.8355 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1607 Approved
0.8333 Intermediate Similarity NPD3749 Approved
0.8323 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1240 Approved
0.8269 Intermediate Similarity NPD7390 Discontinued
0.8261 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8221 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD7473 Discontinued
0.8199 Intermediate Similarity NPD6801 Discontinued
0.8153 Intermediate Similarity NPD1511 Approved
0.8144 Intermediate Similarity NPD6166 Phase 2
0.8144 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD2800 Approved
0.8129 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD3748 Approved
0.8092 Intermediate Similarity NPD6651 Approved
0.805 Intermediate Similarity NPD1512 Approved
0.8037 Intermediate Similarity NPD2801 Approved
0.8024 Intermediate Similarity NPD6232 Discontinued
0.7987 Intermediate Similarity NPD2799 Discontinued
0.7975 Intermediate Similarity NPD1934 Approved
0.7963 Intermediate Similarity NPD6599 Discontinued
0.7949 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD6799 Approved
0.7904 Intermediate Similarity NPD5494 Approved
0.7901 Intermediate Similarity NPD3226 Approved
0.7898 Intermediate Similarity NPD1243 Approved
0.7895 Intermediate Similarity NPD7054 Approved
0.7885 Intermediate Similarity NPD2344 Approved
0.7874 Intermediate Similarity NPD8313 Approved
0.7874 Intermediate Similarity NPD8312 Approved
0.7871 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD7074 Phase 3
0.7849 Intermediate Similarity NPD7472 Approved
0.7848 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD3882 Suspended
0.7821 Intermediate Similarity NPD6099 Approved
0.7821 Intermediate Similarity NPD1551 Phase 2
0.7821 Intermediate Similarity NPD6100 Approved
0.7816 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7816 Intermediate Similarity NPD7808 Phase 3
0.7815 Intermediate Similarity NPD4908 Phase 1
0.7803 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD5844 Phase 1
0.7791 Intermediate Similarity NPD7458 Discontinued
0.7778 Intermediate Similarity NPD5403 Approved
0.7771 Intermediate Similarity NPD3817 Phase 2
0.7759 Intermediate Similarity NPD6559 Discontinued
0.7759 Intermediate Similarity NPD7251 Discontinued
0.7753 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7003 Approved
0.7733 Intermediate Similarity NPD3818 Discontinued
0.7712 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD2313 Discontinued
0.7707 Intermediate Similarity NPD2935 Discontinued
0.7707 Intermediate Similarity NPD5406 Approved
0.7707 Intermediate Similarity NPD5404 Approved
0.7707 Intermediate Similarity NPD5405 Approved
0.7707 Intermediate Similarity NPD5408 Approved
0.7701 Intermediate Similarity NPD6797 Phase 2
0.7701 Intermediate Similarity NPD5953 Discontinued
0.7692 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2309 Approved
0.7682 Intermediate Similarity NPD2798 Approved
0.7669 Intermediate Similarity NPD920 Approved
0.7667 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD2534 Approved
0.7654 Intermediate Similarity NPD2532 Approved
0.7654 Intermediate Similarity NPD5401 Approved
0.7654 Intermediate Similarity NPD2533 Approved
0.764 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD3268 Approved
0.7586 Intermediate Similarity NPD7286 Phase 2
0.756 Intermediate Similarity NPD5402 Approved
0.7547 Intermediate Similarity NPD2346 Discontinued
0.7546 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD4628 Phase 3
0.7516 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1203 Approved
0.75 Intermediate Similarity NPD2797 Approved
0.75 Intermediate Similarity NPD8455 Phase 2
0.7486 Intermediate Similarity NPD4363 Phase 3
0.7486 Intermediate Similarity NPD4360 Phase 2
0.747 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD6832 Phase 2
0.7457 Intermediate Similarity NPD3926 Phase 2
0.7456 Intermediate Similarity NPD4288 Approved
0.7439 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD4308 Phase 3
0.7416 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD1465 Phase 2
0.7389 Intermediate Similarity NPD943 Approved
0.7363 Intermediate Similarity NPD4287 Approved
0.7351 Intermediate Similarity NPD4361 Phase 2
0.7351 Intermediate Similarity NPD1610 Phase 2
0.7351 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD8150 Discontinued
0.7344 Intermediate Similarity NPD8151 Discontinued
0.733 Intermediate Similarity NPD7177 Discontinued
0.7326 Intermediate Similarity NPD919 Approved
0.7316 Intermediate Similarity NPD7870 Phase 2
0.7316 Intermediate Similarity NPD7871 Phase 2
0.7308 Intermediate Similarity NPD4625 Phase 3
0.7303 Intermediate Similarity NPD9717 Approved
0.7299 Intermediate Similarity NPD7229 Phase 3
0.7273 Intermediate Similarity NPD3267 Approved
0.7273 Intermediate Similarity NPD1470 Approved
0.7273 Intermediate Similarity NPD3266 Approved
0.7263 Intermediate Similarity NPD7697 Approved
0.7263 Intermediate Similarity NPD7698 Approved
0.7263 Intermediate Similarity NPD7696 Phase 3
0.7261 Intermediate Similarity NPD3764 Approved
0.7255 Intermediate Similarity NPD4749 Approved
0.7253 Intermediate Similarity NPD8434 Phase 2
0.7241 Intermediate Similarity NPD1247 Approved
0.7237 Intermediate Similarity NPD1201 Approved
0.7237 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD422 Phase 1
0.7233 Intermediate Similarity NPD5124 Phase 1
0.7233 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD3225 Approved
0.7205 Intermediate Similarity NPD7033 Discontinued
0.72 Intermediate Similarity NPD1548 Phase 1
0.7196 Intermediate Similarity NPD6778 Approved
0.7196 Intermediate Similarity NPD6779 Approved
0.7196 Intermediate Similarity NPD6776 Approved
0.7196 Intermediate Similarity NPD6777 Approved
0.7196 Intermediate Similarity NPD6782 Approved
0.7196 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD6780 Approved
0.7196 Intermediate Similarity NPD6781 Approved
0.719 Intermediate Similarity NPD3972 Approved
0.719 Intermediate Similarity NPD1608 Approved
0.7186 Intermediate Similarity NPD6273 Approved
0.7176 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD7435 Discontinued
0.717 Intermediate Similarity NPD4307 Phase 2
0.7152 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD2296 Approved
0.715 Intermediate Similarity NPD7584 Approved
0.7143 Intermediate Similarity NPD7199 Phase 2
0.7135 Intermediate Similarity NPD3751 Discontinued
0.7135 Intermediate Similarity NPD7577 Discontinued
0.7126 Intermediate Similarity NPD7447 Phase 1
0.7119 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD1471 Phase 3
0.7117 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD7701 Phase 2
0.7104 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD5710 Approved
0.7102 Intermediate Similarity NPD5711 Approved
0.7093 Intermediate Similarity NPD5760 Phase 2
0.7093 Intermediate Similarity NPD5761 Phase 2
0.7092 Intermediate Similarity NPD7783 Phase 2
0.7092 Intermediate Similarity NPD7801 Approved
0.7092 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD8166 Discontinued
0.7062 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD1729 Discontinued
0.7051 Intermediate Similarity NPD1164 Approved
0.7044 Intermediate Similarity NPD411 Approved
0.7041 Intermediate Similarity NPD7874 Approved
0.7041 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6823 Phase 2
0.703 Intermediate Similarity NPD2654 Approved
0.7018 Intermediate Similarity NPD6585 Discontinued
0.7006 Intermediate Similarity NPD3787 Discontinued
0.7 Intermediate Similarity NPD7699 Phase 2
0.7 Intermediate Similarity NPD7700 Phase 2
0.6993 Remote Similarity NPD17 Approved
0.6977 Remote Similarity NPD5890 Approved
0.6977 Remote Similarity NPD5889 Approved
0.6971 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7212 Phase 2
0.6964 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6964 Remote Similarity NPD7213 Phase 3
0.6959 Remote Similarity NPD8320 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