Structure

Physi-Chem Properties

Molecular Weight:  708.22
Volume:  703.8
LogP:  6.575
LogD:  3.034
LogS:  -2.877
# Rotatable Bonds:  6
TPSA:  214.44
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.082
Synthetic Accessibility Score:  5.138
Fsp3:  0.25
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:  -5.805
MDCK Permeability:  5.902126304135891e-06
Pgp-inhibitor:  0.139
Pgp-substrate:  0.017
Human Intestinal Absorption (HIA):  0.718
20% Bioavailability (F20%):  0.936
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  97.17955780029297%
Volume Distribution (VD):  0.38
Pgp-substrate:  1.5345652103424072%

ADMET: Metabolism

CYP1A2-inhibitor:  0.259
CYP1A2-substrate:  0.18
CYP2C19-inhibitor:  0.768
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.884
CYP2C9-substrate:  0.958
CYP2D6-inhibitor:  0.625
CYP2D6-substrate:  0.222
CYP3A4-inhibitor:  0.602
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  6.028
Half-life (T1/2):  0.223

ADMET: Toxicity

hERG Blockers:  0.086
Human Hepatotoxicity (H-HT):  0.769
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.575
Rat Oral Acute Toxicity:  0.879
Maximum Recommended Daily Dose:  0.969
Skin Sensitization:  0.933
Carcinogencity:  0.433
Eye Corrosion:  0.003
Eye Irritation:  0.778
Respiratory Toxicity:  0.045

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

  Natural Product: NPC474276

Natural Product ID:  NPC474276
Common Name*:   Sanggenon D
IUPAC Name:   2-[(1S,5R,6S)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,5a,8-tetrahydroxy-10a-(3-methylbut-2-enyl)-[1]benzofuro[3,2-b]chromen-11-one
Synonyms:   Sanggenon D
Standard InCHIKey:  SUOXGDJCEWTZIZ-HCEROAJISA-N
Standard InCHI:  InChI=1S/C40H36O12/c1-18(2)10-11-39-38(49)35-32(52-40(39,50)27-9-6-22(43)16-31(27)51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26-,33-,39?,40?/m0/s1
SMILES:  CC(=CCC12C(=O)c3c(cc(c([C@H]4C=C(C)C[C@@H](c5ccc(cc5O)O)[C@@H]4C(=O)c4ccc(cc4O)O)c3O)O)OC1(c1ccc(cc1O2)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464610
PubChem CID:   9987332
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11429996]
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 n.a. Konya, Turkey 2007-APR PMID[24901948]
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 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]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO9402 Morus mongolica 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]
NPO9402 Morus mongolica 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]
NPO9402 Morus mongolica 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
NPT924 Cell Line HSC-2 Homo sapiens CC50 = 44000.0 nM PMID[486067]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 59000.0 nM PMID[486068]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 = 73000.0 nM PMID[486068]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. CC50 = 64000.0 nM PMID[486067]
NPT27 Others Unspecified CC50 = 140000.0 nM PMID[486067]
NPT27 Others Unspecified Ratio = 3.2 n.a. PMID[486067]
NPT20967 CELL-LINE Platelet n.a. Inhibition = 51.0 % PMID[486069]
NPT20967 CELL-LINE Platelet n.a. Inhibition = 255.5 % PMID[486069]
NPT20967 CELL-LINE Platelet n.a. IC50 = 43300.0 nM PMID[486069]
NPT20967 CELL-LINE Platelet n.a. IC50 = 48300.0 nM PMID[486069]

☑ 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 NPC474276 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 NPC147363
1.0 High Similarity NPC17105
1.0 High Similarity NPC73899
0.963 High Similarity NPC292233
0.9573 High Similarity NPC477529
0.9259 High Similarity NPC172687
0.9255 High Similarity NPC161650
0.9198 High Similarity NPC264932
0.9198 High Similarity NPC311574
0.9162 High Similarity NPC8704
0.9162 High Similarity NPC287884
0.9136 High Similarity NPC210048
0.9074 High Similarity NPC56049
0.9074 High Similarity NPC54830
0.9064 High Similarity NPC121888
0.9059 High Similarity NPC101991
0.9024 High Similarity NPC195136
0.8982 High Similarity NPC82330
0.8976 High Similarity NPC473009
0.8963 High Similarity NPC105584
0.8941 High Similarity NPC59491
0.8941 High Similarity NPC24748
0.8929 High Similarity NPC286230
0.8929 High Similarity NPC253730
0.8922 High Similarity NPC473010
0.8916 High Similarity NPC473012
0.8909 High Similarity NPC121647
0.8909 High Similarity NPC306978
0.8869 High Similarity NPC251336
0.8862 High Similarity NPC63438
0.8855 High Similarity NPC92589
0.8855 High Similarity NPC312273
0.8855 High Similarity NPC301256
0.8848 High Similarity NPC123544
0.8848 High Similarity NPC15815
0.8844 High Similarity NPC244903
0.8837 High Similarity NPC156955
0.883 High Similarity NPC168789
0.8824 High Similarity NPC469344
0.881 High Similarity NPC169471
0.8802 High Similarity NPC475106
0.88 High Similarity NPC75574
0.88 High Similarity NPC106700
0.8795 High Similarity NPC226462
0.8795 High Similarity NPC98023
0.8788 High Similarity NPC257166
0.8788 High Similarity NPC1796
0.878 High Similarity NPC79375
0.878 High Similarity NPC37253
0.8772 High Similarity NPC221288
0.8772 High Similarity NPC101399
0.8772 High Similarity NPC11847
0.8772 High Similarity NPC217822
0.8765 High Similarity NPC158329
0.8765 High Similarity NPC5319
0.8765 High Similarity NPC41598
0.8765 High Similarity NPC476146
0.8765 High Similarity NPC40089
0.875 High Similarity NPC159508
0.8743 High Similarity NPC476929
0.8735 High Similarity NPC295090
0.8735 High Similarity NPC51247
0.8727 High Similarity NPC215917
0.8727 High Similarity NPC10754
0.8727 High Similarity NPC20530
0.8727 High Similarity NPC192587
0.8721 High Similarity NPC476152
0.872 High Similarity NPC100134
0.872 High Similarity NPC121568
0.872 High Similarity NPC209760
0.8713 High Similarity NPC76047
0.8713 High Similarity NPC280642
0.8713 High Similarity NPC92815
0.8713 High Similarity NPC476196
0.8713 High Similarity NPC188815
0.8713 High Similarity NPC96605
0.8713 High Similarity NPC218161
0.8712 High Similarity NPC476162
0.8701 High Similarity NPC282636
0.8701 High Similarity NPC294863
0.869 High Similarity NPC93215
0.869 High Similarity NPC94796
0.8683 High Similarity NPC42965
0.8675 High Similarity NPC323627
0.8675 High Similarity NPC208258
0.8675 High Similarity NPC322459
0.8675 High Similarity NPC475184
0.8675 High Similarity NPC318527
0.8675 High Similarity NPC324358
0.8667 High Similarity NPC158027
0.8667 High Similarity NPC14606
0.8667 High Similarity NPC100049
0.8667 High Similarity NPC215203
0.8667 High Similarity NPC265624
0.8667 High Similarity NPC159707
0.8667 High Similarity NPC469934
0.8667 High Similarity NPC248739
0.8667 High Similarity NPC121649
0.8667 High Similarity NPC52611
0.8667 High Similarity NPC186227
0.8667 High Similarity NPC476169
0.8667 High Similarity NPC150908
0.8667 High Similarity NPC205026
0.8659 High Similarity NPC473996
0.8659 High Similarity NPC477957
0.8659 High Similarity NPC210597
0.8655 High Similarity NPC75141
0.8655 High Similarity NPC476216
0.8655 High Similarity NPC55422
0.8655 High Similarity NPC53252
0.8655 High Similarity NPC47634
0.8647 High Similarity NPC476056
0.8647 High Similarity NPC476255
0.8647 High Similarity NPC62444
0.8642 High Similarity NPC152233
0.8639 High Similarity NPC131578
0.8639 High Similarity NPC183672
0.8639 High Similarity NPC66087
0.8639 High Similarity NPC179198
0.8639 High Similarity NPC278419
0.8636 High Similarity NPC473631
0.8636 High Similarity NPC475662
0.8636 High Similarity NPC293227
0.8636 High Similarity NPC473717
0.8631 High Similarity NPC97812
0.8623 High Similarity NPC51760
0.8623 High Similarity NPC90497
0.8623 High Similarity NPC125969
0.8621 High Similarity NPC231787
0.8614 High Similarity NPC32867
0.8614 High Similarity NPC146636
0.8614 High Similarity NPC69531
0.8613 High Similarity NPC470336
0.8613 High Similarity NPC470335
0.8613 High Similarity NPC476229
0.8613 High Similarity NPC476139
0.8606 High Similarity NPC244250
0.8606 High Similarity NPC71061
0.8606 High Similarity NPC290830
0.8606 High Similarity NPC72425
0.8606 High Similarity NPC236756
0.8606 High Similarity NPC324447
0.8606 High Similarity NPC303485
0.8606 High Similarity NPC20907
0.8606 High Similarity NPC311579
0.8606 High Similarity NPC293286
0.8606 High Similarity NPC194593
0.8605 High Similarity NPC102277
0.8605 High Similarity NPC279209
0.8598 High Similarity NPC472580
0.8598 High Similarity NPC138299
0.8598 High Similarity NPC222713
0.8598 High Similarity NPC111112
0.8598 High Similarity NPC67322
0.8598 High Similarity NPC178484
0.8598 High Similarity NPC471229
0.8598 High Similarity NPC472636
0.8596 High Similarity NPC64755
0.8596 High Similarity NPC193222
0.8596 High Similarity NPC476459
0.8588 High Similarity NPC204088
0.8588 High Similarity NPC329215
0.8588 High Similarity NPC189689
0.8588 High Similarity NPC259007
0.858 High Similarity NPC310603
0.858 High Similarity NPC473011
0.858 High Similarity NPC261271
0.858 High Similarity NPC259834
0.858 High Similarity NPC131745
0.858 High Similarity NPC475348
0.858 High Similarity NPC150164
0.858 High Similarity NPC6709
0.8571 High Similarity NPC286422
0.8571 High Similarity NPC476199
0.8571 High Similarity NPC476210
0.8571 High Similarity NPC43490
0.8571 High Similarity NPC470334
0.8571 High Similarity NPC475107
0.8563 High Similarity NPC99591
0.8563 High Similarity NPC271741
0.8563 High Similarity NPC287789
0.8563 High Similarity NPC162248
0.8555 High Similarity NPC186847
0.8555 High Similarity NPC476159
0.8555 High Similarity NPC257667
0.8555 High Similarity NPC118128
0.8555 High Similarity NPC472454
0.8555 High Similarity NPC474522
0.8554 High Similarity NPC275575
0.8554 High Similarity NPC477958
0.8554 High Similarity NPC111341
0.8554 High Similarity NPC300668
0.8554 High Similarity NPC471116
0.8554 High Similarity NPC66441
0.8554 High Similarity NPC304745
0.8554 High Similarity NPC207809
0.8554 High Similarity NPC217706
0.8554 High Similarity NPC182555
0.8554 High Similarity NPC48579
0.8554 High Similarity NPC259710

  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 NPC474276 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
0.8765 High Similarity NPD7804 Clinical (unspecified phase)
0.8675 High Similarity NPD7075 Discontinued
0.8554 High Similarity NPD8443 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8457 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD4380 Phase 2
0.8304 Intermediate Similarity NPD6959 Discontinued
0.8287 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD7768 Phase 2
0.8266 Intermediate Similarity NPD6166 Phase 2
0.8266 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8266 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7411 Suspended
0.8249 Intermediate Similarity NPD7808 Phase 3
0.8235 Intermediate Similarity NPD3749 Approved
0.8214 Intermediate Similarity NPD6801 Discontinued
0.8192 Intermediate Similarity NPD6559 Discontinued
0.8192 Intermediate Similarity NPD7251 Discontinued
0.8166 Intermediate Similarity NPD7819 Suspended
0.8136 Intermediate Similarity NPD6797 Phase 2
0.8101 Intermediate Similarity NPD8312 Approved
0.8101 Intermediate Similarity NPD8313 Approved
0.8095 Intermediate Similarity NPD6599 Discontinued
0.8079 Intermediate Similarity NPD7074 Phase 3
0.807 Intermediate Similarity NPD3882 Suspended
0.8061 Intermediate Similarity NPD6799 Approved
0.8059 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7054 Approved
0.8011 Intermediate Similarity NPD7473 Discontinued
0.7978 Intermediate Similarity NPD7472 Approved
0.7966 Intermediate Similarity NPD3818 Discontinued
0.7931 Intermediate Similarity NPD5494 Approved
0.7907 Intermediate Similarity NPD3817 Phase 2
0.7895 Intermediate Similarity NPD1934 Approved
0.788 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7866 Intermediate Similarity NPD1549 Phase 2
0.7861 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1512 Approved
0.7845 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD6232 Discontinued
0.7818 Intermediate Similarity NPD2800 Approved
0.7814 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD5403 Approved
0.7805 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3750 Approved
0.7765 Intermediate Similarity NPD3751 Discontinued
0.776 Intermediate Similarity NPD7435 Discontinued
0.7746 Intermediate Similarity NPD8455 Phase 2
0.7746 Intermediate Similarity NPD2801 Approved
0.7738 Intermediate Similarity NPD7390 Discontinued
0.7738 Intermediate Similarity NPD1511 Approved
0.7725 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD5844 Phase 1
0.772 Intermediate Similarity NPD7871 Phase 2
0.772 Intermediate Similarity NPD7870 Phase 2
0.7719 Intermediate Similarity NPD7458 Discontinued
0.7701 Intermediate Similarity NPD5402 Approved
0.7696 Intermediate Similarity NPD6782 Approved
0.7696 Intermediate Similarity NPD6779 Approved
0.7696 Intermediate Similarity NPD6778 Approved
0.7696 Intermediate Similarity NPD6776 Approved
0.7696 Intermediate Similarity NPD6777 Approved
0.7696 Intermediate Similarity NPD6780 Approved
0.7696 Intermediate Similarity NPD6781 Approved
0.7692 Intermediate Similarity NPD5401 Approved
0.7683 Intermediate Similarity NPD1510 Phase 2
0.7676 Intermediate Similarity NPD8150 Discontinued
0.7676 Intermediate Similarity NPD8434 Phase 2
0.7669 Intermediate Similarity NPD1607 Approved
0.7668 Intermediate Similarity NPD7696 Phase 3
0.7668 Intermediate Similarity NPD7697 Approved
0.7668 Intermediate Similarity NPD7698 Approved
0.7654 Intermediate Similarity NPD1240 Approved
0.764 Intermediate Similarity NPD3787 Discontinued
0.7636 Intermediate Similarity NPD2796 Approved
0.7614 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD7874 Approved
0.7605 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7701 Phase 2
0.7598 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7801 Approved
0.7563 Intermediate Similarity NPD8151 Discontinued
0.756 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD8320 Phase 1
0.7538 Intermediate Similarity NPD8319 Approved
0.7514 Intermediate Similarity NPD3226 Approved
0.75 Intermediate Similarity NPD3926 Phase 2
0.75 Intermediate Similarity NPD7699 Phase 2
0.75 Intermediate Similarity NPD7700 Phase 2
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD2344 Approved
0.7485 Intermediate Similarity NPD2532 Approved
0.7485 Intermediate Similarity NPD2533 Approved
0.7485 Intermediate Similarity NPD2534 Approved
0.7472 Intermediate Similarity NPD919 Approved
0.747 Intermediate Similarity NPD3748 Approved
0.747 Intermediate Similarity NPD2799 Discontinued
0.7455 Intermediate Similarity NPD6651 Approved
0.7443 Intermediate Similarity NPD1465 Phase 2
0.7435 Intermediate Similarity NPD6534 Approved
0.7435 Intermediate Similarity NPD6535 Approved
0.7425 Intermediate Similarity NPD6099 Approved
0.7425 Intermediate Similarity NPD6100 Approved
0.7423 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7783 Phase 2
0.7399 Intermediate Similarity NPD920 Approved
0.7389 Intermediate Similarity NPD7199 Phase 2
0.7389 Intermediate Similarity NPD1247 Approved
0.7377 Intermediate Similarity NPD7228 Approved
0.7374 Intermediate Similarity NPD7584 Approved
0.7366 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD4628 Phase 3
0.7347 Intermediate Similarity NPD6823 Phase 2
0.7337 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1551 Phase 2
0.7321 Intermediate Similarity NPD2935 Discontinued
0.7316 Intermediate Similarity NPD4287 Approved
0.731 Intermediate Similarity NPD2309 Approved
0.7301 Intermediate Similarity NPD4908 Phase 1
0.7284 Intermediate Similarity NPD2798 Approved
0.7283 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2346 Discontinued
0.7278 Intermediate Similarity NPD6234 Discontinued
0.7268 Intermediate Similarity NPD2403 Approved
0.7267 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD5953 Discontinued
0.7251 Intermediate Similarity NPD7003 Approved
0.7243 Intermediate Similarity NPD7286 Phase 2
0.7219 Intermediate Similarity NPD5408 Approved
0.7219 Intermediate Similarity NPD5404 Approved
0.7219 Intermediate Similarity NPD5405 Approved
0.7219 Intermediate Similarity NPD5406 Approved
0.7212 Intermediate Similarity NPD2313 Discontinued
0.7212 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD37 Approved
0.7186 Intermediate Similarity NPD6355 Discontinued
0.7184 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD4967 Phase 2
0.7167 Intermediate Similarity NPD4965 Approved
0.7167 Intermediate Similarity NPD4966 Approved
0.7158 Intermediate Similarity NPD7229 Phase 3
0.7151 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD7685 Pre-registration
0.7126 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6798 Discontinued
0.7108 Intermediate Similarity NPD3764 Approved
0.7101 Intermediate Similarity NPD7097 Phase 1
0.7081 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD4360 Phase 2
0.7077 Intermediate Similarity NPD4363 Phase 3
0.7076 Intermediate Similarity NPD1471 Phase 3
0.7065 Intermediate Similarity NPD5710 Approved
0.7065 Intermediate Similarity NPD5711 Approved
0.7045 Intermediate Similarity NPD5049 Phase 3
0.7037 Intermediate Similarity NPD7240 Approved
0.7024 Intermediate Similarity NPD943 Approved
0.7012 Intermediate Similarity NPD1203 Approved
0.7011 Intermediate Similarity NPD2354 Approved
0.7006 Intermediate Similarity NPD3268 Approved
0.7005 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7799 Discontinued
0.6995 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6995 Remote Similarity NPD7585 Approved
0.6989 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6832 Phase 2
0.6985 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6982 Remote Similarity NPD1933 Approved
0.698 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6977 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6233 Phase 2
0.6961 Remote Similarity NPD5761 Phase 2
0.6961 Remote Similarity NPD5760 Phase 2
0.6959 Remote Similarity NPD4308 Phase 3
0.6954 Remote Similarity NPD4361 Phase 2
0.6954 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6946 Remote Similarity NPD4625 Phase 3
0.6946 Remote Similarity NPD7583 Approved
0.6946 Remote Similarity NPD7095 Approved
0.6944 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6213 Phase 3
0.6939 Remote Similarity NPD6212 Phase 3
0.6923 Remote Similarity NPD4060 Phase 1
0.6923 Remote Similarity NPD4288 Approved
0.6919 Remote Similarity NPD8127 Discontinued
0.6919 Remote Similarity NPD8366 Approved
0.6916 Remote Similarity NPD8059 Phase 3
0.6916 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7177 Discontinued
0.6914 Remote Similarity NPD6190 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