Structure

Physi-Chem Properties

Molecular Weight:  558.12
Volume:  535.879
LogP:  3.934
LogD:  2.312
LogS:  -5.257
# Rotatable Bonds:  3
TPSA:  201.28
# H-Bond Aceptor:  11
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.144
Synthetic Accessibility Score:  3.985
Fsp3:  0.1
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.94
MDCK Permeability:  6.146091436676215e-06
Pgp-inhibitor:  0.018
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.165
20% Bioavailability (F20%):  0.795
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  94.8076400756836%
Volume Distribution (VD):  0.422
Pgp-substrate:  5.513161659240723%

ADMET: Metabolism

CYP1A2-inhibitor:  0.483
CYP1A2-substrate:  0.101
CYP2C19-inhibitor:  0.142
CYP2C19-substrate:  0.037
CYP2C9-inhibitor:  0.678
CYP2C9-substrate:  0.912
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.252
CYP3A4-inhibitor:  0.132
CYP3A4-substrate:  0.085

ADMET: Excretion

Clearance (CL):  7.603
Half-life (T1/2):  0.771

ADMET: Toxicity

hERG Blockers:  0.076
Human Hepatotoxicity (H-HT):  0.326
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.702
Rat Oral Acute Toxicity:  0.418
Maximum Recommended Daily Dose:  0.96
Skin Sensitization:  0.926
Carcinogencity:  0.051
Eye Corrosion:  0.003
Eye Irritation:  0.914
Respiratory Toxicity:  0.055

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

  Natural Product: NPC224851

Natural Product ID:  NPC224851
Common Name*:   (2S,2's,3R)-2'-(3,4-Dihydroxyphenyl)-5,5',7,7'-Tetrahydroxy-2-(4-Hydroxyphenyl)-3,8'-Bichroman-4,4'-Dione
IUPAC Name:   (2S)-8-[(2S,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  IMIXFUXOSFSXPC-DETITRACSA-N
Standard InCHI:  InChI=1S/C30H22O11/c31-14-4-1-12(2-5-14)29-27(28(39)25-18(35)8-15(32)9-23(25)41-29)26-20(37)10-19(36)24-21(38)11-22(40-30(24)26)13-3-6-16(33)17(34)7-13/h1-10,22,27,29,31-37H,11H2/t22-,27-,29+/m0/s1
SMILES:  Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1c1c(O)cc(c2c1O[C@@H](CC2=O)c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL445452
PubChem CID:   176988
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
NPO32446 calophyllum panciflorum Species Calophyllaceae Eukaryota n.a. n.a. n.a. PMID[10654415]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO11682 Eusynstyela latericius Species Styelidae Eukaryota n.a. n.a. n.a. PMID[19505081]
NPO11682 Eusynstyela latericius Species Styelidae Eukaryota n.a. Hixson Island (2145.0' S, 15017.5' E); Percy Island Group in the Central Great Barrier Reef, Queensland, Australia; Rib Reef (1828.7' S, 14652.3' E) n.a. PMID[19505081]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13664 Garcinia prainiana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14421 Vellozia compacta Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4680 Neatostema apulum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15065 Daniellia ogea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9336 Rhodococcus jostii Species 0cardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11682 Eusynstyela latericius Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17151 Schizaphis graminum Species Aphididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13172 Xylaria telfairii Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10893 Polyporus ciliatus Species Polyporaceae 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
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 170000.0 nM PMID[518037]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 96.0 % PMID[518037]
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[518038]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[518038]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 42.5 % PMID[518038]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 71.3 % PMID[518038]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 90.6 % PMID[518038]

☑ 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 NPC224851 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
0.9873 High Similarity NPC171985
0.9873 High Similarity NPC320741
0.975 High Similarity NPC472454
0.975 High Similarity NPC186847
0.975 High Similarity NPC257667
0.9748 High Similarity NPC107627
0.9557 High Similarity NPC477841
0.9487 High Similarity NPC69531
0.9437 High Similarity NPC477840
0.9434 High Similarity NPC219927
0.9383 High Similarity NPC300307
0.9383 High Similarity NPC475212
0.9379 High Similarity NPC272560
0.9375 High Similarity NPC63438
0.9371 High Similarity NPC142252
0.9363 High Similarity NPC32867
0.9341 High Similarity NPC132111
0.9337 High Similarity NPC324742
0.9321 High Similarity NPC260266
0.9317 High Similarity NPC259757
0.9304 High Similarity NPC475184
0.9304 High Similarity NPC471209
0.9299 High Similarity NPC258474
0.9299 High Similarity NPC134171
0.9299 High Similarity NPC201227
0.9299 High Similarity NPC300668
0.9277 High Similarity NPC265380
0.9268 High Similarity NPC262580
0.9268 High Similarity NPC81332
0.9268 High Similarity NPC212038
0.9268 High Similarity NPC289396
0.9268 High Similarity NPC4200
0.9268 High Similarity NPC271848
0.925 High Similarity NPC301256
0.925 High Similarity NPC312273
0.9245 High Similarity NPC53545
0.9245 High Similarity NPC117418
0.9245 High Similarity NPC295090
0.9241 High Similarity NPC61112
0.9241 High Similarity NPC309648
0.9241 High Similarity NPC198489
0.9236 High Similarity NPC213896
0.9236 High Similarity NPC192083
0.9226 High Similarity NPC150977
0.9226 High Similarity NPC321916
0.9222 High Similarity NPC185275
0.9212 High Similarity NPC98583
0.9207 High Similarity NPC102277
0.9207 High Similarity NPC279209
0.9202 High Similarity NPC14662
0.9198 High Similarity NPC62261
0.9198 High Similarity NPC58223
0.9198 High Similarity NPC36916
0.9198 High Similarity NPC473010
0.9198 High Similarity NPC7688
0.9198 High Similarity NPC7154
0.9198 High Similarity NPC72787
0.9198 High Similarity NPC36
0.9198 High Similarity NPC125039
0.9193 High Similarity NPC473011
0.9193 High Similarity NPC476247
0.9193 High Similarity NPC474150
0.9193 High Similarity NPC473012
0.9193 High Similarity NPC474162
0.9182 High Similarity NPC1796
0.9182 High Similarity NPC287789
0.9182 High Similarity NPC271741
0.9177 High Similarity NPC321779
0.9177 High Similarity NPC182555
0.9177 High Similarity NPC66441
0.9172 High Similarity NPC174086
0.9172 High Similarity NPC318119
0.9172 High Similarity NPC106976
0.9162 High Similarity NPC471789
0.9152 High Similarity NPC65333
0.9152 High Similarity NPC100251
0.9141 High Similarity NPC120593
0.9136 High Similarity NPC476295
0.9136 High Similarity NPC473009
0.9136 High Similarity NPC12461
0.913 High Similarity NPC158188
0.913 High Similarity NPC472632
0.913 High Similarity NPC134783
0.913 High Similarity NPC289771
0.913 High Similarity NPC228383
0.913 High Similarity NPC66618
0.913 High Similarity NPC266314
0.913 High Similarity NPC305987
0.913 High Similarity NPC288131
0.913 High Similarity NPC471212
0.913 High Similarity NPC26326
0.913 High Similarity NPC84324
0.913 High Similarity NPC471211
0.913 High Similarity NPC113163
0.913 High Similarity NPC165970
0.913 High Similarity NPC471210
0.9125 High Similarity NPC51760
0.9125 High Similarity NPC210459
0.9125 High Similarity NPC123544
0.9125 High Similarity NPC51247
0.9119 High Similarity NPC195796
0.9119 High Similarity NPC35038
0.9119 High Similarity NPC278778
0.9119 High Similarity NPC291878
0.9114 High Similarity NPC74924
0.9114 High Similarity NPC121568
0.9114 High Similarity NPC298692
0.9091 High Similarity NPC476365
0.9091 High Similarity NPC103307
0.9085 High Similarity NPC243877
0.908 High Similarity NPC293319
0.908 High Similarity NPC471788
0.9074 High Similarity NPC220912
0.9074 High Similarity NPC474033
0.9074 High Similarity NPC15374
0.9074 High Similarity NPC206605
0.9074 High Similarity NPC474034
0.9068 High Similarity NPC98023
0.9068 High Similarity NPC321399
0.9068 High Similarity NPC119209
0.9068 High Similarity NPC192686
0.9068 High Similarity NPC101731
0.9068 High Similarity NPC292863
0.9068 High Similarity NPC36217
0.9068 High Similarity NPC184326
0.9068 High Similarity NPC118256
0.9068 High Similarity NPC226462
0.9068 High Similarity NPC42965
0.9068 High Similarity NPC174953
0.9068 High Similarity NPC297212
0.9064 High Similarity NPC73929
0.9064 High Similarity NPC179947
0.9064 High Similarity NPC47905
0.9064 High Similarity NPC139683
0.9062 High Similarity NPC299520
0.9062 High Similarity NPC129684
0.9062 High Similarity NPC291508
0.9062 High Similarity NPC112954
0.9062 High Similarity NPC472598
0.9062 High Similarity NPC27337
0.9062 High Similarity NPC257166
0.9062 High Similarity NPC474055
0.9057 High Similarity NPC67396
0.9057 High Similarity NPC477503
0.9057 High Similarity NPC45849
0.9057 High Similarity NPC200761
0.9057 High Similarity NPC470327
0.9038 High Similarity NPC188679
0.9038 High Similarity NPC122894
0.9038 High Similarity NPC3036
0.9038 High Similarity NPC294852
0.9038 High Similarity NPC321011
0.9036 High Similarity NPC248593
0.9036 High Similarity NPC28589
0.903 High Similarity NPC188079
0.903 High Similarity NPC177480
0.9024 High Similarity NPC13481
0.9024 High Similarity NPC207575
0.9024 High Similarity NPC471213
0.9024 High Similarity NPC251336
0.9018 High Similarity NPC272064
0.9018 High Similarity NPC273959
0.9018 High Similarity NPC186686
0.9012 High Similarity NPC471499
0.9012 High Similarity NPC474038
0.9012 High Similarity NPC18380
0.9012 High Similarity NPC34089
0.9012 High Similarity NPC137232
0.9012 High Similarity NPC472634
0.9012 High Similarity NPC196179
0.9012 High Similarity NPC472275
0.9012 High Similarity NPC473618
0.9012 High Similarity NPC173137
0.9006 High Similarity NPC250214
0.9006 High Similarity NPC46736
0.9006 High Similarity NPC85121
0.9006 High Similarity NPC284127
0.9006 High Similarity NPC476410
0.9006 High Similarity NPC473990
0.9006 High Similarity NPC95936
0.9006 High Similarity NPC22192
0.9006 High Similarity NPC304322
0.9006 High Similarity NPC112380
0.9006 High Similarity NPC195167
0.9006 High Similarity NPC105584
0.9006 High Similarity NPC172202
0.9006 High Similarity NPC15815
0.9 High Similarity NPC78492
0.9 High Similarity NPC209614
0.9 High Similarity NPC208152
0.9 High Similarity NPC472626
0.9 High Similarity NPC24640
0.9 High Similarity NPC470328
0.8994 High Similarity NPC326592
0.8994 High Similarity NPC112701
0.8994 High Similarity NPC109594
0.8994 High Similarity NPC18727
0.8987 High Similarity NPC204515
0.8982 High Similarity NPC168789
0.8981 High Similarity NPC183959

  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 NPC224851 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
0.9236 High Similarity NPD2393 Clinical (unspecified phase)
0.9198 High Similarity NPD6167 Clinical (unspecified phase)
0.9198 High Similarity NPD6168 Clinical (unspecified phase)
0.9198 High Similarity NPD6166 Phase 2
0.9012 High Similarity NPD6959 Discontinued
0.8931 High Similarity NPD1934 Approved
0.8882 High Similarity NPD4868 Clinical (unspecified phase)
0.882 High Similarity NPD8443 Clinical (unspecified phase)
0.881 High Similarity NPD7993 Clinical (unspecified phase)
0.875 High Similarity NPD7074 Phase 3
0.872 High Similarity NPD5494 Approved
0.869 High Similarity NPD7054 Approved
0.8688 High Similarity NPD4380 Phase 2
0.8662 High Similarity NPD1511 Approved
0.8642 High Similarity NPD2801 Approved
0.8639 High Similarity NPD7472 Approved
0.8588 High Similarity NPD6797 Phase 2
0.8553 High Similarity NPD1512 Approved
0.8538 High Similarity NPD7251 Discontinued
0.8521 High Similarity NPD3818 Discontinued
0.8512 High Similarity NPD7852 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7473 Discontinued
0.8424 Intermediate Similarity NPD3882 Suspended
0.8405 Intermediate Similarity NPD7411 Suspended
0.8397 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD6232 Discontinued
0.8382 Intermediate Similarity NPD7808 Phase 3
0.8382 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8375 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD7075 Discontinued
0.8363 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD1549 Phase 2
0.8303 Intermediate Similarity NPD7819 Suspended
0.8256 Intermediate Similarity NPD5844 Phase 1
0.8253 Intermediate Similarity NPD3817 Phase 2
0.8229 Intermediate Similarity NPD8313 Approved
0.8229 Intermediate Similarity NPD8312 Approved
0.8204 Intermediate Similarity NPD7768 Phase 2
0.8193 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD1465 Phase 2
0.8101 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD3749 Approved
0.8038 Intermediate Similarity NPD1510 Phase 2
0.8024 Intermediate Similarity NPD6801 Discontinued
0.8011 Intermediate Similarity NPD6559 Discontinued
0.7987 Intermediate Similarity NPD2796 Approved
0.7975 Intermediate Similarity NPD7390 Discontinued
0.7929 Intermediate Similarity NPD5402 Approved
0.7927 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD943 Approved
0.7814 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD1240 Approved
0.7785 Intermediate Similarity NPD1613 Approved
0.7784 Intermediate Similarity NPD7228 Approved
0.7771 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD8455 Phase 2
0.7759 Intermediate Similarity NPD3787 Discontinued
0.7758 Intermediate Similarity NPD6799 Approved
0.773 Intermediate Similarity NPD2800 Approved
0.773 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD5403 Approved
0.7714 Intermediate Similarity NPD3926 Phase 2
0.7711 Intermediate Similarity NPD2534 Approved
0.7711 Intermediate Similarity NPD2532 Approved
0.7711 Intermediate Similarity NPD2533 Approved
0.7692 Intermediate Similarity NPD6599 Discontinued
0.7688 Intermediate Similarity NPD1607 Approved
0.7688 Intermediate Similarity NPD6234 Discontinued
0.7684 Intermediate Similarity NPD3751 Discontinued
0.7683 Intermediate Similarity NPD3750 Approved
0.7669 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7668 Intermediate Similarity NPD8151 Discontinued
0.7643 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7637 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD3226 Approved
0.7605 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD5401 Approved
0.76 Intermediate Similarity NPD1247 Approved
0.76 Intermediate Similarity NPD7199 Phase 2
0.758 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD2935 Discontinued
0.7529 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD6778 Approved
0.7526 Intermediate Similarity NPD6776 Approved
0.7526 Intermediate Similarity NPD6782 Approved
0.7526 Intermediate Similarity NPD6777 Approved
0.7526 Intermediate Similarity NPD6779 Approved
0.7526 Intermediate Similarity NPD6780 Approved
0.7526 Intermediate Similarity NPD6781 Approved
0.7516 Intermediate Similarity NPD230 Phase 1
0.7515 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD37 Approved
0.75 Intermediate Similarity NPD8150 Discontinued
0.7486 Intermediate Similarity NPD919 Approved
0.7485 Intermediate Similarity NPD2799 Discontinued
0.7485 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD4965 Approved
0.7471 Intermediate Similarity NPD4967 Phase 2
0.7471 Intermediate Similarity NPD4966 Approved
0.7469 Intermediate Similarity NPD6651 Approved
0.7459 Intermediate Similarity NPD5953 Discontinued
0.7447 Intermediate Similarity NPD4360 Phase 2
0.7447 Intermediate Similarity NPD4363 Phase 3
0.7439 Intermediate Similarity NPD1551 Phase 2
0.7439 Intermediate Similarity NPD6099 Approved
0.7439 Intermediate Similarity NPD6100 Approved
0.7425 Intermediate Similarity NPD6190 Approved
0.7412 Intermediate Similarity NPD920 Approved
0.7411 Intermediate Similarity NPD7783 Phase 2
0.7411 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7409 Intermediate Similarity NPD7696 Phase 3
0.7409 Intermediate Similarity NPD7435 Discontinued
0.7409 Intermediate Similarity NPD7697 Approved
0.7409 Intermediate Similarity NPD7698 Approved
0.7396 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD2344 Approved
0.7394 Intermediate Similarity NPD2346 Discontinued
0.7378 Intermediate Similarity NPD3748 Approved
0.7375 Intermediate Similarity NPD3027 Phase 3
0.7371 Intermediate Similarity NPD7871 Phase 2
0.7371 Intermediate Similarity NPD7870 Phase 2
0.7368 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD4628 Phase 3
0.736 Intermediate Similarity NPD7229 Phase 3
0.7348 Intermediate Similarity NPD7286 Phase 2
0.7347 Intermediate Similarity NPD7701 Phase 2
0.7333 Intermediate Similarity NPD5405 Approved
0.7333 Intermediate Similarity NPD5408 Approved
0.7333 Intermediate Similarity NPD5406 Approved
0.7333 Intermediate Similarity NPD5404 Approved
0.7329 Intermediate Similarity NPD2313 Discontinued
0.7329 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7458 Discontinued
0.7322 Intermediate Similarity NPD7240 Approved
0.7322 Intermediate Similarity NPD7685 Pre-registration
0.7308 Intermediate Similarity NPD1610 Phase 2
0.7278 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD6823 Phase 2
0.7267 Intermediate Similarity NPD1653 Approved
0.7263 Intermediate Similarity NPD6535 Approved
0.7263 Intermediate Similarity NPD5710 Approved
0.7263 Intermediate Similarity NPD5711 Approved
0.7263 Intermediate Similarity NPD6534 Approved
0.7262 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD7699 Phase 2
0.724 Intermediate Similarity NPD7700 Phase 2
0.7236 Intermediate Similarity NPD7801 Approved
0.7235 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2309 Approved
0.7219 Intermediate Similarity NPD8434 Phase 2
0.7202 Intermediate Similarity NPD1243 Approved
0.7197 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD447 Suspended
0.7194 Intermediate Similarity NPD8320 Phase 1
0.7194 Intermediate Similarity NPD8319 Approved
0.7186 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7874 Approved
0.716 Intermediate Similarity NPD8166 Discontinued
0.716 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7003 Approved
0.7143 Intermediate Similarity NPD4287 Approved
0.7143 Intermediate Similarity NPD2861 Phase 2
0.7121 Intermediate Similarity NPD7584 Approved
0.7111 Intermediate Similarity NPD8127 Discontinued
0.7104 Intermediate Similarity NPD7177 Discontinued
0.7091 Intermediate Similarity NPD5124 Phase 1
0.7091 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7680 Approved
0.7055 Intermediate Similarity NPD4625 Phase 3
0.7052 Intermediate Similarity NPD6273 Approved
0.7047 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD4361 Phase 2
0.7037 Intermediate Similarity NPD9494 Approved
0.7031 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD6212 Phase 3
0.7031 Intermediate Similarity NPD6213 Phase 3
0.7026 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD1203 Approved
0.7019 Intermediate Similarity NPD1470 Approved
0.7012 Intermediate Similarity NPD3268 Approved
0.7012 Intermediate Similarity NPD6798 Discontinued
0.7006 Intermediate Similarity NPD7097 Phase 1
0.7006 Intermediate Similarity NPD6844 Discontinued
0.7005 Intermediate Similarity NPD7549 Discontinued
0.6994 Remote Similarity NPD6832 Phase 2
0.6988 Remote Similarity NPD1933 Approved
0.6982 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6982 Remote Similarity NPD7266 Discontinued
0.6981 Remote Similarity NPD1201 Approved
0.6975 Remote Similarity NPD2798 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