Structure

Physi-Chem Properties

Molecular Weight:  482.12
Volume:  459.711
LogP:  2.21
LogD:  2.416
LogS:  -4.837
# Rotatable Bonds:  4
TPSA:  155.14
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.374
Synthetic Accessibility Score:  3.992
Fsp3:  0.24
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.4
MDCK Permeability:  8.40742632135516e-06
Pgp-inhibitor:  0.906
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.25
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.024
Plasma Protein Binding (PPB):  97.03462982177734%
Volume Distribution (VD):  0.636
Pgp-substrate:  6.3073530197143555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.054
CYP1A2-substrate:  0.116
CYP2C19-inhibitor:  0.102
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.721
CYP2C9-substrate:  0.778
CYP2D6-inhibitor:  0.268
CYP2D6-substrate:  0.358
CYP3A4-inhibitor:  0.778
CYP3A4-substrate:  0.262

ADMET: Excretion

Clearance (CL):  3.536
Half-life (T1/2):  0.336

ADMET: Toxicity

hERG Blockers:  0.058
Human Hepatotoxicity (H-HT):  0.173
Drug-inuced Liver Injury (DILI):  0.9
AMES Toxicity:  0.311
Rat Oral Acute Toxicity:  0.17
Maximum Recommended Daily Dose:  0.04
Skin Sensitization:  0.141
Carcinogencity:  0.63
Eye Corrosion:  0.003
Eye Irritation:  0.233
Respiratory Toxicity:  0.033

Download Data

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

  Natural Product: NPC72787

Natural Product ID:  NPC72787
Common Name*:   Isosilybin A
IUPAC Name:   (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  FDQAOULAVFHKBX-HKTJVKLFSA-N
Standard InCHI:  InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
SMILES:  OC[C@H]1Oc2cc(ccc2O[C@@H]1c1ccc(c(c1)OC)O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@@H]1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL592676
PubChem CID:   11059920
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001844] Flavonolignans

*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
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[12643908]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[16394559]
NPO21361 Anastatica hierochuntica Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[20189399]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24456525]
NPO5645 Silybum marianum Species Asteraceae Eukaryota Seeds n.a. n.a. PMID[24597776]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21361 Anastatica hierochuntica Species Brassicaceae 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
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 5.1 % PMID[488189]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 7.0 % PMID[488189]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 13.1 % PMID[488189]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 29.4 % PMID[488189]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 42.7 % PMID[488189]
NPT43 Individual Protein Tyrosinase Agaricus bisporus KA = 6.314 10'6L/mol PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus KSV = 0.2668 10'4L/mol PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus TIME = 0.08333 hr PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Kis = 29.5 uM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Ki = 12300.0 nM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Ki = 12400.0 nM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 16700.0 nM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Ki = 1100.0 nM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 2100.0 nM PMID[488195]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Kis = 3.2 uM PMID[488195]
NPT2 Others Unspecified Inhibition = 11.7 % PMID[488189]
NPT2 Others Unspecified Inhibition = 19.8 % PMID[488189]
NPT2 Others Unspecified Inhibition = 50.2 % PMID[488189]
NPT2 Others Unspecified Inhibition = 72.1 % PMID[488189]
NPT27 Others Unspecified Inhibition = -2.2 % PMID[488189]
NPT27 Others Unspecified Inhibition = -1.5 % PMID[488189]
NPT27 Others Unspecified Inhibition = -2.5 % PMID[488189]
NPT27 Others Unspecified Inhibition = 16.0 % PMID[488189]
NPT2 Others Unspecified Ratio = 0.73 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.97 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.85 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.56 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 1.11 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 1.26 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 1.12 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.6 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.68 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.63 n.a. PMID[488189]
NPT2 Others Unspecified Ratio = 0.36 n.a. PMID[488189]
NPT2 Others Unspecified IC50 = 10000.0 nM PMID[488189]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 80000.0 nM PMID[488190]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens FC = 2.08 n.a. PMID[488191]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus EC50 = 32.0 ug.mL-1 PMID[488193]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBIC = 124.0 ug ml-1 PMID[488193]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 1.42 % PMID[488194]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = -1.184 % PMID[488196]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.09 % PMID[488197]

☑ 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 NPC72787 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 NPC36
1.0 High Similarity NPC58223
1.0 High Similarity NPC7154
1.0 High Similarity NPC36916
1.0 High Similarity NPC125039
1.0 High Similarity NPC7688
0.9679 High Similarity NPC165970
0.9679 High Similarity NPC305987
0.9679 High Similarity NPC288131
0.9679 High Similarity NPC158188
0.9679 High Similarity NPC84324
0.9679 High Similarity NPC66618
0.9679 High Similarity NPC113163
0.9623 High Similarity NPC14662
0.9623 High Similarity NPC295082
0.962 High Similarity NPC477840
0.9618 High Similarity NPC477841
0.9615 High Similarity NPC101731
0.956 High Similarity NPC471213
0.9554 High Similarity NPC471499
0.9554 High Similarity NPC142252
0.9551 High Similarity NPC172202
0.9551 High Similarity NPC284127
0.9551 High Similarity NPC476410
0.9548 High Similarity NPC320825
0.9548 High Similarity NPC326037
0.9548 High Similarity NPC13858
0.9548 High Similarity NPC250922
0.9503 High Similarity NPC102277
0.9503 High Similarity NPC279209
0.95 High Similarity NPC260266
0.95 High Similarity NPC243877
0.9494 High Similarity NPC219927
0.9494 High Similarity NPC476247
0.949 High Similarity NPC470326
0.949 High Similarity NPC287328
0.949 High Similarity NPC282009
0.9487 High Similarity NPC471479
0.9487 High Similarity NPC52530
0.9487 High Similarity NPC471515
0.9487 High Similarity NPC183851
0.9487 High Similarity NPC63454
0.9444 High Similarity NPC186847
0.9444 High Similarity NPC472454
0.9444 High Similarity NPC257667
0.9441 High Similarity NPC475212
0.9434 High Similarity NPC472625
0.943 High Similarity NPC472632
0.943 High Similarity NPC289771
0.943 High Similarity NPC173137
0.943 High Similarity NPC26326
0.9427 High Similarity NPC22192
0.9423 High Similarity NPC471500
0.9419 High Similarity NPC18727
0.9375 High Similarity NPC224280
0.9375 High Similarity NPC62261
0.9371 High Similarity NPC474034
0.9371 High Similarity NPC474033
0.9367 High Similarity NPC470183
0.9367 High Similarity NPC174953
0.9367 High Similarity NPC263449
0.9363 High Similarity NPC67876
0.9363 High Similarity NPC472598
0.9363 High Similarity NPC474055
0.9355 High Similarity NPC61506
0.9355 High Similarity NPC240476
0.9355 High Similarity NPC9743
0.9355 High Similarity NPC36835
0.9355 High Similarity NPC302950
0.9355 High Similarity NPC246162
0.9355 High Similarity NPC219582
0.9355 High Similarity NPC19721
0.9355 High Similarity NPC260491
0.9355 High Similarity NPC236637
0.9321 High Similarity NPC270578
0.9321 High Similarity NPC52382
0.9317 High Similarity NPC5778
0.9317 High Similarity NPC477517
0.9317 High Similarity NPC236934
0.9308 High Similarity NPC471211
0.9308 High Similarity NPC474038
0.9308 High Similarity NPC112418
0.9308 High Similarity NPC472634
0.9308 High Similarity NPC471212
0.9308 High Similarity NPC471210
0.9308 High Similarity NPC308992
0.9304 High Similarity NPC473990
0.9304 High Similarity NPC53545
0.9304 High Similarity NPC117418
0.9299 High Similarity NPC195796
0.9299 High Similarity NPC291878
0.9299 High Similarity NPC35038
0.9299 High Similarity NPC278778
0.9295 High Similarity NPC27532
0.9295 High Similarity NPC325028
0.9295 High Similarity NPC246328
0.9295 High Similarity NPC256346
0.9264 High Similarity NPC231194
0.9264 High Similarity NPC177731
0.9264 High Similarity NPC105095
0.9264 High Similarity NPC79056
0.9264 High Similarity NPC285197
0.9264 High Similarity NPC51326
0.9264 High Similarity NPC67105
0.9264 High Similarity NPC476365
0.9264 High Similarity NPC95866
0.9264 High Similarity NPC44328
0.9259 High Similarity NPC160156
0.9259 High Similarity NPC92565
0.9255 High Similarity NPC234052
0.925 High Similarity NPC471745
0.925 High Similarity NPC472635
0.9245 High Similarity NPC192686
0.9245 High Similarity NPC475784
0.9245 High Similarity NPC118256
0.9245 High Similarity NPC119209
0.9245 High Similarity NPC472631
0.9245 High Similarity NPC472630
0.9245 High Similarity NPC471744
0.9241 High Similarity NPC162869
0.9241 High Similarity NPC471209
0.9241 High Similarity NPC474208
0.9241 High Similarity NPC156057
0.9241 High Similarity NPC475267
0.9241 High Similarity NPC474836
0.9241 High Similarity NPC27337
0.9241 High Similarity NPC48208
0.9241 High Similarity NPC291508
0.9236 High Similarity NPC45849
0.9236 High Similarity NPC200761
0.9236 High Similarity NPC470327
0.9236 High Similarity NPC321779
0.9236 High Similarity NPC477503
0.9231 High Similarity NPC472912
0.9226 High Similarity NPC338131
0.9217 High Similarity NPC217520
0.9217 High Similarity NPC139571
0.9212 High Similarity NPC294629
0.9212 High Similarity NPC16194
0.9212 High Similarity NPC220173
0.9212 High Similarity NPC294815
0.9212 High Similarity NPC476472
0.9212 High Similarity NPC473327
0.9212 High Similarity NPC19108
0.9207 High Similarity NPC33054
0.9207 High Similarity NPC471725
0.9207 High Similarity NPC155877
0.9207 High Similarity NPC47140
0.9207 High Similarity NPC26230
0.9207 High Similarity NPC256760
0.9207 High Similarity NPC203259
0.9207 High Similarity NPC81332
0.9207 High Similarity NPC471748
0.9207 High Similarity NPC262580
0.9207 High Similarity NPC134532
0.9207 High Similarity NPC212038
0.9207 High Similarity NPC60735
0.9207 High Similarity NPC289396
0.9207 High Similarity NPC176740
0.9207 High Similarity NPC67134
0.9207 High Similarity NPC271848
0.9202 High Similarity NPC203050
0.9202 High Similarity NPC326877
0.9202 High Similarity NPC195257
0.9202 High Similarity NPC219904
0.9202 High Similarity NPC223747
0.9202 High Similarity NPC177480
0.9202 High Similarity NPC293629
0.9202 High Similarity NPC43587
0.9202 High Similarity NPC227508
0.9202 High Similarity NPC229687
0.9202 High Similarity NPC107627
0.9202 High Similarity NPC209296
0.9202 High Similarity NPC188079
0.9202 High Similarity NPC120099
0.9202 High Similarity NPC225434
0.9198 High Similarity NPC21100
0.9198 High Similarity NPC197285
0.9198 High Similarity NPC115674
0.9198 High Similarity NPC210073
0.9198 High Similarity NPC224851
0.9193 High Similarity NPC29830
0.9187 High Similarity NPC134783
0.9182 High Similarity NPC55738
0.9182 High Similarity NPC123544
0.9182 High Similarity NPC152904
0.9177 High Similarity NPC201837
0.9177 High Similarity NPC235165
0.9177 High Similarity NPC209614
0.9177 High Similarity NPC470328
0.9177 High Similarity NPC208152
0.9177 High Similarity NPC474638
0.9177 High Similarity NPC255106
0.9177 High Similarity NPC472626
0.9177 High Similarity NPC78492
0.9172 High Similarity NPC192083
0.9172 High Similarity NPC213896
0.9172 High Similarity NPC141212
0.9172 High Similarity NPC58382
0.9172 High Similarity NPC162351

  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 NPC72787 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
1.0 High Similarity NPD6166 Phase 2
1.0 High Similarity NPD6167 Clinical (unspecified phase)
1.0 High Similarity NPD6168 Clinical (unspecified phase)
0.9355 High Similarity NPD1934 Approved
0.9264 High Similarity NPD7074 Phase 3
0.9207 High Similarity NPD6797 Phase 2
0.9202 High Similarity NPD7054 Approved
0.9172 High Similarity NPD2393 Clinical (unspecified phase)
0.9152 High Similarity NPD7251 Discontinued
0.9146 High Similarity NPD7472 Approved
0.9096 High Similarity NPD7808 Phase 3
0.8976 High Similarity NPD7993 Clinical (unspecified phase)
0.8938 High Similarity NPD3882 Suspended
0.8938 High Similarity NPD4868 Clinical (unspecified phase)
0.8931 High Similarity NPD2801 Approved
0.8875 High Similarity NPD3817 Phase 2
0.8869 High Similarity NPD4338 Clinical (unspecified phase)
0.8846 High Similarity NPD1512 Approved
0.8795 High Similarity NPD3818 Discontinued
0.8743 High Similarity NPD7804 Clinical (unspecified phase)
0.8742 High Similarity NPD4380 Phase 2
0.8718 High Similarity NPD1511 Approved
0.865 High Similarity NPD4381 Clinical (unspecified phase)
0.865 High Similarity NPD7075 Discontinued
0.8606 High Similarity NPD6959 Discontinued
0.8545 High Similarity NPD5494 Approved
0.8544 High Similarity NPD4378 Clinical (unspecified phase)
0.8528 High Similarity NPD8443 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8412 Intermediate Similarity NPD5844 Phase 1
0.8405 Intermediate Similarity NPD6801 Discontinued
0.8397 Intermediate Similarity NPD1549 Phase 2
0.8344 Intermediate Similarity NPD7411 Suspended
0.8333 Intermediate Similarity NPD6232 Discontinued
0.8313 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8303 Intermediate Similarity NPD5402 Approved
0.8294 Intermediate Similarity NPD7473 Discontinued
0.825 Intermediate Similarity NPD6799 Approved
0.8242 Intermediate Similarity NPD1465 Phase 2
0.821 Intermediate Similarity NPD5403 Approved
0.8161 Intermediate Similarity NPD6559 Discontinued
0.8153 Intermediate Similarity NPD2796 Approved
0.8133 Intermediate Similarity NPD7819 Suspended
0.8129 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD1510 Phase 2
0.8086 Intermediate Similarity NPD5401 Approved
0.807 Intermediate Similarity NPD3926 Phase 2
0.8065 Intermediate Similarity NPD1613 Approved
0.8065 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD6599 Discontinued
0.7949 Intermediate Similarity NPD1240 Approved
0.7931 Intermediate Similarity NPD3751 Discontinued
0.7907 Intermediate Similarity NPD3787 Discontinued
0.7879 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD3027 Phase 3
0.7861 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD1247 Approved
0.7849 Intermediate Similarity NPD7199 Phase 2
0.7848 Intermediate Similarity NPD1607 Approved
0.7845 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD919 Approved
0.7834 Intermediate Similarity NPD943 Approved
0.7829 Intermediate Similarity NPD7228 Approved
0.7824 Intermediate Similarity NPD7768 Phase 2
0.7806 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6190 Approved
0.7778 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD3749 Approved
0.7765 Intermediate Similarity NPD8312 Approved
0.7765 Intermediate Similarity NPD8313 Approved
0.7742 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD6234 Discontinued
0.7622 Intermediate Similarity NPD3750 Approved
0.7622 Intermediate Similarity NPD4628 Phase 3
0.7619 Intermediate Similarity NPD1653 Approved
0.7607 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7390 Discontinued
0.758 Intermediate Similarity NPD4908 Phase 1
0.7566 Intermediate Similarity NPD6778 Approved
0.7566 Intermediate Similarity NPD6782 Approved
0.7566 Intermediate Similarity NPD6776 Approved
0.7566 Intermediate Similarity NPD6777 Approved
0.7566 Intermediate Similarity NPD6781 Approved
0.7566 Intermediate Similarity NPD6780 Approved
0.7566 Intermediate Similarity NPD6779 Approved
0.7562 Intermediate Similarity NPD230 Phase 1
0.7545 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD37 Approved
0.7541 Intermediate Similarity NPD8150 Discontinued
0.7531 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7526 Intermediate Similarity NPD8151 Discontinued
0.7514 Intermediate Similarity NPD4967 Phase 2
0.7514 Intermediate Similarity NPD4966 Approved
0.7514 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD8455 Phase 2
0.7485 Intermediate Similarity NPD1551 Phase 2
0.7485 Intermediate Similarity NPD2935 Discontinued
0.7484 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD6798 Discontinued
0.7484 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7459 Intermediate Similarity NPD7685 Pre-registration
0.7455 Intermediate Similarity NPD2800 Approved
0.7453 Intermediate Similarity NPD447 Suspended
0.7448 Intermediate Similarity NPD7696 Phase 3
0.7448 Intermediate Similarity NPD7698 Approved
0.7448 Intermediate Similarity NPD7435 Discontinued
0.7448 Intermediate Similarity NPD7697 Approved
0.744 Intermediate Similarity NPD2534 Approved
0.744 Intermediate Similarity NPD2532 Approved
0.744 Intermediate Similarity NPD2533 Approved
0.7409 Intermediate Similarity NPD7871 Phase 2
0.7409 Intermediate Similarity NPD7870 Phase 2
0.7385 Intermediate Similarity NPD7701 Phase 2
0.7378 Intermediate Similarity NPD6100 Approved
0.7378 Intermediate Similarity NPD6099 Approved
0.7368 Intermediate Similarity NPD3226 Approved
0.7363 Intermediate Similarity NPD7240 Approved
0.736 Intermediate Similarity NPD7783 Phase 2
0.736 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD8434 Phase 2
0.7346 Intermediate Similarity NPD1933 Approved
0.7337 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2344 Approved
0.7333 Intermediate Similarity NPD7266 Discontinued
0.7329 Intermediate Similarity NPD6233 Phase 2
0.7322 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3748 Approved
0.7308 Intermediate Similarity NPD5953 Discontinued
0.7305 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD4363 Phase 3
0.7302 Intermediate Similarity NPD6535 Approved
0.7302 Intermediate Similarity NPD4360 Phase 2
0.7302 Intermediate Similarity NPD6534 Approved
0.7301 Intermediate Similarity NPD6651 Approved
0.7296 Intermediate Similarity NPD9494 Approved
0.7277 Intermediate Similarity NPD7700 Phase 2
0.7277 Intermediate Similarity NPD7699 Phase 2
0.7267 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD920 Approved
0.7245 Intermediate Similarity NPD7584 Approved
0.7244 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7874 Approved
0.7212 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD7033 Discontinued
0.7198 Intermediate Similarity NPD7286 Phase 2
0.7186 Intermediate Similarity NPD7801 Approved
0.716 Intermediate Similarity NPD2309 Approved
0.7151 Intermediate Similarity NPD8127 Discontinued
0.7143 Intermediate Similarity NPD8320 Phase 1
0.7143 Intermediate Similarity NPD8319 Approved
0.7143 Intermediate Similarity NPD6832 Phase 2
0.7143 Intermediate Similarity NPD6844 Discontinued
0.7143 Intermediate Similarity NPD1243 Approved
0.7135 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7549 Discontinued
0.7134 Intermediate Similarity NPD6355 Discontinued
0.7134 Intermediate Similarity NPD1610 Phase 2
0.7128 Intermediate Similarity NPD6823 Phase 2
0.7127 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD2346 Discontinued
0.7118 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD2799 Discontinued
0.7101 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD7680 Approved
0.7081 Intermediate Similarity NPD7039 Approved
0.7081 Intermediate Similarity NPD7038 Approved
0.7077 Intermediate Similarity NPD2493 Approved
0.7077 Intermediate Similarity NPD2494 Approved
0.7072 Intermediate Similarity NPD5242 Approved
0.7069 Intermediate Similarity NPD7458 Discontinued
0.7063 Intermediate Similarity NPD1203 Approved
0.7062 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5353 Approved
0.7055 Intermediate Similarity NPD2313 Discontinued
0.7049 Intermediate Similarity NPD2163 Approved
0.7041 Intermediate Similarity NPD1652 Phase 2
0.7033 Intermediate Similarity NPD2403 Approved
0.703 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5124 Phase 1
0.7017 Intermediate Similarity NPD7229 Phase 3
0.7017 Intermediate Similarity NPD5710 Approved
0.7017 Intermediate Similarity NPD5711 Approved
0.699 Remote Similarity NPD3450 Approved
0.699 Remote Similarity NPD3452 Approved
0.6989 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1548 Phase 1
0.6982 Remote Similarity NPD2424 Discontinued
0.6977 Remote Similarity NPD7213 Phase 3
0.6977 Remote Similarity NPD7212 Phase 2
0.6975 Remote Similarity NPD2861 Phase 2

  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