Structure

Physi-Chem Properties

Molecular Weight:  464.11
Volume:  448.285
LogP:  3.94
LogD:  2.831
LogS:  -4.642
# Rotatable Bonds:  4
TPSA:  138.82
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.358
Synthetic Accessibility Score:  3.5
Fsp3:  0.16
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.023
MDCK Permeability:  3.32443269144278e-05
Pgp-inhibitor:  0.647
Pgp-substrate:  0.272
Human Intestinal Absorption (HIA):  0.037
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  93.50260162353516%
Volume Distribution (VD):  0.612
Pgp-substrate:  10.02359676361084%

ADMET: Metabolism

CYP1A2-inhibitor:  0.628
CYP1A2-substrate:  0.571
CYP2C19-inhibitor:  0.485
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.834
CYP2C9-substrate:  0.896
CYP2D6-inhibitor:  0.549
CYP2D6-substrate:  0.868
CYP3A4-inhibitor:  0.757
CYP3A4-substrate:  0.249

ADMET: Excretion

Clearance (CL):  7.358
Half-life (T1/2):  0.679

ADMET: Toxicity

hERG Blockers:  0.145
Human Hepatotoxicity (H-HT):  0.236
Drug-inuced Liver Injury (DILI):  0.948
AMES Toxicity:  0.393
Rat Oral Acute Toxicity:  0.101
Maximum Recommended Daily Dose:  0.426
Skin Sensitization:  0.903
Carcinogencity:  0.238
Eye Corrosion:  0.003
Eye Irritation:  0.787
Respiratory Toxicity:  0.06

Download Data

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

  Natural Product: NPC305987

Natural Product ID:  NPC305987
Common Name*:   (-)-Hydnocarpin
IUPAC Name:   5,7-dihydroxy-2-[(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
Synonyms:   (-)-Hydnocarpin
Standard InCHIKey:  NMICSFNNFDNGEL-ZCYQVOJMSA-N
Standard InCHI:  InChI=1S/C25H20O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-10,23,25-29H,11H2,1H3/t23-,25-/m0/s1
SMILES:  OC[C@@H]1Oc2cc(ccc2O[C@H]1c1ccc(c(c1)OC)O)c1cc(=O)c2c(o1)cc(cc2O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL476644
PubChem CID:   44582381
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
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. seed n.a. DOI[10.1016/0031-9422(96)00258-0]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S1383-5769(99)00023-9]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[10086989]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[1512598]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[15165151]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. leaf n.a. PMID[15949825]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota fruit Indonesia n.a. PMID[17896817]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[18723353]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. Vietnam n.a. PMID[19026551]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota seeds n.a. n.a. PMID[20050684]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota Seeds n.a. n.a. PMID[22506620]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[26522747]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[6481366]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7561896]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[8350091]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. leaf n.a. PMID[8699184]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11432 Centrolobium tomentosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12717 Parmelia metastrigosa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9203 Cephalonomia gallicola Species Bethylidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO211 Aplysina cauliformis Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26718 Chelidonura fulvipunctata Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15146 Myrica nana Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11084 Asplenium normale Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14749 Lippia carviodora Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11637 Psilostrophe cooperi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14150 Solanum jamaicense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5303 Castanea crenata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15520 Dracocephalum kotschyi Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14528 Pneumatospora obcoronata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12944 Sideritis tragoriganum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14845 Ceratophyllum submersum Species Ceratophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3164 Yponomeuta malinellus Species Yponomeutidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14948 Brucea javanica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10818 Carpobrotus edulis Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1641 Amycolatopsis azurea Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12089 Trifolium alexandrinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11873 Oecophylla smaragdina Species Formicidae 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
NPT83 Cell Line MCF7 Homo sapiens ED50 > 10.0 uM PMID[536610]
NPT858 Cell Line LNCaP Homo sapiens ED50 > 10.0 uM PMID[536610]
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 10.0 uM PMID[536610]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 uM PMID[536610]

☑ 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 NPC305987 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 NPC113163
1.0 High Similarity NPC66618
1.0 High Similarity NPC165970
1.0 High Similarity NPC84324
1.0 High Similarity NPC288131
0.9934 High Similarity NPC101731
0.9868 High Similarity NPC476410
0.9868 High Similarity NPC172202
0.9868 High Similarity NPC284127
0.9803 High Similarity NPC183851
0.9803 High Similarity NPC63454
0.974 High Similarity NPC158188
0.9682 High Similarity NPC295082
0.9682 High Similarity NPC243877
0.9679 High Similarity NPC58223
0.9679 High Similarity NPC125039
0.9679 High Similarity NPC72787
0.9679 High Similarity NPC7154
0.9679 High Similarity NPC7688
0.9679 High Similarity NPC36916
0.9679 High Similarity NPC36
0.9677 High Similarity NPC219927
0.962 High Similarity NPC475212
0.9613 High Similarity NPC26326
0.9613 High Similarity NPC142252
0.9557 High Similarity NPC14662
0.9554 High Similarity NPC477840
0.9551 High Similarity NPC477841
0.9551 High Similarity NPC476247
0.9487 High Similarity NPC474038
0.9484 High Similarity NPC53545
0.9484 High Similarity NPC117418
0.9477 High Similarity NPC18727
0.9441 High Similarity NPC472993
0.9434 High Similarity NPC260266
0.943 High Similarity NPC311830
0.943 High Similarity NPC22832
0.9423 High Similarity NPC119209
0.9423 High Similarity NPC118256
0.9423 High Similarity NPC475784
0.9423 High Similarity NPC192686
0.9419 High Similarity NPC474055
0.9419 High Similarity NPC112954
0.9419 High Similarity NPC472598
0.9419 High Similarity NPC470402
0.9419 High Similarity NPC183
0.9412 High Similarity NPC302950
0.9412 High Similarity NPC219582
0.9412 High Similarity NPC236637
0.9375 High Similarity NPC209296
0.9375 High Similarity NPC195257
0.9375 High Similarity NPC188079
0.9371 High Similarity NPC115674
0.9371 High Similarity NPC210073
0.9367 High Similarity NPC284960
0.9367 High Similarity NPC272064
0.9367 High Similarity NPC88023
0.9367 High Similarity NPC191306
0.9367 High Similarity NPC19709
0.9367 High Similarity NPC270335
0.9367 High Similarity NPC309025
0.9367 High Similarity NPC472625
0.9367 High Similarity NPC222936
0.9367 High Similarity NPC243930
0.9363 High Similarity NPC289771
0.9363 High Similarity NPC472632
0.9363 High Similarity NPC472634
0.9363 High Similarity NPC471499
0.9355 High Similarity NPC326037
0.9355 High Similarity NPC291878
0.9355 High Similarity NPC195796
0.9355 High Similarity NPC320825
0.9355 High Similarity NPC13858
0.9355 High Similarity NPC35038
0.9355 High Similarity NPC250922
0.9355 High Similarity NPC278778
0.9342 High Similarity NPC287101
0.9342 High Similarity NPC52005
0.9342 High Similarity NPC223579
0.9342 High Similarity NPC48479
0.9342 High Similarity NPC183950
0.9342 High Similarity NPC137062
0.9342 High Similarity NPC177298
0.9317 High Similarity NPC476365
0.9317 High Similarity NPC231194
0.9317 High Similarity NPC279209
0.9317 High Similarity NPC102277
0.9317 High Similarity NPC51326
0.9313 High Similarity NPC229729
0.9304 High Similarity NPC474034
0.9304 High Similarity NPC474033
0.9304 High Similarity NPC473043
0.9304 High Similarity NPC472635
0.9304 High Similarity NPC77660
0.9304 High Similarity NPC189142
0.9299 High Similarity NPC472631
0.9299 High Similarity NPC287328
0.9299 High Similarity NPC470326
0.9299 High Similarity NPC472630
0.9299 High Similarity NPC174953
0.9299 High Similarity NPC282009
0.9295 High Similarity NPC471479
0.9295 High Similarity NPC474208
0.9295 High Similarity NPC48208
0.9295 High Similarity NPC474836
0.9295 High Similarity NPC52530
0.9295 High Similarity NPC475267
0.9295 High Similarity NPC471515
0.9295 High Similarity NPC284820
0.9295 High Similarity NPC27337
0.9295 High Similarity NPC156057
0.9295 High Similarity NPC473272
0.9295 High Similarity NPC162869
0.9295 High Similarity NPC291508
0.929 High Similarity NPC50715
0.929 High Similarity NPC146165
0.929 High Similarity NPC92659
0.929 High Similarity NPC227325
0.929 High Similarity NPC200761
0.929 High Similarity NPC4455
0.929 High Similarity NPC280339
0.929 High Similarity NPC470327
0.929 High Similarity NPC128863
0.929 High Similarity NPC2476
0.929 High Similarity NPC196439
0.929 High Similarity NPC45849
0.929 High Similarity NPC138360
0.929 High Similarity NPC201136
0.929 High Similarity NPC213622
0.929 High Similarity NPC321779
0.929 High Similarity NPC477503
0.929 High Similarity NPC163780
0.929 High Similarity NPC183597
0.929 High Similarity NPC167815
0.9286 High Similarity NPC60972
0.9286 High Similarity NPC257648
0.9286 High Similarity NPC472912
0.9286 High Similarity NPC477231
0.9286 High Similarity NPC39732
0.9281 High Similarity NPC338131
0.9276 High Similarity NPC119059
0.9276 High Similarity NPC195202
0.9276 High Similarity NPC120464
0.9268 High Similarity NPC217520
0.9268 High Similarity NPC139571
0.9259 High Similarity NPC256760
0.9255 High Similarity NPC93337
0.9255 High Similarity NPC105025
0.9255 High Similarity NPC86008
0.9255 High Similarity NPC469931
0.9255 High Similarity NPC201292
0.9255 High Similarity NPC475942
0.9255 High Similarity NPC219904
0.9255 High Similarity NPC58053
0.9255 High Similarity NPC45638
0.9255 High Similarity NPC203050
0.9255 High Similarity NPC120099
0.9255 High Similarity NPC223747
0.9255 High Similarity NPC186807
0.9255 High Similarity NPC226294
0.9255 High Similarity NPC225434
0.925 High Similarity NPC21100
0.925 High Similarity NPC8856
0.925 High Similarity NPC197285
0.925 High Similarity NPC471213
0.925 High Similarity NPC320741
0.925 High Similarity NPC5778
0.925 High Similarity NPC236934
0.925 High Similarity NPC171985
0.9245 High Similarity NPC186686
0.9245 High Similarity NPC168822
0.9241 High Similarity NPC182045
0.9241 High Similarity NPC471211
0.9241 High Similarity NPC34089
0.9241 High Similarity NPC471210
0.9241 High Similarity NPC196179
0.9241 High Similarity NPC471212
0.9236 High Similarity NPC473990
0.9236 High Similarity NPC22192
0.9231 High Similarity NPC472916
0.9231 High Similarity NPC470328
0.9231 High Similarity NPC208152
0.9231 High Similarity NPC235165
0.9231 High Similarity NPC255106
0.9231 High Similarity NPC78492
0.9231 High Similarity NPC471500
0.9231 High Similarity NPC472626
0.9231 High Similarity NPC209614
0.9226 High Similarity NPC183878
0.9226 High Similarity NPC75279
0.9226 High Similarity NPC160951
0.9226 High Similarity NPC255350
0.9226 High Similarity NPC176775
0.9226 High Similarity NPC69394
0.9226 High Similarity NPC213896
0.9226 High Similarity NPC47781
0.9226 High Similarity NPC145379
0.9226 High Similarity NPC276409
0.9226 High Similarity NPC22519
0.9226 High Similarity NPC274327

  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 NPC305987 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
0.9679 High Similarity NPD6168 Clinical (unspecified phase)
0.9679 High Similarity NPD6167 Clinical (unspecified phase)
0.9679 High Similarity NPD6166 Phase 2
0.9412 High Similarity NPD1934 Approved
0.9375 High Similarity NPD7054 Approved
0.9317 High Similarity NPD7472 Approved
0.9226 High Similarity NPD2393 Clinical (unspecified phase)
0.9226 High Similarity NPD2801 Approved
0.9198 High Similarity NPD7074 Phase 3
0.9141 High Similarity NPD6797 Phase 2
0.9085 High Similarity NPD7251 Discontinued
0.903 High Similarity NPD7808 Phase 3
0.9013 High Similarity NPD1511 Approved
0.8987 High Similarity NPD4868 Clinical (unspecified phase)
0.8957 High Similarity NPD3818 Discontinued
0.8924 High Similarity NPD3817 Phase 2
0.8916 High Similarity NPD4338 Clinical (unspecified phase)
0.891 High Similarity NPD4380 Phase 2
0.8896 High Similarity NPD1512 Approved
0.8868 High Similarity NPD3882 Suspended
0.8812 High Similarity NPD4381 Clinical (unspecified phase)
0.8683 High Similarity NPD7993 Clinical (unspecified phase)
0.8571 High Similarity NPD8443 Clinical (unspecified phase)
0.8563 High Similarity NPD7804 Clinical (unspecified phase)
0.8537 High Similarity NPD6959 Discontinued
0.8497 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD5494 Approved
0.8471 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD7075 Discontinued
0.8452 Intermediate Similarity NPD5844 Phase 1
0.8442 Intermediate Similarity NPD1549 Phase 2
0.8385 Intermediate Similarity NPD7411 Suspended
0.8373 Intermediate Similarity NPD6232 Discontinued
0.8344 Intermediate Similarity NPD5402 Approved
0.8333 Intermediate Similarity NPD7473 Discontinued
0.8333 Intermediate Similarity NPD6801 Discontinued
0.8312 Intermediate Similarity NPD2796 Approved
0.8282 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD5403 Approved
0.8247 Intermediate Similarity NPD1510 Phase 2
0.8198 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD6799 Approved
0.8171 Intermediate Similarity NPD7819 Suspended
0.8171 Intermediate Similarity NPD1465 Phase 2
0.8166 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD5401 Approved
0.8105 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD1613 Approved
0.7987 Intermediate Similarity NPD1240 Approved
0.7914 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD3027 Phase 3
0.7895 Intermediate Similarity NPD3926 Phase 2
0.7885 Intermediate Similarity NPD1607 Approved
0.7882 Intermediate Similarity NPD7199 Phase 2
0.7879 Intermediate Similarity NPD6599 Discontinued
0.7877 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD943 Approved
0.7866 Intermediate Similarity NPD1653 Approved
0.7862 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD3751 Discontinued
0.7857 Intermediate Similarity NPD7768 Phase 2
0.7843 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD3787 Discontinued
0.7811 Intermediate Similarity NPD3749 Approved
0.7778 Intermediate Similarity NPD1247 Approved
0.7778 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD919 Approved
0.7764 Intermediate Similarity NPD3750 Approved
0.7759 Intermediate Similarity NPD7228 Approved
0.7716 Intermediate Similarity NPD6190 Approved
0.7707 Intermediate Similarity NPD230 Phase 1
0.7702 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD8312 Approved
0.7697 Intermediate Similarity NPD8313 Approved
0.7692 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD7685 Pre-registration
0.7661 Intermediate Similarity NPD6234 Discontinued
0.7654 Intermediate Similarity NPD4628 Phase 3
0.7628 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD1551 Phase 2
0.7622 Intermediate Similarity NPD7390 Discontinued
0.7622 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD4908 Phase 1
0.7611 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD447 Suspended
0.7576 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD37 Approved
0.7546 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD4966 Approved
0.7544 Intermediate Similarity NPD4967 Phase 2
0.7544 Intermediate Similarity NPD4965 Approved
0.7516 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD2800 Approved
0.7484 Intermediate Similarity NPD1933 Approved
0.747 Intermediate Similarity NPD2534 Approved
0.747 Intermediate Similarity NPD2532 Approved
0.747 Intermediate Similarity NPD2533 Approved
0.7461 Intermediate Similarity NPD8151 Discontinued
0.7453 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3748 Approved
0.7444 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD9494 Approved
0.7427 Intermediate Similarity NPD8455 Phase 2
0.7419 Intermediate Similarity NPD4363 Phase 3
0.7419 Intermediate Similarity NPD4360 Phase 2
0.7407 Intermediate Similarity NPD6780 Approved
0.7407 Intermediate Similarity NPD6778 Approved
0.7407 Intermediate Similarity NPD6777 Approved
0.7407 Intermediate Similarity NPD6100 Approved
0.7407 Intermediate Similarity NPD6782 Approved
0.7407 Intermediate Similarity NPD6781 Approved
0.7407 Intermediate Similarity NPD6779 Approved
0.7407 Intermediate Similarity NPD6099 Approved
0.7407 Intermediate Similarity NPD6776 Approved
0.7403 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD3226 Approved
0.7381 Intermediate Similarity NPD920 Approved
0.7377 Intermediate Similarity NPD8150 Discontinued
0.7368 Intermediate Similarity NPD6844 Discontinued
0.7365 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD7266 Discontinued
0.7362 Intermediate Similarity NPD2344 Approved
0.7358 Intermediate Similarity NPD7584 Approved
0.7346 Intermediate Similarity NPD7033 Discontinued
0.7333 Intermediate Similarity NPD5953 Discontinued
0.7329 Intermediate Similarity NPD6651 Approved
0.7296 Intermediate Similarity NPD6798 Discontinued
0.7296 Intermediate Similarity NPD7783 Phase 2
0.7296 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7240 Approved
0.7292 Intermediate Similarity NPD7435 Discontinued
0.7278 Intermediate Similarity NPD6832 Phase 2
0.7273 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1652 Phase 2
0.7273 Intermediate Similarity NPD1243 Approved
0.7262 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD7870 Phase 2
0.7254 Intermediate Similarity NPD7871 Phase 2
0.7253 Intermediate Similarity NPD7549 Discontinued
0.725 Intermediate Similarity NPD6233 Phase 2
0.7246 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD1548 Phase 1
0.7222 Intermediate Similarity NPD7286 Phase 2
0.7202 Intermediate Similarity NPD7697 Approved
0.7202 Intermediate Similarity NPD7696 Phase 3
0.7202 Intermediate Similarity NPD7698 Approved
0.7198 Intermediate Similarity NPD7039 Approved
0.7198 Intermediate Similarity NPD7038 Approved
0.7197 Intermediate Similarity NPD1203 Approved
0.7189 Intermediate Similarity NPD8434 Phase 2
0.7188 Intermediate Similarity NPD2313 Discontinued
0.7186 Intermediate Similarity NPD2309 Approved
0.7184 Intermediate Similarity NPD5353 Approved
0.7175 Intermediate Similarity NPD8127 Discontinued
0.7161 Intermediate Similarity NPD1610 Phase 2
0.716 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5124 Phase 1
0.716 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD2346 Discontinued
0.7151 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6823 Phase 2
0.7143 Intermediate Similarity NPD7701 Phase 2
0.7143 Intermediate Similarity NPD6535 Approved
0.7143 Intermediate Similarity NPD6534 Approved
0.7134 Intermediate Similarity NPD2799 Discontinued
0.7126 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD3018 Phase 2
0.7101 Intermediate Similarity NPD7213 Phase 3
0.7101 Intermediate Similarity NPD7212 Phase 2
0.7095 Intermediate Similarity NPD5242 Approved
0.7093 Intermediate Similarity NPD7458 Discontinued
0.7081 Intermediate Similarity NPD3268 Approved
0.7071 Intermediate Similarity NPD7874 Approved
0.7071 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7447 Phase 1
0.7051 Intermediate Similarity NPD422 Phase 1
0.7044 Intermediate Similarity NPD2798 Approved
0.7039 Intermediate Similarity NPD5711 Approved
0.7039 Intermediate Similarity NPD7229 Phase 3
0.7039 Intermediate Similarity NPD5710 Approved
0.7035 Intermediate Similarity NPD7801 Approved
0.7031 Intermediate Similarity NPD7700 Phase 2
0.7031 Intermediate Similarity NPD7699 Phase 2
0.7026 Intermediate Similarity NPD7680 Approved
0.7025 Intermediate Similarity NPD3225 Approved
0.7016 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD4361 Phase 2
0.7011 Intermediate Similarity NPD6385 Approved
0.7011 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6386 Approved
0.7006 Intermediate Similarity NPD9269 Phase 2
0.7006 Intermediate Similarity NPD2424 Discontinued

  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