Structure

Physi-Chem Properties

Molecular Weight:  642.17
Volume:  628.513
LogP:  5.003
LogD:  2.579
LogS:  -4.066
# Rotatable Bonds:  8
TPSA:  188.51
# H-Bond Aceptor:  12
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.128
Synthetic Accessibility Score:  4.078
Fsp3:  0.171
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.021
MDCK Permeability:  1.0888408723985776e-05
Pgp-inhibitor:  0.993
Pgp-substrate:  0.06
Human Intestinal Absorption (HIA):  0.759
20% Bioavailability (F20%):  0.096
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  94.2488784790039%
Volume Distribution (VD):  0.505
Pgp-substrate:  11.899067878723145%

ADMET: Metabolism

CYP1A2-inhibitor:  0.295
CYP1A2-substrate:  0.764
CYP2C19-inhibitor:  0.103
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.776
CYP2C9-substrate:  0.527
CYP2D6-inhibitor:  0.033
CYP2D6-substrate:  0.814
CYP3A4-inhibitor:  0.417
CYP3A4-substrate:  0.403

ADMET: Excretion

Clearance (CL):  4.053
Half-life (T1/2):  0.829

ADMET: Toxicity

hERG Blockers:  0.187
Human Hepatotoxicity (H-HT):  0.277
Drug-inuced Liver Injury (DILI):  0.945
AMES Toxicity:  0.604
Rat Oral Acute Toxicity:  0.124
Maximum Recommended Daily Dose:  0.931
Skin Sensitization:  0.944
Carcinogencity:  0.226
Eye Corrosion:  0.003
Eye Irritation:  0.67
Respiratory Toxicity:  0.076

Download Data

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

  Natural Product: NPC475212

Natural Product ID:  NPC475212
Common Name*:   Hydnowightin
IUPAC Name:   5,7-dihydroxy-2-[(2R,3R)-3-[4-hydroxy-3-[(Z)-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)prop-1-en-2-yl]-5-methoxyphenyl]-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
Synonyms:   Hydnowightin
Standard InCHIKey:  KMYJDVOGPCWOTR-UDJTZZNJSA-N
Standard InCHI:  InChI=1S/C35H30O12/c1-43-28-8-17(3-5-23(28)39)7-20(15-36)22-9-19(11-31(44-2)34(22)42)35-32(16-37)45-26-6-4-18(10-29(26)47-35)27-14-25(41)33-24(40)12-21(38)13-30(33)46-27/h3-14,32,35-40,42H,15-16H2,1-2H3/b20-7+/t32-,35-/m1/s1
SMILES:  COC1=CC(=CC(=C1O)C(=CC2=CC(=C(C=C2)O)OC)CO)C3C(OC4=C(O3)C=C(C=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501111
PubChem CID:   21723008
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
NPO14784 Hydnocarpus wightiana Species Achariaceae Eukaryota seeds n.a. n.a. PMID[1800632]
NPO14784 Hydnocarpus wightiana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14784 Hydnocarpus wightiana Species Achariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14784 Hydnocarpus wightiana Species Achariaceae 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
NPT1490 Cell Line Ehrlich Mus musculus Inhibition = 12.1 % PMID[450821]
NPT137 Cell Line L1210 Mus musculus ED50 = 3.07 ug ml-1 PMID[450821]
NPT91 Cell Line KB Homo sapiens ED50 = 1.96 ug ml-1 PMID[450821]
NPT660 Cell Line SW480 Homo sapiens ED50 = 2.38 ug ml-1 PMID[450821]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 3.01 ug ml-1 PMID[450821]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 7.49 ug ml-1 PMID[450821]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 2.5 ug ml-1 PMID[450821]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 5.02 ug ml-1 PMID[450821]
NPT32 Organism Mus musculus Mus musculus Activity = 59.0 % PMID[450821]
NPT32 Organism Mus musculus Mus musculus Activity = 80.0 % PMID[450821]
NPT32 Organism Mus musculus Mus musculus Inhibition = 24.0 % PMID[450821]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 4.33 ug ml-1 PMID[450821]

☑ 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 NPC475212 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
0.9686 High Similarity NPC477840
0.9684 High Similarity NPC219927
0.962 High Similarity NPC113163
0.962 High Similarity NPC84324
0.962 High Similarity NPC288131
0.962 High Similarity NPC142252
0.962 High Similarity NPC165970
0.962 High Similarity NPC66618
0.962 High Similarity NPC26326
0.962 High Similarity NPC305987
0.9576 High Similarity NPC324742
0.956 High Similarity NPC476247
0.956 High Similarity NPC477841
0.9557 High Similarity NPC101731
0.9503 High Similarity NPC171985
0.9503 High Similarity NPC320741
0.9497 High Similarity NPC474038
0.9497 High Similarity NPC158188
0.9494 High Similarity NPC53545
0.9494 High Similarity NPC117418
0.9494 High Similarity NPC284127
0.9494 High Similarity NPC476410
0.9494 High Similarity NPC172202
0.9448 High Similarity NPC476365
0.9444 High Similarity NPC243877
0.9444 High Similarity NPC260266
0.9441 High Similarity NPC72787
0.9441 High Similarity NPC36916
0.9441 High Similarity NPC125039
0.9441 High Similarity NPC7688
0.9441 High Similarity NPC7154
0.9441 High Similarity NPC58223
0.9441 High Similarity NPC36
0.9434 High Similarity NPC118256
0.9434 High Similarity NPC475784
0.9434 High Similarity NPC192686
0.9434 High Similarity NPC119209
0.943 High Similarity NPC63454
0.943 High Similarity NPC474055
0.943 High Similarity NPC183851
0.943 High Similarity NPC472598
0.939 High Similarity NPC472454
0.939 High Similarity NPC186847
0.939 High Similarity NPC257667
0.9387 High Similarity NPC107627
0.9383 High Similarity NPC224851
0.9379 High Similarity NPC472625
0.9375 High Similarity NPC472632
0.9375 High Similarity NPC472634
0.9375 High Similarity NPC471499
0.9375 High Similarity NPC289771
0.9367 High Similarity NPC195796
0.9367 High Similarity NPC35038
0.9367 High Similarity NPC291878
0.9367 High Similarity NPC278778
0.9341 High Similarity NPC185275
0.9329 High Similarity NPC279209
0.9329 High Similarity NPC102277
0.9325 High Similarity NPC14662
0.9325 High Similarity NPC295082
0.9317 High Similarity NPC472635
0.9317 High Similarity NPC474034
0.9317 High Similarity NPC474033
0.9313 High Similarity NPC472631
0.9313 High Similarity NPC470326
0.9313 High Similarity NPC287328
0.9313 High Similarity NPC472630
0.9313 High Similarity NPC174953
0.9313 High Similarity NPC282009
0.9308 High Similarity NPC27337
0.9308 High Similarity NPC284820
0.9308 High Similarity NPC183
0.9308 High Similarity NPC291508
0.9308 High Similarity NPC473272
0.9308 High Similarity NPC112954
0.9304 High Similarity NPC321779
0.9304 High Similarity NPC477503
0.9304 High Similarity NPC470327
0.9304 High Similarity NPC45849
0.9304 High Similarity NPC200761
0.9281 High Similarity NPC265380
0.9277 High Similarity NPC99591
0.9273 High Similarity NPC4200
0.9273 High Similarity NPC256760
0.9268 High Similarity NPC188079
0.9264 High Similarity NPC471213
0.9259 High Similarity NPC272064
0.9259 High Similarity NPC186686
0.9255 High Similarity NPC471210
0.9255 High Similarity NPC471212
0.9255 High Similarity NPC471211
0.925 High Similarity NPC123544
0.925 High Similarity NPC22192
0.925 High Similarity NPC473990
0.9245 High Similarity NPC472626
0.9245 High Similarity NPC209614
0.9245 High Similarity NPC78492
0.9245 High Similarity NPC470328
0.9245 High Similarity NPC208152
0.9241 High Similarity NPC18727
0.9241 High Similarity NPC213896
0.9241 High Similarity NPC192083
0.9231 High Similarity NPC132111
0.9226 High Similarity NPC471030
0.9217 High Similarity NPC208668
0.9212 High Similarity NPC150767
0.9212 High Similarity NPC78734
0.9202 High Similarity NPC471788
0.9198 High Similarity NPC474150
0.9198 High Similarity NPC201800
0.9198 High Similarity NPC474162
0.9193 High Similarity NPC472624
0.9193 High Similarity NPC36217
0.9187 High Similarity NPC471209
0.9187 High Similarity NPC223787
0.9187 High Similarity NPC52889
0.9182 High Similarity NPC226025
0.9181 High Similarity NPC64755
0.9177 High Similarity NPC219582
0.9177 High Similarity NPC56232
0.9177 High Similarity NPC10807
0.9177 High Similarity NPC106976
0.9177 High Similarity NPC236637
0.9177 High Similarity NPC150123
0.9177 High Similarity NPC302950
0.9177 High Similarity NPC471982
0.9177 High Similarity NPC244583
0.9177 High Similarity NPC161881
0.9172 High Similarity NPC117668
0.9157 High Similarity NPC271848
0.9157 High Similarity NPC81332
0.9157 High Similarity NPC262580
0.9157 High Similarity NPC289396
0.9157 High Similarity NPC212038
0.9152 High Similarity NPC300307
0.9146 High Similarity NPC43319
0.9146 High Similarity NPC13481
0.9146 High Similarity NPC272560
0.9146 High Similarity NPC207575
0.9141 High Similarity NPC124038
0.9141 High Similarity NPC476295
0.9136 High Similarity NPC312273
0.9136 High Similarity NPC134783
0.9136 High Similarity NPC301256
0.9136 High Similarity NPC196179
0.9136 High Similarity NPC34089
0.9136 High Similarity NPC266314
0.9136 High Similarity NPC198829
0.913 High Similarity NPC95936
0.913 High Similarity NPC74178
0.913 High Similarity NPC204879
0.913 High Similarity NPC187792
0.913 High Similarity NPC250214
0.913 High Similarity NPC184755
0.9128 High Similarity NPC473618
0.9125 High Similarity NPC320825
0.9125 High Similarity NPC326037
0.9125 High Similarity NPC250922
0.9125 High Similarity NPC471985
0.9125 High Similarity NPC13858
0.9119 High Similarity NPC112701
0.9119 High Similarity NPC109594
0.9119 High Similarity NPC326592
0.9119 High Similarity NPC74924
0.9119 High Similarity NPC298692
0.9118 High Similarity NPC150977
0.9118 High Similarity NPC321916
0.9114 High Similarity NPC328740
0.9114 High Similarity NPC289774
0.9114 High Similarity NPC477897
0.9114 High Similarity NPC209846
0.9107 High Similarity NPC216307
0.9107 High Similarity NPC255799
0.9102 High Similarity NPC476374
0.9102 High Similarity NPC472993
0.9102 High Similarity NPC25724
0.9096 High Similarity NPC231194
0.9096 High Similarity NPC218488
0.9096 High Similarity NPC51326
0.9091 High Similarity NPC477502
0.9091 High Similarity NPC229729
0.9091 High Similarity NPC218226
0.9091 High Similarity NPC474024
0.9085 High Similarity NPC470457
0.9085 High Similarity NPC311830
0.9085 High Similarity NPC259757
0.9085 High Similarity NPC293319
0.9085 High Similarity NPC475888
0.9085 High Similarity NPC62261
0.9085 High Similarity NPC22832
0.9085 High Similarity NPC50960
0.908 High Similarity NPC476371
0.908 High Similarity NPC476372
0.908 High Similarity NPC83922
0.908 High Similarity NPC194427
0.908 High Similarity NPC220912
0.908 High Similarity NPC473012
0.908 High Similarity NPC472448
0.9074 High Similarity NPC204290
0.9074 High Similarity NPC188967

  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 NPC475212 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
0.9441 High Similarity NPD6168 Clinical (unspecified phase)
0.9441 High Similarity NPD6167 Clinical (unspecified phase)
0.9441 High Similarity NPD6166 Phase 2
0.9241 High Similarity NPD2393 Clinical (unspecified phase)
0.9177 High Similarity NPD1934 Approved
0.9036 High Similarity NPD7054 Approved
0.8982 High Similarity NPD7074 Phase 3
0.8982 High Similarity NPD7472 Approved
0.8931 High Similarity NPD4380 Phase 2
0.8882 High Similarity NPD2801 Approved
0.8824 High Similarity NPD7808 Phase 3
0.8817 High Similarity NPD6797 Phase 2
0.8817 High Similarity NPD7993 Clinical (unspecified phase)
0.8788 High Similarity NPD6959 Discontinued
0.8773 High Similarity NPD4868 Clinical (unspecified phase)
0.8765 High Similarity NPD7251 Discontinued
0.875 High Similarity NPD3818 Discontinued
0.8712 High Similarity NPD8443 Clinical (unspecified phase)
0.8698 High Similarity NPD7804 Clinical (unspecified phase)
0.8671 High Similarity NPD1511 Approved
0.8606 High Similarity NPD4381 Clinical (unspecified phase)
0.8605 High Similarity NPD4338 Clinical (unspecified phase)
0.8598 High Similarity NPD3817 Phase 2
0.8562 High Similarity NPD1512 Approved
0.8545 High Similarity NPD3882 Suspended
0.8521 High Similarity NPD7852 Clinical (unspecified phase)
0.8503 High Similarity NPD5494 Approved
0.85 High Similarity NPD4378 Clinical (unspecified phase)
0.85 High Similarity NPD7410 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD7075 Discontinued
0.848 Intermediate Similarity NPD5844 Phase 1
0.8415 Intermediate Similarity NPD7411 Suspended
0.8402 Intermediate Similarity NPD6232 Discontinued
0.8364 Intermediate Similarity NPD6801 Discontinued
0.8363 Intermediate Similarity NPD7473 Discontinued
0.8313 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8313 Intermediate Similarity NPD7819 Suspended
0.8291 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD1549 Phase 2
0.8229 Intermediate Similarity NPD6559 Discontinued
0.8214 Intermediate Similarity NPD7768 Phase 2
0.8212 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD2796 Approved
0.805 Intermediate Similarity NPD1510 Phase 2
0.8047 Intermediate Similarity NPD5402 Approved
0.8034 Intermediate Similarity NPD8312 Approved
0.8034 Intermediate Similarity NPD8313 Approved
0.7988 Intermediate Similarity NPD1465 Phase 2
0.7952 Intermediate Similarity NPD5403 Approved
0.7923 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD1613 Approved
0.7911 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD7390 Discontinued
0.7879 Intermediate Similarity NPD6799 Approved
0.7831 Intermediate Similarity NPD5401 Approved
0.7816 Intermediate Similarity NPD1247 Approved
0.7803 Intermediate Similarity NPD919 Approved
0.7799 Intermediate Similarity NPD1240 Approved
0.7778 Intermediate Similarity NPD8455 Phase 2
0.7754 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD3749 Approved
0.7744 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD3926 Phase 2
0.7722 Intermediate Similarity NPD3027 Phase 3
0.7714 Intermediate Similarity NPD7199 Phase 2
0.7706 Intermediate Similarity NPD6599 Discontinued
0.7702 Intermediate Similarity NPD1607 Approved
0.7697 Intermediate Similarity NPD7228 Approved
0.7688 Intermediate Similarity NPD943 Approved
0.768 Intermediate Similarity NPD8151 Discontinued
0.767 Intermediate Similarity NPD3787 Discontinued
0.7658 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.765 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD6234 Discontinued
0.7598 Intermediate Similarity NPD3751 Discontinued
0.7595 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD3750 Approved
0.7588 Intermediate Similarity NPD1653 Approved
0.7576 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD2935 Discontinued
0.7539 Intermediate Similarity NPD6780 Approved
0.7539 Intermediate Similarity NPD6776 Approved
0.7539 Intermediate Similarity NPD6781 Approved
0.7539 Intermediate Similarity NPD6777 Approved
0.7539 Intermediate Similarity NPD6782 Approved
0.7539 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD6779 Approved
0.7539 Intermediate Similarity NPD6778 Approved
0.753 Intermediate Similarity NPD2800 Approved
0.7528 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7685 Pre-registration
0.7515 Intermediate Similarity NPD2532 Approved
0.7515 Intermediate Similarity NPD2534 Approved
0.7515 Intermediate Similarity NPD2533 Approved
0.7514 Intermediate Similarity NPD8150 Discontinued
0.7514 Intermediate Similarity NPD37 Approved
0.7486 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD4965 Approved
0.7486 Intermediate Similarity NPD4966 Approved
0.7486 Intermediate Similarity NPD4967 Phase 2
0.7485 Intermediate Similarity NPD4628 Phase 3
0.7474 Intermediate Similarity NPD7871 Phase 2
0.7474 Intermediate Similarity NPD7870 Phase 2
0.746 Intermediate Similarity NPD4360 Phase 2
0.746 Intermediate Similarity NPD4363 Phase 3
0.7456 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD3226 Approved
0.744 Intermediate Similarity NPD6190 Approved
0.7438 Intermediate Similarity NPD4908 Phase 1
0.7427 Intermediate Similarity NPD920 Approved
0.7424 Intermediate Similarity NPD7783 Phase 2
0.7424 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7698 Approved
0.7423 Intermediate Similarity NPD7435 Discontinued
0.7423 Intermediate Similarity NPD7696 Phase 3
0.7423 Intermediate Similarity NPD230 Phase 1
0.7423 Intermediate Similarity NPD7697 Approved
0.7412 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD7584 Approved
0.7378 Intermediate Similarity NPD6651 Approved
0.7377 Intermediate Similarity NPD5953 Discontinued
0.736 Intermediate Similarity NPD7701 Phase 2
0.7349 Intermediate Similarity NPD1551 Phase 2
0.7346 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD1243 Approved
0.7318 Intermediate Similarity NPD8127 Discontinued
0.7317 Intermediate Similarity NPD447 Suspended
0.731 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3748 Approved
0.7289 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD7874 Approved
0.7286 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD6823 Phase 2
0.7278 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6535 Approved
0.7277 Intermediate Similarity NPD6534 Approved
0.7268 Intermediate Similarity NPD7286 Phase 2
0.7254 Intermediate Similarity NPD7699 Phase 2
0.7254 Intermediate Similarity NPD7700 Phase 2
0.725 Intermediate Similarity NPD7801 Approved
0.7246 Intermediate Similarity NPD6099 Approved
0.7246 Intermediate Similarity NPD6100 Approved
0.7243 Intermediate Similarity NPD7240 Approved
0.7241 Intermediate Similarity NPD7458 Discontinued
0.7239 Intermediate Similarity NPD2313 Discontinued
0.7234 Intermediate Similarity NPD8434 Phase 2
0.7212 Intermediate Similarity NPD5124 Phase 1
0.7212 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD1933 Approved
0.7202 Intermediate Similarity NPD2344 Approved
0.7202 Intermediate Similarity NPD2346 Discontinued
0.7186 Intermediate Similarity NPD7033 Discontinued
0.7186 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2799 Discontinued
0.716 Intermediate Similarity NPD9494 Approved
0.7143 Intermediate Similarity NPD5406 Approved
0.7143 Intermediate Similarity NPD5408 Approved
0.7143 Intermediate Similarity NPD5405 Approved
0.7143 Intermediate Similarity NPD5404 Approved
0.7134 Intermediate Similarity NPD6798 Discontinued
0.7125 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD8319 Approved
0.7121 Intermediate Similarity NPD8320 Phase 1
0.7119 Intermediate Similarity NPD6844 Discontinued
0.7112 Intermediate Similarity NPD7549 Discontinued
0.7107 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD7266 Discontinued
0.7088 Intermediate Similarity NPD5710 Approved
0.7088 Intermediate Similarity NPD5711 Approved
0.7088 Intermediate Similarity NPD7229 Phase 3
0.7076 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD8166 Discontinued
0.7071 Intermediate Similarity NPD7680 Approved
0.7062 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4361 Phase 2
0.7059 Intermediate Similarity NPD2424 Discontinued
0.7047 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6212 Phase 3
0.7047 Intermediate Similarity NPD6213 Phase 3
0.7035 Intermediate Similarity NPD2309 Approved
0.7027 Intermediate Similarity NPD7177 Discontinued
0.7019 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6674 Discontinued
0.7018 Intermediate Similarity NPD1652 Phase 2
0.7015 Intermediate Similarity NPD7585 Approved
0.7012 Intermediate Similarity NPD6832 Phase 2
0.7011 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1610 Phase 2
0.6988 Remote Similarity NPD6233 Phase 2
0.6977 Remote Similarity NPD7003 Approved
0.6971 Remote Similarity NPD6273 Approved
0.697 Remote Similarity NPD4625 Phase 3
0.6968 Remote Similarity NPD7038 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