Structure

Physi-Chem Properties

Molecular Weight:  344.16
Volume:  356.939
LogP:  3.997
LogD:  3.655
LogS:  -4.087
# Rotatable Bonds:  4
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.87
Synthetic Accessibility Score:  3.409
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.703
MDCK Permeability:  1.646111559239216e-05
Pgp-inhibitor:  0.02
Pgp-substrate:  0.019
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.047
Plasma Protein Binding (PPB):  96.0372543334961%
Volume Distribution (VD):  0.722
Pgp-substrate:  5.3718366622924805%

ADMET: Metabolism

CYP1A2-inhibitor:  0.173
CYP1A2-substrate:  0.953
CYP2C19-inhibitor:  0.707
CYP2C19-substrate:  0.761
CYP2C9-inhibitor:  0.863
CYP2C9-substrate:  0.939
CYP2D6-inhibitor:  0.497
CYP2D6-substrate:  0.902
CYP3A4-inhibitor:  0.732
CYP3A4-substrate:  0.611

ADMET: Excretion

Clearance (CL):  11.533
Half-life (T1/2):  0.589

ADMET: Toxicity

hERG Blockers:  0.074
Human Hepatotoxicity (H-HT):  0.165
Drug-inuced Liver Injury (DILI):  0.738
AMES Toxicity:  0.25
Rat Oral Acute Toxicity:  0.113
Maximum Recommended Daily Dose:  0.127
Skin Sensitization:  0.696
Carcinogencity:  0.151
Eye Corrosion:  0.01
Eye Irritation:  0.912
Respiratory Toxicity:  0.774

Download Data

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

  Natural Product: NPC282703

Natural Product ID:  NPC282703
Common Name*:   Tetrahydrofuroguaiacin B
IUPAC Name:   4-[(2R,3S,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
Synonyms:  
Standard InCHIKey:  GMXMKSFJQLFOSO-SRRICDNISA-N
Standard InCHI:  InChI=1S/C20H24O5/c1-11-12(2)20(14-6-8-16(22)18(10-14)24-4)25-19(11)13-5-7-15(21)17(9-13)23-3/h5-12,19-22H,1-4H3/t11-,12+,19+,20-
SMILES:  C[C@H]1[C@@H](C)[C@@H](c2ccc(c(c2)OC)O)O[C@H]1c1ccc(c(c1)OC)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1170325
PubChem CID:   13870572
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota seeds n.a. n.a. PMID[17998162]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[1955885]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. fruit n.a. PMID[20879744]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[27419473]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Aril n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6113 Piper pedicellosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5162 Comaster multifida Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4539 Ipomoea cristulata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO490 Lophozonia menziesii Species 0thofagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17811 Cephalonoplos segetum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5746 Pancratium trianthum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5241 Myristica fragrans Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7393 Esenbeckia nesiotica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19928 Lachnoanaerobaculum saburreum Species Lachnospiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5334 Rhodotypos scandens Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7237 Xanthostemon oppositifolius Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2665 Andinobates fulguritus Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8303 Catalpa bignonioides Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28409 Lens phaseoloides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8532 Helipterum tenellum Species Asteraceae 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
NPT68 Individual Protein Aldose reductase Rattus norvegicus IC50 = 21379.62 nM PMID[559350]

☑ 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 NPC282703 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 NPC45774
1.0 High Similarity NPC11258
1.0 High Similarity NPC21867
1.0 High Similarity NPC184733
1.0 High Similarity NPC129570
1.0 High Similarity NPC128208
0.9837 High Similarity NPC187998
0.9837 High Similarity NPC145305
0.9837 High Similarity NPC242807
0.9837 High Similarity NPC153739
0.9837 High Similarity NPC241522
0.9837 High Similarity NPC257582
0.9837 High Similarity NPC77040
0.9837 High Similarity NPC64201
0.9837 High Similarity NPC42300
0.9837 High Similarity NPC92164
0.9837 High Similarity NPC174495
0.9758 High Similarity NPC115207
0.9758 High Similarity NPC277804
0.9758 High Similarity NPC40432
0.9758 High Similarity NPC228346
0.9758 High Similarity NPC27843
0.9758 High Similarity NPC158079
0.9758 High Similarity NPC7171
0.9758 High Similarity NPC161557
0.9756 High Similarity NPC475875
0.968 High Similarity NPC181049
0.968 High Similarity NPC207400
0.9675 High Similarity NPC470084
0.9603 High Similarity NPC158331
0.9593 High Similarity NPC165045
0.9593 High Similarity NPC118533
0.959 High Similarity NPC148627
0.9587 High Similarity NPC31344
0.9587 High Similarity NPC317769
0.9528 High Similarity NPC67247
0.9528 High Similarity NPC49603
0.9528 High Similarity NPC187616
0.9528 High Similarity NPC287745
0.9528 High Similarity NPC193026
0.9528 High Similarity NPC471942
0.9524 High Similarity NPC471505
0.9524 High Similarity NPC175067
0.9524 High Similarity NPC4940
0.9524 High Similarity NPC204215
0.9512 High Similarity NPC206882
0.9453 High Similarity NPC135777
0.9453 High Similarity NPC142547
0.9453 High Similarity NPC126409
0.9453 High Similarity NPC99572
0.9435 High Similarity NPC5428
0.9426 High Similarity NPC471693
0.9421 High Similarity NPC126935
0.9421 High Similarity NPC312713
0.9421 High Similarity NPC65933
0.9421 High Similarity NPC216929
0.9421 High Similarity NPC57268
0.9421 High Similarity NPC172676
0.938 High Similarity NPC477939
0.938 High Similarity NPC156502
0.938 High Similarity NPC54743
0.938 High Similarity NPC209985
0.938 High Similarity NPC471988
0.938 High Similarity NPC29799
0.938 High Similarity NPC10737
0.938 High Similarity NPC177160
0.938 High Similarity NPC263367
0.938 High Similarity NPC77861
0.9375 High Similarity NPC244983
0.9375 High Similarity NPC326095
0.937 High Similarity NPC106739
0.936 High Similarity NPC245826
0.936 High Similarity NPC252307
0.936 High Similarity NPC474178
0.9355 High Similarity NPC178284
0.9355 High Similarity NPC58607
0.9355 High Similarity NPC191037
0.9344 High Similarity NPC85488
0.9308 High Similarity NPC281780
0.9302 High Similarity NPC34103
0.9302 High Similarity NPC101624
0.9302 High Similarity NPC141765
0.9302 High Similarity NPC165155
0.9302 High Similarity NPC184938
0.9302 High Similarity NPC24490
0.9291 High Similarity NPC474017
0.928 High Similarity NPC118787
0.928 High Similarity NPC111247
0.928 High Similarity NPC41706
0.928 High Similarity NPC183181
0.928 High Similarity NPC163332
0.928 High Similarity NPC319625
0.928 High Similarity NPC292056
0.928 High Similarity NPC147821
0.9274 High Similarity NPC194519
0.9268 High Similarity NPC280704
0.9268 High Similarity NPC473451
0.9256 High Similarity NPC242885
0.9256 High Similarity NPC232316
0.9256 High Similarity NPC95614
0.9256 High Similarity NPC227217
0.9256 High Similarity NPC117780
0.9256 High Similarity NPC56214
0.9256 High Similarity NPC165133
0.9237 High Similarity NPC193666
0.9237 High Similarity NPC123526
0.9237 High Similarity NPC88640
0.9213 High Similarity NPC275950
0.9213 High Similarity NPC181079
0.9213 High Similarity NPC143483
0.9213 High Similarity NPC173308
0.9194 High Similarity NPC131747
0.9194 High Similarity NPC146355
0.9194 High Similarity NPC18449
0.9194 High Similarity NPC94276
0.9194 High Similarity NPC109822
0.9194 High Similarity NPC257682
0.9194 High Similarity NPC34902
0.9194 High Similarity NPC121783
0.918 High Similarity NPC207613
0.9174 High Similarity NPC281298
0.9174 High Similarity NPC310338
0.9167 High Similarity NPC254759
0.9167 High Similarity NPC160283
0.9167 High Similarity NPC184797
0.9167 High Similarity NPC309124
0.9154 High Similarity NPC93783
0.9147 High Similarity NPC26394
0.9141 High Similarity NPC476345
0.9134 High Similarity NPC5851
0.9134 High Similarity NPC86030
0.9134 High Similarity NPC170844
0.9134 High Similarity NPC476968
0.9127 High Similarity NPC21563
0.9127 High Similarity NPC106511
0.9127 High Similarity NPC127587
0.9106 High Similarity NPC476343
0.9106 High Similarity NPC473853
0.9106 High Similarity NPC262156
0.9106 High Similarity NPC113865
0.9106 High Similarity NPC343720
0.9106 High Similarity NPC470804
0.9106 High Similarity NPC38996
0.9106 High Similarity NPC324571
0.9106 High Similarity NPC312675
0.9106 High Similarity NPC160380
0.9106 High Similarity NPC54872
0.9106 High Similarity NPC184651
0.9106 High Similarity NPC470212
0.9098 High Similarity NPC470372
0.9098 High Similarity NPC471414
0.9098 High Similarity NPC87725
0.9098 High Similarity NPC472711
0.9098 High Similarity NPC263261
0.9091 High Similarity NPC470626
0.9091 High Similarity NPC232164
0.9091 High Similarity NPC236306
0.9091 High Similarity NPC292882
0.9091 High Similarity NPC473739
0.9077 High Similarity NPC478085
0.907 High Similarity NPC259742
0.907 High Similarity NPC147616
0.907 High Similarity NPC104077
0.907 High Similarity NPC230219
0.907 High Similarity NPC201587
0.907 High Similarity NPC219671
0.907 High Similarity NPC253105
0.9055 High Similarity NPC206615
0.9055 High Similarity NPC98631
0.9055 High Similarity NPC470213
0.9055 High Similarity NPC72529
0.9055 High Similarity NPC186843
0.9055 High Similarity NPC472968
0.9048 High Similarity NPC76451
0.9048 High Similarity NPC285725
0.9048 High Similarity NPC274356
0.9048 High Similarity NPC112571
0.9048 High Similarity NPC50683
0.904 High Similarity NPC48990
0.904 High Similarity NPC114901
0.904 High Similarity NPC293701
0.9032 High Similarity NPC71090
0.903 High Similarity NPC131971
0.903 High Similarity NPC476356
0.903 High Similarity NPC107161
0.903 High Similarity NPC67467
0.903 High Similarity NPC253878
0.9023 High Similarity NPC177868
0.9023 High Similarity NPC55793
0.9016 High Similarity NPC320987
0.9016 High Similarity NPC181969
0.9015 High Similarity NPC474039
0.9008 High Similarity NPC293619
0.9 High Similarity NPC170185
0.9 High Similarity NPC169973
0.8992 High Similarity NPC472597
0.8992 High Similarity NPC470096
0.8992 High Similarity NPC470095
0.8976 High Similarity NPC98745
0.8968 High Similarity NPC203133

  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 NPC282703 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
0.9134 High Similarity NPD3027 Phase 3
0.8678 High Similarity NPD5283 Phase 1
0.8512 High Similarity NPD228 Approved
0.8496 Intermediate Similarity NPD1613 Approved
0.8496 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD2861 Phase 2
0.8359 Intermediate Similarity NPD3705 Approved
0.8358 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8358 Intermediate Similarity NPD3620 Phase 2
0.8347 Intermediate Similarity NPD3021 Approved
0.8347 Intermediate Similarity NPD3022 Approved
0.8333 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7984 Intermediate Similarity NPD1357 Approved
0.7956 Intermediate Similarity NPD4060 Phase 1
0.7956 Intermediate Similarity NPD1558 Phase 1
0.7947 Intermediate Similarity NPD6234 Discontinued
0.7926 Intermediate Similarity NPD4908 Phase 1
0.7887 Intermediate Similarity NPD4236 Phase 3
0.7887 Intermediate Similarity NPD4237 Approved
0.7823 Intermediate Similarity NPD2684 Approved
0.782 Intermediate Similarity NPD2983 Phase 2
0.782 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.782 Intermediate Similarity NPD2982 Phase 2
0.7812 Intermediate Similarity NPD7157 Approved
0.781 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD1610 Phase 2
0.7793 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD3060 Approved
0.7746 Intermediate Similarity NPD7266 Discontinued
0.7746 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD2981 Phase 2
0.7733 Intermediate Similarity NPD37 Approved
0.7733 Intermediate Similarity NPD1934 Approved
0.7721 Intermediate Similarity NPD3018 Phase 2
0.7717 Intermediate Similarity NPD7843 Approved
0.7708 Intermediate Similarity NPD6331 Phase 2
0.7708 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD4110 Phase 3
0.7697 Intermediate Similarity NPD4967 Phase 2
0.7697 Intermediate Similarity NPD4966 Approved
0.7697 Intermediate Similarity NPD4965 Approved
0.7692 Intermediate Similarity NPD5536 Phase 2
0.7682 Intermediate Similarity NPD2977 Approved
0.7682 Intermediate Similarity NPD2978 Approved
0.7643 Intermediate Similarity NPD5735 Approved
0.7643 Intermediate Similarity NPD6355 Discontinued
0.7639 Intermediate Similarity NPD6674 Discontinued
0.7639 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD1375 Discontinued
0.7606 Intermediate Similarity NPD5588 Approved
0.7603 Intermediate Similarity NPD3020 Approved
0.7595 Intermediate Similarity NPD7228 Approved
0.7582 Intermediate Similarity NPD3882 Suspended
0.7566 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD5111 Phase 2
0.7554 Intermediate Similarity NPD5110 Phase 2
0.7554 Intermediate Similarity NPD5109 Approved
0.7552 Intermediate Similarity NPD2161 Phase 2
0.7538 Intermediate Similarity NPD6671 Approved
0.7535 Intermediate Similarity NPD4536 Approved
0.7535 Intermediate Similarity NPD4538 Approved
0.7535 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD968 Approved
0.7518 Intermediate Similarity NPD3657 Discovery
0.7518 Intermediate Similarity NPD6584 Phase 3
0.75 Intermediate Similarity NPD5763 Approved
0.75 Intermediate Similarity NPD1548 Phase 1
0.75 Intermediate Similarity NPD2674 Phase 3
0.75 Intermediate Similarity NPD5762 Approved
0.75 Intermediate Similarity NPD8651 Approved
0.75 Intermediate Similarity NPD4123 Phase 3
0.7483 Intermediate Similarity NPD5058 Phase 3
0.7482 Intermediate Similarity NPD7095 Approved
0.7466 Intermediate Similarity NPD4628 Phase 3
0.7451 Intermediate Similarity NPD2801 Approved
0.745 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD2238 Phase 2
0.7445 Intermediate Similarity NPD3094 Phase 2
0.7429 Intermediate Similarity NPD3145 Approved
0.7429 Intermediate Similarity NPD3144 Approved
0.7426 Intermediate Similarity NPD5327 Phase 3
0.7426 Intermediate Similarity NPD4749 Approved
0.7415 Intermediate Similarity NPD2677 Approved
0.741 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD1091 Approved
0.7407 Intermediate Similarity NPD3092 Approved
0.7397 Intermediate Similarity NPD5177 Phase 3
0.7397 Intermediate Similarity NPD4162 Approved
0.7389 Intermediate Similarity NPD7199 Phase 2
0.7388 Intermediate Similarity NPD6516 Phase 2
0.7388 Intermediate Similarity NPD5846 Approved
0.7383 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7375 Intermediate Similarity NPD3818 Discontinued
0.7372 Intermediate Similarity NPD6696 Suspended
0.7361 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD5960 Phase 3
0.7358 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD2489 Approved
0.7358 Intermediate Similarity NPD27 Approved
0.7358 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6166 Phase 2
0.7357 Intermediate Similarity NPD4625 Phase 3
0.7355 Intermediate Similarity NPD2859 Approved
0.7355 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2860 Approved
0.7353 Intermediate Similarity NPD2231 Phase 2
0.7353 Intermediate Similarity NPD2233 Approved
0.7353 Intermediate Similarity NPD1608 Approved
0.7353 Intermediate Similarity NPD2230 Approved
0.7353 Intermediate Similarity NPD2235 Phase 2
0.7353 Intermediate Similarity NPD2232 Approved
0.7351 Intermediate Similarity NPD1653 Approved
0.7343 Intermediate Similarity NPD6653 Approved
0.7338 Intermediate Similarity NPD5772 Approved
0.7338 Intermediate Similarity NPD9494 Approved
0.7338 Intermediate Similarity NPD5773 Approved
0.7333 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD4140 Approved
0.7324 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD290 Approved
0.7305 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD6798 Discontinued
0.7303 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD6583 Phase 3
0.7299 Intermediate Similarity NPD6582 Phase 2
0.7297 Intermediate Similarity NPD5241 Discontinued
0.7297 Intermediate Similarity NPD6190 Approved
0.7296 Intermediate Similarity NPD2970 Approved
0.7296 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2969 Approved
0.7292 Intermediate Similarity NPD6896 Approved
0.7292 Intermediate Similarity NPD6895 Approved
0.729 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD2563 Approved
0.729 Intermediate Similarity NPD2560 Approved
0.7273 Intermediate Similarity NPD9296 Approved
0.7273 Intermediate Similarity NPD2933 Approved
0.7273 Intermediate Similarity NPD2934 Approved
0.7266 Intermediate Similarity NPD4624 Approved
0.7266 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD5126 Approved
0.7259 Intermediate Similarity NPD5125 Phase 3
0.7259 Intermediate Similarity NPD2668 Approved
0.7259 Intermediate Similarity NPD2667 Approved
0.7255 Intermediate Similarity NPD4678 Approved
0.7255 Intermediate Similarity NPD4675 Approved
0.7254 Intermediate Similarity NPD6233 Phase 2
0.7248 Intermediate Similarity NPD7124 Phase 2
0.7239 Intermediate Similarity NPD3091 Approved
0.7239 Intermediate Similarity NPD1182 Approved
0.7237 Intermediate Similarity NPD3686 Approved
0.7237 Intermediate Similarity NPD4210 Discontinued
0.7237 Intermediate Similarity NPD3687 Approved
0.7233 Intermediate Similarity NPD3051 Approved
0.723 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1840 Phase 2
0.7222 Intermediate Similarity NPD6353 Approved
0.7219 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7526 Approved
0.7219 Intermediate Similarity NPD52 Approved
0.7215 Intermediate Similarity NPD5494 Approved
0.7212 Intermediate Similarity NPD7313 Approved
0.7212 Intermediate Similarity NPD7310 Approved
0.7212 Intermediate Similarity NPD7312 Approved
0.7212 Intermediate Similarity NPD7311 Approved
0.7211 Intermediate Similarity NPD7037 Approved
0.7209 Intermediate Similarity NPD5451 Approved
0.7203 Intermediate Similarity NPD3062 Approved
0.7203 Intermediate Similarity NPD3061 Approved
0.7203 Intermediate Similarity NPD3059 Approved
0.72 Intermediate Similarity NPD1511 Approved
0.72 Intermediate Similarity NPD4357 Discontinued
0.72 Intermediate Similarity NPD291 Approved
0.7197 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7685 Pre-registration
0.719 Intermediate Similarity NPD4005 Discontinued
0.7185 Intermediate Similarity NPD5585 Approved
0.7178 Intermediate Similarity NPD7074 Phase 3
0.7176 Intermediate Similarity NPD5535 Approved
0.717 Intermediate Similarity NPD8127 Discontinued
0.7169 Intermediate Similarity NPD7309 Approved
0.7153 Intermediate Similarity NPD4340 Discontinued
0.7152 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3540 Phase 1
0.7133 Intermediate Similarity NPD4062 Phase 3
0.7132 Intermediate Similarity NPD9384 Approved
0.7132 Intermediate Similarity NPD9381 Approved
0.7132 Intermediate Similarity NPD17 Approved
0.7132 Intermediate Similarity NPD4626 Approved
0.7122 Intermediate Similarity NPD1283 Approved
0.7122 Intermediate Similarity NPD2922 Phase 1
0.7117 Intermediate Similarity NPD7054 Approved
0.7115 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD8166 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