Structure

Physi-Chem Properties

Molecular Weight:  416.18
Volume:  417.851
LogP:  2.991
LogD:  3.2
LogS:  -4.009
# Rotatable Bonds:  7
TPSA:  64.61
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.68
Synthetic Accessibility Score:  3.594
Fsp3:  0.478
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.803
MDCK Permeability:  5.794649769086391e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.242
Plasma Protein Binding (PPB):  55.72899627685547%
Volume Distribution (VD):  0.53
Pgp-substrate:  17.34419822692871%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.961
CYP2C19-inhibitor:  0.087
CYP2C19-substrate:  0.937
CYP2C9-inhibitor:  0.095
CYP2C9-substrate:  0.529
CYP2D6-inhibitor:  0.046
CYP2D6-substrate:  0.917
CYP3A4-inhibitor:  0.448
CYP3A4-substrate:  0.921

ADMET: Excretion

Clearance (CL):  8.852
Half-life (T1/2):  0.333

ADMET: Toxicity

hERG Blockers:  0.67
Human Hepatotoxicity (H-HT):  0.112
Drug-inuced Liver Injury (DILI):  0.916
AMES Toxicity:  0.119
Rat Oral Acute Toxicity:  0.049
Maximum Recommended Daily Dose:  0.407
Skin Sensitization:  0.942
Carcinogencity:  0.052
Eye Corrosion:  0.003
Eye Irritation:  0.041
Respiratory Toxicity:  0.351

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

  Natural Product: NPC82862

Natural Product ID:  NPC82862
Common Name*:   (+)-Magnolin
IUPAC Name:   (3S,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-6-(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
Synonyms:   (+)-Magnolin
Standard InCHIKey:  MFIHSKBTNZNJIK-RZTYQLBFSA-N
Standard InCHI:  InChI=1S/C23H28O7/c1-24-17-7-6-13(8-18(17)25-2)21-15-11-30-22(16(15)12-29-21)14-9-19(26-3)23(28-5)20(10-14)27-4/h6-10,15-16,21-22H,11-12H2,1-5H3/t15-,16-,21+,22+/m0/s1
SMILES:  COc1cc(ccc1OC)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL519926
PubChem CID:   169234
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans

*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
NPO9825 Actinoplanes durhamensis Species Micromonosporaceae Bacteria n.a. n.a. n.a. PMID[12193009]
NPO11997 Leucophyllum ambiguum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. PMID[12608853]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[17628872]
NPO17167 Magnolia fargesii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[19110419]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[19370929]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21563811]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[22080044]
NPO25682 Acorus calamus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22671987]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[23373216]
NPO16126 Vitex peduncularis Species Lamiaceae Eukaryota leaves n.a. n.a. PMID[25264585]
NPO11997 Leucophyllum ambiguum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. PMID[32239935]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. flower bud n.a. PMID[7779269]
NPO17167 Magnolia fargesii Species Magnoliaceae Eukaryota flower buds n.a. n.a. PMID[9644071]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18524 Scenedesmus basiliensis Species Scenedesmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15064 Magnolia denudata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17167 Magnolia fargesii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18811 Magnolia biondii Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1918 Magnolia kobus Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25197 Magnolia sprengeri Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25682 Acorus calamus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11997 Leucophyllum ambiguum Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16126 Vitex peduncularis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17721 Oenothera odorata Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15294 Magnolia salicifolia Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9825 Actinoplanes durhamensis Species Micromonosporaceae Bacteria 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
NPT34 Cell Line BV-2 Mus musculus IC50 = 20500.0 nM PMID[448146]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 903.0 nM PMID[448147]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition > 90.0 % PMID[448147]

☑ 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 NPC82862 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 NPC222127
0.9917 High Similarity NPC8050
0.9917 High Similarity NPC473092
0.9917 High Similarity NPC473093
0.9836 High Similarity NPC328682
0.9836 High Similarity NPC281864
0.9836 High Similarity NPC54321
0.9835 High Similarity NPC50683
0.9835 High Similarity NPC285725
0.9835 High Similarity NPC112571
0.9672 High Similarity NPC88297
0.9672 High Similarity NPC186845
0.9672 High Similarity NPC9891
0.9669 High Similarity NPC121783
0.9669 High Similarity NPC18449
0.9669 High Similarity NPC34902
0.9603 High Similarity NPC136750
0.9603 High Similarity NPC266848
0.9524 High Similarity NPC72046
0.9524 High Similarity NPC261812
0.9524 High Similarity NPC65183
0.9453 High Similarity NPC126409
0.9453 High Similarity NPC189474
0.9453 High Similarity NPC99572
0.9444 High Similarity NPC192255
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 NPC78047
0.9375 High Similarity NPC31530
0.9365 High Similarity NPC470624
0.9365 High Similarity NPC237169
0.9302 High Similarity NPC34103
0.9302 High Similarity NPC141765
0.9302 High Similarity NPC49235
0.9302 High Similarity NPC24490
0.9302 High Similarity NPC148893
0.9302 High Similarity NPC165155
0.9302 High Similarity NPC25333
0.9297 High Similarity NPC158331
0.9262 High Similarity NPC477886
0.9231 High Similarity NPC121651
0.9225 High Similarity NPC287745
0.9225 High Similarity NPC474478
0.9219 High Similarity NPC204215
0.9219 High Similarity NPC7744
0.9219 High Similarity NPC475856
0.9219 High Similarity NPC175067
0.9206 High Similarity NPC165128
0.9206 High Similarity NPC158471
0.9206 High Similarity NPC57119
0.9206 High Similarity NPC226862
0.92 High Similarity NPC206882
0.9187 High Similarity NPC261661
0.9174 High Similarity NPC475961
0.9174 High Similarity NPC254625
0.916 High Similarity NPC185908
0.9147 High Similarity NPC1474
0.9141 High Similarity NPC161557
0.9141 High Similarity NPC228346
0.9141 High Similarity NPC115207
0.9141 High Similarity NPC40432
0.9141 High Similarity NPC158079
0.9141 High Similarity NPC7171
0.9141 High Similarity NPC82111
0.9141 High Similarity NPC227160
0.9141 High Similarity NPC27843
0.9098 High Similarity NPC312199
0.9091 High Similarity NPC113550
0.9084 High Similarity NPC11453
0.9077 High Similarity NPC244983
0.9077 High Similarity NPC326095
0.907 High Similarity NPC181049
0.907 High Similarity NPC207400
0.9062 High Similarity NPC271208
0.9062 High Similarity NPC233224
0.9055 High Similarity NPC31707
0.9055 High Similarity NPC470084
0.903 High Similarity NPC472562
0.903 High Similarity NPC80326
0.9024 High Similarity NPC472596
0.9023 High Similarity NPC46591
0.9023 High Similarity NPC177868
0.9023 High Similarity NPC103448
0.9023 High Similarity NPC216434
0.9016 High Similarity NPC15805
0.9015 High Similarity NPC283949
0.9015 High Similarity NPC477938
0.9008 High Similarity NPC150534
0.9 High Similarity NPC196937
0.8992 High Similarity NPC474017
0.8992 High Similarity NPC184928
0.8992 High Similarity NPC141493
0.8976 High Similarity NPC98745
0.8976 High Similarity NPC242032
0.8963 High Similarity NPC255566
0.8963 High Similarity NPC298317
0.8955 High Similarity NPC300798
0.8955 High Similarity NPC58137
0.8939 High Similarity NPC143895
0.8931 High Similarity NPC145769
0.8926 High Similarity NPC123948
0.8923 High Similarity NPC171928
0.8923 High Similarity NPC129687
0.8923 High Similarity NPC100223
0.8923 High Similarity NPC158526
0.8923 High Similarity NPC4940
0.8923 High Similarity NPC16830
0.8923 High Similarity NPC33611
0.8915 High Similarity NPC64201
0.8915 High Similarity NPC187998
0.8915 High Similarity NPC42300
0.8915 High Similarity NPC145305
0.8915 High Similarity NPC174495
0.8915 High Similarity NPC242807
0.8915 High Similarity NPC257582
0.8915 High Similarity NPC153739
0.8915 High Similarity NPC92164
0.8915 High Similarity NPC241522
0.8915 High Similarity NPC77040
0.8906 High Similarity NPC45774
0.8906 High Similarity NPC11258
0.8906 High Similarity NPC21867
0.8906 High Similarity NPC184733
0.8906 High Similarity NPC128208
0.8906 High Similarity NPC282703
0.8906 High Similarity NPC210674
0.8906 High Similarity NPC129570
0.8897 High Similarity NPC471415
0.8897 High Similarity NPC470097
0.8897 High Similarity NPC114119
0.8889 High Similarity NPC287124
0.8889 High Similarity NPC474295
0.8889 High Similarity NPC311057
0.8889 High Similarity NPC174522
0.8881 High Similarity NPC160283
0.8881 High Similarity NPC254759
0.8881 High Similarity NPC309124
0.8881 High Similarity NPC27495
0.8881 High Similarity NPC226547
0.8881 High Similarity NPC56091
0.8881 High Similarity NPC184797
0.8864 High Similarity NPC236522
0.8864 High Similarity NPC474139
0.8864 High Similarity NPC211386
0.8846 High Similarity NPC277804
0.8837 High Similarity NPC210623
0.8837 High Similarity NPC226788
0.8837 High Similarity NPC218856
0.8837 High Similarity NPC190629
0.8837 High Similarity NPC476968
0.8837 High Similarity NPC170844
0.8837 High Similarity NPC202582
0.8837 High Similarity NPC285339
0.8837 High Similarity NPC222004
0.8837 High Similarity NPC475875
0.8837 High Similarity NPC273295
0.8837 High Similarity NPC470258
0.8837 High Similarity NPC3439
0.8832 High Similarity NPC180953
0.8828 High Similarity NPC202904
0.8828 High Similarity NPC474119
0.8828 High Similarity NPC127587
0.8828 High Similarity NPC189248
0.8824 High Similarity NPC474808
0.8824 High Similarity NPC12728
0.8824 High Similarity NPC185071
0.8815 High Similarity NPC263261
0.8815 High Similarity NPC87725
0.881 High Similarity NPC233526
0.881 High Similarity NPC282496
0.8806 High Similarity NPC232164
0.8806 High Similarity NPC473739
0.8806 High Similarity NPC236306
0.8806 High Similarity NPC292882
0.8797 High Similarity NPC32189
0.8788 High Similarity NPC47181
0.8788 High Similarity NPC170779
0.8788 High Similarity NPC90083
0.8779 High Similarity NPC201587
0.8779 High Similarity NPC104077
0.8779 High Similarity NPC219671
0.8779 High Similarity NPC147616
0.8779 High Similarity NPC253105
0.8779 High Similarity NPC230219
0.8779 High Similarity NPC259742
0.877 High Similarity NPC81067
0.877 High Similarity NPC9341
0.8769 High Similarity NPC307042
0.8769 High Similarity NPC192687
0.8769 High Similarity NPC476399
0.8769 High Similarity NPC79184
0.8769 High Similarity NPC224157
0.8768 High Similarity NPC324492
0.8768 High Similarity NPC317053
0.876 High Similarity NPC470213
0.876 High Similarity NPC207702

  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 NPC82862 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
0.8837 High Similarity NPD3027 Phase 3
0.8678 High Similarity NPD5283 Phase 1
0.8438 Intermediate Similarity NPD2981 Phase 2
0.8372 Intermediate Similarity NPD2983 Phase 2
0.8372 Intermediate Similarity NPD2982 Phase 2
0.8359 Intermediate Similarity NPD3705 Approved
0.8258 Intermediate Similarity NPD3018 Phase 2
0.8222 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD1613 Approved
0.8156 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.806 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD4965 Approved
0.8054 Intermediate Similarity NPD4967 Phase 2
0.8054 Intermediate Similarity NPD4966 Approved
0.7985 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD6234 Discontinued
0.7926 Intermediate Similarity NPD4908 Phase 1
0.7891 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD37 Approved
0.7847 Intermediate Similarity NPD7124 Phase 2
0.781 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7803 Intermediate Similarity NPD1610 Phase 2
0.7778 Intermediate Similarity NPD5494 Approved
0.7721 Intermediate Similarity NPD2861 Phase 2
0.7692 Intermediate Similarity NPD5536 Phase 2
0.7676 Intermediate Similarity NPD3539 Phase 1
0.766 Intermediate Similarity NPD6111 Discontinued
0.7635 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD3540 Phase 1
0.7613 Intermediate Similarity NPD7199 Phase 2
0.7595 Intermediate Similarity NPD7228 Approved
0.7554 Intermediate Similarity NPD5109 Approved
0.7554 Intermediate Similarity NPD5110 Phase 2
0.7554 Intermediate Similarity NPD5111 Phase 2
0.7518 Intermediate Similarity NPD3657 Discovery
0.7517 Intermediate Similarity NPD4237 Approved
0.7517 Intermediate Similarity NPD4236 Phase 3
0.7516 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1548 Phase 1
0.75 Intermediate Similarity NPD228 Approved
0.75 Intermediate Similarity NPD1934 Approved
0.745 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD3620 Phase 2
0.7444 Intermediate Similarity NPD1357 Approved
0.7432 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4749 Approved
0.7426 Intermediate Similarity NPD5327 Phase 3
0.7419 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD4005 Discontinued
0.741 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7240 Approved
0.7405 Intermediate Similarity NPD7157 Approved
0.7402 Intermediate Similarity NPD2684 Approved
0.7391 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1375 Discontinued
0.7368 Intermediate Similarity NPD4678 Approved
0.7368 Intermediate Similarity NPD4675 Approved
0.7361 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD4625 Phase 3
0.7355 Intermediate Similarity NPD3882 Suspended
0.7351 Intermediate Similarity NPD4210 Discontinued
0.7347 Intermediate Similarity NPD7466 Approved
0.7347 Intermediate Similarity NPD4110 Phase 3
0.7347 Intermediate Similarity NPD6331 Phase 2
0.7347 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7344 Intermediate Similarity NPD3021 Approved
0.7344 Intermediate Similarity NPD3022 Approved
0.7338 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD4357 Discontinued
0.731 Intermediate Similarity NPD2161 Phase 2
0.7308 Intermediate Similarity NPD7843 Approved
0.7305 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD6895 Approved
0.7292 Intermediate Similarity NPD6896 Approved
0.729 Intermediate Similarity NPD3817 Phase 2
0.7279 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6674 Discontinued
0.7273 Intermediate Similarity NPD5735 Approved
0.7241 Intermediate Similarity NPD5588 Approved
0.723 Intermediate Similarity NPD3892 Phase 2
0.723 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD2801 Approved
0.7219 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD5451 Approved
0.7203 Intermediate Similarity NPD4060 Phase 1
0.7203 Intermediate Similarity NPD2238 Phase 2
0.72 Intermediate Similarity NPD5297 Approved
0.7192 Intermediate Similarity NPD2438 Suspended
0.7192 Intermediate Similarity NPD2796 Approved
0.7188 Intermediate Similarity NPD5242 Approved
0.7188 Intermediate Similarity NPD3926 Phase 2
0.7185 Intermediate Similarity NPD5585 Approved
0.7181 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD5535 Approved
0.7174 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD4538 Approved
0.7172 Intermediate Similarity NPD4536 Approved
0.7162 Intermediate Similarity NPD3060 Approved
0.7162 Intermediate Similarity NPD5177 Phase 3
0.7161 Intermediate Similarity NPD3382 Approved
0.7161 Intermediate Similarity NPD3383 Approved
0.7161 Intermediate Similarity NPD3384 Approved
0.716 Intermediate Similarity NPD3818 Discontinued
0.7153 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6166 Phase 2
0.7143 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD5058 Phase 3
0.7133 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD17 Approved
0.7124 Intermediate Similarity NPD1653 Approved
0.7122 Intermediate Similarity NPD8651 Approved
0.7122 Intermediate Similarity NPD2922 Phase 1
0.7117 Intermediate Similarity NPD5844 Phase 1
0.7111 Intermediate Similarity NPD1182 Approved
0.7105 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1840 Phase 2
0.7089 Intermediate Similarity NPD4055 Discovery
0.7083 Intermediate Similarity NPD2979 Phase 3
0.7083 Intermediate Similarity NPD1558 Phase 1
0.707 Intermediate Similarity NPD5353 Approved
0.7067 Intermediate Similarity NPD2219 Phase 1
0.7066 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5718 Phase 2
0.7063 Intermediate Similarity NPD1247 Approved
0.7059 Intermediate Similarity NPD1651 Approved
0.7059 Intermediate Similarity NPD5691 Approved
0.7059 Intermediate Similarity NPD5976 Discontinued
0.7054 Intermediate Similarity NPD1358 Approved
0.7047 Intermediate Similarity NPD4162 Approved
0.7044 Intermediate Similarity NPD919 Approved
0.7039 Intermediate Similarity NPD4123 Phase 3
0.7029 Intermediate Similarity NPD1091 Approved
0.7027 Intermediate Similarity NPD5763 Approved
0.7027 Intermediate Similarity NPD5762 Approved
0.7027 Intermediate Similarity NPD7266 Discontinued
0.702 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6232 Discontinued
0.7007 Intermediate Similarity NPD5846 Approved
0.7007 Intermediate Similarity NPD6516 Phase 2
0.7007 Intermediate Similarity NPD5960 Phase 3
0.6994 Remote Similarity NPD7473 Discontinued
0.6993 Remote Similarity NPD7526 Approved
0.6993 Remote Similarity NPD52 Approved
0.6993 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6993 Remote Similarity NPD7095 Approved
0.6986 Remote Similarity NPD6353 Approved
0.6984 Remote Similarity NPD1242 Phase 1
0.698 Remote Similarity NPD1372 Clinical (unspecified phase)
0.698 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6978 Remote Similarity NPD1608 Approved
0.6977 Remote Similarity NPD3134 Approved
0.6974 Remote Similarity NPD1511 Approved
0.697 Remote Similarity NPD7074 Phase 3
0.6966 Remote Similarity NPD4140 Approved
0.6963 Remote Similarity NPD3596 Phase 2
0.6962 Remote Similarity NPD2563 Approved
0.6962 Remote Similarity NPD2560 Approved
0.6954 Remote Similarity NPD2677 Approved
0.6947 Remote Similarity NPD4750 Phase 3
0.6946 Remote Similarity NPD7549 Discontinued
0.6933 Remote Similarity NPD1652 Phase 2
0.6929 Remote Similarity NPD4359 Approved
0.6923 Remote Similarity NPD290 Approved
0.6923 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6923 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4380 Phase 2
0.6918 Remote Similarity NPD5124 Phase 1
0.6918 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6918 Remote Similarity NPD6788 Approved
0.6914 Remote Similarity NPD7229 Phase 3
0.6913 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6912 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6909 Remote Similarity NPD8156 Discontinued
0.6909 Remote Similarity NPD7054 Approved
0.6906 Remote Similarity NPD422 Phase 1
0.6906 Remote Similarity NPD1281 Approved
0.6905 Remote Similarity NPD3020 Approved
0.6901 Remote Similarity NPD6584 Phase 3
0.6901 Remote Similarity NPD4624 Approved
0.6899 Remote Similarity NPD5772 Approved
0.6899 Remote Similarity NPD5773 Approved
0.6899 Remote Similarity NPD2978 Approved
0.6899 Remote Similarity NPD2977 Approved
0.6897 Remote Similarity NPD6233 Phase 2
0.6892 Remote Similarity NPD3748 Approved
0.6892 Remote Similarity NPD4108 Discontinued
0.6889 Remote Similarity NPD6671 Approved
0.6887 Remote Similarity NPD4628 Phase 3
0.6884 Remote Similarity NPD2667 Approved
0.6884 Remote Similarity NPD2668 Approved
0.6884 Remote Similarity NPD5126 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