Structure

Physi-Chem Properties

Molecular Weight:  362.17
Volume:  374.286
LogP:  2.082
LogD:  2.471
LogS:  -3.411
# Rotatable Bonds:  10
TPSA:  88.38
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.601
Synthetic Accessibility Score:  2.715
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.488
MDCK Permeability:  1.8678963897400536e-05
Pgp-inhibitor:  0.019
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.237
Plasma Protein Binding (PPB):  91.97761535644531%
Volume Distribution (VD):  0.701
Pgp-substrate:  3.135850191116333%

ADMET: Metabolism

CYP1A2-inhibitor:  0.675
CYP1A2-substrate:  0.879
CYP2C19-inhibitor:  0.429
CYP2C19-substrate:  0.617
CYP2C9-inhibitor:  0.388
CYP2C9-substrate:  0.762
CYP2D6-inhibitor:  0.87
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.844
CYP3A4-substrate:  0.736

ADMET: Excretion

Clearance (CL):  11.072
Half-life (T1/2):  0.902

ADMET: Toxicity

hERG Blockers:  0.102
Human Hepatotoxicity (H-HT):  0.322
Drug-inuced Liver Injury (DILI):  0.233
AMES Toxicity:  0.108
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.751
Skin Sensitization:  0.541
Carcinogencity:  0.561
Eye Corrosion:  0.003
Eye Irritation:  0.033
Respiratory Toxicity:  0.035

Download Data

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

  Natural Product: NPC194519

Natural Product ID:  NPC194519
Common Name*:   Ligraminol E
IUPAC Name:   4-[(2R)-3-hydroxy-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propyl]-2-methoxyphenol
Synonyms:   Ligraminol E
Standard InCHIKey:  UAGBDLXEDIGWJU-MRXNPFEDSA-N
Standard InCHI:  InChI=1S/C20H26O6/c1-24-19-12-15(5-7-17(19)23)10-16(13-22)26-18-8-6-14(4-3-9-21)11-20(18)25-2/h5-8,11-12,16,21-23H,3-4,9-10,13H2,1-2H3/t16-/m1/s1
SMILES:  OCCCc1ccc(c(c1)OC)O[C@H](Cc1ccc(c(c1)OC)O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1928005
PubChem CID:   56600272
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21936523]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[21936523]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22951040]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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
NPT81 Cell Line A549 Homo sapiens IC50 > 10000.0 nM PMID[464552]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 10000.0 nM PMID[464552]
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 > 10000.0 nM PMID[464552]
NPT34 Cell Line BV-2 Mus musculus IC50 > 200000.0 nM PMID[464552]
NPT34 Cell Line BV-2 Mus musculus Activity = 97.1 % PMID[464552]

☑ 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 NPC194519 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
0.9916 High Similarity NPC58607
0.9916 High Similarity NPC191037
0.9916 High Similarity NPC178284
0.9833 High Similarity NPC183181
0.9833 High Similarity NPC163332
0.9833 High Similarity NPC292056
0.9833 High Similarity NPC147821
0.9833 High Similarity NPC118787
0.9833 High Similarity NPC319625
0.9833 High Similarity NPC41706
0.9833 High Similarity NPC111247
0.9748 High Similarity NPC48990
0.9748 High Similarity NPC109822
0.9748 High Similarity NPC94276
0.9748 High Similarity NPC114901
0.9748 High Similarity NPC293701
0.9746 High Similarity NPC71090
0.9672 High Similarity NPC5851
0.9672 High Similarity NPC86030
0.9664 High Similarity NPC471693
0.9593 High Similarity NPC472338
0.959 High Similarity NPC72529
0.9516 High Similarity NPC472597
0.9504 High Similarity NPC148627
0.9496 High Similarity NPC127389
0.9496 High Similarity NPC290451
0.944 High Similarity NPC184447
0.944 High Similarity NPC35932
0.944 High Similarity NPC16208
0.944 High Similarity NPC7903
0.944 High Similarity NPC160991
0.9431 High Similarity NPC474178
0.9431 High Similarity NPC252307
0.9431 High Similarity NPC245826
0.9412 High Similarity NPC207613
0.9365 High Similarity NPC475840
0.9355 High Similarity NPC470258
0.9355 High Similarity NPC218856
0.9355 High Similarity NPC210623
0.9355 High Similarity NPC285339
0.9355 High Similarity NPC226788
0.9355 High Similarity NPC273295
0.9355 High Similarity NPC222004
0.9355 High Similarity NPC202582
0.9355 High Similarity NPC190629
0.9355 High Similarity NPC3439
0.935 High Similarity NPC165045
0.935 High Similarity NPC118533
0.935 High Similarity NPC210355
0.935 High Similarity NPC474119
0.9333 High Similarity NPC473853
0.9333 High Similarity NPC54872
0.9333 High Similarity NPC324571
0.9333 High Similarity NPC470804
0.9333 High Similarity NPC343720
0.9333 High Similarity NPC113865
0.9333 High Similarity NPC312675
0.9333 High Similarity NPC262156
0.9333 High Similarity NPC470212
0.9333 High Similarity NPC184651
0.9322 High Similarity NPC255675
0.9291 High Similarity NPC170694
0.9291 High Similarity NPC249791
0.9291 High Similarity NPC119060
0.9291 High Similarity NPC310854
0.9291 High Similarity NPC476387
0.9291 High Similarity NPC237594
0.9291 High Similarity NPC478085
0.9286 High Similarity NPC470752
0.928 High Similarity NPC77040
0.928 High Similarity NPC174495
0.928 High Similarity NPC92164
0.928 High Similarity NPC64201
0.928 High Similarity NPC241522
0.928 High Similarity NPC153739
0.928 High Similarity NPC187998
0.928 High Similarity NPC42300
0.928 High Similarity NPC257582
0.928 High Similarity NPC242807
0.928 High Similarity NPC145305
0.9274 High Similarity NPC128208
0.9274 High Similarity NPC98631
0.9274 High Similarity NPC129570
0.9274 High Similarity NPC206615
0.9274 High Similarity NPC45774
0.9274 High Similarity NPC470213
0.9274 High Similarity NPC186843
0.9274 High Similarity NPC11258
0.9274 High Similarity NPC184733
0.9274 High Similarity NPC282703
0.9274 High Similarity NPC21867
0.9244 High Similarity NPC181969
0.9244 High Similarity NPC320987
0.9237 High Similarity NPC86947
0.9219 High Similarity NPC472337
0.9206 High Similarity NPC277804
0.9206 High Similarity NPC470096
0.9206 High Similarity NPC30043
0.9206 High Similarity NPC469613
0.9206 High Similarity NPC309787
0.9206 High Similarity NPC469625
0.9206 High Similarity NPC470095
0.92 High Similarity NPC170844
0.92 High Similarity NPC476968
0.92 High Similarity NPC475875
0.9194 High Similarity NPC5428
0.9167 High Similarity NPC177475
0.9167 High Similarity NPC148615
0.9167 High Similarity NPC35071
0.916 High Similarity NPC470626
0.9153 High Similarity NPC221049
0.9147 High Similarity NPC263367
0.9147 High Similarity NPC177160
0.9147 High Similarity NPC16435
0.9147 High Similarity NPC477939
0.9147 High Similarity NPC77861
0.9147 High Similarity NPC29799
0.9147 High Similarity NPC209985
0.9147 High Similarity NPC472334
0.9147 High Similarity NPC54743
0.9147 High Similarity NPC306441
0.9147 High Similarity NPC10737
0.9147 High Similarity NPC156502
0.9147 High Similarity NPC472336
0.9141 High Similarity NPC193026
0.9141 High Similarity NPC187616
0.9141 High Similarity NPC49603
0.9134 High Similarity NPC201587
0.9134 High Similarity NPC253105
0.9127 High Similarity NPC143483
0.9127 High Similarity NPC469614
0.9127 High Similarity NPC469612
0.912 High Similarity NPC470084
0.9106 High Similarity NPC228972
0.9106 High Similarity NPC122792
0.9098 High Similarity NPC209567
0.9098 High Similarity NPC85488
0.9083 High Similarity NPC135961
0.9083 High Similarity NPC311595
0.9083 High Similarity NPC24474
0.9077 High Similarity NPC138738
0.9077 High Similarity NPC126206
0.9077 High Similarity NPC470413
0.9076 High Similarity NPC293619
0.9076 High Similarity NPC164386
0.907 High Similarity NPC112939
0.907 High Similarity NPC112246
0.907 High Similarity NPC474206
0.907 High Similarity NPC470356
0.907 High Similarity NPC234333
0.907 High Similarity NPC94750
0.907 High Similarity NPC61946
0.907 High Similarity NPC47398
0.907 High Similarity NPC260898
0.907 High Similarity NPC214729
0.907 High Similarity NPC121812
0.9062 High Similarity NPC168059
0.9062 High Similarity NPC229442
0.9055 High Similarity NPC228346
0.9055 High Similarity NPC7171
0.9055 High Similarity NPC474017
0.9055 High Similarity NPC27843
0.9055 High Similarity NPC115207
0.9055 High Similarity NPC40432
0.9055 High Similarity NPC161557
0.9055 High Similarity NPC158079
0.9048 High Similarity NPC212015
0.904 High Similarity NPC106511
0.904 High Similarity NPC470699
0.9032 High Similarity NPC251855
0.9032 High Similarity NPC117214
0.9032 High Similarity NPC233410
0.9032 High Similarity NPC203133
0.9032 High Similarity NPC193544
0.9032 High Similarity NPC208950
0.9032 High Similarity NPC17943
0.9032 High Similarity NPC57490
0.9032 High Similarity NPC472093
0.9032 High Similarity NPC475169
0.9032 High Similarity NPC221077
0.9032 High Similarity NPC116907
0.9032 High Similarity NPC298757
0.9024 High Similarity NPC31344
0.9024 High Similarity NPC317769
0.9024 High Similarity NPC280704
0.9016 High Similarity NPC476343
0.9008 High Similarity NPC227217
0.9008 High Similarity NPC95614
0.9008 High Similarity NPC117780
0.9008 High Similarity NPC56214
0.9008 High Similarity NPC165133
0.9008 High Similarity NPC232316
0.9008 High Similarity NPC242885
0.9008 High Similarity NPC22517
0.9 High Similarity NPC269091
0.9 High Similarity NPC474639
0.9 High Similarity NPC230734
0.9 High Similarity NPC471664
0.9 High Similarity NPC227503
0.9 High Similarity NPC474214

  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 NPC194519 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
0.92 High Similarity NPD3027 Phase 3
0.8837 High Similarity NPD1612 Clinical (unspecified phase)
0.8837 High Similarity NPD1613 Approved
0.8729 High Similarity NPD228 Approved
0.8527 High Similarity NPD1529 Clinical (unspecified phase)
0.845 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD5283 Phase 1
0.8425 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8409 Intermediate Similarity NPD1558 Phase 1
0.8319 Intermediate Similarity NPD2684 Approved
0.8197 Intermediate Similarity NPD7843 Approved
0.8168 Intermediate Similarity NPD2861 Phase 2
0.8145 Intermediate Similarity NPD7157 Approved
0.8134 Intermediate Similarity NPD3620 Phase 2
0.8134 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8099 Intermediate Similarity NPD3021 Approved
0.8099 Intermediate Similarity NPD3022 Approved
0.8058 Intermediate Similarity NPD3060 Approved
0.8031 Intermediate Similarity NPD1357 Approved
0.8 Intermediate Similarity NPD2983 Phase 2
0.8 Intermediate Similarity NPD2982 Phase 2
0.8 Intermediate Similarity NPD4060 Phase 1
0.7984 Intermediate Similarity NPD3705 Approved
0.797 Intermediate Similarity NPD4908 Phase 1
0.7953 Intermediate Similarity NPD1548 Phase 1
0.7934 Intermediate Similarity NPD290 Approved
0.7929 Intermediate Similarity NPD4237 Approved
0.7929 Intermediate Similarity NPD4236 Phase 3
0.7929 Intermediate Similarity NPD4162 Approved
0.7923 Intermediate Similarity NPD2981 Phase 2
0.7914 Intermediate Similarity NPD7266 Discontinued
0.7895 Intermediate Similarity NPD3018 Phase 2
0.7891 Intermediate Similarity NPD1934 Approved
0.7874 Intermediate Similarity NPD5536 Phase 2
0.7852 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7851 Intermediate Similarity NPD968 Approved
0.7846 Intermediate Similarity NPD1091 Approved
0.7846 Intermediate Similarity NPD1610 Phase 2
0.7836 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD5846 Approved
0.7829 Intermediate Similarity NPD6516 Phase 2
0.7826 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD4536 Approved
0.7826 Intermediate Similarity NPD4538 Approved
0.782 Intermediate Similarity NPD6584 Phase 3
0.7815 Intermediate Similarity NPD291 Approved
0.7803 Intermediate Similarity NPD8651 Approved
0.7801 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD4123 Phase 3
0.7746 Intermediate Similarity NPD4628 Phase 3
0.774 Intermediate Similarity NPD1653 Approved
0.7733 Intermediate Similarity NPD3882 Suspended
0.7718 Intermediate Similarity NPD2801 Approved
0.7718 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD6671 Approved
0.7692 Intermediate Similarity NPD2677 Approved
0.7681 Intermediate Similarity NPD5735 Approved
0.7676 Intermediate Similarity NPD6674 Discontinued
0.7664 Intermediate Similarity NPD2674 Phase 3
0.7664 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7652 Intermediate Similarity NPD2235 Phase 2
0.7652 Intermediate Similarity NPD2231 Phase 2
0.7647 Intermediate Similarity NPD7095 Approved
0.7643 Intermediate Similarity NPD5588 Approved
0.7643 Intermediate Similarity NPD5960 Phase 3
0.7622 Intermediate Similarity NPD6331 Phase 2
0.7622 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD4110 Phase 3
0.7619 Intermediate Similarity NPD3687 Approved
0.7619 Intermediate Similarity NPD3686 Approved
0.7613 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6166 Phase 2
0.7613 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD2977 Approved
0.76 Intermediate Similarity NPD2978 Approved
0.7594 Intermediate Similarity NPD6582 Phase 2
0.7594 Intermediate Similarity NPD6583 Phase 3
0.7594 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD6798 Discontinued
0.7586 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD6355 Discontinued
0.7554 Intermediate Similarity NPD4340 Discontinued
0.7536 Intermediate Similarity NPD4062 Phase 3
0.7536 Intermediate Similarity NPD6233 Phase 2
0.7535 Intermediate Similarity NPD5763 Approved
0.7535 Intermediate Similarity NPD1375 Discontinued
0.7535 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD5762 Approved
0.7518 Intermediate Similarity NPD3179 Approved
0.7518 Intermediate Similarity NPD3180 Approved
0.7518 Intermediate Similarity NPD4625 Phase 3
0.7517 Intermediate Similarity NPD4678 Approved
0.7517 Intermediate Similarity NPD4675 Approved
0.7517 Intermediate Similarity NPD5058 Phase 3
0.75 Intermediate Similarity NPD3054 Approved
0.75 Intermediate Similarity NPD3052 Approved
0.75 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9494 Approved
0.7483 Intermediate Similarity NPD5772 Approved
0.7483 Intermediate Similarity NPD5773 Approved
0.7482 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD5535 Approved
0.748 Intermediate Similarity NPD821 Approved
0.7468 Intermediate Similarity NPD7054 Approved
0.7466 Intermediate Similarity NPD1774 Approved
0.7466 Intermediate Similarity NPD1511 Approved
0.7465 Intermediate Similarity NPD2161 Phase 2
0.7464 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD3144 Approved
0.7464 Intermediate Similarity NPD3145 Approved
0.7463 Intermediate Similarity NPD4749 Approved
0.7458 Intermediate Similarity NPD2934 Approved
0.7458 Intermediate Similarity NPD9296 Approved
0.7458 Intermediate Similarity NPD2933 Approved
0.7448 Intermediate Similarity NPD6190 Approved
0.7448 Intermediate Similarity NPD5241 Discontinued
0.7421 Intermediate Similarity NPD7472 Approved
0.7421 Intermediate Similarity NPD7074 Phase 3
0.7415 Intermediate Similarity NPD3536 Discontinued
0.7405 Intermediate Similarity NPD3818 Discontinued
0.7403 Intermediate Similarity NPD6234 Discontinued
0.7395 Intermediate Similarity NPD2860 Approved
0.7395 Intermediate Similarity NPD2859 Approved
0.7394 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD1608 Approved
0.7379 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD6653 Approved
0.7368 Intermediate Similarity NPD3496 Discontinued
0.7365 Intermediate Similarity NPD1512 Approved
0.7357 Intermediate Similarity NPD3062 Approved
0.7357 Intermediate Similarity NPD3059 Approved
0.7357 Intermediate Similarity NPD4140 Approved
0.7357 Intermediate Similarity NPD3061 Approved
0.7355 Intermediate Similarity NPD3020 Approved
0.7338 Intermediate Similarity NPD5109 Approved
0.7338 Intermediate Similarity NPD5111 Phase 2
0.7338 Intermediate Similarity NPD5110 Phase 2
0.7333 Intermediate Similarity NPD5327 Phase 3
0.7333 Intermediate Similarity NPD3685 Discontinued
0.7329 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD2563 Approved
0.732 Intermediate Similarity NPD2560 Approved
0.732 Intermediate Similarity NPD3817 Phase 2
0.7313 Intermediate Similarity NPD422 Phase 1
0.731 Intermediate Similarity NPD5177 Phase 3
0.7308 Intermediate Similarity NPD7199 Phase 2
0.7303 Intermediate Similarity NPD37 Approved
0.7293 Intermediate Similarity NPD9384 Approved
0.7293 Intermediate Similarity NPD9381 Approved
0.7293 Intermediate Similarity NPD1778 Approved
0.7292 Intermediate Similarity NPD3540 Phase 1
0.7279 Intermediate Similarity NPD2922 Phase 1
0.7278 Intermediate Similarity NPD27 Approved
0.7278 Intermediate Similarity NPD2489 Approved
0.7273 Intermediate Similarity NPD1894 Discontinued
0.7273 Intermediate Similarity NPD2154 Approved
0.7273 Intermediate Similarity NPD1182 Approved
0.7273 Intermediate Similarity NPD7033 Discontinued
0.7273 Intermediate Similarity NPD4965 Approved
0.7273 Intermediate Similarity NPD4966 Approved
0.7273 Intermediate Similarity NPD2156 Approved
0.7273 Intermediate Similarity NPD4967 Phase 2
0.7273 Intermediate Similarity NPD2155 Approved
0.7267 Intermediate Similarity NPD6797 Phase 2
0.726 Intermediate Similarity NPD4535 Phase 3
0.7255 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD5314 Approved
0.7252 Intermediate Similarity NPD3596 Phase 2
0.7248 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD52 Approved
0.7248 Intermediate Similarity NPD7526 Approved
0.7244 Intermediate Similarity NPD556 Approved
0.7244 Intermediate Similarity NPD5451 Approved
0.7241 Intermediate Similarity NPD7153 Discontinued
0.7234 Intermediate Similarity NPD2238 Phase 2
0.723 Intermediate Similarity NPD4357 Discontinued
0.7226 Intermediate Similarity NPD1818 Approved
0.7226 Intermediate Similarity NPD1819 Approved
0.7226 Intermediate Similarity NPD1817 Approved
0.7226 Intermediate Similarity NPD1820 Approved
0.7222 Intermediate Similarity NPD3539 Phase 1
0.7222 Intermediate Similarity NPD6032 Approved
0.7222 Intermediate Similarity NPD1358 Approved
0.7222 Intermediate Similarity NPD7251 Discontinued
0.7219 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4005 Discontinued
0.7218 Intermediate Similarity NPD5585 Approved
0.7215 Intermediate Similarity NPD2969 Approved
0.7215 Intermediate Similarity NPD2970 Approved
0.7214 Intermediate Similarity NPD5718 Phase 2
0.7206 Intermediate Similarity NPD9622 Approved
0.7203 Intermediate Similarity NPD9365 Approved
0.72 Intermediate Similarity NPD2122 Discontinued
0.7192 Intermediate Similarity NPD1652 Phase 2
0.7188 Intermediate Similarity NPD7228 Approved
0.7185 Intermediate Similarity NPD3092 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