Structure

Physi-Chem Properties

Molecular Weight:  346.14
Volume:  354.353
LogP:  1.901
LogD:  2.213
LogS:  -2.63
# Rotatable Bonds:  7
TPSA:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.614
Synthetic Accessibility Score:  3.277
Fsp3:  0.263
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:  -4.896
MDCK Permeability:  1.0871899576159194e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.85
Human Intestinal Absorption (HIA):  0.051
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.363

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.3
Plasma Protein Binding (PPB):  97.1308364868164%
Volume Distribution (VD):  0.554
Pgp-substrate:  5.587038516998291%

ADMET: Metabolism

CYP1A2-inhibitor:  0.077
CYP1A2-substrate:  0.822
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.495
CYP2C9-inhibitor:  0.067
CYP2C9-substrate:  0.798
CYP2D6-inhibitor:  0.103
CYP2D6-substrate:  0.784
CYP3A4-inhibitor:  0.481
CYP3A4-substrate:  0.721

ADMET: Excretion

Clearance (CL):  14.009
Half-life (T1/2):  0.875

ADMET: Toxicity

hERG Blockers:  0.072
Human Hepatotoxicity (H-HT):  0.506
Drug-inuced Liver Injury (DILI):  0.044
AMES Toxicity:  0.086
Rat Oral Acute Toxicity:  0.537
Maximum Recommended Daily Dose:  0.583
Skin Sensitization:  0.935
Carcinogencity:  0.501
Eye Corrosion:  0.003
Eye Irritation:  0.035
Respiratory Toxicity:  0.909

Download Data

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

  Natural Product: NPC148627

Natural Product ID:  NPC148627
Common Name*:   Metasequirin D
IUPAC Name:   (E,2S,3S)-3,5-bis(4-hydroxy-3-methoxyphenyl)pent-4-ene-1,2-diol
Synonyms:   Metasequirin D
Standard InCHIKey:  DCEHETRPHUXAHR-ORCRKBFJSA-N
Standard InCHI:  InChI=1S/C19H22O6/c1-24-18-9-12(4-7-15(18)21)3-6-14(17(23)11-20)13-5-8-16(22)19(10-13)25-2/h3-10,14,17,20-23H,11H2,1-2H3/b6-3+/t14-,17+/m0/s1
SMILES:  OC[C@H]([C@H](c1ccc(c(c1)OC)O)/C=C/c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1689209
PubChem CID:   51040471
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
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. stem n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. leaf n.a. PMID[21226514]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6741 Metasequoia glyptostroboides Species Cupressaceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000.0 nM PMID[490610]

☑ 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 NPC148627 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
0.9833 High Similarity NPC165045
0.9833 High Similarity NPC118533
0.9831 High Similarity NPC471693
0.9669 High Similarity NPC5428
0.9593 High Similarity NPC42300
0.9593 High Similarity NPC187998
0.9593 High Similarity NPC77040
0.9593 High Similarity NPC153739
0.9593 High Similarity NPC242807
0.9593 High Similarity NPC92164
0.9593 High Similarity NPC64201
0.9593 High Similarity NPC145305
0.9593 High Similarity NPC257582
0.9593 High Similarity NPC241522
0.9593 High Similarity NPC174495
0.959 High Similarity NPC128208
0.959 High Similarity NPC21867
0.959 High Similarity NPC11258
0.959 High Similarity NPC184733
0.959 High Similarity NPC45774
0.959 High Similarity NPC129570
0.959 High Similarity NPC282703
0.958 High Similarity NPC85488
0.9576 High Similarity NPC207613
0.9516 High Similarity NPC474017
0.9516 High Similarity NPC277804
0.9512 High Similarity NPC475875
0.9504 High Similarity NPC194519
0.95 High Similarity NPC280704
0.9496 High Similarity NPC473853
0.9496 High Similarity NPC343720
0.9496 High Similarity NPC113865
0.9496 High Similarity NPC324571
0.9496 High Similarity NPC312675
0.9496 High Similarity NPC54872
0.9496 High Similarity NPC470212
0.9496 High Similarity NPC184651
0.9496 High Similarity NPC262156
0.9492 High Similarity NPC227217
0.9492 High Similarity NPC232316
0.9492 High Similarity NPC165133
0.9492 High Similarity NPC95614
0.9492 High Similarity NPC242885
0.9492 High Similarity NPC117780
0.9492 High Similarity NPC56214
0.9435 High Similarity NPC143483
0.9431 High Similarity NPC98631
0.9431 High Similarity NPC206615
0.9431 High Similarity NPC474178
0.9431 High Similarity NPC186843
0.9431 High Similarity NPC252307
0.9431 High Similarity NPC245826
0.9431 High Similarity NPC470213
0.9431 High Similarity NPC470084
0.9426 High Similarity NPC191037
0.9426 High Similarity NPC58607
0.9426 High Similarity NPC178284
0.9407 High Similarity NPC281298
0.9407 High Similarity NPC310338
0.936 High Similarity NPC158079
0.936 High Similarity NPC115207
0.936 High Similarity NPC161557
0.936 High Similarity NPC40432
0.936 High Similarity NPC27843
0.936 High Similarity NPC7171
0.936 High Similarity NPC228346
0.9355 High Similarity NPC170844
0.9355 High Similarity NPC476968
0.935 High Similarity NPC319625
0.935 High Similarity NPC147821
0.935 High Similarity NPC41706
0.935 High Similarity NPC127587
0.935 High Similarity NPC111247
0.935 High Similarity NPC118787
0.935 High Similarity NPC106511
0.935 High Similarity NPC292056
0.935 High Similarity NPC183181
0.935 High Similarity NPC163332
0.9339 High Similarity NPC31344
0.9339 High Similarity NPC317769
0.9333 High Similarity NPC160380
0.9333 High Similarity NPC476343
0.9333 High Similarity NPC38996
0.9322 High Similarity NPC474040
0.9322 High Similarity NPC470626
0.9322 High Similarity NPC255675
0.9291 High Similarity NPC478085
0.9291 High Similarity NPC287745
0.9286 High Similarity NPC181049
0.9286 High Similarity NPC106739
0.9286 High Similarity NPC471505
0.9286 High Similarity NPC207400
0.9274 High Similarity NPC472968
0.9268 High Similarity NPC206882
0.9268 High Similarity NPC76451
0.9262 High Similarity NPC94276
0.9262 High Similarity NPC293701
0.9262 High Similarity NPC48990
0.9262 High Similarity NPC114901
0.9262 High Similarity NPC109822
0.9256 High Similarity NPC71090
0.9244 High Similarity NPC181969
0.9244 High Similarity NPC311595
0.9244 High Similarity NPC24474
0.9244 High Similarity NPC320987
0.9237 High Similarity NPC164386
0.9237 High Similarity NPC293619
0.9213 High Similarity NPC158331
0.92 High Similarity NPC212015
0.92 High Similarity NPC86030
0.92 High Similarity NPC5851
0.9194 High Similarity NPC21563
0.9187 High Similarity NPC193544
0.9187 High Similarity NPC475169
0.9187 High Similarity NPC17943
0.9187 High Similarity NPC116907
0.9187 High Similarity NPC208950
0.9187 High Similarity NPC203133
0.9187 High Similarity NPC233410
0.9187 High Similarity NPC221077
0.9187 High Similarity NPC57490
0.9187 High Similarity NPC472093
0.9187 High Similarity NPC251855
0.9187 High Similarity NPC298757
0.9187 High Similarity NPC117214
0.9174 High Similarity NPC290451
0.9174 High Similarity NPC470804
0.9174 High Similarity NPC127389
0.9167 High Similarity NPC177475
0.9167 High Similarity NPC148615
0.9167 High Similarity NPC35071
0.916 High Similarity NPC474214
0.9153 High Similarity NPC221049
0.9147 High Similarity NPC263367
0.9147 High Similarity NPC177160
0.9147 High Similarity NPC477939
0.9147 High Similarity NPC77861
0.9147 High Similarity NPC29799
0.9147 High Similarity NPC209985
0.9147 High Similarity NPC10737
0.9147 High Similarity NPC156502
0.9147 High Similarity NPC54743
0.9141 High Similarity NPC193026
0.9141 High Similarity NPC67247
0.9141 High Similarity NPC187616
0.9141 High Similarity NPC471942
0.9141 High Similarity NPC326095
0.9141 High Similarity NPC244983
0.9141 High Similarity NPC311256
0.9141 High Similarity NPC49603
0.9134 High Similarity NPC175067
0.9134 High Similarity NPC201587
0.9134 High Similarity NPC204215
0.9134 High Similarity NPC253105
0.9134 High Similarity NPC4940
0.9127 High Similarity NPC472338
0.912 High Similarity NPC307050
0.912 High Similarity NPC277458
0.912 High Similarity NPC72529
0.9083 High Similarity NPC135961
0.9083 High Similarity NPC474320
0.907 High Similarity NPC99572
0.907 High Similarity NPC256262
0.907 High Similarity NPC142547
0.907 High Similarity NPC184938
0.907 High Similarity NPC135777
0.907 High Similarity NPC101624
0.907 High Similarity NPC126409
0.9062 High Similarity NPC475840
0.9062 High Similarity NPC170185
0.9055 High Similarity NPC470096
0.9055 High Similarity NPC470095
0.9055 High Similarity NPC472597
0.904 High Similarity NPC236791
0.904 High Similarity NPC293054
0.904 High Similarity NPC324112
0.904 High Similarity NPC169474
0.904 High Similarity NPC246620
0.904 High Similarity NPC159968
0.904 High Similarity NPC282000
0.904 High Similarity NPC124452
0.904 High Similarity NPC82679
0.904 High Similarity NPC74817
0.9032 High Similarity NPC29008
0.9032 High Similarity NPC228771
0.9032 High Similarity NPC266705
0.9032 High Similarity NPC9067
0.9024 High Similarity NPC228922
0.9024 High Similarity NPC473451
0.9024 High Similarity NPC197757
0.9024 High Similarity NPC282496
0.9024 High Similarity NPC233526
0.9024 High Similarity NPC136319
0.9016 High Similarity NPC216929
0.9016 High Similarity NPC312713
0.9016 High Similarity NPC65933
0.9016 High Similarity NPC126935
0.9016 High Similarity NPC172676
0.9016 High Similarity NPC57268
0.9 High Similarity NPC471988

  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 NPC148627 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
0.9355 High Similarity NPD3027 Phase 3
0.8898 High Similarity NPD5283 Phase 1
0.8729 High Similarity NPD228 Approved
0.8559 High Similarity NPD3022 Approved
0.8559 High Similarity NPD3021 Approved
0.855 High Similarity NPD3619 Clinical (unspecified phase)
0.855 High Similarity NPD1612 Clinical (unspecified phase)
0.855 High Similarity NPD3620 Phase 2
0.855 High Similarity NPD1613 Approved
0.8425 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8244 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD2861 Phase 2
0.8168 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8058 Intermediate Similarity NPD3060 Approved
0.8031 Intermediate Similarity NPD1357 Approved
0.8017 Intermediate Similarity NPD2684 Approved
0.8 Intermediate Similarity NPD2983 Phase 2
0.8 Intermediate Similarity NPD1558 Phase 1
0.8 Intermediate Similarity NPD7157 Approved
0.8 Intermediate Similarity NPD2982 Phase 2
0.8 Intermediate Similarity NPD4060 Phase 1
0.8 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7984 Intermediate Similarity NPD3705 Approved
0.797 Intermediate Similarity NPD4908 Phase 1
0.7923 Intermediate Similarity NPD2981 Phase 2
0.7903 Intermediate Similarity NPD7843 Approved
0.7895 Intermediate Similarity NPD3018 Phase 2
0.7874 Intermediate Similarity NPD5536 Phase 2
0.7852 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7846 Intermediate Similarity NPD1610 Phase 2
0.7801 Intermediate Similarity NPD4237 Approved
0.7801 Intermediate Similarity NPD4236 Phase 3
0.7797 Intermediate Similarity NPD3020 Approved
0.7786 Intermediate Similarity NPD7266 Discontinued
0.7721 Intermediate Similarity NPD5111 Phase 2
0.7721 Intermediate Similarity NPD5109 Approved
0.7721 Intermediate Similarity NPD5110 Phase 2
0.7681 Intermediate Similarity NPD5735 Approved
0.7676 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD6674 Discontinued
0.7669 Intermediate Similarity NPD8651 Approved
0.7664 Intermediate Similarity NPD2674 Phase 3
0.766 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD37 Approved
0.7651 Intermediate Similarity NPD1934 Approved
0.7632 Intermediate Similarity NPD6234 Discontinued
0.7622 Intermediate Similarity NPD6331 Phase 2
0.7622 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD4628 Phase 3
0.7622 Intermediate Similarity NPD4110 Phase 3
0.7609 Intermediate Similarity NPD2238 Phase 2
0.76 Intermediate Similarity NPD2977 Approved
0.76 Intermediate Similarity NPD2978 Approved
0.7591 Intermediate Similarity NPD3145 Approved
0.7591 Intermediate Similarity NPD3144 Approved
0.7586 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD3092 Approved
0.7571 Intermediate Similarity NPD4538 Approved
0.7571 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD4536 Approved
0.7569 Intermediate Similarity NPD5241 Discontinued
0.7557 Intermediate Similarity NPD6516 Phase 2
0.7557 Intermediate Similarity NPD5846 Approved
0.7556 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD6584 Phase 3
0.7554 Intermediate Similarity NPD3657 Discovery
0.7554 Intermediate Similarity NPD6355 Discontinued
0.7552 Intermediate Similarity NPD4162 Approved
0.7552 Intermediate Similarity NPD5177 Phase 3
0.7542 Intermediate Similarity NPD2860 Approved
0.7542 Intermediate Similarity NPD2859 Approved
0.7538 Intermediate Similarity NPD1548 Phase 1
0.7535 Intermediate Similarity NPD5763 Approved
0.7535 Intermediate Similarity NPD5762 Approved
0.7518 Intermediate Similarity NPD7095 Approved
0.75 Intermediate Similarity NPD290 Approved
0.75 Intermediate Similarity NPD9494 Approved
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.7483 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD3094 Phase 2
0.7465 Intermediate Similarity NPD2161 Phase 2
0.7464 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD4749 Approved
0.7458 Intermediate Similarity NPD2934 Approved
0.7458 Intermediate Similarity NPD9296 Approved
0.7458 Intermediate Similarity NPD2933 Approved
0.745 Intermediate Similarity NPD4005 Discontinued
0.7448 Intermediate Similarity NPD2677 Approved
0.7448 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6896 Approved
0.7447 Intermediate Similarity NPD6895 Approved
0.7445 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD1091 Approved
0.7442 Intermediate Similarity NPD6671 Approved
0.7424 Intermediate Similarity NPD2667 Approved
0.7424 Intermediate Similarity NPD2668 Approved
0.7419 Intermediate Similarity NPD968 Approved
0.7415 Intermediate Similarity NPD4123 Phase 3
0.7413 Intermediate Similarity NPD1375 Discontinued
0.7405 Intermediate Similarity NPD3091 Approved
0.7405 Intermediate Similarity NPD7228 Approved
0.7397 Intermediate Similarity NPD7124 Phase 2
0.7394 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD5588 Approved
0.7394 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD5960 Phase 3
0.7391 Intermediate Similarity NPD4625 Phase 3
0.7389 Intermediate Similarity NPD6166 Phase 2
0.7389 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7388 Intermediate Similarity NPD1608 Approved
0.7388 Intermediate Similarity NPD2233 Approved
0.7388 Intermediate Similarity NPD2231 Phase 2
0.7388 Intermediate Similarity NPD2230 Approved
0.7388 Intermediate Similarity NPD2232 Approved
0.7388 Intermediate Similarity NPD2235 Phase 2
0.7386 Intermediate Similarity NPD3882 Suspended
0.7383 Intermediate Similarity NPD1653 Approved
0.7381 Intermediate Similarity NPD5451 Approved
0.7377 Intermediate Similarity NPD291 Approved
0.7368 Intermediate Similarity NPD2801 Approved
0.7368 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD3062 Approved
0.7357 Intermediate Similarity NPD3059 Approved
0.7357 Intermediate Similarity NPD4140 Approved
0.7357 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7357 Intermediate Similarity NPD3061 Approved
0.7338 Intermediate Similarity NPD6798 Discontinued
0.7338 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5327 Phase 3
0.7333 Intermediate Similarity NPD6583 Phase 3
0.7333 Intermediate Similarity NPD6582 Phase 2
0.7329 Intermediate Similarity NPD6190 Approved
0.7308 Intermediate Similarity NPD7199 Phase 2
0.7299 Intermediate Similarity NPD4624 Approved
0.7297 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD9384 Approved
0.7293 Intermediate Similarity NPD9381 Approved
0.7293 Intermediate Similarity NPD4626 Approved
0.7292 Intermediate Similarity NPD3540 Phase 1
0.7286 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD5058 Phase 3
0.7279 Intermediate Similarity NPD2922 Phase 1
0.7279 Intermediate Similarity NPD1283 Approved
0.7278 Intermediate Similarity NPD27 Approved
0.7278 Intermediate Similarity NPD2489 Approved
0.7273 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3687 Approved
0.7267 Intermediate Similarity NPD3686 Approved
0.726 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD6653 Approved
0.7254 Intermediate Similarity NPD5314 Approved
0.7248 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD52 Approved
0.7248 Intermediate Similarity NPD7526 Approved
0.7239 Intermediate Similarity NPD3847 Discontinued
0.723 Intermediate Similarity NPD4357 Discontinued
0.7222 Intermediate Similarity NPD3539 Phase 1
0.7218 Intermediate Similarity NPD1651 Approved
0.7215 Intermediate Similarity NPD2969 Approved
0.7215 Intermediate Similarity NPD2970 Approved
0.7214 Intermediate Similarity NPD5718 Phase 2
0.7209 Intermediate Similarity NPD5535 Approved
0.7208 Intermediate Similarity NPD2560 Approved
0.7208 Intermediate Similarity NPD2563 Approved
0.7206 Intermediate Similarity NPD9622 Approved
0.7206 Intermediate Similarity NPD3685 Discontinued
0.7206 Intermediate Similarity NPD1669 Approved
0.7205 Intermediate Similarity NPD7074 Phase 3
0.7203 Intermediate Similarity NPD6111 Discontinued
0.7188 Intermediate Similarity NPD3818 Discontinued
0.7183 Intermediate Similarity NPD4340 Discontinued
0.7181 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD4678 Approved
0.7171 Intermediate Similarity NPD4675 Approved
0.7167 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD17 Approved
0.7164 Intermediate Similarity NPD3095 Discontinued
0.7163 Intermediate Similarity NPD4062 Phase 3
0.7163 Intermediate Similarity NPD6233 Phase 2
0.7154 Intermediate Similarity NPD1242 Phase 1
0.7152 Intermediate Similarity NPD3051 Approved
0.7143 Intermediate Similarity NPD3179 Approved
0.7143 Intermediate Similarity NPD8166 Discontinued
0.7143 Intermediate Similarity NPD5772 Approved
0.7143 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD3180 Approved
0.7143 Intermediate Similarity NPD5773 Approved
0.7133 Intermediate Similarity NPD3052 Approved
0.7133 Intermediate Similarity NPD6353 Approved
0.7133 Intermediate Similarity NPD3054 Approved
0.7123 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD7685 Pre-registration
0.7114 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1511 Approved
0.7114 Intermediate Similarity NPD7041 Phase 2

  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