Structure

Physi-Chem Properties

Molecular Weight:  348.16
Volume:  356.99
LogP:  1.271
LogD:  1.632
LogS:  -2.249
# Rotatable Bonds:  9
TPSA:  99.38
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.551
Synthetic Accessibility Score:  2.984
Fsp3:  0.368
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.78
MDCK Permeability:  9.043131285579875e-06
Pgp-inhibitor:  0.006
Pgp-substrate:  0.012
Human Intestinal Absorption (HIA):  0.039
20% Bioavailability (F20%):  0.399
30% Bioavailability (F30%):  0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.229
Plasma Protein Binding (PPB):  65.41896057128906%
Volume Distribution (VD):  1.745
Pgp-substrate:  11.93115234375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.258
CYP1A2-substrate:  0.239
CYP2C19-inhibitor:  0.148
CYP2C19-substrate:  0.395
CYP2C9-inhibitor:  0.089
CYP2C9-substrate:  0.64
CYP2D6-inhibitor:  0.32
CYP2D6-substrate:  0.814
CYP3A4-inhibitor:  0.208
CYP3A4-substrate:  0.633

ADMET: Excretion

Clearance (CL):  11.512
Half-life (T1/2):  0.9

ADMET: Toxicity

hERG Blockers:  0.162
Human Hepatotoxicity (H-HT):  0.069
Drug-inuced Liver Injury (DILI):  0.05
AMES Toxicity:  0.054
Rat Oral Acute Toxicity:  0.019
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.252
Carcinogencity:  0.197
Eye Corrosion:  0.003
Eye Irritation:  0.069
Respiratory Toxicity:  0.006

Download Data

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

  Natural Product: NPC293701

Natural Product ID:  NPC293701
Common Name*:   Chushizisins D
IUPAC Name:   (1S,2R)-1-(4-hydroxyphenyl)-2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]propane-1,3-diol
Synonyms:   chushizisins D
Standard InCHIKey:  KMRAGNBQNZWMMG-MOPGFXCFSA-N
Standard InCHI:  InChI=1S/C19H24O6/c1-24-17-11-13(3-2-10-20)4-9-16(17)25-18(12-21)19(23)14-5-7-15(22)8-6-14/h4-9,11,18-23H,2-3,10,12H2,1H3/t18-,19+/m1/s1
SMILES:  COc1cc(CCCO)ccc1O[C@H](CO)[C@H](c1ccc(cc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL550571
PubChem CID:   45269748
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
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5495 Broussonetia papyrifera Species Moraceae 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
NPT1 Others Radical scavenging activity IC50 = 273900.0 nM PMID[572715]

☑ 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 NPC293701 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 NPC114901
1.0 High Similarity NPC48990
0.975 High Similarity NPC147821
0.975 High Similarity NPC118787
0.975 High Similarity NPC292056
0.975 High Similarity NPC163332
0.975 High Similarity NPC111247
0.975 High Similarity NPC41706
0.975 High Similarity NPC183181
0.975 High Similarity NPC319625
0.9748 High Similarity NPC194519
0.9667 High Similarity NPC178284
0.9667 High Similarity NPC58607
0.9667 High Similarity NPC191037
0.9664 High Similarity NPC109822
0.9664 High Similarity NPC94276
0.9661 High Similarity NPC71090
0.959 High Similarity NPC5851
0.959 High Similarity NPC86030
0.9512 High Similarity NPC472338
0.9508 High Similarity NPC72529
0.9435 High Similarity NPC472597
0.9431 High Similarity NPC470258
0.9431 High Similarity NPC273295
0.9431 High Similarity NPC202582
0.9431 High Similarity NPC218856
0.9431 High Similarity NPC285339
0.9431 High Similarity NPC3439
0.9431 High Similarity NPC190629
0.9431 High Similarity NPC226788
0.9431 High Similarity NPC222004
0.9431 High Similarity NPC210623
0.9426 High Similarity NPC474119
0.9417 High Similarity NPC471693
0.9412 High Similarity NPC127389
0.9412 High Similarity NPC184651
0.9412 High Similarity NPC473853
0.9412 High Similarity NPC324571
0.9412 High Similarity NPC113865
0.9412 High Similarity NPC312675
0.9412 High Similarity NPC54872
0.9412 High Similarity NPC470212
0.9412 High Similarity NPC262156
0.9412 High Similarity NPC290451
0.9412 High Similarity NPC343720
0.936 High Similarity NPC7903
0.936 High Similarity NPC16208
0.936 High Similarity NPC160991
0.936 High Similarity NPC184447
0.936 High Similarity NPC35932
0.935 High Similarity NPC245826
0.935 High Similarity NPC252307
0.935 High Similarity NPC474178
0.9328 High Similarity NPC207613
0.9286 High Similarity NPC475840
0.928 High Similarity NPC30043
0.928 High Similarity NPC469613
0.928 High Similarity NPC469625
0.9274 High Similarity NPC475875
0.9268 High Similarity NPC165045
0.9268 High Similarity NPC118533
0.9268 High Similarity NPC210355
0.9262 High Similarity NPC148627
0.925 High Similarity NPC470804
0.9237 High Similarity NPC474214
0.9213 High Similarity NPC237594
0.9213 High Similarity NPC119060
0.9213 High Similarity NPC478085
0.9213 High Similarity NPC310854
0.9213 High Similarity NPC476387
0.9213 High Similarity NPC170694
0.9213 High Similarity NPC249791
0.9206 High Similarity NPC470752
0.92 High Similarity NPC145305
0.92 High Similarity NPC42300
0.92 High Similarity NPC92164
0.92 High Similarity NPC242807
0.92 High Similarity NPC187998
0.92 High Similarity NPC469612
0.92 High Similarity NPC77040
0.92 High Similarity NPC64201
0.92 High Similarity NPC257582
0.92 High Similarity NPC469614
0.92 High Similarity NPC241522
0.92 High Similarity NPC174495
0.92 High Similarity NPC153739
0.9194 High Similarity NPC98631
0.9194 High Similarity NPC470084
0.9194 High Similarity NPC186843
0.9194 High Similarity NPC470213
0.9194 High Similarity NPC206615
0.916 High Similarity NPC135961
0.916 High Similarity NPC474320
0.916 High Similarity NPC24474
0.916 High Similarity NPC311595
0.9153 High Similarity NPC86947
0.9141 High Similarity NPC61946
0.9141 High Similarity NPC472337
0.9127 High Similarity NPC277804
0.9127 High Similarity NPC470095
0.9127 High Similarity NPC309787
0.9127 High Similarity NPC470096
0.912 High Similarity NPC212015
0.912 High Similarity NPC476968
0.912 High Similarity NPC170844
0.9113 High Similarity NPC5428
0.9098 High Similarity NPC280704
0.9091 High Similarity NPC476343
0.9083 High Similarity NPC148615
0.9083 High Similarity NPC35071
0.9083 High Similarity NPC177475
0.9076 High Similarity NPC470626
0.9076 High Similarity NPC255675
0.907 High Similarity NPC472334
0.907 High Similarity NPC472336
0.907 High Similarity NPC29799
0.907 High Similarity NPC177160
0.907 High Similarity NPC10737
0.907 High Similarity NPC263367
0.907 High Similarity NPC477939
0.907 High Similarity NPC54743
0.907 High Similarity NPC156502
0.907 High Similarity NPC209985
0.907 High Similarity NPC16435
0.907 High Similarity NPC306441
0.9055 High Similarity NPC253105
0.9055 High Similarity NPC201587
0.904 High Similarity NPC282703
0.904 High Similarity NPC11258
0.904 High Similarity NPC45774
0.904 High Similarity NPC184733
0.904 High Similarity NPC129570
0.904 High Similarity NPC128208
0.904 High Similarity NPC21867
0.9032 High Similarity NPC206882
0.9024 High Similarity NPC122792
0.9024 High Similarity NPC228972
0.9016 High Similarity NPC85488
0.9016 High Similarity NPC261661
0.9016 High Similarity NPC209567
0.9 High Similarity NPC181969
0.9 High Similarity NPC138738
0.9 High Similarity NPC126206
0.9 High Similarity NPC470413
0.9 High Similarity NPC320987
0.8992 High Similarity NPC293619
0.8992 High Similarity NPC121812
0.8992 High Similarity NPC112939
0.8992 High Similarity NPC234333
0.8992 High Similarity NPC112246
0.8992 High Similarity NPC164386
0.8992 High Similarity NPC260898
0.8992 High Similarity NPC214729
0.8992 High Similarity NPC47398
0.8992 High Similarity NPC94750
0.8992 High Similarity NPC474206
0.8992 High Similarity NPC470356
0.8984 High Similarity NPC263064
0.8984 High Similarity NPC168059
0.8984 High Similarity NPC229442
0.8984 High Similarity NPC26394
0.8976 High Similarity NPC40432
0.8976 High Similarity NPC115207
0.8976 High Similarity NPC27843
0.8976 High Similarity NPC161557
0.8976 High Similarity NPC474017
0.8976 High Similarity NPC228346
0.8976 High Similarity NPC7171
0.8976 High Similarity NPC158079
0.8968 High Similarity NPC26653
0.8968 High Similarity NPC270849
0.896 High Similarity NPC470699
0.8952 High Similarity NPC251855
0.8952 High Similarity NPC221077
0.8952 High Similarity NPC193544
0.8952 High Similarity NPC17943
0.8952 High Similarity NPC208950
0.8952 High Similarity NPC116907
0.8952 High Similarity NPC475169
0.8952 High Similarity NPC57490
0.8952 High Similarity NPC298757
0.8952 High Similarity NPC233410
0.8952 High Similarity NPC117214
0.8952 High Similarity NPC203133
0.8952 High Similarity NPC472093
0.8943 High Similarity NPC282496
0.8943 High Similarity NPC197757
0.8943 High Similarity NPC31344
0.8943 High Similarity NPC317769
0.8943 High Similarity NPC233526
0.8943 High Similarity NPC228922
0.8931 High Similarity NPC22517
0.8926 High Similarity NPC117780
0.8926 High Similarity NPC95614
0.8926 High Similarity NPC474565
0.8926 High Similarity NPC227217
0.8926 High Similarity NPC232316
0.8926 High Similarity NPC165133
0.8926 High Similarity NPC56214
0.8926 High Similarity NPC242885

  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 NPC293701 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
0.912 High Similarity NPD3027 Phase 3
0.876 High Similarity NPD1612 Clinical (unspecified phase)
0.876 High Similarity NPD1613 Approved
0.8644 High Similarity NPD228 Approved
0.85 High Similarity NPD5283 Phase 1
0.845 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.839 Intermediate Similarity NPD2684 Approved
0.8372 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8346 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.8264 Intermediate Similarity NPD7843 Approved
0.8211 Intermediate Similarity NPD7157 Approved
0.8195 Intermediate Similarity NPD1558 Phase 1
0.8151 Intermediate Similarity NPD290 Approved
0.8116 Intermediate Similarity NPD3060 Approved
0.8095 Intermediate Similarity NPD1357 Approved
0.8092 Intermediate Similarity NPD2861 Phase 2
0.8062 Intermediate Similarity NPD2983 Phase 2
0.8062 Intermediate Similarity NPD2982 Phase 2
0.806 Intermediate Similarity NPD3620 Phase 2
0.806 Intermediate Similarity NPD4060 Phase 1
0.806 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.8034 Intermediate Similarity NPD291 Approved
0.803 Intermediate Similarity NPD4908 Phase 1
0.8017 Intermediate Similarity NPD3022 Approved
0.8017 Intermediate Similarity NPD3021 Approved
0.8016 Intermediate Similarity NPD1548 Phase 1
0.8015 Intermediate Similarity NPD4536 Approved
0.8015 Intermediate Similarity NPD4538 Approved
0.8015 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD4162 Approved
0.7984 Intermediate Similarity NPD2981 Phase 2
0.7955 Intermediate Similarity NPD3018 Phase 2
0.7937 Intermediate Similarity NPD5536 Phase 2
0.7917 Intermediate Similarity NPD968 Approved
0.791 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD3705 Approved
0.7907 Intermediate Similarity NPD1610 Phase 2
0.7907 Intermediate Similarity NPD1091 Approved
0.7895 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7891 Intermediate Similarity NPD6516 Phase 2
0.7891 Intermediate Similarity NPD5846 Approved
0.7879 Intermediate Similarity NPD6584 Phase 3
0.7857 Intermediate Similarity NPD4236 Phase 3
0.7857 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD4237 Approved
0.7842 Intermediate Similarity NPD7266 Discontinued
0.7826 Intermediate Similarity NPD5960 Phase 3
0.7826 Intermediate Similarity NPD5588 Approved
0.7823 Intermediate Similarity NPD1934 Approved
0.7778 Intermediate Similarity NPD6671 Approved
0.7737 Intermediate Similarity NPD5735 Approved
0.773 Intermediate Similarity NPD6674 Discontinued
0.7727 Intermediate Similarity NPD8651 Approved
0.7721 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD6233 Phase 2
0.771 Intermediate Similarity NPD2231 Phase 2
0.771 Intermediate Similarity NPD2235 Phase 2
0.7708 Intermediate Similarity NPD4123 Phase 3
0.7704 Intermediate Similarity NPD7095 Approved
0.7676 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD6331 Phase 2
0.7676 Intermediate Similarity NPD4628 Phase 3
0.7676 Intermediate Similarity NPD4110 Phase 3
0.7671 Intermediate Similarity NPD1653 Approved
0.7667 Intermediate Similarity NPD3882 Suspended
0.7652 Intermediate Similarity NPD6582 Phase 2
0.7652 Intermediate Similarity NPD6583 Phase 3
0.7652 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD2801 Approved
0.7651 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6798 Discontinued
0.7622 Intermediate Similarity NPD2677 Approved
0.7609 Intermediate Similarity NPD6355 Discontinued
0.7591 Intermediate Similarity NPD4062 Phase 3
0.7591 Intermediate Similarity NPD2674 Phase 3
0.7589 Intermediate Similarity NPD5762 Approved
0.7589 Intermediate Similarity NPD5763 Approved
0.7574 Intermediate Similarity NPD4625 Phase 3
0.7569 Intermediate Similarity NPD5058 Phase 3
0.7568 Intermediate Similarity NPD4678 Approved
0.7568 Intermediate Similarity NPD4675 Approved
0.7554 Intermediate Similarity NPD6653 Approved
0.7554 Intermediate Similarity NPD3054 Approved
0.7554 Intermediate Similarity NPD3052 Approved
0.7551 Intermediate Similarity NPD3686 Approved
0.7551 Intermediate Similarity NPD3687 Approved
0.7548 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6166 Phase 2
0.754 Intermediate Similarity NPD5535 Approved
0.754 Intermediate Similarity NPD821 Approved
0.7536 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD2977 Approved
0.7533 Intermediate Similarity NPD2978 Approved
0.7521 Intermediate Similarity NPD2933 Approved
0.7521 Intermediate Similarity NPD2934 Approved
0.7519 Intermediate Similarity NPD4749 Approved
0.7518 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD2161 Phase 2
0.7518 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5241 Discontinued
0.7483 Intermediate Similarity NPD5177 Phase 3
0.7482 Intermediate Similarity NPD4340 Discontinued
0.7466 Intermediate Similarity NPD3536 Discontinued
0.7465 Intermediate Similarity NPD1375 Discontinued
0.7458 Intermediate Similarity NPD2860 Approved
0.7458 Intermediate Similarity NPD2859 Approved
0.7447 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD3179 Approved
0.7445 Intermediate Similarity NPD3180 Approved
0.744 Intermediate Similarity NPD556 Approved
0.7434 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD4535 Phase 3
0.7426 Intermediate Similarity NPD9494 Approved
0.7424 Intermediate Similarity NPD3496 Discontinued
0.7417 Intermediate Similarity NPD5773 Approved
0.7417 Intermediate Similarity NPD3020 Approved
0.7417 Intermediate Similarity NPD5772 Approved
0.7415 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7415 Intermediate Similarity NPD7526 Approved
0.7415 Intermediate Similarity NPD52 Approved
0.741 Intermediate Similarity NPD4140 Approved
0.741 Intermediate Similarity NPD2238 Phase 2
0.7405 Intermediate Similarity NPD7054 Approved
0.7397 Intermediate Similarity NPD1774 Approved
0.7397 Intermediate Similarity NPD1511 Approved
0.7391 Intermediate Similarity NPD3144 Approved
0.7391 Intermediate Similarity NPD5110 Phase 2
0.7391 Intermediate Similarity NPD3145 Approved
0.7391 Intermediate Similarity NPD5109 Approved
0.7391 Intermediate Similarity NPD5111 Phase 2
0.7388 Intermediate Similarity NPD3685 Discontinued
0.7388 Intermediate Similarity NPD5327 Phase 3
0.7379 Intermediate Similarity NPD6190 Approved
0.7379 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7373 Intermediate Similarity NPD9296 Approved
0.7368 Intermediate Similarity NPD3817 Phase 2
0.7368 Intermediate Similarity NPD2563 Approved
0.7368 Intermediate Similarity NPD422 Phase 1
0.7368 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD2560 Approved
0.7358 Intermediate Similarity NPD7074 Phase 3
0.7358 Intermediate Similarity NPD7472 Approved
0.7355 Intermediate Similarity NPD7199 Phase 2
0.7355 Intermediate Similarity NPD1242 Phase 1
0.7351 Intermediate Similarity NPD37 Approved
0.7343 Intermediate Similarity NPD3540 Phase 1
0.7343 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD3818 Discontinued
0.7338 Intermediate Similarity NPD6234 Discontinued
0.7333 Intermediate Similarity NPD2922 Phase 1
0.7328 Intermediate Similarity NPD1182 Approved
0.7328 Intermediate Similarity NPD1894 Discontinued
0.7324 Intermediate Similarity NPD2154 Approved
0.7324 Intermediate Similarity NPD7033 Discontinued
0.7324 Intermediate Similarity NPD2156 Approved
0.7324 Intermediate Similarity NPD2155 Approved
0.732 Intermediate Similarity NPD4967 Phase 2
0.732 Intermediate Similarity NPD4966 Approved
0.732 Intermediate Similarity NPD4965 Approved
0.7313 Intermediate Similarity NPD1608 Approved
0.7308 Intermediate Similarity NPD3596 Phase 2
0.7302 Intermediate Similarity NPD5451 Approved
0.7297 Intermediate Similarity NPD1512 Approved
0.7292 Intermediate Similarity NPD7153 Discontinued
0.7292 Intermediate Similarity NPD2424 Discontinued
0.7286 Intermediate Similarity NPD3061 Approved
0.7286 Intermediate Similarity NPD3059 Approved
0.7286 Intermediate Similarity NPD3062 Approved
0.728 Intermediate Similarity NPD1358 Approved
0.7279 Intermediate Similarity NPD1819 Approved
0.7279 Intermediate Similarity NPD1818 Approved
0.7279 Intermediate Similarity NPD1817 Approved
0.7279 Intermediate Similarity NPD4357 Discontinued
0.7279 Intermediate Similarity NPD1820 Approved
0.7279 Intermediate Similarity NPD3094 Phase 2
0.7273 Intermediate Similarity NPD6032 Approved
0.7273 Intermediate Similarity NPD3539 Phase 1
0.7273 Intermediate Similarity NPD5585 Approved
0.7267 Intermediate Similarity NPD4005 Discontinued
0.7267 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD5718 Phase 2
0.7266 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD9365 Approved
0.7241 Intermediate Similarity NPD1652 Phase 2
0.7239 Intermediate Similarity NPD1535 Discovery
0.7239 Intermediate Similarity NPD3092 Approved
0.7234 Intermediate Similarity NPD3657 Discovery
0.7226 Intermediate Similarity NPD558 Phase 2
0.7226 Intermediate Similarity NPD3691 Phase 2
0.7226 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3690 Phase 2
0.7222 Intermediate Similarity NPD7808 Phase 3
0.7218 Intermediate Similarity NPD1778 Approved
0.7218 Intermediate Similarity NPD9381 Approved
0.7218 Intermediate Similarity NPD9384 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