Structure

Physi-Chem Properties

Molecular Weight:  646.19
Volume:  595.599
LogP:  1.981
LogD:  0.911
LogS:  -3.531
# Rotatable Bonds:  11
TPSA:  220.13
# H-Bond Aceptor:  15
# H-Bond Donor:  6
# Rings:  9
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.159
Synthetic Accessibility Score:  6.412
Fsp3:  0.548
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.585
MDCK Permeability:  2.5858957087621093e-05
Pgp-inhibitor:  0.089
Pgp-substrate:  0.988
Human Intestinal Absorption (HIA):  0.842
20% Bioavailability (F20%):  0.728
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.145
Plasma Protein Binding (PPB):  97.10953521728516%
Volume Distribution (VD):  0.419
Pgp-substrate:  9.49251651763916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.984
CYP2C19-inhibitor:  0.026
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.183
CYP2C9-substrate:  0.063
CYP2D6-inhibitor:  0.044
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.824
CYP3A4-substrate:  0.172

ADMET: Excretion

Clearance (CL):  6.607
Half-life (T1/2):  0.939

ADMET: Toxicity

hERG Blockers:  0.08
Human Hepatotoxicity (H-HT):  0.04
Drug-inuced Liver Injury (DILI):  0.773
AMES Toxicity:  0.92
Rat Oral Acute Toxicity:  0.012
Maximum Recommended Daily Dose:  0.106
Skin Sensitization:  0.957
Carcinogencity:  0.825
Eye Corrosion:  0.003
Eye Irritation:  0.462
Respiratory Toxicity:  0.822

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

  Natural Product: NPC260300

Natural Product ID:  NPC260300
Common Name*:   VQNYYCZTWCMUQV-NYQDJGBXSA-N
IUPAC Name:   n.a.
Synonyms:   4-O-Methylgalloylpaeoniflorin
Standard InCHIKey:  VQNYYCZTWCMUQV-NYQDJGBXSA-N
Standard InCHI:  InChI=1S/C31H34O15/c1-28-12-30(40-2)19-10-31(28,29(19,27(45-28)46-30)13-42-24(38)14-6-4-3-5-7-14)44-26-23(37)22(36)21(35)18(43-26)11-41-25(39)15-8-16(32)20(34)17(33)9-15/h3-9,18-19,21-23,26-27,32-37H,10-13H2,1-2H3/t18-,19+,21-,22+,23-,26+,27-,28+,29+,30-,31-/m1/s1
SMILES:  CO[C@@]12O[C@@H]3[C@@]4([C@@H]2C[C@]4([C@](C1)(O3)C)O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O)COC(=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1078418
PubChem CID:   46883518
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides

*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
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Anhui province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Gansu province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Henan province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shandong province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shanxi province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. DOI[10.2174/092986712800229032]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[19402674]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota roots n.a. n.a. PMID[19691309]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19721258]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19772486]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[20806783]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21782011]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22190295]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[26838074]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27313650]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27429639]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[29741372]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds HeZe, ShanDong, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[32951423]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Xinjiang,China PMID[33063333]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30226 Paeonia albiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9798 Paeonia lactiflora Species Paeoniaceae 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
NPT848 Cell Line N9 Homo sapiens Inhibition = 80.8 % PMID[571415]
NPT848 Cell Line N9 Homo sapiens Inhibition = 113.4 % PMID[571415]
NPT848 Cell Line N9 Homo sapiens Inhibition = 108.4 % PMID[571415]
NPT848 Cell Line N9 Homo sapiens Inhibition = 101.5 % PMID[571415]
NPT848 Cell Line N9 Homo sapiens IC50 > 100000.0 nM PMID[571415]

☑ 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 NPC260300 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
0.9879 High Similarity NPC80360
0.9819 High Similarity NPC195114
0.9641 High Similarity NPC469418
0.9512 High Similarity NPC469458
0.9512 High Similarity NPC88176
0.9512 High Similarity NPC149002
0.9512 High Similarity NPC469396
0.9412 High Similarity NPC188217
0.9394 High Similarity NPC469459
0.929 High Similarity NPC469438
0.9286 High Similarity NPC148185
0.9286 High Similarity NPC477617
0.9235 High Similarity NPC469397
0.9162 High Similarity NPC469419
0.9152 High Similarity NPC293568
0.9152 High Similarity NPC117943
0.9064 High Similarity NPC469354
0.8988 High Similarity NPC265600
0.897 High Similarity NPC4747
0.897 High Similarity NPC104275
0.8922 High Similarity NPC477627
0.8857 High Similarity NPC102367
0.8848 High Similarity NPC156624
0.8848 High Similarity NPC172920
0.8848 High Similarity NPC203757
0.8817 High Similarity NPC120012
0.878 High Similarity NPC34066
0.8779 High Similarity NPC475058
0.8757 High Similarity NPC14030
0.8757 High Similarity NPC291957
0.8735 High Similarity NPC469399
0.8729 High Similarity NPC476358
0.8721 High Similarity NPC476017
0.872 High Similarity NPC140151
0.8706 High Similarity NPC470898
0.8706 High Similarity NPC116759
0.8706 High Similarity NPC14294
0.8698 High Similarity NPC266365
0.8667 High Similarity NPC469422
0.8667 High Similarity NPC221249
0.8663 High Similarity NPC185498
0.8614 High Similarity NPC3746
0.8614 High Similarity NPC16024
0.8614 High Similarity NPC205037
0.8614 High Similarity NPC44260
0.8614 High Similarity NPC61152
0.8598 High Similarity NPC92117
0.8598 High Similarity NPC75945
0.8596 High Similarity NPC100420
0.8588 High Similarity NPC100465
0.8588 High Similarity NPC152424
0.858 High Similarity NPC67629
0.858 High Similarity NPC79736
0.858 High Similarity NPC196771
0.8571 High Similarity NPC316539
0.8563 High Similarity NPC470272
0.8563 High Similarity NPC179240
0.8563 High Similarity NPC469417
0.8555 High Similarity NPC470271
0.8555 High Similarity NPC311389
0.8547 High Similarity NPC475738
0.8545 High Similarity NPC116292
0.8545 High Similarity NPC87630
0.8545 High Similarity NPC179128
0.8545 High Similarity NPC267469
0.8539 High Similarity NPC53680
0.8539 High Similarity NPC208797
0.8537 High Similarity NPC469448
0.8537 High Similarity NPC120621
0.8537 High Similarity NPC248257
0.8531 High Similarity NPC267549
0.8529 High Similarity NPC268718
0.8529 High Similarity NPC91634
0.8529 High Similarity NPC150943
0.8523 High Similarity NPC169645
0.8523 High Similarity NPC84482
0.8523 High Similarity NPC171706
0.8521 High Similarity NPC49173
0.8521 High Similarity NPC226759
0.8521 High Similarity NPC472860
0.8521 High Similarity NPC135222
0.8521 High Similarity NPC474010
0.8497 Intermediate Similarity NPC175793
0.8494 Intermediate Similarity NPC469477
0.8494 Intermediate Similarity NPC133430
0.8492 Intermediate Similarity NPC473205
0.8492 Intermediate Similarity NPC473776
0.8488 Intermediate Similarity NPC109990
0.8485 Intermediate Similarity NPC469415
0.8483 Intermediate Similarity NPC93685
0.8483 Intermediate Similarity NPC108191
0.8475 Intermediate Similarity NPC473713
0.8462 Intermediate Similarity NPC477623
0.8453 Intermediate Similarity NPC475360
0.8448 Intermediate Similarity NPC190204
0.8448 Intermediate Similarity NPC261411
0.8448 Intermediate Similarity NPC43918
0.8443 Intermediate Similarity NPC469398
0.8439 Intermediate Similarity NPC222531
0.8434 Intermediate Similarity NPC35160
0.8434 Intermediate Similarity NPC306343
0.8434 Intermediate Similarity NPC162569
0.843 Intermediate Similarity NPC33298
0.843 Intermediate Similarity NPC41009
0.843 Intermediate Similarity NPC285108
0.843 Intermediate Similarity NPC90905
0.843 Intermediate Similarity NPC4013
0.843 Intermediate Similarity NPC145847
0.8424 Intermediate Similarity NPC303429
0.8424 Intermediate Similarity NPC222102
0.8421 Intermediate Similarity NPC203020
0.8421 Intermediate Similarity NPC239966
0.8421 Intermediate Similarity NPC289346
0.8418 Intermediate Similarity NPC193377
0.8415 Intermediate Similarity NPC473867
0.8412 Intermediate Similarity NPC172419
0.8412 Intermediate Similarity NPC187205
0.8412 Intermediate Similarity NPC238419
0.84 Intermediate Similarity NPC88557
0.84 Intermediate Similarity NPC117911
0.8391 Intermediate Similarity NPC306475
0.838 Intermediate Similarity NPC198902
0.8373 Intermediate Similarity NPC42464
0.8372 Intermediate Similarity NPC69868
0.8372 Intermediate Similarity NPC472859
0.8372 Intermediate Similarity NPC25389
0.8372 Intermediate Similarity NPC115624
0.8372 Intermediate Similarity NPC311803
0.8371 Intermediate Similarity NPC472723
0.8363 Intermediate Similarity NPC104222
0.8363 Intermediate Similarity NPC287872
0.8363 Intermediate Similarity NPC210501
0.8363 Intermediate Similarity NPC114791
0.8363 Intermediate Similarity NPC289811
0.8363 Intermediate Similarity NPC141331
0.8363 Intermediate Similarity NPC160780
0.8363 Intermediate Similarity NPC74319
0.8363 Intermediate Similarity NPC318826
0.8354 Intermediate Similarity NPC108455
0.8353 Intermediate Similarity NPC237946
0.8353 Intermediate Similarity NPC247629
0.8353 Intermediate Similarity NPC32373
0.8353 Intermediate Similarity NPC239019
0.8352 Intermediate Similarity NPC47521
0.8352 Intermediate Similarity NPC469421
0.8352 Intermediate Similarity NPC212748
0.8352 Intermediate Similarity NPC105591
0.8343 Intermediate Similarity NPC311912
0.8343 Intermediate Similarity NPC79322
0.8343 Intermediate Similarity NPC31034
0.8333 Intermediate Similarity NPC469420
0.8333 Intermediate Similarity NPC170203
0.8333 Intermediate Similarity NPC5115
0.8333 Intermediate Similarity NPC469371
0.8324 Intermediate Similarity NPC148273
0.8324 Intermediate Similarity NPC35266
0.8324 Intermediate Similarity NPC241196
0.8324 Intermediate Similarity NPC76687
0.8314 Intermediate Similarity NPC166277
0.8314 Intermediate Similarity NPC474770
0.8314 Intermediate Similarity NPC119125
0.8314 Intermediate Similarity NPC24627
0.8313 Intermediate Similarity NPC142528
0.8313 Intermediate Similarity NPC81835
0.8313 Intermediate Similarity NPC43123
0.8305 Intermediate Similarity NPC471920
0.8305 Intermediate Similarity NPC129930
0.8305 Intermediate Similarity NPC235575
0.8305 Intermediate Similarity NPC114550
0.8305 Intermediate Similarity NPC261254
0.8305 Intermediate Similarity NPC292712
0.8305 Intermediate Similarity NPC20114
0.8305 Intermediate Similarity NPC471921
0.8305 Intermediate Similarity NPC312006
0.8305 Intermediate Similarity NPC474075
0.8305 Intermediate Similarity NPC102851
0.8305 Intermediate Similarity NPC5786
0.8305 Intermediate Similarity NPC471922
0.8304 Intermediate Similarity NPC19947
0.8304 Intermediate Similarity NPC1913
0.8304 Intermediate Similarity NPC207584
0.8304 Intermediate Similarity NPC181168
0.8304 Intermediate Similarity NPC115281
0.8304 Intermediate Similarity NPC163527
0.8304 Intermediate Similarity NPC257309
0.8303 Intermediate Similarity NPC208293
0.8295 Intermediate Similarity NPC658
0.8295 Intermediate Similarity NPC202428
0.8295 Intermediate Similarity NPC266545
0.8295 Intermediate Similarity NPC197708
0.8295 Intermediate Similarity NPC21956
0.8294 Intermediate Similarity NPC472835
0.8293 Intermediate Similarity NPC229036
0.8293 Intermediate Similarity NPC121573
0.8293 Intermediate Similarity NPC190587
0.8293 Intermediate Similarity NPC22176
0.8293 Intermediate Similarity NPC226738
0.8287 Intermediate Similarity NPC199172
0.8287 Intermediate Similarity NPC473883
0.8287 Intermediate Similarity NPC35924

  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 NPC260300 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
0.8663 High Similarity NPD7228 Approved
0.8483 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD6234 Discontinued
0.8353 Intermediate Similarity NPD4967 Phase 2
0.8353 Intermediate Similarity NPD4966 Approved
0.8353 Intermediate Similarity NPD4965 Approved
0.8176 Intermediate Similarity NPD37 Approved
0.8156 Intermediate Similarity NPD7240 Approved
0.814 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD3818 Discontinued
0.8056 Intermediate Similarity NPD7685 Pre-registration
0.8045 Intermediate Similarity NPD7074 Phase 3
0.8011 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7989 Intermediate Similarity NPD7054 Approved
0.7989 Intermediate Similarity NPD5844 Phase 1
0.7957 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD7472 Approved
0.7904 Intermediate Similarity NPD6190 Approved
0.7879 Intermediate Similarity NPD7266 Discontinued
0.7857 Intermediate Similarity NPD7251 Discontinued
0.7853 Intermediate Similarity NPD7199 Phase 2
0.7802 Intermediate Similarity NPD6797 Phase 2
0.7801 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7473 Discontinued
0.7778 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.776 Intermediate Similarity NPD6559 Discontinued
0.7732 Intermediate Similarity NPD7680 Approved
0.7717 Intermediate Similarity NPD7808 Phase 3
0.7709 Intermediate Similarity NPD6232 Discontinued
0.7705 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD230 Phase 1
0.7667 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8434 Phase 2
0.7647 Intermediate Similarity NPD8150 Discontinued
0.7624 Intermediate Similarity NPD6166 Phase 2
0.7624 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7624 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD1465 Phase 2
0.7614 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD5494 Approved
0.7596 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD8312 Approved
0.7581 Intermediate Similarity NPD8313 Approved
0.7557 Intermediate Similarity NPD1934 Approved
0.7551 Intermediate Similarity NPD7435 Discontinued
0.7543 Intermediate Similarity NPD4380 Phase 2
0.754 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD8166 Discontinued
0.7513 Intermediate Similarity NPD8320 Phase 1
0.7513 Intermediate Similarity NPD8319 Approved
0.75 Intermediate Similarity NPD6535 Approved
0.75 Intermediate Similarity NPD6534 Approved
0.7486 Intermediate Similarity NPD7458 Discontinued
0.7486 Intermediate Similarity NPD7075 Discontinued
0.7474 Intermediate Similarity NPD7700 Phase 2
0.7474 Intermediate Similarity NPD7699 Phase 2
0.745 Intermediate Similarity NPD8151 Discontinued
0.7446 Intermediate Similarity NPD7799 Discontinued
0.743 Intermediate Similarity NPD3882 Suspended
0.7429 Intermediate Similarity NPD1653 Approved
0.7427 Intermediate Similarity NPD4628 Phase 3
0.7416 Intermediate Similarity NPD7819 Suspended
0.7416 Intermediate Similarity NPD2801 Approved
0.7405 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD6779 Approved
0.7398 Intermediate Similarity NPD6776 Approved
0.7398 Intermediate Similarity NPD6780 Approved
0.7398 Intermediate Similarity NPD6777 Approved
0.7398 Intermediate Similarity NPD6781 Approved
0.7398 Intermediate Similarity NPD6778 Approved
0.7398 Intermediate Similarity NPD6782 Approved
0.7363 Intermediate Similarity NPD8127 Discontinued
0.7327 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7874 Approved
0.7318 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD7783 Phase 2
0.7291 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3764 Approved
0.7286 Intermediate Similarity NPD7696 Phase 3
0.7286 Intermediate Similarity NPD7698 Approved
0.7286 Intermediate Similarity NPD7697 Approved
0.7278 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3817 Phase 2
0.7263 Intermediate Similarity NPD8407 Phase 2
0.7258 Intermediate Similarity NPD3751 Discontinued
0.7257 Intermediate Similarity NPD2533 Approved
0.7257 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD2532 Approved
0.7257 Intermediate Similarity NPD2534 Approved
0.725 Intermediate Similarity NPD7870 Phase 2
0.725 Intermediate Similarity NPD7871 Phase 2
0.7236 Intermediate Similarity NPD6823 Phase 2
0.7228 Intermediate Similarity NPD7701 Phase 2
0.7225 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD8455 Phase 2
0.7207 Intermediate Similarity NPD7411 Suspended
0.7206 Intermediate Similarity NPD7801 Approved
0.7202 Intermediate Similarity NPD8361 Approved
0.7202 Intermediate Similarity NPD8360 Approved
0.7198 Intermediate Similarity NPD3749 Approved
0.7196 Intermediate Similarity NPD8368 Discontinued
0.7182 Intermediate Similarity NPD5402 Approved
0.7179 Intermediate Similarity NPD6213 Phase 3
0.7179 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6212 Phase 3
0.7174 Intermediate Similarity NPD6959 Discontinued
0.7167 Intermediate Similarity NPD6801 Discontinued
0.7151 Intermediate Similarity NPD6599 Discontinued
0.7135 Intermediate Similarity NPD3787 Discontinued
0.7126 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6273 Approved
0.7113 Intermediate Similarity NPD8435 Approved
0.7102 Intermediate Similarity NPD1511 Approved
0.7101 Intermediate Similarity NPD943 Approved
0.7062 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7028 Phase 2
0.7049 Intermediate Similarity NPD7768 Phase 2
0.7045 Intermediate Similarity NPD7236 Approved
0.7033 Intermediate Similarity NPD5760 Phase 2
0.7033 Intermediate Similarity NPD5761 Phase 2
0.703 Intermediate Similarity NPD7497 Discontinued
0.7029 Intermediate Similarity NPD3750 Approved
0.7022 Intermediate Similarity NPD1512 Approved
0.7019 Intermediate Similarity NPD7930 Approved
0.7012 Intermediate Similarity NPD9269 Phase 2
0.7011 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6100 Approved
0.6994 Remote Similarity NPD6099 Approved
0.6981 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6976 Remote Similarity NPD7585 Approved
0.6971 Remote Similarity NPD6674 Discontinued
0.6966 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6965 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7999 Approved
0.6952 Remote Similarity NPD7229 Phase 3
0.6944 Remote Similarity NPD7239 Suspended
0.6941 Remote Similarity NPD6663 Approved
0.6936 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6927 Remote Similarity NPD7583 Approved
0.6923 Remote Similarity NPD3027 Phase 3
0.6916 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1549 Phase 2
0.691 Remote Similarity NPD7390 Discontinued
0.691 Remote Similarity NPD6799 Approved
0.6902 Remote Similarity NPD5353 Approved
0.6901 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1613 Approved
0.6897 Remote Similarity NPD2935 Discontinued
0.6889 Remote Similarity NPD5403 Approved
0.6875 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6872 Remote Similarity NPD8404 Phase 2
0.6862 Remote Similarity NPD5711 Approved
0.6862 Remote Similarity NPD5710 Approved
0.6857 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7584 Approved
0.6839 Remote Similarity NPD1510 Phase 2
0.6839 Remote Similarity NPD651 Clinical (unspecified phase)
0.6836 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6836 Remote Similarity NPD7003 Approved
0.6825 Remote Similarity NPD5242 Approved
0.6816 Remote Similarity NPD8485 Approved
0.6814 Remote Similarity NPD5006 Approved
0.6814 Remote Similarity NPD5005 Approved
0.6813 Remote Similarity NPD3226 Approved
0.6808 Remote Similarity NPD4665 Approved
0.6805 Remote Similarity NPD5736 Approved
0.6802 Remote Similarity NPD7966 Clinical (unspecified phase)
0.68 Remote Similarity NPD5408 Approved
0.68 Remote Similarity NPD5405 Approved
0.68 Remote Similarity NPD5406 Approved
0.68 Remote Similarity NPD5404 Approved
0.6791 Remote Similarity NPD919 Approved
0.6784 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6782 Remote Similarity NPD7097 Phase 1
0.6778 Remote Similarity NPD5401 Approved
0.6768 Remote Similarity NPD9268 Approved
0.6762 Remote Similarity NPD7827 Phase 1
0.6743 Remote Similarity NPD3748 Approved
0.6743 Remote Similarity NPD8059 Phase 3
0.6743 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6737 Remote Similarity NPD3926 Phase 2
0.6724 Remote Similarity NPD1607 Approved
0.6721 Remote Similarity NPD3455 Phase 2
0.672 Remote Similarity NPD1247 Approved
0.6707 Remote Similarity NPD9545 Approved
0.6705 Remote Similarity NPD1240 Approved
0.6705 Remote Similarity NPD2796 Approved
0.67 Remote Similarity NPD4420 Approved
0.6685 Remote Similarity NPD2800 Approved
0.6683 Remote Similarity NPD2494 Approved
0.6683 Remote Similarity NPD2493 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