Structure

Physi-Chem Properties

Molecular Weight:  780.23
Volume:  750.205
LogP:  2.905
LogD:  1.955
LogS:  -3.102
# Rotatable Bonds:  17
TPSA:  268.43
# H-Bond Aceptor:  17
# H-Bond Donor:  8
# Rings:  5
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.063
Synthetic Accessibility Score:  5.048
Fsp3:  0.308
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.511
MDCK Permeability:  2.6036674171336927e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.932
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  99.88478088378906%
Volume Distribution (VD):  0.378
Pgp-substrate:  1.5031182765960693%

ADMET: Metabolism

CYP1A2-inhibitor:  0.136
CYP1A2-substrate:  0.009
CYP2C19-inhibitor:  0.305
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.662
CYP2C9-substrate:  0.888
CYP2D6-inhibitor:  0.036
CYP2D6-substrate:  0.208
CYP3A4-inhibitor:  0.808
CYP3A4-substrate:  0.188

ADMET: Excretion

Clearance (CL):  2.971
Half-life (T1/2):  0.908

ADMET: Toxicity

hERG Blockers:  0.289
Human Hepatotoxicity (H-HT):  0.047
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.182
Rat Oral Acute Toxicity:  0.245
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.98
Carcinogencity:  0.154
Eye Corrosion:  0.003
Eye Irritation:  0.026
Respiratory Toxicity:  0.007

Download Data

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

  Natural Product: NPC28637

Natural Product ID:  NPC28637
Common Name*:   Hydropiperoside
IUPAC Name:   [(2R,3R,4S,5S)-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:   Hydropiperoside
Standard InCHIKey:  VJVCHSAJVKCENR-QDCYMVOUSA-N
Standard InCHI:  InChI=1S/C39H40O17/c40-19-28-33(47)35(49)36(50)38(53-28)56-39(21-52-31(45)17-8-23-3-12-26(42)13-4-23)37(54-32(46)18-9-24-5-14-27(43)15-6-24)34(48)29(55-39)20-51-30(44)16-7-22-1-10-25(41)11-2-22/h1-18,28-29,33-38,40-43,47-50H,19-21H2/b16-7+,17-8+,18-9+/t28-,29-,33-,34-,35+,36-,37+,38-,39+/m1/s1
SMILES:  c1cc(ccc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@@](COC(=O)/C=C/c2ccc(cc2)O)(O1)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC(=O)/C=C/c1ccc(cc1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL448091
PubChem CID:   10350284
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives
          • [CHEMONTID:0003002] Hydroxycinnamic acid esters
            • [CHEMONTID:0000465] Coumaric acid esters

*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
NPO7193 Persicaria lapathifolia Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11678656]
NPO30740 Polygonum lapathifolium Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30896 Polygonum hydropiper Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30896 Polygonum hydropiper Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[Nippon Kogaku Zasshi, 91, (1970), 762]
NPO7193 Persicaria lapathifolia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29082 Persicaria hydropiper Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30896 Polygonum hydropiper Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30740 Polygonum lapathifolium Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29082 Persicaria hydropiper Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6826 Persicaria perfoliata Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7193 Persicaria lapathifolia Species Polygonaceae 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
NPT80 Cell Line Raji Homo sapiens Activity = 70.0 % PMID[528482]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[528482]
NPT2 Others Unspecified Activity = 10.6 % PMID[528482]
NPT2 Others Unspecified Activity = 39.6 % PMID[528482]
NPT2 Others Unspecified Activity = 71.5 % PMID[528482]
NPT2 Others Unspecified Activity = 100.0 % PMID[528482]

☑ 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 NPC28637 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
0.9603 High Similarity NPC225307
0.938 High Similarity NPC478255
0.937 High Similarity NPC471881
0.937 High Similarity NPC35288
0.937 High Similarity NPC45224
0.937 High Similarity NPC173150
0.937 High Similarity NPC471882
0.937 High Similarity NPC156692
0.9242 High Similarity NPC263829
0.9231 High Similarity NPC138777
0.9231 High Similarity NPC235294
0.9231 High Similarity NPC246869
0.9231 High Similarity NPC225384
0.9231 High Similarity NPC46137
0.9219 High Similarity NPC288416
0.9219 High Similarity NPC103533
0.9213 High Similarity NPC83218
0.9213 High Similarity NPC126991
0.9141 High Similarity NPC61181
0.9141 High Similarity NPC471157
0.9127 High Similarity NPC52097
0.907 High Similarity NPC106677
0.9051 High Similarity NPC105005
0.9048 High Similarity NPC11724
0.9 High Similarity NPC28651
0.9 High Similarity NPC215095
0.9 High Similarity NPC80732
0.9 High Similarity NPC210611
0.9 High Similarity NPC300262
0.9 High Similarity NPC192763
0.9 High Similarity NPC199311
0.9 High Similarity NPC3460
0.9 High Similarity NPC201148
0.9 High Similarity NPC261122
0.8992 High Similarity NPC252114
0.8986 High Similarity NPC141455
0.8986 High Similarity NPC300894
0.8986 High Similarity NPC296954
0.8986 High Similarity NPC196063
0.8968 High Similarity NPC476872
0.8913 High Similarity NPC40305
0.8905 High Similarity NPC476377
0.8905 High Similarity NPC47471
0.8897 High Similarity NPC328273
0.8897 High Similarity NPC321638
0.8897 High Similarity NPC321184
0.8897 High Similarity NPC205195
0.8897 High Similarity NPC171134
0.8881 High Similarity NPC471883
0.8857 High Similarity NPC229505
0.8832 High Similarity NPC475530
0.8832 High Similarity NPC473799
0.8824 High Similarity NPC260425
0.8815 High Similarity NPC476870
0.8811 High Similarity NPC143480
0.8811 High Similarity NPC7145
0.8811 High Similarity NPC125823
0.8811 High Similarity NPC85192
0.8797 High Similarity NPC219677
0.8797 High Similarity NPC254819
0.8797 High Similarity NPC281798
0.8788 High Similarity NPC253595
0.8786 High Similarity NPC216819
0.8786 High Similarity NPC83743
0.8786 High Similarity NPC287615
0.8786 High Similarity NPC262182
0.8777 High Similarity NPC76406
0.8777 High Similarity NPC112
0.8777 High Similarity NPC476380
0.8777 High Similarity NPC476375
0.8777 High Similarity NPC269141
0.8777 High Similarity NPC476397
0.8777 High Similarity NPC264632
0.8777 High Similarity NPC476378
0.8777 High Similarity NPC476381
0.8777 High Similarity NPC205864
0.8777 High Similarity NPC298257
0.8777 High Similarity NPC96795
0.8777 High Similarity NPC247032
0.8777 High Similarity NPC119537
0.8777 High Similarity NPC476384
0.8777 High Similarity NPC175214
0.8768 High Similarity NPC134405
0.8768 High Similarity NPC476385
0.8759 High Similarity NPC64141
0.8759 High Similarity NPC197316
0.8759 High Similarity NPC472350
0.8759 High Similarity NPC68092
0.8759 High Similarity NPC476383
0.8759 High Similarity NPC89105
0.8759 High Similarity NPC81515
0.875 High Similarity NPC472611
0.875 High Similarity NPC289967
0.875 High Similarity NPC472612
0.8741 High Similarity NPC886
0.8741 High Similarity NPC34293
0.8741 High Similarity NPC287597
0.8731 High Similarity NPC473924
0.8714 High Similarity NPC64195
0.8686 High Similarity NPC78363
0.8686 High Similarity NPC476376
0.8682 High Similarity NPC471067
0.8667 High Similarity NPC254398
0.8647 High Similarity NPC477294
0.8647 High Similarity NPC229784
0.8647 High Similarity NPC477293
0.8643 High Similarity NPC293154
0.8643 High Similarity NPC478250
0.8636 High Similarity NPC469687
0.8621 High Similarity NPC478268
0.8615 High Similarity NPC232454
0.8615 High Similarity NPC178449
0.8615 High Similarity NPC470907
0.8613 High Similarity NPC471345
0.8613 High Similarity NPC166180
0.8611 High Similarity NPC476871
0.8611 High Similarity NPC188393
0.8611 High Similarity NPC470934
0.8593 High Similarity NPC473285
0.8582 High Similarity NPC476867
0.8582 High Similarity NPC110063
0.8571 High Similarity NPC265648
0.8571 High Similarity NPC222433
0.8571 High Similarity NPC232880
0.8551 High Similarity NPC65262
0.8551 High Similarity NPC469364
0.8551 High Similarity NPC101686
0.8542 High Similarity NPC283839
0.8542 High Similarity NPC90896
0.8527 High Similarity NPC469703
0.8527 High Similarity NPC229600
0.8527 High Similarity NPC160854
0.8527 High Similarity NPC469704
0.8527 High Similarity NPC201402
0.8521 High Similarity NPC476868
0.8521 High Similarity NPC476869
0.8521 High Similarity NPC476864
0.8521 High Similarity NPC476866
0.8521 High Similarity NPC138915
0.8496 Intermediate Similarity NPC476873
0.8478 Intermediate Similarity NPC472132
0.8478 Intermediate Similarity NPC470572
0.8472 Intermediate Similarity NPC473138
0.8472 Intermediate Similarity NPC28776
0.8467 Intermediate Similarity NPC169398
0.8462 Intermediate Similarity NPC469686
0.8462 Intermediate Similarity NPC476865
0.845 Intermediate Similarity NPC282409
0.845 Intermediate Similarity NPC469702
0.844 Intermediate Similarity NPC148080
0.844 Intermediate Similarity NPC469623
0.8414 Intermediate Similarity NPC476398
0.8414 Intermediate Similarity NPC259347
0.8414 Intermediate Similarity NPC306890
0.8414 Intermediate Similarity NPC470933
0.8414 Intermediate Similarity NPC473427
0.8414 Intermediate Similarity NPC471062
0.8414 Intermediate Similarity NPC476386
0.8414 Intermediate Similarity NPC94871
0.8413 Intermediate Similarity NPC313193
0.8392 Intermediate Similarity NPC100998
0.8392 Intermediate Similarity NPC34927
0.8392 Intermediate Similarity NPC252292
0.8392 Intermediate Similarity NPC34587
0.8392 Intermediate Similarity NPC476382
0.8389 Intermediate Similarity NPC11411
0.8385 Intermediate Similarity NPC476448
0.8385 Intermediate Similarity NPC476445
0.8385 Intermediate Similarity NPC469548
0.838 Intermediate Similarity NPC204644
0.837 Intermediate Similarity NPC295970
0.8369 Intermediate Similarity NPC186406
0.8367 Intermediate Similarity NPC106818
0.8357 Intermediate Similarity NPC49597
0.8357 Intermediate Similarity NPC226005
0.8357 Intermediate Similarity NPC31745
0.8357 Intermediate Similarity NPC220942
0.8357 Intermediate Similarity NPC220936
0.8356 Intermediate Similarity NPC257970
0.8356 Intermediate Similarity NPC470927
0.8345 Intermediate Similarity NPC120728
0.8333 Intermediate Similarity NPC320734
0.8321 Intermediate Similarity NPC471095
0.8321 Intermediate Similarity NPC471066
0.8321 Intermediate Similarity NPC55608
0.8311 Intermediate Similarity NPC87403
0.8311 Intermediate Similarity NPC471874
0.831 Intermediate Similarity NPC157816
0.831 Intermediate Similarity NPC140502
0.831 Intermediate Similarity NPC145319
0.8289 Intermediate Similarity NPC7191
0.8289 Intermediate Similarity NPC149873
0.8286 Intermediate Similarity NPC469696
0.8281 Intermediate Similarity NPC175771
0.8278 Intermediate Similarity NPC478269
0.8276 Intermediate Similarity NPC232992
0.8276 Intermediate Similarity NPC97240
0.8261 Intermediate Similarity NPC164172
0.8252 Intermediate Similarity NPC478239
0.8239 Intermediate Similarity NPC46644

  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 NPC28637 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
0.8759 High Similarity NPD7266 Discontinued
0.7778 Intermediate Similarity NPD8455 Phase 2
0.7635 Intermediate Similarity NPD6190 Approved
0.7566 Intermediate Similarity NPD1653 Approved
0.7518 Intermediate Similarity NPD1091 Approved
0.7405 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7685 Pre-registration
0.7348 Intermediate Similarity NPD969 Suspended
0.7305 Intermediate Similarity NPD8312 Approved
0.7305 Intermediate Similarity NPD8313 Approved
0.7303 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD3764 Approved
0.7279 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7228 Approved
0.7186 Intermediate Similarity NPD6559 Discontinued
0.7162 Intermediate Similarity NPD7097 Phase 1
0.7125 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD6233 Phase 2
0.7122 Intermediate Similarity NPD5125 Phase 3
0.7122 Intermediate Similarity NPD5126 Approved
0.7118 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD7472 Approved
0.7048 Intermediate Similarity NPD3818 Discontinued
0.7045 Intermediate Similarity NPD1358 Approved
0.7044 Intermediate Similarity NPD37 Approved
0.7041 Intermediate Similarity NPD7808 Phase 3
0.7037 Intermediate Similarity NPD6234 Discontinued
0.7027 Intermediate Similarity NPD4340 Discontinued
0.7025 Intermediate Similarity NPD4380 Phase 2
0.7019 Intermediate Similarity NPD4965 Approved
0.7019 Intermediate Similarity NPD4966 Approved
0.7019 Intermediate Similarity NPD4967 Phase 2
0.7013 Intermediate Similarity NPD5058 Phase 3
0.7006 Intermediate Similarity NPD7054 Approved
0.6993 Remote Similarity NPD4628 Phase 3
0.6982 Remote Similarity NPD7251 Discontinued
0.6982 Remote Similarity NPD7240 Approved
0.6978 Remote Similarity NPD9545 Approved
0.6964 Remote Similarity NPD7074 Phase 3
0.6943 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6798 Discontinued
0.6928 Remote Similarity NPD1652 Phase 2
0.6923 Remote Similarity NPD6797 Phase 2
0.6923 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4908 Phase 1
0.6914 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6883 Remote Similarity NPD8166 Discontinued
0.6871 Remote Similarity NPD7075 Discontinued
0.6871 Remote Similarity NPD3027 Phase 3
0.6848 Remote Similarity NPD7199 Phase 2
0.6846 Remote Similarity NPD1613 Approved
0.6846 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6846 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6842 Remote Similarity NPD3134 Approved
0.6835 Remote Similarity NPD5403 Approved
0.6824 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6674 Discontinued
0.6809 Remote Similarity NPD1357 Approved
0.6806 Remote Similarity NPD4379 Clinical (unspecified phase)
0.68 Remote Similarity NPD5124 Phase 1
0.68 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6788 Remote Similarity NPD7843 Approved
0.6776 Remote Similarity NPD5588 Approved
0.677 Remote Similarity NPD7411 Suspended
0.6759 Remote Similarity NPD3225 Approved
0.675 Remote Similarity NPD7458 Discontinued
0.6735 Remote Similarity NPD2861 Phase 2
0.6711 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6709 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6709 Remote Similarity NPD5401 Approved
0.6707 Remote Similarity NPD7768 Phase 2
0.6705 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6689 Remote Similarity NPD230 Phase 1
0.6689 Remote Similarity NPD6355 Discontinued
0.6687 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7033 Discontinued
0.6667 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6667 Remote Similarity NPD422 Phase 1
0.6667 Remote Similarity NPD5535 Approved
0.6667 Remote Similarity NPD3705 Approved
0.6647 Remote Similarity NPD8127 Discontinued
0.6646 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5402 Approved
0.6644 Remote Similarity NPD7095 Approved
0.6644 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6643 Remote Similarity NPD5846 Approved
0.6643 Remote Similarity NPD6516 Phase 2
0.663 Remote Similarity NPD7680 Approved
0.6627 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6166 Phase 2
0.6627 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6626 Remote Similarity NPD6801 Discontinued
0.6623 Remote Similarity NPD4060 Phase 1
0.6622 Remote Similarity NPD5736 Approved
0.662 Remote Similarity NPD1548 Phase 1
0.6608 Remote Similarity NPD5844 Phase 1
0.6601 Remote Similarity NPD4538 Approved
0.6601 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6601 Remote Similarity NPD4536 Approved
0.6599 Remote Similarity NPD3094 Phase 2
0.6589 Remote Similarity NPD2933 Approved
0.6589 Remote Similarity NPD2934 Approved
0.6582 Remote Similarity NPD7440 Discontinued
0.6577 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6561 Remote Similarity NPD3750 Approved
0.6558 Remote Similarity NPD5960 Phase 3
0.6556 Remote Similarity NPD4062 Phase 3
0.6554 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6552 Remote Similarity NPD1610 Phase 2
0.655 Remote Similarity NPD3751 Discontinued
0.6543 Remote Similarity NPD8151 Discontinued
0.6541 Remote Similarity NPD6799 Approved
0.6538 Remote Similarity NPD1549 Phase 2
0.6538 Remote Similarity NPD2859 Approved
0.6538 Remote Similarity NPD2860 Approved
0.6536 Remote Similarity NPD6653 Approved
0.6529 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6525 Remote Similarity NPD7157 Approved
0.651 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6505 Remote Similarity NPD8320 Phase 1
0.6505 Remote Similarity NPD8319 Approved
0.6503 Remote Similarity NPD7237 Clinical (unspecified phase)
0.65 Remote Similarity NPD8389 Clinical (unspecified phase)
0.65 Remote Similarity NPD3536 Discontinued
0.6497 Remote Similarity NPD8150 Discontinued
0.6496 Remote Similarity NPD2684 Approved
0.6485 Remote Similarity NPD7819 Suspended
0.6479 Remote Similarity NPD694 Clinical (unspecified phase)
0.6474 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6474 Remote Similarity NPD5763 Approved
0.6474 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6474 Remote Similarity NPD5762 Approved
0.6471 Remote Similarity NPD1933 Approved
0.6471 Remote Similarity NPD968 Approved
0.6467 Remote Similarity NPD3749 Approved
0.6466 Remote Similarity NPD1242 Phase 1
0.6457 Remote Similarity NPD689 Discontinued
0.6456 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6453 Remote Similarity NPD7799 Discontinued
0.6452 Remote Similarity NPD7435 Discontinued
0.6448 Remote Similarity NPD7699 Phase 2
0.6448 Remote Similarity NPD7700 Phase 2
0.6447 Remote Similarity NPD6663 Approved
0.6442 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6438 Remote Similarity NPD1535 Discovery
0.6438 Remote Similarity NPD3092 Approved
0.6434 Remote Similarity NPD5536 Phase 2
0.6433 Remote Similarity NPD2424 Discontinued
0.6424 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6424 Remote Similarity NPD1934 Approved
0.6423 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6423 Remote Similarity NPD290 Approved
0.6419 Remote Similarity NPD8651 Approved
0.6414 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6412 Remote Similarity NPD3787 Discontinued
0.641 Remote Similarity NPD2935 Discontinued
0.641 Remote Similarity NPD5408 Approved
0.641 Remote Similarity NPD5404 Approved
0.641 Remote Similarity NPD1551 Phase 2
0.641 Remote Similarity NPD5405 Approved
0.641 Remote Similarity NPD5406 Approved
0.6408 Remote Similarity NPD4198 Discontinued
0.6405 Remote Similarity NPD4140 Approved
0.6404 Remote Similarity NPD8434 Phase 2
0.6398 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6395 Remote Similarity NPD1481 Phase 2
0.6392 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6391 Remote Similarity NPD3020 Approved
0.6389 Remote Similarity NPD7741 Discontinued
0.6389 Remote Similarity NPD1894 Discontinued
0.6387 Remote Similarity NPD7783 Phase 2
0.6387 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6386 Remote Similarity NPD2977 Approved
0.6386 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6386 Remote Similarity NPD2978 Approved
0.6376 Remote Similarity NPD2797 Approved
0.6376 Remote Similarity NPD1203 Approved
0.6374 Remote Similarity NPD6535 Approved
0.6374 Remote Similarity NPD6534 Approved
0.637 Remote Similarity NPD3847 Discontinued
0.637 Remote Similarity NPD3496 Discontinued
0.6369 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6364 Remote Similarity NPD9493 Approved
0.6364 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6358 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6358 Remote Similarity NPD6273 Approved
0.6358 Remote Similarity NPD6832 Phase 2
0.6351 Remote Similarity NPD7876 Discontinued
0.6351 Remote Similarity NPD6583 Phase 3
0.6351 Remote Similarity NPD6582 Phase 2
0.6347 Remote Similarity NPD3817 Phase 2
0.6346 Remote Similarity NPD1510 Phase 2
0.6341 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6341 Remote Similarity NPD3455 Phase 2
0.6335 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6335 Remote Similarity NPD7874 Approved
0.6335 Remote Similarity NPD7212 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