Structure

Physi-Chem Properties

Molecular Weight:  202.03
Volume:  192.485
LogP:  1.819
LogD:  1.709
LogS:  -3.147
# Rotatable Bonds:  0
TPSA:  63.58
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.568
Synthetic Accessibility Score:  2.741
Fsp3:  0.0
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:  -4.835
MDCK Permeability:  1.90919545275392e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.068
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.316
30% Bioavailability (F30%):  0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.023
Plasma Protein Binding (PPB):  90.26410675048828%
Volume Distribution (VD):  0.669
Pgp-substrate:  10.264388084411621%

ADMET: Metabolism

CYP1A2-inhibitor:  0.985
CYP1A2-substrate:  0.501
CYP2C19-inhibitor:  0.168
CYP2C19-substrate:  0.061
CYP2C9-inhibitor:  0.337
CYP2C9-substrate:  0.498
CYP2D6-inhibitor:  0.784
CYP2D6-substrate:  0.444
CYP3A4-inhibitor:  0.503
CYP3A4-substrate:  0.126

ADMET: Excretion

Clearance (CL):  13.333
Half-life (T1/2):  0.837

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.646
Drug-inuced Liver Injury (DILI):  0.97
AMES Toxicity:  0.28
Rat Oral Acute Toxicity:  0.428
Maximum Recommended Daily Dose:  0.257
Skin Sensitization:  0.526
Carcinogencity:  0.908
Eye Corrosion:  0.004
Eye Irritation:  0.154
Respiratory Toxicity:  0.85

Download Data

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC15819

Natural Product ID:  NPC15819
Common Name*:   Xanthotoxol
IUPAC Name:   9-hydroxyfuro[3,2-g]chromen-7-one
Synonyms:   8-Hydroxypsoralen; Xanthotoxol; Xanthoxol
Standard InCHIKey:  JWVYQQGERKEAHW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H
SMILES:  O=c1ccc2c(o1)c(O)c1c(c2)cco1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1192
PubChem CID:   65090
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0000358] Furanocoumarins
          • [CHEMONTID:0002569] Linear furanocoumarins
            • [CHEMONTID:0000202] Psoralens
              • [CHEMONTID:0002831] 8-hydroxypsoralens

*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
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[10785419]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[1453177]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[17666859]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21800857]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota fruits n.a. n.a. PMID[22932311]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. fruit n.a. PMID[23721280]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24813739]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Root Essent. Oil n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota Roots n.a. Database[FooDB]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30713 Angelica talwaniana Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17866 Peucedanum rubricaule Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31471 Poncirus trifoliata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO900 Cnidium monieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16675 Peucedanum japonicum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12662 Torilis japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15544 Cnidium monnieri Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13642 Pastinaca sativa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6190 Angelica archangelica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16696 Cryptodiscus didymus Species Stictidaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 > 500000.0 nM PMID[548537]
NPT520 Cell Line 3T3-L1 Mus musculus IC50 > 500000.0 nM PMID[548537]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[548542]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 19.8 % PMID[548538]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 10.5 % PMID[548538]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 5.2 % PMID[548538]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 0.7 % PMID[548538]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = 2.7 % PMID[548538]
NPT963 Organism Hepatitis B virus Hepatitis B virus Inhibition = -5.0 % PMID[548538]
NPT27 Others Unspecified Inhibition = 17.0 % PMID[548538]
NPT27 Others Unspecified Inhibition = 12.2 % PMID[548538]
NPT27 Others Unspecified Inhibition = 7.8 % PMID[548538]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 10300.0 nM PMID[548540]
NPT1 Others Radical scavenging activity IC50 = 69600.0 nM PMID[548540]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 188300.0 nM PMID[548540]
NPT452 Organism Helicobacter pylori SS1 Helicobacter pylori SS1 MIC > 50.0 ug.mL-1 PMID[548541]
NPT2 Others Unspecified Potency n.a. 163.6 nM PMID[548542]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[548543]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens Inhibition = 32.8 % PMID[548543]
NPT2 Others Unspecified Potency n.a. 1000.0 nM PMID[548542]
NPT1 Others Radical scavenging activity Activity = 25.0 % PMID[548545]
NPT35 Others n.a. Inhibition = 5.0 % PMID[548545]
NPT2 Others Unspecified IC50 = 89000.0 nM PMID[548545]
NPT1 Others Radical scavenging activity Activity = 22.0 % PMID[548545]

☑ 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 NPC15819 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
0.9565 High Similarity NPC233956
0.9563 High Similarity NPC281835
0.9363 High Similarity NPC33320
0.9321 High Similarity NPC51404
0.9304 High Similarity NPC243509
0.9245 High Similarity NPC216092
0.9236 High Similarity NPC19860
0.9212 High Similarity NPC107244
0.913 High Similarity NPC179464
0.908 High Similarity NPC241820
0.9074 High Similarity NPC179015
0.9074 High Similarity NPC173149
0.9068 High Similarity NPC78612
0.9068 High Similarity NPC234536
0.9038 High Similarity NPC155882
0.9036 High Similarity NPC53917
0.9036 High Similarity NPC224165
0.9018 High Similarity NPC67450
0.9018 High Similarity NPC193881
0.9018 High Similarity NPC210460
0.9018 High Similarity NPC155264
0.8994 High Similarity NPC472461
0.8957 High Similarity NPC38914
0.8947 High Similarity NPC73703
0.8944 High Similarity NPC169
0.8861 High Similarity NPC98028
0.8855 High Similarity NPC131866
0.8834 High Similarity NPC272722
0.8831 High Similarity NPC166858
0.8831 High Similarity NPC51146
0.8805 High Similarity NPC304954
0.8797 High Similarity NPC260582
0.878 High Similarity NPC1755
0.878 High Similarity NPC263092
0.878 High Similarity NPC39305
0.878 High Similarity NPC59295
0.878 High Similarity NPC1706
0.8773 High Similarity NPC264293
0.8773 High Similarity NPC14822
0.8765 High Similarity NPC16935
0.875 High Similarity NPC189130
0.875 High Similarity NPC475895
0.875 High Similarity NPC277510
0.8743 High Similarity NPC144288
0.8735 High Similarity NPC247973
0.8727 High Similarity NPC36320
0.8726 High Similarity NPC140840
0.8726 High Similarity NPC86847
0.872 High Similarity NPC238995
0.8718 High Similarity NPC246903
0.8712 High Similarity NPC49009
0.8712 High Similarity NPC239270
0.8712 High Similarity NPC328102
0.8712 High Similarity NPC303210
0.8712 High Similarity NPC95472
0.8704 High Similarity NPC269495
0.8704 High Similarity NPC270044
0.8696 High Similarity NPC234255
0.8688 High Similarity NPC199773
0.8688 High Similarity NPC55205
0.8671 High Similarity NPC19545
0.8667 High Similarity NPC472582
0.8659 High Similarity NPC188486
0.865 High Similarity NPC196879
0.865 High Similarity NPC184755
0.865 High Similarity NPC74178
0.8642 High Similarity NPC474638
0.8642 High Similarity NPC472455
0.8639 High Similarity NPC310794
0.8639 High Similarity NPC261471
0.8634 High Similarity NPC256346
0.8634 High Similarity NPC27532
0.8634 High Similarity NPC141212
0.8634 High Similarity NPC325028
0.8634 High Similarity NPC246328
0.8634 High Similarity NPC131725
0.8631 High Similarity NPC28042
0.8625 High Similarity NPC200740
0.8625 High Similarity NPC125062
0.8625 High Similarity NPC256406
0.8625 High Similarity NPC252933
0.8625 High Similarity NPC54394
0.8623 High Similarity NPC186392
0.8616 High Similarity NPC88445
0.8614 High Similarity NPC204088
0.8614 High Similarity NPC29411
0.8614 High Similarity NPC259007
0.8614 High Similarity NPC329215
0.8614 High Similarity NPC45449
0.8608 High Similarity NPC74539
0.8608 High Similarity NPC125449
0.8608 High Similarity NPC51443
0.8608 High Similarity NPC168803
0.8608 High Similarity NPC188074
0.8608 High Similarity NPC304443
0.8608 High Similarity NPC74881
0.8606 High Similarity NPC81679
0.8606 High Similarity NPC471745
0.8606 High Similarity NPC84515
0.8606 High Similarity NPC193998
0.8606 High Similarity NPC312056
0.8598 High Similarity NPC287328
0.8598 High Similarity NPC130955
0.8598 High Similarity NPC282009
0.8598 High Similarity NPC471744
0.8598 High Similarity NPC472624
0.8598 High Similarity NPC292415
0.8596 High Similarity NPC98546
0.8596 High Similarity NPC297807
0.8589 High Similarity NPC291508
0.8589 High Similarity NPC35598
0.8589 High Similarity NPC67876
0.8589 High Similarity NPC52530
0.8589 High Similarity NPC52889
0.8589 High Similarity NPC222689
0.858 High Similarity NPC57674
0.858 High Similarity NPC230149
0.858 High Similarity NPC117992
0.858 High Similarity NPC472280
0.858 High Similarity NPC20541
0.858 High Similarity NPC152951
0.858 High Similarity NPC157522
0.858 High Similarity NPC133392
0.858 High Similarity NPC168247
0.8571 High Similarity NPC165456
0.8571 High Similarity NPC237994
0.8571 High Similarity NPC157784
0.8571 High Similarity NPC471982
0.8571 High Similarity NPC36835
0.8571 High Similarity NPC82325
0.8571 High Similarity NPC61506
0.8571 High Similarity NPC37684
0.8571 High Similarity NPC63187
0.8571 High Similarity NPC279989
0.8571 High Similarity NPC9743
0.8571 High Similarity NPC246162
0.8571 High Similarity NPC125300
0.8571 High Similarity NPC253872
0.8571 High Similarity NPC240476
0.8571 High Similarity NPC260491
0.8563 High Similarity NPC277480
0.8563 High Similarity NPC323137
0.8562 High Similarity NPC191104
0.8562 High Similarity NPC29231
0.8554 High Similarity NPC234004
0.8554 High Similarity NPC124038
0.8554 High Similarity NPC472625
0.8553 High Similarity NPC266743
0.8553 High Similarity NPC139364
0.8553 High Similarity NPC203747
0.8553 High Similarity NPC254702
0.8553 High Similarity NPC272721
0.8553 High Similarity NPC194653
0.8553 High Similarity NPC43669
0.8553 High Similarity NPC196277
0.8553 High Similarity NPC80710
0.8547 High Similarity NPC104682
0.8545 High Similarity NPC94155
0.8545 High Similarity NPC289771
0.8545 High Similarity NPC349525
0.8545 High Similarity NPC112418
0.8545 High Similarity NPC103201
0.8545 High Similarity NPC473106
0.8545 High Similarity NPC187354
0.8545 High Similarity NPC471499
0.8544 High Similarity NPC179271
0.8544 High Similarity NPC20791
0.8538 High Similarity NPC8127
0.8538 High Similarity NPC49667
0.8538 High Similarity NPC164384
0.8537 High Similarity NPC168616
0.8537 High Similarity NPC55738
0.8537 High Similarity NPC204879
0.8537 High Similarity NPC22192
0.8537 High Similarity NPC195832
0.8537 High Similarity NPC83763
0.8535 High Similarity NPC38065
0.8535 High Similarity NPC242893
0.8529 High Similarity NPC72455
0.8528 High Similarity NPC5322
0.8528 High Similarity NPC265511
0.8528 High Similarity NPC6633
0.8528 High Similarity NPC13858
0.8528 High Similarity NPC278778
0.8528 High Similarity NPC282307
0.8528 High Similarity NPC320825
0.8528 High Similarity NPC326037
0.8528 High Similarity NPC170026
0.8528 High Similarity NPC195796
0.8528 High Similarity NPC291878
0.8528 High Similarity NPC35038
0.8528 High Similarity NPC45131
0.8528 High Similarity NPC133970
0.8521 High Similarity NPC78830
0.8521 High Similarity NPC218533
0.8519 High Similarity NPC49402
0.8519 High Similarity NPC469550
0.8519 High Similarity NPC33051
0.8519 High Similarity NPC78326
0.8519 High Similarity NPC179126

  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 NPC15819 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
0.9363 High Similarity NPD919 Approved
0.8831 High Similarity NPD643 Clinical (unspecified phase)
0.8773 High Similarity NPD1247 Approved
0.8758 High Similarity NPD3882 Suspended
0.8718 High Similarity NPD642 Clinical (unspecified phase)
0.8608 High Similarity NPD920 Approved
0.8544 High Similarity NPD1512 Approved
0.8466 Intermediate Similarity NPD3817 Phase 2
0.8457 Intermediate Similarity NPD1934 Approved
0.8418 Intermediate Similarity NPD1511 Approved
0.8405 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD3818 Discontinued
0.8397 Intermediate Similarity NPD1243 Approved
0.8364 Intermediate Similarity NPD7075 Discontinued
0.8293 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8293 Intermediate Similarity NPD2801 Approved
0.8232 Intermediate Similarity NPD6801 Discontinued
0.8208 Intermediate Similarity NPD6559 Discontinued
0.8187 Intermediate Similarity NPD6799 Approved
0.8182 Intermediate Similarity NPD1465 Phase 2
0.8176 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD6166 Phase 2
0.8161 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8084 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD3749 Approved
0.8025 Intermediate Similarity NPD1510 Phase 2
0.8012 Intermediate Similarity NPD3926 Phase 2
0.8 Intermediate Similarity NPD6599 Discontinued
0.8 Intermediate Similarity NPD4380 Phase 2
0.7987 Intermediate Similarity NPD1549 Phase 2
0.7975 Intermediate Similarity NPD1551 Phase 2
0.7964 Intermediate Similarity NPD7819 Suspended
0.7953 Intermediate Similarity NPD6232 Discontinued
0.7943 Intermediate Similarity NPD6797 Phase 2
0.7941 Intermediate Similarity NPD5494 Approved
0.7931 Intermediate Similarity NPD5844 Phase 1
0.7931 Intermediate Similarity NPD7054 Approved
0.7925 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7473 Discontinued
0.7898 Intermediate Similarity NPD7251 Discontinued
0.7886 Intermediate Similarity NPD7472 Approved
0.7886 Intermediate Similarity NPD7074 Phase 3
0.7875 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD7808 Phase 3
0.7844 Intermediate Similarity NPD7411 Suspended
0.7841 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7824 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD5403 Approved
0.7811 Intermediate Similarity NPD5402 Approved
0.7805 Intermediate Similarity NPD5401 Approved
0.7771 Intermediate Similarity NPD943 Approved
0.7771 Intermediate Similarity NPD1240 Approved
0.7727 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD230 Phase 1
0.7722 Intermediate Similarity NPD447 Suspended
0.7697 Intermediate Similarity NPD2533 Approved
0.7697 Intermediate Similarity NPD2534 Approved
0.7697 Intermediate Similarity NPD2532 Approved
0.7697 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1607 Approved
0.7669 Intermediate Similarity NPD3750 Approved
0.7661 Intermediate Similarity NPD7768 Phase 2
0.7657 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD2796 Approved
0.7605 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2800 Approved
0.7486 Intermediate Similarity NPD8434 Phase 2
0.7485 Intermediate Similarity NPD2344 Approved
0.7469 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD1653 Approved
0.7455 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD9494 Approved
0.7436 Intermediate Similarity NPD1203 Approved
0.7405 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6959 Discontinued
0.7386 Intermediate Similarity NPD7199 Phase 2
0.7378 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD3748 Approved
0.7349 Intermediate Similarity NPD4628 Phase 3
0.7348 Intermediate Similarity NPD5953 Discontinued
0.7337 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD1613 Approved
0.7329 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD2313 Discontinued
0.7312 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD3226 Approved
0.7305 Intermediate Similarity NPD2309 Approved
0.7296 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6234 Discontinued
0.7263 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD2799 Discontinued
0.7244 Intermediate Similarity NPD9269 Phase 2
0.7244 Intermediate Similarity NPD9717 Approved
0.7238 Intermediate Similarity NPD7286 Phase 2
0.7233 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD411 Approved
0.7202 Intermediate Similarity NPD6190 Approved
0.7182 Intermediate Similarity NPD3751 Discontinued
0.7179 Intermediate Similarity NPD422 Phase 1
0.7178 Intermediate Similarity NPD1933 Approved
0.7174 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD5710 Approved
0.7151 Intermediate Similarity NPD5711 Approved
0.7143 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4287 Approved
0.7088 Intermediate Similarity NPD2163 Approved
0.7086 Intermediate Similarity NPD37 Approved
0.7081 Intermediate Similarity NPD6832 Phase 2
0.7073 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD1471 Phase 3
0.7066 Intermediate Similarity NPD2346 Discontinued
0.7062 Intermediate Similarity NPD4965 Approved
0.7062 Intermediate Similarity NPD4966 Approved
0.7062 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4967 Phase 2
0.7048 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3027 Phase 3
0.703 Intermediate Similarity NPD6651 Approved
0.7012 Intermediate Similarity NPD4060 Phase 1
0.7011 Intermediate Similarity NPD1729 Discontinued
0.6995 Remote Similarity NPD7228 Approved
0.6995 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6994 Remote Similarity NPD1296 Phase 2
0.6987 Remote Similarity NPD9268 Approved
0.6977 Remote Similarity NPD7004 Clinical (unspecified phase)
0.697 Remote Similarity NPD6355 Discontinued
0.6961 Remote Similarity NPD7229 Phase 3
0.6961 Remote Similarity NPD3787 Discontinued
0.6952 Remote Similarity NPD8312 Approved
0.6952 Remote Similarity NPD8313 Approved
0.6949 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6946 Remote Similarity NPD7033 Discontinued
0.6946 Remote Similarity NPD4308 Phase 3
0.6935 Remote Similarity NPD7685 Pre-registration
0.6923 Remote Similarity NPD9545 Approved
0.6923 Remote Similarity NPD5242 Approved
0.6918 Remote Similarity NPD1608 Approved
0.6914 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2354 Approved
0.6894 Remote Similarity NPD1164 Approved
0.6893 Remote Similarity NPD4665 Approved
0.6893 Remote Similarity NPD4111 Phase 1
0.689 Remote Similarity NPD6798 Discontinued
0.689 Remote Similarity NPD3268 Approved
0.6889 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6867 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6867 Remote Similarity NPD5124 Phase 1
0.6855 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6852 Remote Similarity NPD1019 Discontinued
0.6842 Remote Similarity NPD8150 Discontinued
0.6839 Remote Similarity NPD5049 Phase 3
0.6832 Remote Similarity NPD3225 Approved
0.6827 Remote Similarity NPD7907 Approved
0.6818 Remote Similarity NPD7458 Discontinued
0.6816 Remote Similarity NPD2296 Approved
0.6816 Remote Similarity NPD4288 Approved
0.6816 Remote Similarity NPD5353 Approved
0.6815 Remote Similarity NPD1548 Phase 1
0.6805 Remote Similarity NPD5404 Approved
0.6805 Remote Similarity NPD5406 Approved
0.6805 Remote Similarity NPD5408 Approved
0.6805 Remote Similarity NPD5405 Approved
0.6795 Remote Similarity NPD9493 Approved
0.6793 Remote Similarity NPD2403 Approved
0.6793 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6793 Remote Similarity NPD7784 Clinical (unspecified phase)
0.679 Remote Similarity NPD2797 Approved
0.6788 Remote Similarity NPD3764 Approved
0.6784 Remote Similarity NPD1652 Phase 2
0.6784 Remote Similarity NPD7435 Discontinued
0.6782 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6782 Remote Similarity NPD8151 Discontinued
0.6776 Remote Similarity NPD6808 Phase 2
0.6769 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6769 Remote Similarity NPD4361 Phase 2
0.6762 Remote Similarity NPD5619 Clinical (unspecified phase)
0.675 Remote Similarity NPD1610 Phase 2
0.6742 Remote Similarity NPD6386 Approved
0.6742 Remote Similarity NPD6385 Approved
0.6734 Remote Similarity NPD3057 Approved
0.6734 Remote Similarity NPD3448 Approved
0.6734 Remote Similarity NPD2491 Approved
0.673 Remote Similarity NPD17 Approved
0.6724 Remote Similarity NPD7390 Discontinued
0.6721 Remote Similarity NPD8127 Discontinued
0.6717 Remote Similarity NPD6780 Approved
0.6717 Remote Similarity NPD6781 Approved
0.6717 Remote Similarity NPD6782 Approved
0.6717 Remote Similarity NPD6776 Approved
0.6717 Remote Similarity NPD4107 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