Structure

Physi-Chem Properties

Molecular Weight:  202.03
Volume:  192.485
LogP:  1.896
LogD:  1.748
LogS:  -3.018
# 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:  2.451
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:  -4.831
MDCK Permeability:  1.4872313840896823e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.991
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  91.62765502929688%
Volume Distribution (VD):  0.554
Pgp-substrate:  12.259520530700684%

ADMET: Metabolism

CYP1A2-inhibitor:  0.981
CYP1A2-substrate:  0.825
CYP2C19-inhibitor:  0.347
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.133
CYP2C9-substrate:  0.78
CYP2D6-inhibitor:  0.771
CYP2D6-substrate:  0.806
CYP3A4-inhibitor:  0.442
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  12.042
Half-life (T1/2):  0.757

ADMET: Toxicity

hERG Blockers:  0.15
Human Hepatotoxicity (H-HT):  0.162
Drug-inuced Liver Injury (DILI):  0.93
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.186
Maximum Recommended Daily Dose:  0.271
Skin Sensitization:  0.714
Carcinogencity:  0.849
Eye Corrosion:  0.009
Eye Irritation:  0.959
Respiratory Toxicity:  0.557

Download Data

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

  Natural Product: NPC155882

Natural Product ID:  NPC155882
Common Name*:   Bergaptol
IUPAC Name:   4-hydroxyfuro[3,2-g]chromen-7-one
Synonyms:   5-Hydroxy-Psoralen; 5-Hydroxypsoralen; Bergaptol
Standard InCHIKey:  GIJHDGJRTUSBJR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
SMILES:  O=c1ccc2c(o1)cc1c(c2O)cco1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL242711
PubChem CID:   5280371
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:0002830] 5-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
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. root n.a. PMID[20707067]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. rhizome n.a. PMID[20707067]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[25333853]
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]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO662 Angelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2392 Hansenia weberbaueriana 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]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30526 0topterygium incisum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30125 0topterygium forbesii n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2392 Hansenia weberbaueriana 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]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO662 Angelica officinalis 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]
NPO16614 Zanthoxylum spinosum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2953 Ostericum grosseserratum Species Apiaceae 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
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens IC50 = 24920.0 nM PMID[462983]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Inhibition = 98.9 % PMID[462983]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 500000.0 nM PMID[462984]
NPT520 Cell Line 3T3-L1 Mus musculus IC50 > 500000.0 nM PMID[462984]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[462985]
NPT583 Individual Protein Inositol monophosphatase 1 Rattus norvegicus Potency = 2511.9 nM PMID[462985]
NPT442 Individual Protein Ferritin light chain Equus caballus Potency = 31622.8 nM PMID[462985]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 15848.9 nM PMID[462985]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 15848.9 nM PMID[462985]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 15848.9 nM PMID[462985]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 23099.9 nM PMID[462986]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens Ki = 11600.0 nM PMID[462987]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens Kinact = 0.02 min-1 PMID[462987]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 100000.0 nM PMID[462986]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 501.2 nM PMID[462986]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 19952.6 nM PMID[462985]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 183.6 nM PMID[462986]
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency n.a. 5623.4 nM PMID[462986]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 12995.3 nM PMID[462985]
NPT446 Individual Protein Rap guanine nucleotide exchange factor 3 Homo sapiens Potency n.a. 89125.1 nM PMID[462986]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 29.7 % PMID[462983]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 91.1 % PMID[462983]
NPT35 Others n.a. Activity = 82.9 % PMID[462983]
NPT35 Others n.a. Activity = 42.5 % PMID[462983]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 28183.8 nM PMID[462985]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 89125.1 nM PMID[462986]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[462986]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 > 500000.0 nM PMID[462988]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens Inhibition = 11.1 % PMID[462988]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens EC200 = 0.3 uM PMID[462989]
NPT1 Others Radical scavenging activity Activity = 34.0 % PMID[462990]
NPT35 Others n.a. Inhibition = 95.0 % PMID[462990]
NPT2 Others Unspecified IC50 = 41500.0 nM PMID[462990]
NPT1 Others Radical scavenging activity Activity = 36.0 % PMID[462990]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 100.0 ug.mL-1 PMID[462991]

☑ 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 NPC155882 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
0.9597 High Similarity NPC270044
0.9517 High Similarity NPC304443
0.9517 High Similarity NPC74539
0.9514 High Similarity NPC246903
0.9467 High Similarity NPC269495
0.9388 High Similarity NPC88445
0.9375 High Similarity NPC51146
0.9375 High Similarity NPC166858
0.9342 High Similarity NPC169
0.9324 High Similarity NPC191104
0.9216 High Similarity NPC95472
0.9216 High Similarity NPC239270
0.9216 High Similarity NPC49009
0.9216 High Similarity NPC303210
0.9156 High Similarity NPC14822
0.9133 High Similarity NPC116604
0.9116 High Similarity NPC208584
0.911 High Similarity NPC313036
0.9079 High Similarity NPC250769
0.9079 High Similarity NPC278010
0.9079 High Similarity NPC295608
0.9073 High Similarity NPC263676
0.9073 High Similarity NPC253872
0.906 High Similarity NPC266743
0.9054 High Similarity NPC190572
0.9038 High Similarity NPC15819
0.902 High Similarity NPC160015
0.902 High Similarity NPC247677
0.9 High Similarity NPC37226
0.9 High Similarity NPC226644
0.8994 High Similarity NPC281835
0.8968 High Similarity NPC115432
0.8968 High Similarity NPC260296
0.8961 High Similarity NPC260902
0.8961 High Similarity NPC296957
0.8947 High Similarity NPC41326
0.8947 High Similarity NPC67654
0.8912 High Similarity NPC254010
0.8904 High Similarity NPC262635
0.8903 High Similarity NPC244750
0.8903 High Similarity NPC476350
0.8903 High Similarity NPC476349
0.8889 High Similarity NPC1477
0.8889 High Similarity NPC213608
0.8889 High Similarity NPC122365
0.8889 High Similarity NPC131725
0.8882 High Similarity NPC233956
0.8882 High Similarity NPC290671
0.8882 High Similarity NPC170169
0.8882 High Similarity NPC156244
0.8874 High Similarity NPC296030
0.8874 High Similarity NPC317492
0.8874 High Similarity NPC39929
0.8867 High Similarity NPC12148
0.8867 High Similarity NPC130581
0.8859 High Similarity NPC155144
0.8854 High Similarity NPC193998
0.8851 High Similarity NPC53192
0.8839 High Similarity NPC65504
0.8831 High Similarity NPC198490
0.8831 High Similarity NPC474542
0.8824 High Similarity NPC5871
0.8816 High Similarity NPC230713
0.8816 High Similarity NPC148423
0.8816 High Similarity NPC135303
0.8816 High Similarity NPC78335
0.8808 High Similarity NPC135325
0.8808 High Similarity NPC168085
0.8808 High Similarity NPC306788
0.8805 High Similarity NPC323137
0.88 High Similarity NPC210826
0.88 High Similarity NPC300267
0.88 High Similarity NPC51641
0.8797 High Similarity NPC155640
0.8792 High Similarity NPC225884
0.8792 High Similarity NPC302181
0.879 High Similarity NPC304387
0.8776 High Similarity NPC137009
0.8774 High Similarity NPC13879
0.8774 High Similarity NPC19860
0.8767 High Similarity NPC332594
0.8766 High Similarity NPC183874
0.8766 High Similarity NPC472462
0.8758 High Similarity NPC472407
0.875 High Similarity NPC37208
0.875 High Similarity NPC320789
0.875 High Similarity NPC221868
0.875 High Similarity NPC178202
0.8742 High Similarity NPC198427
0.8742 High Similarity NPC259007
0.8742 High Similarity NPC17816
0.8742 High Similarity NPC329215
0.8742 High Similarity NPC38914
0.8742 High Similarity NPC204088
0.8734 High Similarity NPC78612
0.8734 High Similarity NPC234536
0.8733 High Similarity NPC230943
0.8733 High Similarity NPC98926
0.8725 High Similarity NPC162476
0.8716 High Similarity NPC470856
0.8716 High Similarity NPC28337
0.871 High Similarity NPC108937
0.871 High Similarity NPC148938
0.871 High Similarity NPC279218
0.871 High Similarity NPC473193
0.8701 High Similarity NPC38361
0.8701 High Similarity NPC130015
0.8701 High Similarity NPC271681
0.8693 High Similarity NPC474735
0.8684 High Similarity NPC272194
0.8679 High Similarity NPC179464
0.8675 High Similarity NPC470322
0.8675 High Similarity NPC154217
0.8662 High Similarity NPC40583
0.8662 High Similarity NPC472877
0.8662 High Similarity NPC33320
0.8659 High Similarity NPC107244
0.8654 High Similarity NPC469936
0.8654 High Similarity NPC78554
0.8654 High Similarity NPC474738
0.8654 High Similarity NPC321372
0.8654 High Similarity NPC129053
0.8654 High Similarity NPC474609
0.8654 High Similarity NPC109967
0.8654 High Similarity NPC475797
0.8649 High Similarity NPC473076
0.8649 High Similarity NPC37206
0.8649 High Similarity NPC472515
0.8645 High Similarity NPC235333
0.8645 High Similarity NPC41719
0.8642 High Similarity NPC120220
0.8636 High Similarity NPC98028
0.8636 High Similarity NPC318424
0.8636 High Similarity NPC115324
0.8634 High Similarity NPC241820
0.863 High Similarity NPC60667
0.8625 High Similarity NPC136641
0.8616 High Similarity NPC219861
0.8609 High Similarity NPC470857
0.8609 High Similarity NPC1886
0.8609 High Similarity NPC316535
0.8609 High Similarity NPC311741
0.8609 High Similarity NPC196137
0.8609 High Similarity NPC297788
0.8609 High Similarity NPC469953
0.8609 High Similarity NPC234629
0.8608 High Similarity NPC243509
0.86 High Similarity NPC294432
0.86 High Similarity NPC470556
0.86 High Similarity NPC36181
0.86 High Similarity NPC112829
0.86 High Similarity NPC472344
0.8599 High Similarity NPC268360
0.8599 High Similarity NPC164110
0.8599 High Similarity NPC96342
0.8599 High Similarity NPC212967
0.8599 High Similarity NPC246647
0.8598 High Similarity NPC53917
0.8598 High Similarity NPC224165
0.8591 High Similarity NPC101366
0.859 High Similarity NPC233776
0.859 High Similarity NPC297531
0.859 High Similarity NPC213936
0.8589 High Similarity NPC472584
0.8581 High Similarity NPC476238
0.8581 High Similarity NPC36414
0.8581 High Similarity NPC327269
0.8581 High Similarity NPC207624
0.8581 High Similarity NPC31627
0.8571 High Similarity NPC321896
0.8571 High Similarity NPC155264
0.8571 High Similarity NPC472516
0.8571 High Similarity NPC193881
0.8571 High Similarity NPC472406
0.8571 High Similarity NPC472421
0.8571 High Similarity NPC67450
0.8571 High Similarity NPC167576
0.8571 High Similarity NPC119929
0.8571 High Similarity NPC210460
0.8571 High Similarity NPC235428
0.8571 High Similarity NPC87545
0.8571 High Similarity NPC476185
0.8571 High Similarity NPC180351
0.8562 High Similarity NPC266572
0.8562 High Similarity NPC125920
0.8562 High Similarity NPC39195
0.8553 High Similarity NPC73320
0.8553 High Similarity NPC24761
0.8553 High Similarity NPC216092
0.8553 High Similarity NPC181388
0.8545 High Similarity NPC325176
0.8543 High Similarity NPC470553
0.8543 High Similarity NPC474939
0.8543 High Similarity NPC184738
0.8543 High Similarity NPC112791
0.8543 High Similarity NPC196459
0.8543 High Similarity NPC470296
0.8543 High Similarity NPC188632
0.8543 High Similarity NPC307895
0.8543 High Similarity NPC87609

  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 NPC155882 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
0.9517 High Similarity NPD920 Approved
0.9514 High Similarity NPD642 Clinical (unspecified phase)
0.9375 High Similarity NPD643 Clinical (unspecified phase)
0.8904 High Similarity NPD1243 Approved
0.8662 High Similarity NPD919 Approved
0.8599 High Similarity NPD3749 Approved
0.8503 High Similarity NPD1510 Phase 2
0.8487 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD1549 Phase 2
0.8446 Intermediate Similarity NPD1551 Phase 2
0.8389 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8389 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD1247 Approved
0.828 Intermediate Similarity NPD7411 Suspended
0.8278 Intermediate Similarity NPD2800 Approved
0.825 Intermediate Similarity NPD7075 Discontinued
0.8231 Intermediate Similarity NPD1240 Approved
0.8228 Intermediate Similarity NPD6801 Discontinued
0.8217 Intermediate Similarity NPD4380 Phase 2
0.8204 Intermediate Similarity NPD6559 Discontinued
0.8176 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD7819 Suspended
0.8129 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD2533 Approved
0.8129 Intermediate Similarity NPD2532 Approved
0.8129 Intermediate Similarity NPD2534 Approved
0.8121 Intermediate Similarity NPD1607 Approved
0.8105 Intermediate Similarity NPD3750 Approved
0.8092 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD2796 Approved
0.8075 Intermediate Similarity NPD7768 Phase 2
0.8065 Intermediate Similarity NPD6799 Approved
0.8065 Intermediate Similarity NPD1511 Approved
0.8063 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8026 Intermediate Similarity NPD2344 Approved
0.8025 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7973 Intermediate Similarity NPD2313 Discontinued
0.7964 Intermediate Similarity NPD3818 Discontinued
0.7963 Intermediate Similarity NPD3882 Suspended
0.7962 Intermediate Similarity NPD1512 Approved
0.7922 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD7286 Phase 2
0.7901 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD1934 Approved
0.7877 Intermediate Similarity NPD1203 Approved
0.7875 Intermediate Similarity NPD6599 Discontinued
0.7843 Intermediate Similarity NPD2935 Discontinued
0.784 Intermediate Similarity NPD2801 Approved
0.784 Intermediate Similarity NPD1465 Phase 2
0.7824 Intermediate Similarity NPD5953 Discontinued
0.7821 Intermediate Similarity NPD2309 Approved
0.7791 Intermediate Similarity NPD3817 Phase 2
0.7778 Intermediate Similarity NPD3748 Approved
0.7778 Intermediate Similarity NPD2799 Discontinued
0.7771 Intermediate Similarity NPD6959 Discontinued
0.7744 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD6232 Discontinued
0.7711 Intermediate Similarity NPD5494 Approved
0.7706 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD3226 Approved
0.7692 Intermediate Similarity NPD7473 Discontinued
0.7688 Intermediate Similarity NPD5403 Approved
0.7683 Intermediate Similarity NPD5402 Approved
0.7673 Intermediate Similarity NPD5401 Approved
0.7671 Intermediate Similarity NPD9717 Approved
0.7603 Intermediate Similarity NPD422 Phase 1
0.7602 Intermediate Similarity NPD5844 Phase 1
0.7571 Intermediate Similarity NPD4287 Approved
0.7532 Intermediate Similarity NPD6651 Approved
0.7529 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD5711 Approved
0.7515 Intermediate Similarity NPD5710 Approved
0.7483 Intermediate Similarity NPD6832 Phase 2
0.7471 Intermediate Similarity NPD3926 Phase 2
0.7468 Intermediate Similarity NPD447 Suspended
0.7468 Intermediate Similarity NPD230 Phase 1
0.7457 Intermediate Similarity NPD1729 Discontinued
0.7452 Intermediate Similarity NPD2346 Discontinued
0.7442 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD6166 Phase 2
0.7421 Intermediate Similarity NPD4628 Phase 3
0.7403 Intermediate Similarity NPD943 Approved
0.7399 Intermediate Similarity NPD7054 Approved
0.7386 Intermediate Similarity NPD411 Approved
0.7386 Intermediate Similarity NPD1296 Phase 2
0.736 Intermediate Similarity NPD8434 Phase 2
0.7356 Intermediate Similarity NPD7074 Phase 3
0.7356 Intermediate Similarity NPD7472 Approved
0.7355 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1019 Discontinued
0.7329 Intermediate Similarity NPD9545 Approved
0.7325 Intermediate Similarity NPD4308 Phase 3
0.7325 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD7033 Discontinued
0.7314 Intermediate Similarity NPD6797 Phase 2
0.7314 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7229 Phase 3
0.7285 Intermediate Similarity NPD1164 Approved
0.7273 Intermediate Similarity NPD3268 Approved
0.7273 Intermediate Similarity NPD3764 Approved
0.7273 Intermediate Similarity NPD7251 Discontinued
0.7262 Intermediate Similarity NPD2296 Approved
0.7248 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD5124 Phase 1
0.7233 Intermediate Similarity NPD1471 Phase 3
0.7232 Intermediate Similarity NPD7808 Phase 3
0.7219 Intermediate Similarity NPD3225 Approved
0.7211 Intermediate Similarity NPD1548 Phase 1
0.7209 Intermediate Similarity NPD6808 Phase 2
0.7205 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD9493 Approved
0.7186 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD2797 Approved
0.716 Intermediate Similarity NPD4288 Approved
0.7152 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1610 Phase 2
0.7101 Intermediate Similarity NPD5760 Phase 2
0.7101 Intermediate Similarity NPD5761 Phase 2
0.7086 Intermediate Similarity NPD1608 Approved
0.7081 Intermediate Similarity NPD4361 Phase 2
0.7081 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD4307 Phase 2
0.7066 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3267 Approved
0.7059 Intermediate Similarity NPD3266 Approved
0.7051 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD6279 Approved
0.7041 Intermediate Similarity NPD6280 Approved
0.7037 Intermediate Similarity NPD2654 Approved
0.7035 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD4360 Phase 2
0.7027 Intermediate Similarity NPD4363 Phase 3
0.7019 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD6005 Phase 3
0.7019 Intermediate Similarity NPD6004 Phase 3
0.7019 Intermediate Similarity NPD6002 Phase 3
0.7013 Intermediate Similarity NPD2798 Approved
0.7011 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD8312 Approved
0.7 Intermediate Similarity NPD8313 Approved
0.6995 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1481 Phase 2
0.6974 Remote Similarity NPD9269 Phase 2
0.697 Remote Similarity NPD7390 Discontinued
0.6964 Remote Similarity NPD7458 Discontinued
0.6957 Remote Similarity NPD5405 Approved
0.6957 Remote Similarity NPD5408 Approved
0.6957 Remote Similarity NPD5404 Approved
0.6957 Remote Similarity NPD5406 Approved
0.6949 Remote Similarity NPD3751 Discontinued
0.6933 Remote Similarity NPD9268 Approved
0.6933 Remote Similarity NPD1652 Phase 2
0.6932 Remote Similarity NPD2403 Approved
0.6923 Remote Similarity NPD4908 Phase 1
0.6923 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6918 Remote Similarity NPD1933 Approved
0.6908 Remote Similarity NPD1535 Discovery
0.6905 Remote Similarity NPD1653 Approved
0.689 Remote Similarity NPD7003 Approved
0.6887 Remote Similarity NPD17 Approved
0.6882 Remote Similarity NPD5889 Approved
0.6882 Remote Similarity NPD5890 Approved
0.6875 Remote Similarity NPD9266 Approved
0.6875 Remote Similarity NPD74 Approved
0.6871 Remote Similarity NPD1241 Discontinued
0.6867 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6859 Remote Similarity NPD9494 Approved
0.6857 Remote Similarity NPD7199 Phase 2
0.6855 Remote Similarity NPD1613 Approved
0.6855 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6852 Remote Similarity NPD6100 Approved
0.6852 Remote Similarity NPD6099 Approved
0.6842 Remote Similarity NPD37 Approved
0.6839 Remote Similarity NPD6234 Discontinued
0.6839 Remote Similarity NPD1470 Approved
0.6821 Remote Similarity NPD4965 Approved
0.6821 Remote Similarity NPD4967 Phase 2
0.6821 Remote Similarity NPD4966 Approved
0.6815 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6355 Discontinued
0.6806 Remote Similarity NPD9267 Approved
0.6806 Remote Similarity NPD9263 Approved
0.6806 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6806 Remote Similarity NPD9264 Approved
0.6804 Remote Similarity NPD7584 Approved
0.6802 Remote Similarity NPD8455 Phase 2
0.6796 Remote Similarity NPD3658 Clinical (unspecified phase)

  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