Structure

Physi-Chem Properties

Molecular Weight:  424.19
Volume:  444.3
LogP:  5.479
LogD:  3.696
LogS:  -3.251
# Rotatable Bonds:  6
TPSA:  107.22
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.363
Synthetic Accessibility Score:  3.561
Fsp3:  0.32
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.904
MDCK Permeability:  1.581869219080545e-05
Pgp-inhibitor:  0.564
Pgp-substrate:  0.89
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.924
30% Bioavailability (F30%):  0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  96.92051696777344%
Volume Distribution (VD):  0.39
Pgp-substrate:  1.7626447677612305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.855
CYP1A2-substrate:  0.493
CYP2C19-inhibitor:  0.929
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.904
CYP2C9-substrate:  0.956
CYP2D6-inhibitor:  0.952
CYP2D6-substrate:  0.717
CYP3A4-inhibitor:  0.439
CYP3A4-substrate:  0.133

ADMET: Excretion

Clearance (CL):  13.174
Half-life (T1/2):  0.784

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.769
Drug-inuced Liver Injury (DILI):  0.759
AMES Toxicity:  0.076
Rat Oral Acute Toxicity:  0.722
Maximum Recommended Daily Dose:  0.749
Skin Sensitization:  0.947
Carcinogencity:  0.155
Eye Corrosion:  0.003
Eye Irritation:  0.9
Respiratory Toxicity:  0.928

Download Data

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

  Natural Product: NPC67396

Natural Product ID:  NPC67396
Common Name*:   Nymphaeol B
IUPAC Name:   (2S)-2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  ILCMVLORKWIOOH-CEMXSPGASA-N
Standard InCHI:  InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)7-8-18-17(9-10-19(27)25(18)30)22-13-21(29)24-20(28)11-16(26)12-23(24)31-22/h5,7,9-12,22,26-28,30H,4,6,8,13H2,1-3H3/b15-7+/t22-/m0/s1
SMILES:  C/C(=CCc1c(ccc(c1O)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)/CCC=C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464364
PubChem CID:   10387631
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003645] 2'-prenylated flavans
            • [CHEMONTID:0003588] 2'-prenylated flavanones

*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
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. stem n.a. DOI[10.1021/np960034d]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/R-1980-04-0397]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[11087590]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[11421757]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11975480]
NPO31282 Propolis (taiwanese) Species Rhytismataceae Eukaryota n.a. n.a. n.a. PMID[12713401]
NPO31347 Propolis (okinawa, japan) Species Rhytismataceae Eukaryota n.a. n.a. n.a. PMID[14745198]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. PMID[14987061]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[15620255]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[15974621]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves Krachong waterfall area, Trang Province, Thailand 2001-APR PMID[15974621]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota leaves n.a. n.a. PMID[17451272]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota leaves n.a. n.a. PMID[18844422]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. leaf n.a. PMID[18844422]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota epidermis of the sclerotia n.a. n.a. PMID[19746919]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[23265519]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[24698790]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[27808511]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. PMID[27934031]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[28972755]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[8984162]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6330 Croton caudatus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17376 Bacillus amyloliquefaciens Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12330 Pseudophryne coriacea Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3280 Penicillium crustaceum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10729 Lechevalieria aerocolonigenes Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19369 Bacillus thuringiensis Species Bacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO477 Lepraria xanthina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11884 Macaranga tanarius Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7087 Oxera splendida Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO305 Vitex pinnata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8543 Meconopsis horridula Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3453 Elaeocarpus fuscoides Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23577 Wolfiporia cocos Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16803 Libanothamnus occultus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1209 Swartzia madagascariensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5508 Stevia purpurea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15164 Jacobaea adonidifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19778 Streptomyces flaveus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO896 Streptomyces kanamyceticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5344 Calodendrum capense Species Rutaceae 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
NPT581 Individual Protein Cyclooxygenase-2 Mus musculus IC50 = 3.7 ug.mL-1 PMID[501740]
NPT81 Cell Line A549 Homo sapiens IC50 = 4000.0 nM PMID[501741]
NPT1 Others Radical scavenging activity IC50 = 13000.0 nM PMID[501740]

☑ 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 NPC67396 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
0.9932 High Similarity NPC24640
0.98 High Similarity NPC210459
0.9735 High Similarity NPC36217
0.9735 High Similarity NPC321399
0.9669 High Similarity NPC329091
0.9669 High Similarity NPC85121
0.9664 High Similarity NPC213896
0.9664 High Similarity NPC18727
0.9664 High Similarity NPC192083
0.9608 High Similarity NPC201800
0.9608 High Similarity NPC472964
0.9605 High Similarity NPC472902
0.96 High Similarity NPC321779
0.9597 High Similarity NPC106976
0.9597 High Similarity NPC219582
0.9597 High Similarity NPC236637
0.9597 High Similarity NPC302950
0.9592 High Similarity NPC294852
0.9592 High Similarity NPC321011
0.9592 High Similarity NPC188679
0.9545 High Similarity NPC186686
0.9536 High Similarity NPC291878
0.9536 High Similarity NPC278778
0.9536 High Similarity NPC35038
0.9536 High Similarity NPC195796
0.9536 High Similarity NPC471500
0.9533 High Similarity NPC298692
0.9533 High Similarity NPC89474
0.9533 High Similarity NPC74924
0.9527 High Similarity NPC183959
0.9527 High Similarity NPC1612
0.9484 High Similarity NPC293319
0.9481 High Similarity NPC211107
0.9477 High Similarity NPC474960
0.9477 High Similarity NPC299436
0.9477 High Similarity NPC470183
0.9474 High Similarity NPC474836
0.9474 High Similarity NPC471515
0.9474 High Similarity NPC129684
0.9474 High Similarity NPC241904
0.9474 High Similarity NPC48208
0.9474 High Similarity NPC471209
0.9474 High Similarity NPC291508
0.9474 High Similarity NPC299520
0.9474 High Similarity NPC162869
0.9474 High Similarity NPC156057
0.9474 High Similarity NPC472598
0.9474 High Similarity NPC300727
0.9474 High Similarity NPC475267
0.9474 High Similarity NPC27337
0.9474 High Similarity NPC474208
0.9474 High Similarity NPC471479
0.9474 High Similarity NPC474055
0.9474 High Similarity NPC472963
0.947 High Similarity NPC470327
0.947 High Similarity NPC477503
0.947 High Similarity NPC56786
0.947 High Similarity NPC200761
0.947 High Similarity NPC80534
0.947 High Similarity NPC45849
0.9467 High Similarity NPC472912
0.9467 High Similarity NPC260979
0.9463 High Similarity NPC338131
0.9463 High Similarity NPC85131
0.9459 High Similarity NPC3036
0.9423 High Similarity NPC477517
0.9423 High Similarity NPC43319
0.9419 High Similarity NPC475985
0.9416 High Similarity NPC32694
0.9412 High Similarity NPC22192
0.9412 High Similarity NPC476242
0.9408 High Similarity NPC472626
0.9408 High Similarity NPC255106
0.9408 High Similarity NPC470328
0.9408 High Similarity NPC235165
0.9408 High Similarity NPC142339
0.9408 High Similarity NPC13858
0.9408 High Similarity NPC472907
0.9408 High Similarity NPC227062
0.9408 High Similarity NPC326037
0.9408 High Similarity NPC274730
0.9408 High Similarity NPC320825
0.9408 High Similarity NPC209614
0.9404 High Similarity NPC472905
0.9404 High Similarity NPC469550
0.94 High Similarity NPC202157
0.94 High Similarity NPC204515
0.9396 High Similarity NPC105512
0.9392 High Similarity NPC108406
0.9392 High Similarity NPC95864
0.9363 High Similarity NPC218226
0.9359 High Similarity NPC473286
0.9359 High Similarity NPC326520
0.9359 High Similarity NPC475888
0.9351 High Similarity NPC228785
0.9351 High Similarity NPC45146
0.9351 High Similarity NPC119209
0.9351 High Similarity NPC14353
0.9351 High Similarity NPC56085
0.9351 High Similarity NPC476283
0.9351 High Similarity NPC118256
0.9351 High Similarity NPC235018
0.9351 High Similarity NPC192686
0.9351 High Similarity NPC287328
0.9351 High Similarity NPC282009
0.9351 High Similarity NPC472624
0.9346 High Similarity NPC223787
0.9346 High Similarity NPC96167
0.9346 High Similarity NPC472914
0.9346 High Similarity NPC245758
0.9346 High Similarity NPC469584
0.9346 High Similarity NPC472911
0.9346 High Similarity NPC67876
0.9346 High Similarity NPC472913
0.9346 High Similarity NPC222814
0.9346 High Similarity NPC111969
0.9346 High Similarity NPC136674
0.9346 High Similarity NPC210084
0.9346 High Similarity NPC236796
0.9346 High Similarity NPC99597
0.9346 High Similarity NPC472910
0.9346 High Similarity NPC273843
0.9346 High Similarity NPC52530
0.9342 High Similarity NPC255807
0.9342 High Similarity NPC31018
0.9342 High Similarity NPC37392
0.9342 High Similarity NPC226025
0.9338 High Similarity NPC240476
0.9338 High Similarity NPC61506
0.9338 High Similarity NPC246162
0.9338 High Similarity NPC9743
0.9338 High Similarity NPC477231
0.9338 High Similarity NPC36835
0.9338 High Similarity NPC260491
0.9338 High Similarity NPC474843
0.9338 High Similarity NPC257648
0.9333 High Similarity NPC62042
0.9333 High Similarity NPC3825
0.9333 High Similarity NPC151473
0.9333 High Similarity NPC88804
0.9329 High Similarity NPC119059
0.9304 High Similarity NPC300307
0.9299 High Similarity NPC170245
0.9295 High Similarity NPC7483
0.9295 High Similarity NPC474240
0.9295 High Similarity NPC220313
0.9295 High Similarity NPC476295
0.929 High Similarity NPC26326
0.929 High Similarity NPC472632
0.929 High Similarity NPC471499
0.929 High Similarity NPC112418
0.929 High Similarity NPC142252
0.929 High Similarity NPC471210
0.929 High Similarity NPC158188
0.929 High Similarity NPC40491
0.929 High Similarity NPC472634
0.929 High Similarity NPC278052
0.929 High Similarity NPC474186
0.929 High Similarity NPC61010
0.929 High Similarity NPC474038
0.929 High Similarity NPC474187
0.929 High Similarity NPC173137
0.9286 High Similarity NPC250214
0.9286 High Similarity NPC95936
0.9286 High Similarity NPC235448
0.9286 High Similarity NPC53545
0.9286 High Similarity NPC100123
0.9286 High Similarity NPC55738
0.9286 High Similarity NPC117418
0.9281 High Similarity NPC250922
0.9281 High Similarity NPC475799
0.9281 High Similarity NPC13779
0.9281 High Similarity NPC472916
0.9281 High Similarity NPC153512
0.9276 High Similarity NPC27532
0.9276 High Similarity NPC325028
0.9276 High Similarity NPC246328
0.9276 High Similarity NPC256346
0.9276 High Similarity NPC141212
0.9272 High Similarity NPC31363
0.9267 High Similarity NPC87125
0.9267 High Similarity NPC177298
0.9267 High Similarity NPC223579
0.9267 High Similarity NPC287101
0.9267 High Similarity NPC48479
0.9267 High Similarity NPC183950
0.9267 High Similarity NPC137062
0.9267 High Similarity NPC270465
0.9267 High Similarity NPC52005
0.9252 High Similarity NPC73028
0.9252 High Similarity NPC310340
0.9241 High Similarity NPC117854
0.9241 High Similarity NPC474024
0.9241 High Similarity NPC6588
0.9241 High Similarity NPC477154
0.9236 High Similarity NPC275780
0.9236 High Similarity NPC472450
0.9236 High Similarity NPC224280
0.9236 High Similarity NPC239752
0.9236 High Similarity NPC472277

  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 NPC67396 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
0.9664 High Similarity NPD2393 Clinical (unspecified phase)
0.9597 High Similarity NPD1934 Approved
0.9189 High Similarity NPD1511 Approved
0.915 High Similarity NPD2801 Approved
0.9114 High Similarity NPD6166 Phase 2
0.9114 High Similarity NPD6168 Clinical (unspecified phase)
0.9114 High Similarity NPD6167 Clinical (unspecified phase)
0.9067 High Similarity NPD1512 Approved
0.8912 High Similarity NPD1552 Clinical (unspecified phase)
0.8912 High Similarity NPD1550 Clinical (unspecified phase)
0.891 High Similarity NPD3882 Suspended
0.8889 High Similarity NPD7074 Phase 3
0.8851 High Similarity NPD1549 Phase 2
0.8827 High Similarity NPD7054 Approved
0.879 High Similarity NPD4868 Clinical (unspecified phase)
0.8782 High Similarity NPD7819 Suspended
0.8773 High Similarity NPD7472 Approved
0.8765 High Similarity NPD3818 Discontinued
0.875 High Similarity NPD4378 Clinical (unspecified phase)
0.8726 High Similarity NPD3817 Phase 2
0.872 High Similarity NPD6797 Phase 2
0.871 High Similarity NPD4380 Phase 2
0.8688 High Similarity NPD6959 Discontinued
0.8667 High Similarity NPD7251 Discontinued
0.8625 High Similarity NPD5494 Approved
0.8616 High Similarity NPD7075 Discontinued
0.8616 High Similarity NPD4381 Clinical (unspecified phase)
0.8608 High Similarity NPD8443 Clinical (unspecified phase)
0.8591 High Similarity NPD2796 Approved
0.8544 High Similarity NPD7096 Clinical (unspecified phase)
0.8523 High Similarity NPD1510 Phase 2
0.8519 High Similarity NPD6232 Discontinued
0.8503 High Similarity NPD4338 Clinical (unspecified phase)
0.8503 High Similarity NPD7808 Phase 3
0.8485 Intermediate Similarity NPD5844 Phase 1
0.8476 Intermediate Similarity NPD7473 Discontinued
0.8428 Intermediate Similarity NPD1465 Phase 2
0.8378 Intermediate Similarity NPD1240 Approved
0.8355 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD6799 Approved
0.8302 Intermediate Similarity NPD7411 Suspended
0.8274 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8267 Intermediate Similarity NPD1607 Approved
0.8263 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8255 Intermediate Similarity NPD943 Approved
0.8255 Intermediate Similarity NPD1613 Approved
0.8255 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.825 Intermediate Similarity NPD6801 Discontinued
0.8247 Intermediate Similarity NPD3750 Approved
0.8239 Intermediate Similarity NPD6599 Discontinued
0.816 Intermediate Similarity NPD3749 Approved
0.8153 Intermediate Similarity NPD2532 Approved
0.8153 Intermediate Similarity NPD2533 Approved
0.8153 Intermediate Similarity NPD2534 Approved
0.8118 Intermediate Similarity NPD6559 Discontinued
0.8108 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8084 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD5402 Approved
0.7988 Intermediate Similarity NPD7768 Phase 2
0.7987 Intermediate Similarity NPD6099 Approved
0.7987 Intermediate Similarity NPD6100 Approved
0.7961 Intermediate Similarity NPD230 Phase 1
0.7949 Intermediate Similarity NPD2800 Approved
0.7937 Intermediate Similarity NPD5403 Approved
0.7933 Intermediate Similarity NPD3027 Phase 3
0.7922 Intermediate Similarity NPD3748 Approved
0.7917 Intermediate Similarity NPD3926 Phase 2
0.7904 Intermediate Similarity NPD7199 Phase 2
0.7898 Intermediate Similarity NPD4628 Phase 3
0.7892 Intermediate Similarity NPD6234 Discontinued
0.7882 Intermediate Similarity NPD3751 Discontinued
0.7881 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD2935 Discontinued
0.7871 Intermediate Similarity NPD1551 Phase 2
0.7857 Intermediate Similarity NPD3787 Discontinued
0.784 Intermediate Similarity NPD3226 Approved
0.7834 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD2346 Discontinued
0.7812 Intermediate Similarity NPD5401 Approved
0.7811 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD1247 Approved
0.7797 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD919 Approved
0.775 Intermediate Similarity NPD7390 Discontinued
0.7748 Intermediate Similarity NPD4908 Phase 1
0.7716 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD2344 Approved
0.7697 Intermediate Similarity NPD37 Approved
0.7674 Intermediate Similarity NPD7228 Approved
0.7665 Intermediate Similarity NPD4967 Phase 2
0.7665 Intermediate Similarity NPD4966 Approved
0.7665 Intermediate Similarity NPD4965 Approved
0.7657 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5710 Approved
0.7647 Intermediate Similarity NPD5711 Approved
0.7647 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1610 Phase 2
0.7627 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7614 Intermediate Similarity NPD8312 Approved
0.7614 Intermediate Similarity NPD8313 Approved
0.7613 Intermediate Similarity NPD447 Suspended
0.7607 Intermediate Similarity NPD920 Approved
0.7593 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD4625 Phase 3
0.758 Intermediate Similarity NPD2799 Discontinued
0.7564 Intermediate Similarity NPD6651 Approved
0.7562 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD1653 Approved
0.7543 Intermediate Similarity NPD5953 Discontinued
0.7531 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7286 Phase 2
0.7527 Intermediate Similarity NPD4360 Phase 2
0.7527 Intermediate Similarity NPD4363 Phase 3
0.7516 Intermediate Similarity NPD6190 Approved
0.7516 Intermediate Similarity NPD2309 Approved
0.7515 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD1243 Approved
0.7485 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7033 Discontinued
0.7451 Intermediate Similarity NPD2861 Phase 2
0.7451 Intermediate Similarity NPD9494 Approved
0.7442 Intermediate Similarity NPD7229 Phase 3
0.7434 Intermediate Similarity NPD1203 Approved
0.7419 Intermediate Similarity NPD2313 Discontinued
0.7419 Intermediate Similarity NPD6782 Approved
0.7419 Intermediate Similarity NPD6778 Approved
0.7419 Intermediate Similarity NPD3268 Approved
0.7419 Intermediate Similarity NPD6776 Approved
0.7419 Intermediate Similarity NPD6777 Approved
0.7419 Intermediate Similarity NPD6779 Approved
0.7419 Intermediate Similarity NPD6780 Approved
0.7419 Intermediate Similarity NPD6781 Approved
0.7417 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6832 Phase 2
0.7401 Intermediate Similarity NPD7685 Pre-registration
0.74 Intermediate Similarity NPD1201 Approved
0.7391 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD8434 Phase 2
0.7389 Intermediate Similarity NPD8150 Discontinued
0.7386 Intermediate Similarity NPD2798 Approved
0.7382 Intermediate Similarity NPD8151 Discontinued
0.7365 Intermediate Similarity NPD1548 Phase 1
0.7351 Intermediate Similarity NPD1608 Approved
0.7325 Intermediate Similarity NPD4060 Phase 1
0.7321 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD2797 Approved
0.732 Intermediate Similarity NPD1470 Approved
0.7308 Intermediate Similarity NPD6798 Discontinued
0.7303 Intermediate Similarity NPD4749 Approved
0.7302 Intermediate Similarity NPD7435 Discontinued
0.7299 Intermediate Similarity NPD5242 Approved
0.7294 Intermediate Similarity NPD4288 Approved
0.7278 Intermediate Similarity NPD6844 Discontinued
0.7278 Intermediate Similarity NPD6355 Discontinued
0.7258 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD9717 Approved
0.7237 Intermediate Similarity NPD9269 Phase 2
0.7229 Intermediate Similarity NPD6273 Approved
0.7216 Intermediate Similarity NPD7783 Phase 2
0.7216 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7213 Intermediate Similarity NPD4287 Approved
0.7211 Intermediate Similarity NPD7698 Approved
0.7211 Intermediate Similarity NPD7696 Phase 3
0.7211 Intermediate Similarity NPD7697 Approved
0.7207 Intermediate Similarity NPD7240 Approved
0.7205 Intermediate Similarity NPD5406 Approved
0.7205 Intermediate Similarity NPD5408 Approved
0.7205 Intermediate Similarity NPD5405 Approved
0.7205 Intermediate Similarity NPD5404 Approved
0.7204 Intermediate Similarity NPD4361 Phase 2
0.7204 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3764 Approved
0.7193 Intermediate Similarity NPD5353 Approved
0.7188 Intermediate Similarity NPD7584 Approved
0.7178 Intermediate Similarity NPD1652 Phase 2
0.7178 Intermediate Similarity NPD2654 Approved
0.7173 Intermediate Similarity NPD7870 Phase 2
0.7173 Intermediate Similarity NPD7871 Phase 2
0.7171 Intermediate Similarity NPD422 Phase 1
0.717 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5124 Phase 1
0.716 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1471 Phase 3
0.716 Intermediate Similarity NPD7266 Discontinued
0.7159 Intermediate Similarity NPD2403 Approved
0.7158 Intermediate Similarity NPD6823 Phase 2
0.7152 Intermediate Similarity NPD6233 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