Structure

Physi-Chem Properties

Molecular Weight:  118.08
Volume:  145.118
LogP:  2.525
LogD:  2.658
LogS:  -2.533
# Rotatable Bonds:  1
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.532
Synthetic Accessibility Score:  1.63
Fsp3:  0.111
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.295
MDCK Permeability:  2.0815919924643822e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.032
30% Bioavailability (F30%):  0.098

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.781
Plasma Protein Binding (PPB):  94.08527374267578%
Volume Distribution (VD):  1.341
Pgp-substrate:  6.680141925811768%

ADMET: Metabolism

CYP1A2-inhibitor:  0.99
CYP1A2-substrate:  0.9
CYP2C19-inhibitor:  0.726
CYP2C19-substrate:  0.577
CYP2C9-inhibitor:  0.208
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.068
CYP2D6-substrate:  0.688
CYP3A4-inhibitor:  0.029
CYP3A4-substrate:  0.297

ADMET: Excretion

Clearance (CL):  7.572
Half-life (T1/2):  0.622

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.033
Drug-inuced Liver Injury (DILI):  0.311
AMES Toxicity:  0.035
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.034
Skin Sensitization:  0.857
Carcinogencity:  0.422
Eye Corrosion:  0.972
Eye Irritation:  0.996
Respiratory Toxicity:  0.092

Download Data

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

  Natural Product: NPC269586

Natural Product ID:  NPC269586
Common Name*:   [(E)-Prop-1-Enyl]Benzene
IUPAC Name:   [(E)-prop-1-enyl]benzene
Synonyms:   Trans-Beta-Methylstyrene
Standard InCHIKey:  QROGIFZRVHSFLM-QHHAFSJGSA-N
Standard InCHI:  InChI=1S/C9H10/c1-2-6-9-7-4-3-5-8-9/h2-8H,1H3/b6-2+
SMILES:  C/C=C/c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL506013
PubChem CID:   252325
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000037] Styrenes

*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
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/S0031-9422(00)94055-X]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. flower n.a. DOI[10.3390/70200245]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[10364842]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[12392098]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. root n.a. PMID[18409040]
NPO30603 Saussurea lappa n.a. n.a. n.a. roots n.a. n.a. PMID[18579374]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23451797]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24617303]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24996657]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. n.a. n.a. PMID[25068579]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[25767328]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. root n.a. PMID[8541643]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. root n.a. Database[Article]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26596 Inula royleana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26596 Inula royleana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26596 Inula royleana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16481 Xanthium canadense Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28295 Foeniculum vulgare Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10256 Liquidambar orientalis Species Altingiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae 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
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae MIC = 400.0 ug.mL-1 PMID[515869]
NPT20 Organism Candida albicans Candida albicans MIC = 400.0 ug.mL-1 PMID[515869]
NPT523 Organism Malassezia furfur Malassezia furfur MIC > 800.0 ug.mL-1 PMID[515869]

☑ 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 NPC269586 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
0.9815 High Similarity NPC212114
0.9815 High Similarity NPC300345
0.9815 High Similarity NPC120441
0.9815 High Similarity NPC65873
0.9811 High Similarity NPC277704
0.9811 High Similarity NPC149436
0.9636 High Similarity NPC8235
0.963 High Similarity NPC198841
0.9464 High Similarity NPC147062
0.9464 High Similarity NPC169110
0.9298 High Similarity NPC310758
0.9298 High Similarity NPC135924
0.9298 High Similarity NPC54368
0.9298 High Similarity NPC248705
0.9298 High Similarity NPC210849
0.9298 High Similarity NPC150196
0.9298 High Similarity NPC238023
0.9286 High Similarity NPC114327
0.9286 High Similarity NPC64270
0.9286 High Similarity NPC36357
0.9138 High Similarity NPC29680
0.8983 High Similarity NPC88566
0.8966 High Similarity NPC246588
0.8833 High Similarity NPC198023
0.8833 High Similarity NPC32312
0.8833 High Similarity NPC155172
0.8814 High Similarity NPC22786
0.8814 High Similarity NPC66517
0.8814 High Similarity NPC71009
0.8814 High Similarity NPC200745
0.8689 High Similarity NPC178527
0.8667 High Similarity NPC21211
0.8667 High Similarity NPC113670
0.8667 High Similarity NPC45756
0.8644 High Similarity NPC45255
0.8548 High Similarity NPC6107
0.8548 High Similarity NPC267443
0.8525 High Similarity NPC291066
0.8475 Intermediate Similarity NPC147578
0.8413 Intermediate Similarity NPC311343
0.8387 Intermediate Similarity NPC113837
0.8387 Intermediate Similarity NPC36440
0.8387 Intermediate Similarity NPC289915
0.8361 Intermediate Similarity NPC50266
0.8333 Intermediate Similarity NPC200624
0.8281 Intermediate Similarity NPC139416
0.8281 Intermediate Similarity NPC246822
0.8281 Intermediate Similarity NPC98880
0.8281 Intermediate Similarity NPC213570
0.8154 Intermediate Similarity NPC95289
0.8125 Intermediate Similarity NPC82770
0.8125 Intermediate Similarity NPC78954
0.8125 Intermediate Similarity NPC239931
0.8113 Intermediate Similarity NPC11150
0.803 Intermediate Similarity NPC280135
0.803 Intermediate Similarity NPC158028
0.803 Intermediate Similarity NPC326200
0.803 Intermediate Similarity NPC74458
0.803 Intermediate Similarity NPC1008
0.803 Intermediate Similarity NPC226999
0.803 Intermediate Similarity NPC87099
0.803 Intermediate Similarity NPC193578
0.803 Intermediate Similarity NPC39799
0.803 Intermediate Similarity NPC135433
0.8 Intermediate Similarity NPC169222
0.8 Intermediate Similarity NPC200936
0.8 Intermediate Similarity NPC5324
0.8 Intermediate Similarity NPC235059
0.8 Intermediate Similarity NPC473206
0.8 Intermediate Similarity NPC16190
0.7969 Intermediate Similarity NPC52330
0.7937 Intermediate Similarity NPC264470
0.791 Intermediate Similarity NPC285679
0.791 Intermediate Similarity NPC54269
0.791 Intermediate Similarity NPC212463
0.7879 Intermediate Similarity NPC263385
0.7879 Intermediate Similarity NPC251490
0.7879 Intermediate Similarity NPC72670
0.7879 Intermediate Similarity NPC229235
0.7846 Intermediate Similarity NPC22760
0.7794 Intermediate Similarity NPC122327
0.7794 Intermediate Similarity NPC112609
0.7794 Intermediate Similarity NPC113000
0.7761 Intermediate Similarity NPC208302
0.7761 Intermediate Similarity NPC155429
0.7727 Intermediate Similarity NPC297358
0.7681 Intermediate Similarity NPC276699
0.7681 Intermediate Similarity NPC189371
0.7681 Intermediate Similarity NPC307195
0.7681 Intermediate Similarity NPC98976
0.7647 Intermediate Similarity NPC271437
0.7647 Intermediate Similarity NPC244738
0.7647 Intermediate Similarity NPC1901
0.7612 Intermediate Similarity NPC219246
0.7576 Intermediate Similarity NPC181786
0.7571 Intermediate Similarity NPC271642
0.7571 Intermediate Similarity NPC110264
0.7571 Intermediate Similarity NPC175393
0.7571 Intermediate Similarity NPC139658
0.7536 Intermediate Similarity NPC258492
0.7536 Intermediate Similarity NPC96835
0.7536 Intermediate Similarity NPC108218
0.7536 Intermediate Similarity NPC208075
0.7465 Intermediate Similarity NPC325662
0.7465 Intermediate Similarity NPC298023
0.7465 Intermediate Similarity NPC3190
0.7465 Intermediate Similarity NPC3672
0.7465 Intermediate Similarity NPC249018
0.7465 Intermediate Similarity NPC290638
0.7465 Intermediate Similarity NPC98269
0.7465 Intermediate Similarity NPC287790
0.7465 Intermediate Similarity NPC329318
0.7429 Intermediate Similarity NPC32203
0.7429 Intermediate Similarity NPC206800
0.7361 Intermediate Similarity NPC137847
0.7361 Intermediate Similarity NPC2785
0.7361 Intermediate Similarity NPC285470
0.7361 Intermediate Similarity NPC76455
0.7361 Intermediate Similarity NPC224544
0.7361 Intermediate Similarity NPC103488
0.7361 Intermediate Similarity NPC50192
0.7361 Intermediate Similarity NPC12857
0.7361 Intermediate Similarity NPC36342
0.7324 Intermediate Similarity NPC302129
0.7286 Intermediate Similarity NPC299134
0.726 Intermediate Similarity NPC469894
0.726 Intermediate Similarity NPC78517
0.726 Intermediate Similarity NPC170484
0.726 Intermediate Similarity NPC167577
0.726 Intermediate Similarity NPC159661
0.726 Intermediate Similarity NPC300205
0.7258 Intermediate Similarity NPC469807
0.7246 Intermediate Similarity NPC121708
0.7246 Intermediate Similarity NPC125144
0.7222 Intermediate Similarity NPC179726
0.7222 Intermediate Similarity NPC245966
0.7222 Intermediate Similarity NPC9796
0.7162 Intermediate Similarity NPC17408
0.7162 Intermediate Similarity NPC328178
0.7162 Intermediate Similarity NPC475573
0.7162 Intermediate Similarity NPC315216
0.7162 Intermediate Similarity NPC157055
0.7162 Intermediate Similarity NPC190567
0.7162 Intermediate Similarity NPC285716
0.7162 Intermediate Similarity NPC475289
0.7162 Intermediate Similarity NPC121800
0.7162 Intermediate Similarity NPC164086
0.7123 Intermediate Similarity NPC176228
0.7123 Intermediate Similarity NPC255345
0.7123 Intermediate Similarity NPC66270
0.7123 Intermediate Similarity NPC245896
0.7067 Intermediate Similarity NPC303245
0.7067 Intermediate Similarity NPC231986
0.7067 Intermediate Similarity NPC145053
0.7067 Intermediate Similarity NPC133050
0.7067 Intermediate Similarity NPC100039
0.7067 Intermediate Similarity NPC89950
0.7067 Intermediate Similarity NPC242628
0.7027 Intermediate Similarity NPC139901
0.7027 Intermediate Similarity NPC151405
0.7027 Intermediate Similarity NPC272260
0.6986 Remote Similarity NPC66655
0.6974 Remote Similarity NPC106313
0.6974 Remote Similarity NPC103326
0.6974 Remote Similarity NPC14326
0.6974 Remote Similarity NPC99240
0.6974 Remote Similarity NPC99394
0.6974 Remote Similarity NPC329319
0.6974 Remote Similarity NPC323103
0.6974 Remote Similarity NPC87299
0.6974 Remote Similarity NPC230068
0.6974 Remote Similarity NPC103387
0.6935 Remote Similarity NPC56072
0.6933 Remote Similarity NPC192623
0.6933 Remote Similarity NPC184030
0.6933 Remote Similarity NPC309279
0.6933 Remote Similarity NPC71664
0.6933 Remote Similarity NPC477703
0.6933 Remote Similarity NPC50063
0.6933 Remote Similarity NPC127343
0.6933 Remote Similarity NPC164449
0.6933 Remote Similarity NPC95868
0.6883 Remote Similarity NPC270507
0.6883 Remote Similarity NPC474088
0.6883 Remote Similarity NPC477770
0.6883 Remote Similarity NPC104070
0.6883 Remote Similarity NPC197581
0.6883 Remote Similarity NPC172984
0.6883 Remote Similarity NPC39600
0.6883 Remote Similarity NPC288903
0.6849 Remote Similarity NPC78500
0.6842 Remote Similarity NPC165212
0.6842 Remote Similarity NPC71795
0.6842 Remote Similarity NPC117180
0.6842 Remote Similarity NPC12936
0.6842 Remote Similarity NPC273033
0.6795 Remote Similarity NPC304538
0.6795 Remote Similarity NPC133162
0.6795 Remote Similarity NPC95429
0.6795 Remote Similarity NPC168855

  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 NPC269586 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
0.8667 High Similarity NPD675 Discontinued
0.8525 High Similarity NPD173 Clinical (unspecified phase)
0.803 Intermediate Similarity NPD294 Approved
0.803 Intermediate Similarity NPD292 Approved
0.8 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD9593 Approved
0.7794 Intermediate Similarity NPD9589 Approved
0.7794 Intermediate Similarity NPD9588 Approved
0.7794 Intermediate Similarity NPD80 Approved
0.7794 Intermediate Similarity NPD9594 Approved
0.7794 Intermediate Similarity NPD9591 Approved
0.7794 Intermediate Similarity NPD9592 Approved
0.7794 Intermediate Similarity NPD9590 Approved
0.7727 Intermediate Similarity NPD1673 Approved
0.7647 Intermediate Similarity NPD9728 Phase 1
0.7536 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4147 Approved
0.7465 Intermediate Similarity NPD603 Approved
0.7465 Intermediate Similarity NPD4144 Approved
0.7429 Intermediate Similarity NPD9716 Approved
0.7361 Intermediate Similarity NPD295 Approved
0.7361 Intermediate Similarity NPD296 Approved
0.7361 Intermediate Similarity NPD293 Approved
0.726 Intermediate Similarity NPD508 Approved
0.726 Intermediate Similarity NPD590 Approved
0.726 Intermediate Similarity NPD589 Approved
0.726 Intermediate Similarity NPD1052 Approved
0.726 Intermediate Similarity NPD1053 Approved
0.726 Intermediate Similarity NPD507 Approved
0.726 Intermediate Similarity NPD1051 Approved
0.7162 Intermediate Similarity NPD260 Discontinued
0.7162 Intermediate Similarity NPD3903 Approved
0.7162 Intermediate Similarity NPD5371 Approved
0.7162 Intermediate Similarity NPD3904 Approved
0.7162 Intermediate Similarity NPD3981 Approved
0.7162 Intermediate Similarity NPD5372 Approved
0.7162 Intermediate Similarity NPD3979 Approved
0.7123 Intermediate Similarity NPD9393 Approved
0.7123 Intermediate Similarity NPD9563 Approved
0.7123 Intermediate Similarity NPD9564 Approved
0.7123 Intermediate Similarity NPD227 Approved
0.7123 Intermediate Similarity NPD79 Approved
0.7123 Intermediate Similarity NPD225 Approved
0.7123 Intermediate Similarity NPD9397 Approved
0.7067 Intermediate Similarity NPD4027 Approved
0.7067 Intermediate Similarity NPD4026 Approved
0.7067 Intermediate Similarity NPD3035 Approved
0.7067 Intermediate Similarity NPD472 Approved
0.7027 Intermediate Similarity NPD1475 Approved
0.6986 Remote Similarity NPD9294 Approved
0.6974 Remote Similarity NPD4170 Approved
0.6974 Remote Similarity NPD4169 Approved
0.6974 Remote Similarity NPD4701 Clinical (unspecified phase)
0.6949 Remote Similarity NPD9072 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1617 Discontinued
0.6883 Remote Similarity NPD262 Approved
0.6883 Remote Similarity NPD830 Approved
0.6883 Remote Similarity NPD831 Approved
0.6883 Remote Similarity NPD3971 Phase 1
0.6883 Remote Similarity NPD4635 Approved
0.6883 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6883 Remote Similarity NPD263 Approved
0.6883 Remote Similarity NPD2001 Discontinued
0.6842 Remote Similarity NPD226 Approved
0.6842 Remote Similarity NPD942 Approved
0.68 Remote Similarity NPD9490 Approved
0.6795 Remote Similarity NPD3427 Approved
0.6795 Remote Similarity NPD5178 Approved
0.6795 Remote Similarity NPD4544 Approved
0.6795 Remote Similarity NPD785 Approved
0.6795 Remote Similarity NPD3429 Approved
0.6795 Remote Similarity NPD9395 Approved
0.6795 Remote Similarity NPD2539 Approved
0.6795 Remote Similarity NPD2538 Approved
0.6711 Remote Similarity NPD914 Suspended
0.6709 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6709 Remote Similarity NPD2208 Approved
0.6709 Remote Similarity NPD2205 Approved
0.6667 Remote Similarity NPD9491 Approved
0.6667 Remote Similarity NPD5288 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1185 Approved
0.6625 Remote Similarity NPD4636 Approved
0.6625 Remote Similarity NPD4406 Approved
0.6625 Remote Similarity NPD4409 Approved
0.6625 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6543 Remote Similarity NPD783 Approved
0.6543 Remote Similarity NPD780 Approved
0.6543 Remote Similarity NPD782 Approved
0.6543 Remote Similarity NPD2002 Discontinued
0.6543 Remote Similarity NPD781 Approved
0.6543 Remote Similarity NPD1282 Approved
0.6543 Remote Similarity NPD3428 Approved
0.6543 Remote Similarity NPD1087 Approved
0.6543 Remote Similarity NPD4145 Approved
0.6543 Remote Similarity NPD4146 Approved
0.6543 Remote Similarity NPD650 Approved
0.6543 Remote Similarity NPD506 Clinical (unspecified phase)
0.6543 Remote Similarity NPD3426 Approved
0.65 Remote Similarity NPD9505 Clinical (unspecified phase)
0.65 Remote Similarity NPD5916 Discontinued
0.65 Remote Similarity NPD111 Approved
0.6463 Remote Similarity NPD587 Approved
0.6463 Remote Similarity NPD588 Approved
0.6463 Remote Similarity NPD3345 Approved
0.6463 Remote Similarity NPD5675 Discontinued
0.6463 Remote Similarity NPD1101 Approved
0.6456 Remote Similarity NPD4000 Phase 3
0.6456 Remote Similarity NPD423 Phase 3
0.642 Remote Similarity NPD304 Approved
0.642 Remote Similarity NPD305 Approved
0.642 Remote Similarity NPD3099 Discontinued
0.641 Remote Similarity NPD9250 Approved
0.6386 Remote Similarity NPD5347 Phase 2
0.6386 Remote Similarity NPD5346 Phase 2
0.6386 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6386 Remote Similarity NPD800 Approved
0.6386 Remote Similarity NPD297 Approved
0.6386 Remote Similarity NPD9 Approved
0.6386 Remote Similarity NPD771 Phase 3
0.6341 Remote Similarity NPD4793 Discontinued
0.6341 Remote Similarity NPD9538 Approved
0.6341 Remote Similarity NPD187 Approved
0.631 Remote Similarity NPD1090 Approved
0.631 Remote Similarity NPD3672 Approved
0.631 Remote Similarity NPD2811 Clinical (unspecified phase)
0.631 Remote Similarity NPD3346 Approved
0.631 Remote Similarity NPD4728 Approved
0.631 Remote Similarity NPD3673 Approved
0.631 Remote Similarity NPD3344 Approved
0.631 Remote Similarity NPD5915 Approved
0.631 Remote Similarity NPD1089 Approved
0.631 Remote Similarity NPD1086 Approved
0.6265 Remote Similarity NPD531 Approved
0.6235 Remote Similarity NPD1007 Discontinued
0.6235 Remote Similarity NPD2998 Approved
0.6235 Remote Similarity NPD4543 Discontinued
0.6235 Remote Similarity NPD517 Discontinued
0.6235 Remote Similarity NPD2997 Approved
0.6235 Remote Similarity NPD7609 Phase 3
0.6235 Remote Similarity NPD530 Approved
0.6235 Remote Similarity NPD3000 Approved
0.622 Remote Similarity NPD1697 Approved
0.619 Remote Similarity NPD9350 Approved
0.619 Remote Similarity NPD9349 Approved
0.619 Remote Similarity NPD9348 Approved
0.619 Remote Similarity NPD1628 Approved
0.619 Remote Similarity NPD689 Discontinued
0.619 Remote Similarity NPD1629 Approved
0.619 Remote Similarity NPD9351 Phase 3
0.6163 Remote Similarity NPD1088 Approved
0.6163 Remote Similarity NPD6690 Approved
0.6163 Remote Similarity NPD4407 Approved
0.6163 Remote Similarity NPD4408 Approved
0.6163 Remote Similarity NPD4405 Approved
0.6163 Remote Similarity NPD7631 Approved
0.6163 Remote Similarity NPD752 Approved
0.6163 Remote Similarity NPD1812 Approved
0.6163 Remote Similarity NPD1814 Approved
0.6092 Remote Similarity NPD1563 Approved
0.6092 Remote Similarity NPD1066 Discontinued
0.6092 Remote Similarity NPD719 Approved
0.6092 Remote Similarity NPD1409 Phase 3
0.6092 Remote Similarity NPD3980 Approved
0.6092 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6092 Remote Similarity NPD3718 Approved
0.6092 Remote Similarity NPD4542 Approved
0.6092 Remote Similarity NPD2878 Approved
0.6092 Remote Similarity NPD845 Approved
0.6092 Remote Similarity NPD3982 Approved
0.6092 Remote Similarity NPD4545 Approved
0.6092 Remote Similarity NPD1080 Approved
0.6092 Remote Similarity NPD720 Approved
0.6092 Remote Similarity NPD837 Approved
0.6092 Remote Similarity NPD3719 Approved
0.6071 Remote Similarity NPD9186 Approved
0.6071 Remote Similarity NPD9184 Approved
0.6047 Remote Similarity NPD7160 Approved
0.6047 Remote Similarity NPD1239 Approved
0.6024 Remote Similarity NPD9259 Approved
0.6024 Remote Similarity NPD9257 Approved
0.6023 Remote Similarity NPD1693 Approved
0.6023 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6023 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6023 Remote Similarity NPD2655 Approved
0.6023 Remote Similarity NPD2656 Approved
0.6023 Remote Similarity NPD7343 Discovery
0.6023 Remote Similarity NPD2933 Approved
0.6023 Remote Similarity NPD4094 Approved
0.6023 Remote Similarity NPD2934 Approved
0.6023 Remote Similarity NPD1081 Clinical (unspecified phase)
0.6023 Remote Similarity NPD5554 Approved
0.6023 Remote Similarity NPD4814 Discontinued
0.6023 Remote Similarity NPD7344 Phase 1
0.6023 Remote Similarity NPD6049 Phase 2
0.5977 Remote Similarity NPD1508 Approved
0.5977 Remote Similarity NPD9361 Approved
0.5977 Remote Similarity NPD159 Clinical (unspecified phase)
0.5955 Remote Similarity NPD838 Approved
0.5955 Remote Similarity NPD3457 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