Structure

Physi-Chem Properties

Molecular Weight:  182.11
Volume:  217.769
LogP:  4.292
LogD:  3.897
LogS:  -4.69
# Rotatable Bonds:  3
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.681
Synthetic Accessibility Score:  1.014
Fsp3:  0.143
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.464
MDCK Permeability:  1.933588646352291e-05
Pgp-inhibitor:  0.039
Pgp-substrate:  0.2
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.998
30% Bioavailability (F30%):  0.313

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.53
Plasma Protein Binding (PPB):  97.07544708251953%
Volume Distribution (VD):  0.922
Pgp-substrate:  1.671678066253662%

ADMET: Metabolism

CYP1A2-inhibitor:  0.975
CYP1A2-substrate:  0.483
CYP2C19-inhibitor:  0.945
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.808
CYP2C9-substrate:  0.129
CYP2D6-inhibitor:  0.263
CYP2D6-substrate:  0.122
CYP3A4-inhibitor:  0.064
CYP3A4-substrate:  0.389

ADMET: Excretion

Clearance (CL):  10.042
Half-life (T1/2):  0.515

ADMET: Toxicity

hERG Blockers:  0.188
Human Hepatotoxicity (H-HT):  0.101
Drug-inuced Liver Injury (DILI):  0.025
AMES Toxicity:  0.049
Rat Oral Acute Toxicity:  0.03
Maximum Recommended Daily Dose:  0.227
Skin Sensitization:  0.841
Carcinogencity:  0.675
Eye Corrosion:  0.88
Eye Irritation:  0.991
Respiratory Toxicity:  0.051

Download Data

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

  Natural Product: NPC246588

Natural Product ID:  NPC246588
Common Name*:   Bibenzyl
IUPAC Name:   2-phenylethylbenzene
Synonyms:   1,2-Diphenylethane
Standard InCHIKey:  QWUWMCYKGHVNAV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H14/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H,11-12H2
SMILES:  c1ccc(cc1)CCc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL440895
PubChem CID:   7647
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

*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
NPO88 Rheum undulatum Species Polygonaceae Eukaryota rhizome n.a. n.a. PMID[10714491]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15686910]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota Fibrous Roots n.a. n.a. PMID[25760525]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[31415170]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10780 Bletilla striata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO27620.1 Pteris cretica var. nervosa Varieties Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO88 Rheum undulatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10780 Bletilla striata Species Orchidaceae 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
NPT32 Organism Mus musculus Mus musculus IC50 > 100000.0 nM PMID[529461]
NPT32 Organism Mus musculus Mus musculus Inhibition = 26.0 % PMID[529461]
NPT35 Others n.a. LogP = 4.888 n.a. PMID[529462]
NPT2 Others Unspecified Activity = 8.3 % PMID[529464]
NPT2 Others Unspecified Potency n.a. 61659.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34376.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 138 nM PubChem BioAssay data set

☑ 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 NPC246588 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
0.9661 High Similarity NPC113670
0.9649 High Similarity NPC36357
0.9649 High Similarity NPC114327
0.9492 High Similarity NPC22786
0.9298 High Similarity NPC198841
0.9194 High Similarity NPC267443
0.918 High Similarity NPC291066
0.9167 High Similarity NPC200745
0.9167 High Similarity NPC71009
0.9138 High Similarity NPC120441
0.9138 High Similarity NPC212114
0.9138 High Similarity NPC65873
0.9138 High Similarity NPC300345
0.9123 High Similarity NPC149436
0.9 High Similarity NPC210849
0.9 High Similarity NPC135924
0.9 High Similarity NPC150196
0.9 High Similarity NPC54368
0.9 High Similarity NPC248705
0.8966 High Similarity NPC269586
0.8906 High Similarity NPC139416
0.8906 High Similarity NPC213570
0.8906 High Similarity NPC246822
0.8906 High Similarity NPC473206
0.8852 High Similarity NPC29680
0.8833 High Similarity NPC147062
0.8793 High Similarity NPC277704
0.8769 High Similarity NPC251490
0.8769 High Similarity NPC72670
0.8769 High Similarity NPC263385
0.873 High Similarity NPC36440
0.871 High Similarity NPC88566
0.8689 High Similarity NPC238023
0.8689 High Similarity NPC310758
0.8667 High Similarity NPC8235
0.8667 High Similarity NPC64270
0.8636 High Similarity NPC135433
0.8636 High Similarity NPC87099
0.8636 High Similarity NPC280135
0.8636 High Similarity NPC1008
0.8636 High Similarity NPC226999
0.8636 High Similarity NPC39799
0.8636 High Similarity NPC193578
0.8636 High Similarity NPC158028
0.8571 High Similarity NPC198023
0.8571 High Similarity NPC155172
0.8571 High Similarity NPC32312
0.8548 High Similarity NPC66517
0.8525 High Similarity NPC169110
0.8507 High Similarity NPC1901
0.8438 Intermediate Similarity NPC178527
0.8413 Intermediate Similarity NPC21211
0.8413 Intermediate Similarity NPC45756
0.8382 Intermediate Similarity NPC96835
0.8382 Intermediate Similarity NPC258492
0.8333 Intermediate Similarity NPC5324
0.8308 Intermediate Similarity NPC6107
0.8281 Intermediate Similarity NPC264470
0.8261 Intermediate Similarity NPC307195
0.8235 Intermediate Similarity NPC54269
0.8154 Intermediate Similarity NPC113837
0.8154 Intermediate Similarity NPC289915
0.8125 Intermediate Similarity NPC50266
0.8095 Intermediate Similarity NPC45255
0.8028 Intermediate Similarity NPC9796
0.7937 Intermediate Similarity NPC147578
0.7917 Intermediate Similarity NPC255345
0.7917 Intermediate Similarity NPC66270
0.7917 Intermediate Similarity NPC245896
0.791 Intermediate Similarity NPC22760
0.7812 Intermediate Similarity NPC200624
0.7808 Intermediate Similarity NPC159661
0.7808 Intermediate Similarity NPC272260
0.7794 Intermediate Similarity NPC297358
0.7778 Intermediate Similarity NPC3190
0.7778 Intermediate Similarity NPC249018
0.7714 Intermediate Similarity NPC212463
0.7703 Intermediate Similarity NPC315216
0.7703 Intermediate Similarity NPC50063
0.7703 Intermediate Similarity NPC95868
0.7703 Intermediate Similarity NPC184030
0.7703 Intermediate Similarity NPC164449
0.7681 Intermediate Similarity NPC229235
0.7647 Intermediate Similarity NPC82770
0.7647 Intermediate Similarity NPC239931
0.7647 Intermediate Similarity NPC311343
0.7647 Intermediate Similarity NPC78954
0.76 Intermediate Similarity NPC273033
0.76 Intermediate Similarity NPC12936
0.7571 Intermediate Similarity NPC74458
0.7571 Intermediate Similarity NPC208302
0.7568 Intermediate Similarity NPC139901
0.7568 Intermediate Similarity NPC151405
0.7544 Intermediate Similarity NPC11150
0.7536 Intermediate Similarity NPC98880
0.7536 Intermediate Similarity NPC235059
0.7536 Intermediate Similarity NPC200936
0.7536 Intermediate Similarity NPC16190
0.7536 Intermediate Similarity NPC169222
0.7534 Intermediate Similarity NPC179726
0.75 Intermediate Similarity NPC121478
0.75 Intermediate Similarity NPC73637
0.75 Intermediate Similarity NPC189371
0.75 Intermediate Similarity NPC276699
0.75 Intermediate Similarity NPC52330
0.7467 Intermediate Similarity NPC71664
0.7467 Intermediate Similarity NPC477703
0.7465 Intermediate Similarity NPC271437
0.7465 Intermediate Similarity NPC285679
0.7465 Intermediate Similarity NPC244738
0.7429 Intermediate Similarity NPC95289
0.7403 Intermediate Similarity NPC273758
0.7403 Intermediate Similarity NPC119677
0.7397 Intermediate Similarity NPC110264
0.7361 Intermediate Similarity NPC122327
0.7361 Intermediate Similarity NPC113000
0.7361 Intermediate Similarity NPC108218
0.7361 Intermediate Similarity NPC112609
0.7361 Intermediate Similarity NPC208075
0.7324 Intermediate Similarity NPC326200
0.7324 Intermediate Similarity NPC155429
0.7308 Intermediate Similarity NPC95429
0.7308 Intermediate Similarity NPC133162
0.7297 Intermediate Similarity NPC290638
0.7297 Intermediate Similarity NPC298023
0.7273 Intermediate Similarity NPC283012
0.7273 Intermediate Similarity NPC475199
0.7215 Intermediate Similarity NPC99482
0.7215 Intermediate Similarity NPC475710
0.72 Intermediate Similarity NPC103488
0.72 Intermediate Similarity NPC224544
0.7183 Intermediate Similarity NPC219246
0.7162 Intermediate Similarity NPC139658
0.7143 Intermediate Similarity NPC165212
0.7143 Intermediate Similarity NPC181786
0.7125 Intermediate Similarity NPC148231
0.7089 Intermediate Similarity NPC169016
0.7067 Intermediate Similarity NPC325662
0.7067 Intermediate Similarity NPC98269
0.7067 Intermediate Similarity NPC245966
0.7059 Intermediate Similarity NPC22627
0.7037 Intermediate Similarity NPC69057
0.7027 Intermediate Similarity NPC206800
0.7027 Intermediate Similarity NPC32203
0.7027 Intermediate Similarity NPC98976
0.7013 Intermediate Similarity NPC328178
0.7013 Intermediate Similarity NPC190567
0.7013 Intermediate Similarity NPC157055
0.7013 Intermediate Similarity NPC17408
0.7013 Intermediate Similarity NPC285716
0.7 Intermediate Similarity NPC123476
0.6974 Remote Similarity NPC76455
0.6974 Remote Similarity NPC2785
0.6974 Remote Similarity NPC137847
0.6974 Remote Similarity NPC285470
0.6974 Remote Similarity NPC36342
0.6962 Remote Similarity NPC477770
0.6962 Remote Similarity NPC243289
0.6962 Remote Similarity NPC208183
0.6951 Remote Similarity NPC267262
0.6933 Remote Similarity NPC271642
0.6933 Remote Similarity NPC175393
0.6923 Remote Similarity NPC242628
0.6923 Remote Similarity NPC145053
0.6923 Remote Similarity NPC231986
0.6923 Remote Similarity NPC133050
0.6914 Remote Similarity NPC203076
0.6892 Remote Similarity NPC299134
0.6883 Remote Similarity NPC300205
0.6883 Remote Similarity NPC170484
0.6867 Remote Similarity NPC176858
0.6867 Remote Similarity NPC418308
0.6867 Remote Similarity NPC325709
0.6867 Remote Similarity NPC113307
0.6867 Remote Similarity NPC199567
0.6867 Remote Similarity NPC231591
0.6849 Remote Similarity NPC125144
0.6849 Remote Similarity NPC121708
0.6842 Remote Similarity NPC329318
0.6842 Remote Similarity NPC287790
0.6842 Remote Similarity NPC3672
0.6835 Remote Similarity NPC230068
0.6829 Remote Similarity NPC60408
0.6795 Remote Similarity NPC192623
0.6795 Remote Similarity NPC127343
0.6795 Remote Similarity NPC121800
0.6795 Remote Similarity NPC309279
0.6795 Remote Similarity NPC164086
0.6786 Remote Similarity NPC277277
0.6786 Remote Similarity NPC19256
0.6786 Remote Similarity NPC191444
0.6753 Remote Similarity NPC12857
0.6753 Remote Similarity NPC176228
0.6753 Remote Similarity NPC50192
0.675 Remote Similarity NPC44830
0.675 Remote Similarity NPC197581
0.675 Remote Similarity NPC104070
0.6711 Remote Similarity NPC302129
0.6709 Remote Similarity NPC71795
0.6709 Remote Similarity NPC117180

  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 NPC246588 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
0.9661 High Similarity NPD675 Discontinued
0.8281 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD294 Approved
0.7826 Intermediate Similarity NPD292 Approved
0.7808 Intermediate Similarity NPD1475 Approved
0.7794 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD1673 Approved
0.7778 Intermediate Similarity NPD4147 Approved
0.7778 Intermediate Similarity NPD4144 Approved
0.7703 Intermediate Similarity NPD3981 Approved
0.7703 Intermediate Similarity NPD1617 Discontinued
0.7703 Intermediate Similarity NPD3903 Approved
0.7703 Intermediate Similarity NPD3979 Approved
0.7703 Intermediate Similarity NPD3904 Approved
0.7703 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD942 Approved
0.76 Intermediate Similarity NPD4027 Approved
0.76 Intermediate Similarity NPD4026 Approved
0.76 Intermediate Similarity NPD3035 Approved
0.75 Intermediate Similarity NPD4170 Approved
0.75 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4169 Approved
0.7467 Intermediate Similarity NPD914 Suspended
0.7465 Intermediate Similarity NPD9728 Phase 1
0.7403 Intermediate Similarity NPD4635 Approved
0.7403 Intermediate Similarity NPD1185 Approved
0.7403 Intermediate Similarity NPD2001 Discontinued
0.7361 Intermediate Similarity NPD9593 Approved
0.7361 Intermediate Similarity NPD9588 Approved
0.7361 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD9589 Approved
0.7361 Intermediate Similarity NPD9592 Approved
0.7361 Intermediate Similarity NPD9594 Approved
0.7361 Intermediate Similarity NPD80 Approved
0.7361 Intermediate Similarity NPD9591 Approved
0.7361 Intermediate Similarity NPD9590 Approved
0.7308 Intermediate Similarity NPD3429 Approved
0.7308 Intermediate Similarity NPD3427 Approved
0.7308 Intermediate Similarity NPD4544 Approved
0.7308 Intermediate Similarity NPD5178 Approved
0.7237 Intermediate Similarity NPD260 Discontinued
0.7215 Intermediate Similarity NPD5916 Discontinued
0.72 Intermediate Similarity NPD79 Approved
0.72 Intermediate Similarity NPD9564 Approved
0.72 Intermediate Similarity NPD9563 Approved
0.7179 Intermediate Similarity NPD5288 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4636 Approved
0.7125 Intermediate Similarity NPD4409 Approved
0.7125 Intermediate Similarity NPD4406 Approved
0.7105 Intermediate Similarity NPD589 Approved
0.7105 Intermediate Similarity NPD590 Approved
0.7089 Intermediate Similarity NPD2539 Approved
0.7089 Intermediate Similarity NPD2538 Approved
0.7037 Intermediate Similarity NPD4146 Approved
0.7037 Intermediate Similarity NPD3428 Approved
0.7037 Intermediate Similarity NPD3426 Approved
0.7037 Intermediate Similarity NPD4145 Approved
0.7037 Intermediate Similarity NPD2002 Discontinued
0.7027 Intermediate Similarity NPD9716 Approved
0.6974 Remote Similarity NPD225 Approved
0.6974 Remote Similarity NPD9393 Approved
0.6974 Remote Similarity NPD9397 Approved
0.6974 Remote Similarity NPD227 Approved
0.6974 Remote Similarity NPD296 Approved
0.6974 Remote Similarity NPD295 Approved
0.6974 Remote Similarity NPD293 Approved
0.6962 Remote Similarity NPD3971 Phase 1
0.6962 Remote Similarity NPD423 Phase 3
0.6951 Remote Similarity NPD3345 Approved
0.6951 Remote Similarity NPD5675 Discontinued
0.6914 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1053 Approved
0.6883 Remote Similarity NPD1051 Approved
0.6883 Remote Similarity NPD1052 Approved
0.6867 Remote Similarity NPD1629 Approved
0.6867 Remote Similarity NPD1628 Approved
0.6867 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6842 Remote Similarity NPD603 Approved
0.6795 Remote Similarity NPD5371 Approved
0.6795 Remote Similarity NPD5372 Approved
0.6786 Remote Similarity NPD4728 Approved
0.6786 Remote Similarity NPD3344 Approved
0.6786 Remote Similarity NPD2811 Clinical (unspecified phase)
0.6786 Remote Similarity NPD3346 Approved
0.6786 Remote Similarity NPD5915 Approved
0.675 Remote Similarity NPD263 Approved
0.675 Remote Similarity NPD262 Approved
0.6709 Remote Similarity NPD472 Approved
0.6709 Remote Similarity NPD226 Approved
0.6706 Remote Similarity NPD4543 Discontinued
0.6706 Remote Similarity NPD2997 Approved
0.6706 Remote Similarity NPD3000 Approved
0.6706 Remote Similarity NPD2998 Approved
0.6706 Remote Similarity NPD1239 Approved
0.6667 Remote Similarity NPD9490 Approved
0.6667 Remote Similarity NPD507 Approved
0.6667 Remote Similarity NPD508 Approved
0.6628 Remote Similarity NPD4408 Approved
0.6628 Remote Similarity NPD4405 Approved
0.6628 Remote Similarity NPD4407 Approved
0.6628 Remote Similarity NPD1508 Approved
0.6623 Remote Similarity NPD9294 Approved
0.6585 Remote Similarity NPD2208 Approved
0.6585 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6585 Remote Similarity NPD2205 Approved
0.6552 Remote Similarity NPD2878 Approved
0.6552 Remote Similarity NPD6548 Approved
0.6552 Remote Similarity NPD3980 Approved
0.6552 Remote Similarity NPD4545 Approved
0.6552 Remote Similarity NPD3982 Approved
0.6552 Remote Similarity NPD1563 Approved
0.6552 Remote Similarity NPD6549 Approved
0.6552 Remote Similarity NPD4542 Approved
0.6543 Remote Similarity NPD830 Approved
0.6543 Remote Similarity NPD4000 Phase 3
0.6543 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6543 Remote Similarity NPD9491 Approved
0.6543 Remote Similarity NPD831 Approved
0.6508 Remote Similarity NPD9072 Clinical (unspecified phase)
0.6506 Remote Similarity NPD3099 Discontinued
0.6477 Remote Similarity NPD5554 Approved
0.6477 Remote Similarity NPD4094 Approved
0.6477 Remote Similarity NPD688 Clinical (unspecified phase)
0.6477 Remote Similarity NPD3772 Phase 3
0.6463 Remote Similarity NPD785 Approved
0.6463 Remote Similarity NPD9395 Approved
0.6429 Remote Similarity NPD650 Approved
0.6429 Remote Similarity NPD783 Approved
0.6429 Remote Similarity NPD780 Approved
0.6429 Remote Similarity NPD4793 Discontinued
0.6429 Remote Similarity NPD782 Approved
0.6429 Remote Similarity NPD1087 Approved
0.6429 Remote Similarity NPD781 Approved
0.6404 Remote Similarity NPD5964 Phase 2
0.6404 Remote Similarity NPD3458 Approved
0.6404 Remote Similarity NPD5963 Phase 2
0.6404 Remote Similarity NPD2859 Approved
0.6404 Remote Similarity NPD1989 Approved
0.6404 Remote Similarity NPD1843 Approved
0.6404 Remote Similarity NPD3832 Clinical (unspecified phase)
0.6404 Remote Similarity NPD2860 Approved
0.6404 Remote Similarity NPD2895 Discontinued
0.6404 Remote Similarity NPD6472 Discontinued
0.6404 Remote Similarity NPD3457 Approved
0.6404 Remote Similarity NPD2507 Clinical (unspecified phase)
0.6404 Remote Similarity NPD3456 Approved
0.6404 Remote Similarity NPD2005 Discontinued
0.6404 Remote Similarity NPD3093 Approved
0.6386 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6353 Remote Similarity NPD531 Approved
0.6353 Remote Similarity NPD1101 Approved
0.6333 Remote Similarity NPD1565 Approved
0.6333 Remote Similarity NPD4657 Approved
0.6333 Remote Similarity NPD4655 Approved
0.6333 Remote Similarity NPD5597 Approved
0.6333 Remote Similarity NPD1875 Phase 1
0.6333 Remote Similarity NPD5598 Approved
0.6333 Remote Similarity NPD2487 Clinical (unspecified phase)
0.6333 Remote Similarity NPD1566 Phase 3
0.6333 Remote Similarity NPD1564 Approved
0.6322 Remote Similarity NPD517 Discontinued
0.6322 Remote Similarity NPD7609 Phase 3
0.631 Remote Similarity NPD1697 Approved
0.631 Remote Similarity NPD304 Approved
0.631 Remote Similarity NPD305 Approved
0.6292 Remote Similarity NPD2933 Approved
0.6292 Remote Similarity NPD6049 Phase 2
0.6292 Remote Similarity NPD2934 Approved
0.6292 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6279 Remote Similarity NPD5346 Phase 2
0.6279 Remote Similarity NPD800 Approved
0.6279 Remote Similarity NPD5347 Phase 2
0.6279 Remote Similarity NPD771 Phase 3
0.6264 Remote Similarity NPD5926 Approved
0.6264 Remote Similarity NPD6499 Approved
0.6264 Remote Similarity NPD6498 Approved
0.6264 Remote Similarity NPD5832 Phase 3
0.6264 Remote Similarity NPD4117 Approved
0.625 Remote Similarity NPD752 Approved
0.625 Remote Similarity NPD7631 Approved
0.6235 Remote Similarity NPD506 Clinical (unspecified phase)
0.6235 Remote Similarity NPD9538 Approved
0.6235 Remote Similarity NPD1282 Approved
0.6222 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6207 Remote Similarity NPD3673 Approved
0.6207 Remote Similarity NPD1090 Approved
0.6207 Remote Similarity NPD1089 Approved
0.6207 Remote Similarity NPD1086 Approved
0.6207 Remote Similarity NPD3672 Approved
0.6196 Remote Similarity NPD4007 Approved
0.6196 Remote Similarity NPD4737 Phase 2
0.6196 Remote Similarity NPD3020 Approved
0.6196 Remote Similarity NPD1946 Clinical (unspecified phase)
0.6196 Remote Similarity NPD4008 Approved
0.618 Remote Similarity NPD1202 Approved
0.618 Remote Similarity NPD720 Approved
0.618 Remote Similarity NPD5122 Clinical (unspecified phase)
0.618 Remote Similarity NPD719 Approved
0.6154 Remote Similarity NPD3495 Discontinued
0.6136 Remote Similarity NPD530 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