Structure

Physi-Chem Properties

Molecular Weight:  328.24
Volume:  382.273
LogP:  6.676
LogD:  5.039
LogS:  -4.079
# Rotatable Bonds:  8
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.544
Synthetic Accessibility Score:  2.874
Fsp3:  0.455
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:  -4.853
MDCK Permeability:  2.640685488586314e-05
Pgp-inhibitor:  0.28
Pgp-substrate:  0.037
Human Intestinal Absorption (HIA):  0.03
20% Bioavailability (F20%):  0.966
30% Bioavailability (F30%):  0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.031
Plasma Protein Binding (PPB):  99.21602630615234%
Volume Distribution (VD):  1.408
Pgp-substrate:  0.6980175375938416%

ADMET: Metabolism

CYP1A2-inhibitor:  0.903
CYP1A2-substrate:  0.312
CYP2C19-inhibitor:  0.786
CYP2C19-substrate:  0.194
CYP2C9-inhibitor:  0.61
CYP2C9-substrate:  0.968
CYP2D6-inhibitor:  0.918
CYP2D6-substrate:  0.845
CYP3A4-inhibitor:  0.353
CYP3A4-substrate:  0.165

ADMET: Excretion

Clearance (CL):  7.291
Half-life (T1/2):  0.505

ADMET: Toxicity

hERG Blockers:  0.018
Human Hepatotoxicity (H-HT):  0.461
Drug-inuced Liver Injury (DILI):  0.013
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.005
Maximum Recommended Daily Dose:  0.74
Skin Sensitization:  0.949
Carcinogencity:  0.024
Eye Corrosion:  0.095
Eye Irritation:  0.932
Respiratory Toxicity:  0.123

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC12640

Natural Product ID:  NPC12640
Common Name*:   Grifolin
IUPAC Name:   5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,3-diol
Synonyms:   Grifolin
Standard InCHIKey:  PZHNKNRPGLTZPO-VZRGJMDUSA-N
Standard InCHI:  InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+
SMILES:  CC(=CCC/C(=C/CC/C(=C/Cc1c(cc(C)cc1O)O)/C)/C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487804
PubChem CID:   5372312
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO40323 Rhododendron nyingchiense Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[30067363]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO17403 Peperomia galioides Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[7769398]
NPO17403 Peperomia galioides Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8759169]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4414 Lilium lancifolium Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4414 Lilium lancifolium Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4414 Lilium lancifolium Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21029 Euphorbia prostrata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17403 Peperomia galioides Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8517 Adenia hastata Species Passifloraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5198 Menegazzia terebrata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7187 Polyporus dispansus Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8897 Streptomyces flavogriseus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10626 Elsholtzia oldhami Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6415 Juniperus excelsa Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14844 Eurotia ceratoides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5371 Ainsliaea fragrans Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10962 Parsonsia spiralis Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4414 Lilium lancifolium Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 5700.0 nM PMID[554259]
NPT2 Others Unspecified IC50 = 81.6 uL PMID[554257]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 68.0 % PMID[554258]
NPT78 Individual Protein Beta amyloid A4 protein Homo sapiens IC50 = 148800.0 nM PMID[554260]

☑ 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 NPC12640 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
1.0 High Similarity NPC99836
1.0 High Similarity NPC201662
0.9899 High Similarity NPC204901
0.9899 High Similarity NPC158253
0.9899 High Similarity NPC232523
0.9898 High Similarity NPC37802
0.9796 High Similarity NPC244513
0.9796 High Similarity NPC227458
0.9796 High Similarity NPC218879
0.9592 High Similarity NPC192032
0.9592 High Similarity NPC24407
0.9592 High Similarity NPC11280
0.9592 High Similarity NPC294186
0.9592 High Similarity NPC166313
0.9592 High Similarity NPC147310
0.9592 High Similarity NPC137415
0.951 High Similarity NPC299568
0.951 High Similarity NPC33728
0.951 High Similarity NPC186385
0.951 High Similarity NPC19808
0.9495 High Similarity NPC168303
0.9495 High Similarity NPC106396
0.9495 High Similarity NPC24404
0.9495 High Similarity NPC242342
0.9495 High Similarity NPC146798
0.9495 High Similarity NPC85479
0.9495 High Similarity NPC302219
0.9495 High Similarity NPC222522
0.9495 High Similarity NPC313030
0.9495 High Similarity NPC249828
0.9495 High Similarity NPC71002
0.9495 High Similarity NPC53051
0.9495 High Similarity NPC94351
0.9423 High Similarity NPC166995
0.9412 High Similarity NPC174981
0.9394 High Similarity NPC72947
0.9394 High Similarity NPC284011
0.9333 High Similarity NPC23804
0.9333 High Similarity NPC263753
0.9327 High Similarity NPC224527
0.9293 High Similarity NPC166761
0.9293 High Similarity NPC10588
0.9151 High Similarity NPC117846
0.9151 High Similarity NPC319803
0.9126 High Similarity NPC305603
0.9126 High Similarity NPC61033
0.9118 High Similarity NPC134829
0.9118 High Similarity NPC246056
0.9048 High Similarity NPC224870
0.9029 High Similarity NPC470700
0.9029 High Similarity NPC118286
0.9029 High Similarity NPC302681
0.9029 High Similarity NPC39097
0.9029 High Similarity NPC109691
0.9029 High Similarity NPC39664
0.902 High Similarity NPC102216
0.902 High Similarity NPC241891
0.901 High Similarity NPC477685
0.8981 High Similarity NPC246760
0.8981 High Similarity NPC84999
0.8972 High Similarity NPC261343
0.8962 High Similarity NPC476632
0.8962 High Similarity NPC165770
0.8962 High Similarity NPC225679
0.8962 High Similarity NPC4493
0.8942 High Similarity NPC54844
0.8909 High Similarity NPC48781
0.8909 High Similarity NPC206
0.8909 High Similarity NPC9592
0.8899 High Similarity NPC115808
0.8879 High Similarity NPC43525
0.8878 High Similarity NPC295295
0.8824 High Similarity NPC100340
0.8824 High Similarity NPC252105
0.8824 High Similarity NPC143659
0.8818 High Similarity NPC470760
0.8812 High Similarity NPC80027
0.875 High Similarity NPC474839
0.8739 High Similarity NPC144343
0.8739 High Similarity NPC190514
0.8725 High Similarity NPC129373
0.8725 High Similarity NPC248396
0.8725 High Similarity NPC48730
0.8725 High Similarity NPC72729
0.8716 High Similarity NPC107240
0.8713 High Similarity NPC79241
0.8713 High Similarity NPC6597
0.8704 High Similarity NPC473521
0.8687 High Similarity NPC94139
0.8687 High Similarity NPC306884
0.8687 High Similarity NPC147284
0.8687 High Similarity NPC162314
0.8687 High Similarity NPC210497
0.8687 High Similarity NPC3358
0.8679 High Similarity NPC61885
0.8679 High Similarity NPC63698
0.8673 High Similarity NPC24125
0.8667 High Similarity NPC469913
0.8661 High Similarity NPC184302
0.8661 High Similarity NPC191866
0.8654 High Similarity NPC119860
0.8654 High Similarity NPC30506
0.8641 High Similarity NPC80800
0.8627 High Similarity NPC33675
0.8627 High Similarity NPC260775
0.8627 High Similarity NPC299762
0.8624 High Similarity NPC62546
0.8624 High Similarity NPC162113
0.8614 High Similarity NPC312132
0.8614 High Similarity NPC259512
0.8611 High Similarity NPC469912
0.8596 High Similarity NPC39029
0.8586 High Similarity NPC231150
0.8585 High Similarity NPC66834
0.8571 High Similarity NPC292452
0.8571 High Similarity NPC47284
0.8558 High Similarity NPC315022
0.8558 High Similarity NPC471228
0.8558 High Similarity NPC235762
0.8544 High Similarity NPC174911
0.8544 High Similarity NPC70677
0.8544 High Similarity NPC130756
0.8544 High Similarity NPC12931
0.8529 High Similarity NPC152097
0.8529 High Similarity NPC291789
0.8522 High Similarity NPC122175
0.8519 High Similarity NPC168657
0.8509 High Similarity NPC218753
0.8505 High Similarity NPC306295
0.8491 Intermediate Similarity NPC248904
0.8491 Intermediate Similarity NPC53740
0.8485 Intermediate Similarity NPC192
0.8482 Intermediate Similarity NPC69261
0.8482 Intermediate Similarity NPC33270
0.8482 Intermediate Similarity NPC277588
0.8476 Intermediate Similarity NPC315936
0.8476 Intermediate Similarity NPC475225
0.8468 Intermediate Similarity NPC808
0.8426 Intermediate Similarity NPC202647
0.8421 Intermediate Similarity NPC69006
0.8396 Intermediate Similarity NPC471350
0.8396 Intermediate Similarity NPC117115
0.8393 Intermediate Similarity NPC123559
0.8393 Intermediate Similarity NPC150624
0.8393 Intermediate Similarity NPC114064
0.8381 Intermediate Similarity NPC108497
0.8378 Intermediate Similarity NPC249270
0.8376 Intermediate Similarity NPC139774
0.8376 Intermediate Similarity NPC174729
0.8365 Intermediate Similarity NPC248573
0.8365 Intermediate Similarity NPC275053
0.8365 Intermediate Similarity NPC161571
0.8364 Intermediate Similarity NPC302371
0.8364 Intermediate Similarity NPC228452
0.8362 Intermediate Similarity NPC77789
0.8362 Intermediate Similarity NPC18128
0.835 Intermediate Similarity NPC475078
0.8349 Intermediate Similarity NPC475018
0.8333 Intermediate Similarity NPC85895
0.8333 Intermediate Similarity NPC137294
0.8333 Intermediate Similarity NPC32714
0.8333 Intermediate Similarity NPC217174
0.8319 Intermediate Similarity NPC127894
0.8319 Intermediate Similarity NPC470759
0.8319 Intermediate Similarity NPC320864
0.8319 Intermediate Similarity NPC219070
0.8319 Intermediate Similarity NPC15860
0.8318 Intermediate Similarity NPC155072
0.8318 Intermediate Similarity NPC310456
0.8304 Intermediate Similarity NPC53906
0.8304 Intermediate Similarity NPC232165
0.8302 Intermediate Similarity NPC272029
0.8291 Intermediate Similarity NPC96940
0.8283 Intermediate Similarity NPC27974
0.8276 Intermediate Similarity NPC237667
0.8273 Intermediate Similarity NPC151537
0.8273 Intermediate Similarity NPC54373
0.8261 Intermediate Similarity NPC223451
0.8241 Intermediate Similarity NPC474352
0.8241 Intermediate Similarity NPC151477
0.8235 Intermediate Similarity NPC111723
0.8235 Intermediate Similarity NPC76938
0.8235 Intermediate Similarity NPC152415
0.8235 Intermediate Similarity NPC91204
0.8235 Intermediate Similarity NPC237517
0.8235 Intermediate Similarity NPC82299
0.8235 Intermediate Similarity NPC245187
0.822 Intermediate Similarity NPC224342
0.8214 Intermediate Similarity NPC22610
0.8214 Intermediate Similarity NPC276737
0.8208 Intermediate Similarity NPC168393
0.8208 Intermediate Similarity NPC269212
0.819 Intermediate Similarity NPC130103
0.8182 Intermediate Similarity NPC407
0.8182 Intermediate Similarity NPC132720
0.8182 Intermediate Similarity NPC242178
0.8182 Intermediate Similarity NPC307235
0.8174 Intermediate Similarity NPC121866
0.8173 Intermediate Similarity NPC474073
0.8167 Intermediate Similarity NPC257947

  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 NPC12640 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
0.951 High Similarity NPD4750 Phase 3
0.901 High Similarity NPD940 Approved
0.901 High Similarity NPD846 Approved
0.8889 High Similarity NPD844 Approved
0.8614 High Similarity NPD288 Approved
0.8365 Intermediate Similarity NPD1242 Phase 1
0.8291 Intermediate Similarity NPD4749 Approved
0.819 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.8083 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD7635 Approved
0.7981 Intermediate Similarity NPD2859 Approved
0.7981 Intermediate Similarity NPD2860 Approved
0.7967 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD845 Approved
0.7925 Intermediate Similarity NPD3020 Approved
0.7886 Intermediate Similarity NPD4625 Phase 3
0.7885 Intermediate Similarity NPD2933 Approved
0.7885 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD2934 Approved
0.781 Intermediate Similarity NPD1809 Phase 2
0.7748 Intermediate Similarity NPD2342 Discontinued
0.7672 Intermediate Similarity NPD6671 Approved
0.7653 Intermediate Similarity NPD9093 Approved
0.7611 Intermediate Similarity NPD3021 Approved
0.7611 Intermediate Similarity NPD3022 Approved
0.7576 Intermediate Similarity NPD9089 Approved
0.7538 Intermediate Similarity NPD6100 Approved
0.7538 Intermediate Similarity NPD6099 Approved
0.7525 Intermediate Similarity NPD111 Approved
0.75 Intermediate Similarity NPD1445 Approved
0.75 Intermediate Similarity NPD1444 Approved
0.748 Intermediate Similarity NPD6696 Suspended
0.7381 Intermediate Similarity NPD4908 Phase 1
0.7377 Intermediate Similarity NPD1610 Phase 2
0.7339 Intermediate Similarity NPD9273 Approved
0.7333 Intermediate Similarity NPD1548 Phase 1
0.7328 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD3027 Phase 3
0.7313 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD1792 Phase 2
0.7302 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD422 Phase 1
0.7232 Intermediate Similarity NPD9500 Approved
0.7222 Intermediate Similarity NPD602 Approved
0.7222 Intermediate Similarity NPD858 Approved
0.7222 Intermediate Similarity NPD599 Approved
0.7222 Intermediate Similarity NPD859 Approved
0.7213 Intermediate Similarity NPD4626 Approved
0.7203 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD3091 Approved
0.7167 Intermediate Similarity NPD7325 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9094 Approved
0.7097 Intermediate Similarity NPD1201 Approved
0.7097 Intermediate Similarity NPD3092 Approved
0.7073 Intermediate Similarity NPD2932 Approved
0.7073 Intermediate Similarity NPD4059 Approved
0.7073 Intermediate Similarity NPD3019 Approved
0.7059 Intermediate Similarity NPD2229 Approved
0.7059 Intermediate Similarity NPD2228 Approved
0.7059 Intermediate Similarity NPD2234 Approved
0.7049 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD228 Approved
0.7029 Intermediate Similarity NPD7390 Discontinued
0.7025 Intermediate Similarity NPD7340 Approved
0.7023 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD1613 Approved
0.7023 Intermediate Similarity NPD943 Approved
0.7008 Intermediate Similarity NPD3094 Phase 2
0.7 Intermediate Similarity NPD1791 Approved
0.7 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD497 Approved
0.7 Intermediate Similarity NPD1793 Approved
0.6984 Remote Similarity NPD3600 Clinical (unspecified phase)
0.696 Remote Similarity NPD5350 Clinical (unspecified phase)
0.696 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6935 Remote Similarity NPD1778 Approved
0.6935 Remote Similarity NPD2286 Discontinued
0.6917 Remote Similarity NPD2568 Approved
0.6917 Remote Similarity NPD495 Approved
0.6917 Remote Similarity NPD498 Approved
0.6917 Remote Similarity NPD1607 Approved
0.6917 Remote Similarity NPD1398 Phase 1
0.6917 Remote Similarity NPD496 Approved
0.6911 Remote Similarity NPD7330 Discontinued
0.6903 Remote Similarity NPD3028 Approved
0.6899 Remote Similarity NPD2861 Phase 2
0.6899 Remote Similarity NPD3018 Phase 2
0.688 Remote Similarity NPD1981 Approved
0.688 Remote Similarity NPD1980 Approved
0.688 Remote Similarity NPD1983 Approved
0.6875 Remote Similarity NPD1131 Approved
0.6875 Remote Similarity NPD1133 Approved
0.6875 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1135 Approved
0.6875 Remote Similarity NPD1129 Approved
0.6875 Remote Similarity NPD1470 Approved
0.6875 Remote Similarity NPD1134 Approved
0.687 Remote Similarity NPD9610 Approved
0.687 Remote Similarity NPD9608 Approved
0.687 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6864 Remote Similarity NPD9380 Clinical (unspecified phase)
0.686 Remote Similarity NPD9618 Approved
0.686 Remote Similarity NPD9614 Approved
0.6855 Remote Similarity NPD4093 Discontinued
0.6855 Remote Similarity NPD5691 Approved
0.6838 Remote Similarity NPD290 Approved
0.6833 Remote Similarity NPD9379 Approved
0.6833 Remote Similarity NPD9377 Approved
0.6818 Remote Similarity NPD6405 Approved
0.6818 Remote Similarity NPD6407 Approved
0.6807 Remote Similarity NPD9280 Clinical (unspecified phase)
0.68 Remote Similarity NPD5238 Clinical (unspecified phase)
0.68 Remote Similarity NPD4589 Approved
0.68 Remote Similarity NPD3095 Discontinued
0.68 Remote Similarity NPD1751 Approved
0.6791 Remote Similarity NPD4097 Suspended
0.678 Remote Similarity NPD9266 Approved
0.678 Remote Similarity NPD2684 Approved
0.678 Remote Similarity NPD74 Approved
0.6774 Remote Similarity NPD5303 Approved
0.6774 Remote Similarity NPD1759 Phase 1
0.6774 Remote Similarity NPD5304 Approved
0.6772 Remote Similarity NPD2233 Approved
0.6772 Remote Similarity NPD2230 Approved
0.6772 Remote Similarity NPD9269 Phase 2
0.6772 Remote Similarity NPD2232 Approved
0.6769 Remote Similarity NPD5736 Approved
0.6768 Remote Similarity NPD9087 Approved
0.6767 Remote Similarity NPD2238 Phase 2
0.6767 Remote Similarity NPD1240 Approved
0.6765 Remote Similarity NPD5406 Approved
0.6765 Remote Similarity NPD5404 Approved
0.6765 Remote Similarity NPD5405 Approved
0.6765 Remote Similarity NPD5408 Approved
0.6748 Remote Similarity NPD9493 Approved
0.6748 Remote Similarity NPD405 Clinical (unspecified phase)
0.6748 Remote Similarity NPD7636 Approved
0.6746 Remote Similarity NPD3496 Discontinued
0.672 Remote Similarity NPD9268 Approved
0.672 Remote Similarity NPD4196 Clinical (unspecified phase)
0.672 Remote Similarity NPD4235 Clinical (unspecified phase)
0.6719 Remote Similarity NPD2982 Phase 2
0.6719 Remote Similarity NPD2983 Phase 2
0.6695 Remote Similarity NPD9263 Approved
0.6695 Remote Similarity NPD9264 Approved
0.6695 Remote Similarity NPD9267 Approved
0.6694 Remote Similarity NPD9616 Approved
0.6694 Remote Similarity NPD9613 Approved
0.6694 Remote Similarity NPD1758 Phase 1
0.6694 Remote Similarity NPD856 Approved
0.6694 Remote Similarity NPD9615 Approved
0.6694 Remote Similarity NPD16 Approved
0.6694 Remote Similarity NPD7843 Approved
0.6691 Remote Similarity NPD651 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9088 Approved
0.6667 Remote Similarity NPD709 Approved
0.6667 Remote Similarity NPD9384 Approved
0.6667 Remote Similarity NPD9381 Approved
0.6667 Remote Similarity NPD970 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7157 Approved
0.6642 Remote Similarity NPD1555 Discontinued
0.6641 Remote Similarity NPD2981 Phase 2
0.664 Remote Similarity NPD316 Approved
0.6639 Remote Similarity NPD5283 Phase 1
0.6638 Remote Similarity NPD5700 Clinical (unspecified phase)
0.662 Remote Similarity NPD2534 Approved
0.662 Remote Similarity NPD7447 Phase 1
0.662 Remote Similarity NPD2533 Approved
0.662 Remote Similarity NPD2532 Approved
0.6615 Remote Similarity NPD2797 Approved
0.6614 Remote Similarity NPD3143 Discontinued
0.661 Remote Similarity NPD968 Approved
0.6593 Remote Similarity NPD230 Phase 1
0.6591 Remote Similarity NPD600 Approved
0.6591 Remote Similarity NPD596 Approved
0.6589 Remote Similarity NPD9622 Approved
0.6589 Remote Similarity NPD4659 Approved
0.6589 Remote Similarity NPD1755 Approved
0.6571 Remote Similarity NPD3892 Phase 2
0.6569 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6569 Remote Similarity NPD9294 Approved
0.6569 Remote Similarity NPD1510 Phase 2
0.6567 Remote Similarity NPD6663 Approved
0.6565 Remote Similarity NPD2194 Approved
0.6565 Remote Similarity NPD2195 Approved
0.6565 Remote Similarity NPD6584 Phase 3
0.6562 Remote Similarity NPD1091 Approved
0.656 Remote Similarity NPD317 Approved
0.656 Remote Similarity NPD318 Approved
0.6555 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6549 Remote Similarity NPD7837 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5310 Approved
0.6538 Remote Similarity NPD5311 Approved
0.6532 Remote Similarity NPD255 Approved
0.6532 Remote Similarity NPD256 Approved
0.6522 Remote Similarity NPD2935 Discontinued
0.6522 Remote Similarity NPD1551 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