Structure

Physi-Chem Properties

Molecular Weight:  538.09
Volume:  521.816
LogP:  5.742
LogD:  2.38
LogS:  -4.276
# Rotatable Bonds:  4
TPSA:  170.8
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.192
Synthetic Accessibility Score:  2.946
Fsp3:  0.0
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.114
MDCK Permeability:  1.1190809345862363e-05
Pgp-inhibitor:  0.074
Pgp-substrate:  0.036
Human Intestinal Absorption (HIA):  0.107
20% Bioavailability (F20%):  0.995
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  99.5940933227539%
Volume Distribution (VD):  0.432
Pgp-substrate:  4.8893938064575195%

ADMET: Metabolism

CYP1A2-inhibitor:  0.86
CYP1A2-substrate:  0.093
CYP2C19-inhibitor:  0.82
CYP2C19-substrate:  0.038
CYP2C9-inhibitor:  0.613
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.162
CYP2D6-substrate:  0.525
CYP3A4-inhibitor:  0.253
CYP3A4-substrate:  0.084

ADMET: Excretion

Clearance (CL):  3.02
Half-life (T1/2):  0.735

ADMET: Toxicity

hERG Blockers:  0.091
Human Hepatotoxicity (H-HT):  0.027
Drug-inuced Liver Injury (DILI):  0.975
AMES Toxicity:  0.289
Rat Oral Acute Toxicity:  0.385
Maximum Recommended Daily Dose:  0.947
Skin Sensitization:  0.954
Carcinogencity:  0.175
Eye Corrosion:  0.003
Eye Irritation:  0.903
Respiratory Toxicity:  0.095

Download Data

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

  Natural Product: NPC196179

Natural Product ID:  NPC196179
Common Name*:   Hinokiflavone
IUPAC Name:   6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms:   Hinokiflavone
Standard InCHIKey:  WTDHMFBJQJSTMH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H18O10/c31-16-5-1-14(2-6-16)24-12-21(35)28-26(40-24)13-22(36)30(29(28)37)38-18-7-3-15(4-8-18)23-11-20(34)27-19(33)9-17(32)10-25(27)39-23/h1-13,31-33,36-37H
SMILES:  Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(c(c2O)Oc1ccc(cc1)c1cc(=O)c2c(o1)cc(cc2O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL291426
PubChem CID:   5281627
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones

*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
NPO33250 rhus succedanea Species Anacardiaceae Eukaryota sap n.a. n.a. PMID[12444713]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota stems n.a. n.a. PMID[12932126]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota leaves Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota Leaves and branches Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota bark n.a. n.a. PMID[18549276]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[20335035]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota feces n.a. n.a. PMID[20402524]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20681570]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[25559759]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[29144743]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. PMID[31244143]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota Twigs and leaves Taichung, Taiwan 1993-Aug PMID[9322359]
NPO33250 rhus succedanea Species Anacardiaceae Eukaryota seed kernels Fukuoka, Japan n.a. PMID[9322359]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO31129 Podocarpus macrophyflus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30638 Cryptomeria fortunei Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14158 Selaginella tamariscina Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27558 Podocarpus macrophyllus Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28400 Selaginella pulvinata Species Selaginellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5082 Cycas revoluta Species Cycadaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5049 Garcinia multiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390 Juniperus rigida Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO882 Trogopterus xanthipes Species Sciuridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24652 Toxicodendron succedaneum Species Anacardiaceae 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
NPT3595 Individual Protein Cathepsin K Homo sapiens IC50 = 0.83 ug.mL-1 PMID[558269]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 = 62000.0 nM PMID[558271]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 Inhibition = 89.9 % PMID[558271]
NPT927 Cell Line PBMC Homo sapiens IC50 = 9000.0 nM PMID[558271]
NPT1602 Individual Protein Neuraminidase Influenza A virus (A/Puerto Rico/8/1934(H1N1)) IC50 = 41.8 ug.mL-1 PMID[558272]
NPT1602 Individual Protein Neuraminidase Influenza A virus (A/Puerto Rico/8/1934(H1N1)) logIC50 = 1.621 n.a. PMID[558272]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis Inhibition = 0.0 % PMID[558268]
NPT2 Others Unspecified Activity = 0.0 n.a. PMID[558270]
NPT2 Others Unspecified IC50 = 18.0 nM PMID[558270]
NPT2 Others Unspecified IC50 = 48.0 nM PMID[558270]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 4100.0 nM PMID[558271]
NPT2 Others Unspecified Selectivity Index = 2.2 n.a. PMID[558271]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 > 10000.0 nM PMID[558273]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 38.7 % PMID[558274]
NPT2 Others Unspecified IC50 = 450.0 nM PMID[558275]
NPT78 Individual Protein Beta amyloid A4 protein Homo sapiens IC50 = 9500.0 nM PMID[558276]

☑ 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 NPC196179 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 NPC34089
0.987 High Similarity NPC272064
0.9803 High Similarity NPC112954
0.9673 High Similarity NPC185526
0.9554 High Similarity NPC259757
0.9545 High Similarity NPC183
0.9484 High Similarity NPC154304
0.9484 High Similarity NPC190487
0.9427 High Similarity NPC219927
0.9423 High Similarity NPC188967
0.9416 High Similarity NPC163780
0.9416 High Similarity NPC2476
0.9416 High Similarity NPC196439
0.9416 High Similarity NPC167815
0.9416 High Similarity NPC50715
0.9416 High Similarity NPC201136
0.9416 High Similarity NPC146165
0.9416 High Similarity NPC280339
0.9416 High Similarity NPC4455
0.9416 High Similarity NPC92659
0.9416 High Similarity NPC183597
0.9416 High Similarity NPC227325
0.9416 High Similarity NPC138360
0.9416 High Similarity NPC128863
0.9383 High Similarity NPC99591
0.9371 High Similarity NPC272560
0.9351 High Similarity NPC231018
0.9351 High Similarity NPC276409
0.9351 High Similarity NPC183878
0.9351 High Similarity NPC250822
0.9351 High Similarity NPC176775
0.9351 High Similarity NPC75279
0.9351 High Similarity NPC69394
0.9351 High Similarity NPC47781
0.9351 High Similarity NPC160951
0.9351 High Similarity NPC22519
0.9351 High Similarity NPC255350
0.9351 High Similarity NPC145379
0.9351 High Similarity NPC274327
0.9342 High Similarity NPC296197
0.9342 High Similarity NPC259713
0.9342 High Similarity NPC17286
0.9342 High Similarity NPC216318
0.9313 High Similarity NPC295082
0.9313 High Similarity NPC243877
0.9304 High Similarity NPC477841
0.9295 High Similarity NPC75215
0.9295 High Similarity NPC227192
0.9295 High Similarity NPC189179
0.9295 High Similarity NPC224137
0.9295 High Similarity NPC93376
0.929 High Similarity NPC20830
0.929 High Similarity NPC208197
0.929 High Similarity NPC213622
0.929 High Similarity NPC256612
0.9286 High Similarity NPC187498
0.9286 High Similarity NPC241498
0.9286 High Similarity NPC131624
0.9286 High Similarity NPC198826
0.9286 High Similarity NPC142540
0.9286 High Similarity NPC275722
0.9286 High Similarity NPC212678
0.9286 High Similarity NPC222830
0.9286 High Similarity NPC293183
0.9286 High Similarity NPC301323
0.9286 High Similarity NPC25270
0.9286 High Similarity NPC120163
0.9286 High Similarity NPC275836
0.9286 High Similarity NPC100887
0.9286 High Similarity NPC256283
0.9286 High Similarity NPC57030
0.9286 High Similarity NPC71334
0.9286 High Similarity NPC156222
0.9286 High Similarity NPC239128
0.9286 High Similarity NPC188203
0.9286 High Similarity NPC83508
0.9286 High Similarity NPC162313
0.9286 High Similarity NPC27208
0.9281 High Similarity NPC45873
0.9241 High Similarity NPC165970
0.9241 High Similarity NPC305987
0.9241 High Similarity NPC288131
0.9241 High Similarity NPC259456
0.9241 High Similarity NPC66618
0.9241 High Similarity NPC113163
0.9241 High Similarity NPC84324
0.9236 High Similarity NPC105242
0.9236 High Similarity NPC115798
0.9236 High Similarity NPC284127
0.9236 High Similarity NPC25495
0.9236 High Similarity NPC9609
0.9236 High Similarity NPC19687
0.9236 High Similarity NPC172202
0.9236 High Similarity NPC261004
0.9236 High Similarity NPC143828
0.9236 High Similarity NPC176300
0.9236 High Similarity NPC18607
0.9236 High Similarity NPC4481
0.9236 High Similarity NPC476410
0.9236 High Similarity NPC22472
0.9236 High Similarity NPC191459
0.9236 High Similarity NPC204854
0.9236 High Similarity NPC130894
0.9236 High Similarity NPC288669
0.9236 High Similarity NPC18772
0.9236 High Similarity NPC300943
0.9236 High Similarity NPC152166
0.9236 High Similarity NPC253634
0.9236 High Similarity NPC7846
0.9231 High Similarity NPC474520
0.9231 High Similarity NPC247017
0.9231 High Similarity NPC49824
0.9231 High Similarity NPC98661
0.9221 High Similarity NPC208043
0.9221 High Similarity NPC226973
0.9221 High Similarity NPC225731
0.9211 High Similarity NPC130230
0.9211 High Similarity NPC239312
0.9211 High Similarity NPC275772
0.9193 High Similarity NPC14662
0.9187 High Similarity NPC477840
0.9177 High Similarity NPC101731
0.9177 High Similarity NPC204290
0.9172 High Similarity NPC7973
0.9172 High Similarity NPC63454
0.9172 High Similarity NPC203891
0.9172 High Similarity NPC101830
0.9172 High Similarity NPC110070
0.9172 High Similarity NPC305663
0.9172 High Similarity NPC78302
0.9172 High Similarity NPC183851
0.9172 High Similarity NPC29841
0.9172 High Similarity NPC163524
0.9172 High Similarity NPC287979
0.9172 High Similarity NPC470402
0.9172 High Similarity NPC472438
0.9172 High Similarity NPC176665
0.9172 High Similarity NPC235215
0.9167 High Similarity NPC44079
0.9167 High Similarity NPC201451
0.9167 High Similarity NPC26227
0.9161 High Similarity NPC39732
0.9161 High Similarity NPC60972
0.9156 High Similarity NPC61620
0.9156 High Similarity NPC306821
0.9156 High Similarity NPC184136
0.9156 High Similarity NPC77858
0.915 High Similarity NPC12367
0.915 High Similarity NPC118726
0.9136 High Similarity NPC475212
0.9136 High Similarity NPC280493
0.913 High Similarity NPC171985
0.913 High Similarity NPC320741
0.9119 High Similarity NPC29876
0.9119 High Similarity NPC167678
0.9114 High Similarity NPC193842
0.9108 High Similarity NPC276444
0.9108 High Similarity NPC200388
0.9108 High Similarity NPC472916
0.9108 High Similarity NPC55619
0.9108 High Similarity NPC68093
0.9108 High Similarity NPC178854
0.9108 High Similarity NPC100916
0.9108 High Similarity NPC43243
0.9108 High Similarity NPC245546
0.9108 High Similarity NPC191146
0.9108 High Similarity NPC471985
0.9108 High Similarity NPC266960
0.9108 High Similarity NPC268161
0.9108 High Similarity NPC292107
0.9103 High Similarity NPC86485
0.9097 High Similarity NPC308451
0.9097 High Similarity NPC251110
0.9096 High Similarity NPC324742
0.9091 High Similarity NPC137062
0.9091 High Similarity NPC287101
0.9091 High Similarity NPC183950
0.9091 High Similarity NPC223579
0.9091 High Similarity NPC52005
0.9091 High Similarity NPC48479
0.9091 High Similarity NPC177298
0.9091 High Similarity NPC195351
0.9091 High Similarity NPC328119
0.9091 High Similarity NPC216307
0.9085 High Similarity NPC168803
0.9085 High Similarity NPC149846
0.9068 High Similarity NPC50960
0.9062 High Similarity NPC472448
0.9062 High Similarity NPC261470
0.9062 High Similarity NPC83922
0.9057 High Similarity NPC476980
0.9057 High Similarity NPC139036
0.9051 High Similarity NPC472911
0.9051 High Similarity NPC218871
0.9051 High Similarity NPC48208
0.9051 High Similarity NPC162869
0.9051 High Similarity NPC472914
0.9051 High Similarity NPC476630
0.9051 High Similarity NPC78225
0.9051 High Similarity NPC222814

  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 NPC196179 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
0.9351 High Similarity NPD2801 Approved
0.9013 High Similarity NPD1511 Approved
0.8951 High Similarity NPD6168 Clinical (unspecified phase)
0.8951 High Similarity NPD6167 Clinical (unspecified phase)
0.8951 High Similarity NPD6166 Phase 2
0.8896 High Similarity NPD1512 Approved
0.8797 High Similarity NPD1934 Approved
0.869 High Similarity NPD4338 Clinical (unspecified phase)
0.8675 High Similarity NPD7054 Approved
0.8634 High Similarity NPD4868 Clinical (unspecified phase)
0.8634 High Similarity NPD3882 Suspended
0.8625 High Similarity NPD2393 Clinical (unspecified phase)
0.8623 High Similarity NPD7472 Approved
0.8614 High Similarity NPD3818 Discontinued
0.8571 High Similarity NPD3817 Phase 2
0.8512 High Similarity NPD7074 Phase 3
0.8462 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD6797 Phase 2
0.8412 Intermediate Similarity NPD7251 Discontinued
0.8363 Intermediate Similarity NPD7808 Phase 3
0.8354 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD5402 Approved
0.8323 Intermediate Similarity NPD4380 Phase 2
0.8263 Intermediate Similarity NPD6232 Discontinued
0.8253 Intermediate Similarity NPD5494 Approved
0.8242 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD7473 Discontinued
0.8204 Intermediate Similarity NPD6959 Discontinued
0.8171 Intermediate Similarity NPD1465 Phase 2
0.8025 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD5844 Phase 1
0.8013 Intermediate Similarity NPD1510 Phase 2
0.8012 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD943 Approved
0.7978 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1549 Phase 2
0.7953 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD7411 Suspended
0.7919 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD3749 Approved
0.7917 Intermediate Similarity NPD7075 Discontinued
0.7914 Intermediate Similarity NPD5403 Approved
0.7848 Intermediate Similarity NPD2796 Approved
0.784 Intermediate Similarity NPD6799 Approved
0.7791 Intermediate Similarity NPD3926 Phase 2
0.7791 Intermediate Similarity NPD5401 Approved
0.7784 Intermediate Similarity NPD6801 Discontinued
0.7778 Intermediate Similarity NPD1247 Approved
0.7764 Intermediate Similarity NPD3750 Approved
0.7756 Intermediate Similarity NPD1240 Approved
0.7751 Intermediate Similarity NPD7768 Phase 2
0.7738 Intermediate Similarity NPD7819 Suspended
0.7738 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD7390 Discontinued
0.7727 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD1607 Approved
0.764 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD3787 Discontinued
0.7595 Intermediate Similarity NPD447 Suspended
0.7584 Intermediate Similarity NPD6559 Discontinued
0.7562 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6599 Discontinued
0.7557 Intermediate Similarity NPD3751 Discontinued
0.7545 Intermediate Similarity NPD1653 Approved
0.7532 Intermediate Similarity NPD1613 Approved
0.7532 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2935 Discontinued
0.75 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6190 Approved
0.75 Intermediate Similarity NPD8312 Approved
0.75 Intermediate Similarity NPD8313 Approved
0.7485 Intermediate Similarity NPD2800 Approved
0.7484 Intermediate Similarity NPD230 Phase 1
0.7471 Intermediate Similarity NPD7199 Phase 2
0.7457 Intermediate Similarity NPD919 Approved
0.7453 Intermediate Similarity NPD3748 Approved
0.741 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD1551 Phase 2
0.7396 Intermediate Similarity NPD3226 Approved
0.7386 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD2344 Approved
0.7356 Intermediate Similarity NPD6234 Discontinued
0.7342 Intermediate Similarity NPD3027 Phase 3
0.7322 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD2313 Discontinued
0.7296 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7228 Approved
0.7262 Intermediate Similarity NPD2534 Approved
0.7262 Intermediate Similarity NPD2532 Approved
0.7262 Intermediate Similarity NPD2533 Approved
0.7239 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6781 Approved
0.7225 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6776 Approved
0.7225 Intermediate Similarity NPD6778 Approved
0.7225 Intermediate Similarity NPD6782 Approved
0.7225 Intermediate Similarity NPD6779 Approved
0.7225 Intermediate Similarity NPD6780 Approved
0.7225 Intermediate Similarity NPD6777 Approved
0.7215 Intermediate Similarity NPD9494 Approved
0.7198 Intermediate Similarity NPD7685 Pre-registration
0.7197 Intermediate Similarity NPD1203 Approved
0.7195 Intermediate Similarity NPD6100 Approved
0.7195 Intermediate Similarity NPD6099 Approved
0.7186 Intermediate Similarity NPD2309 Approved
0.7179 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD920 Approved
0.717 Intermediate Similarity NPD4908 Phase 1
0.7169 Intermediate Similarity NPD1243 Approved
0.7168 Intermediate Similarity NPD37 Approved
0.716 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1933 Approved
0.7158 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4966 Approved
0.7143 Intermediate Similarity NPD5953 Discontinued
0.7143 Intermediate Similarity NPD4965 Approved
0.7143 Intermediate Similarity NPD4967 Phase 2
0.7134 Intermediate Similarity NPD3225 Approved
0.7134 Intermediate Similarity NPD2799 Discontinued
0.7126 Intermediate Similarity NPD4628 Phase 3
0.7126 Intermediate Similarity NPD8455 Phase 2
0.7117 Intermediate Similarity NPD6651 Approved
0.7115 Intermediate Similarity NPD9269 Phase 2
0.7113 Intermediate Similarity NPD7435 Discontinued
0.7107 Intermediate Similarity NPD8151 Discontinued
0.7091 Intermediate Similarity NPD5405 Approved
0.7091 Intermediate Similarity NPD5404 Approved
0.7091 Intermediate Similarity NPD5408 Approved
0.7091 Intermediate Similarity NPD5406 Approved
0.7081 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD7870 Phase 2
0.7077 Intermediate Similarity NPD7871 Phase 2
0.7069 Intermediate Similarity NPD6844 Discontinued
0.7065 Intermediate Similarity NPD7549 Discontinued
0.7065 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD2346 Discontinued
0.7041 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6233 Phase 2
0.7035 Intermediate Similarity NPD7783 Phase 2
0.7035 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD7286 Phase 2
0.7026 Intermediate Similarity NPD7698 Approved
0.7026 Intermediate Similarity NPD7697 Approved
0.7026 Intermediate Similarity NPD7696 Phase 3
0.7021 Intermediate Similarity NPD4287 Approved
0.7013 Intermediate Similarity NPD1548 Phase 1
0.7005 Intermediate Similarity NPD8150 Discontinued
0.6975 Remote Similarity NPD3268 Approved
0.6974 Remote Similarity NPD6823 Phase 2
0.697 Remote Similarity NPD7701 Phase 2
0.6963 Remote Similarity NPD6535 Approved
0.6963 Remote Similarity NPD6534 Approved
0.6957 Remote Similarity NPD6832 Phase 2
0.6943 Remote Similarity NPD422 Phase 1
0.6937 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6915 Remote Similarity NPD8434 Phase 2
0.6906 Remote Similarity NPD5242 Approved
0.69 Remote Similarity NPD7875 Clinical (unspecified phase)
0.69 Remote Similarity NPD7874 Approved
0.6899 Remote Similarity NPD9717 Approved
0.6897 Remote Similarity NPD7458 Discontinued
0.6894 Remote Similarity NPD3018 Phase 2
0.6893 Remote Similarity NPD4288 Approved
0.6875 Remote Similarity NPD2797 Approved
0.6875 Remote Similarity NPD4363 Phase 3
0.6875 Remote Similarity NPD1470 Approved
0.6875 Remote Similarity NPD4360 Phase 2
0.6871 Remote Similarity NPD3764 Approved
0.6871 Remote Similarity NPD6798 Discontinued
0.6868 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6866 Remote Similarity NPD7801 Approved
0.6859 Remote Similarity NPD9268 Approved
0.6856 Remote Similarity NPD7700 Phase 2
0.6856 Remote Similarity NPD7699 Phase 2
0.6851 Remote Similarity NPD7229 Phase 3
0.6848 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6835 Remote Similarity NPD1201 Approved
0.6835 Remote Similarity NPD1610 Phase 2
0.6835 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6834 Remote Similarity NPD7584 Approved
0.6828 Remote Similarity NPD7240 Approved
0.6826 Remote Similarity NPD7033 Discontinued
0.6826 Remote Similarity NPD4308 Phase 3
0.6818 Remote Similarity NPD6386 Approved
0.6818 Remote Similarity NPD6385 Approved
0.6802 Remote Similarity NPD4357 Discontinued
0.68 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6798 Remote Similarity NPD5353 Approved
0.6796 Remote Similarity NPD8127 Discontinued
0.6792 Remote Similarity NPD1481 Phase 2
0.6792 Remote Similarity NPD1608 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