Structure

Physi-Chem Properties

Molecular Weight:  184.1
Volume:  205.17
LogP:  1.98
LogD:  1.677
LogS:  -2.279
# Rotatable Bonds:  1
TPSA:  52.04
# H-Bond Aceptor:  2
# H-Bond Donor:  4
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.669
Synthetic Accessibility Score:  1.377
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.911
MDCK Permeability:  1.7099431715905666e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.965
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.599
30% Bioavailability (F30%):  0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.482
Plasma Protein Binding (PPB):  78.461181640625%
Volume Distribution (VD):  2.022
Pgp-substrate:  23.173311233520508%

ADMET: Metabolism

CYP1A2-inhibitor:  0.987
CYP1A2-substrate:  0.092
CYP2C19-inhibitor:  0.698
CYP2C19-substrate:  0.092
CYP2C9-inhibitor:  0.689
CYP2C9-substrate:  0.369
CYP2D6-inhibitor:  0.16
CYP2D6-substrate:  0.893
CYP3A4-inhibitor:  0.916
CYP3A4-substrate:  0.221

ADMET: Excretion

Clearance (CL):  11.377
Half-life (T1/2):  0.173

ADMET: Toxicity

hERG Blockers:  0.092
Human Hepatotoxicity (H-HT):  0.1
Drug-inuced Liver Injury (DILI):  0.578
AMES Toxicity:  0.98
Rat Oral Acute Toxicity:  0.875
Maximum Recommended Daily Dose:  0.176
Skin Sensitization:  0.942
Carcinogencity:  0.906
Eye Corrosion:  0.065
Eye Irritation:  0.982
Respiratory Toxicity:  0.988

Download Data

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

  Natural Product: NPC191444

Natural Product ID:  NPC191444
Common Name*:   Benzidine
IUPAC Name:   4-(4-aminophenyl)aniline
Synonyms:   Benzidine
Standard InCHIKey:  HFACYLZERDEVSX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
SMILES:  Nc1ccc(cc1)c1ccc(cc1)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL15901
PubChem CID:   7111
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000041] Biphenyls and derivatives
          • [CHEMONTID:0003955] Benzidines

*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
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[12932131]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[20460582]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[25172746]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[8910532]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota Tissue Culture n.a. n.a. Database[FooDB]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16501 Capsicum annuum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28251 Typha orientalis Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9822 Typha angustifolia Species Typhaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16501 Capsicum annuum Species Solanaceae 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
NPT839 Cell Line L6 Rattus norvegicus IC50 > 217000.0 nM PMID[501044]
NPT839 Cell Line L6 Rattus norvegicus Ratio > 152.0 n.a. PMID[501044]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 50118.7 nM PMID[501049]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 7.9 nM PMID[501049]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 25118.9 nM PMID[501049]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 44668.4 nM PMID[501049]
NPT1852 Individual Protein Rac GTPase-activating protein 1 Homo sapiens IC50 n.a. 7390.0 nM PMID[501051]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 19952.6 nM PMID[501051]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 19952.6 nM PMID[501051]
NPT158 Individual Protein Nuclear receptor subfamily 1 group I member 2 Rattus norvegicus Potency n.a. 44668.4 nM PMID[501049]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 10749.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 4855.8 nM PubChem BioAssay data set
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 1420.0 nM PMID[501044]
NPT35 Others n.a. Log S = -2.7 n.a. PMID[501045]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Km = 460000.0 nM PMID[501046]
NPT35 Others n.a. LogP = 1.34 n.a. PMID[501047]
NPT27 Others Unspecified log Pe = -4.46 n.a. PMID[501047]
NPT27 Others Unspecified log Ks = 3.35 n.a. PMID[501048]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 35481.3 nM PMID[501049]
NPT694 Individual Protein UDP-glucuronosyltransferase 1-3 Homo sapiens Activity = 5.0 pm/min/mg PMID[501050]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Activity = 240.0 pm/min/mg PMID[501050]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Activity = 204.0 pm/min/mg PMID[501050]
NPT2 Others Unspecified IC50 n.a. 8000.0 nM PMID[501051]
NPT2 Others Unspecified Potency n.a. 42163.2 nM PMID[501049]
NPT2 Others Unspecified Inhibition = 23.35 % PMID[501052]
NPT2 Others Unspecified Potency n.a. 2433.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24064.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15355.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10870.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9580.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5387.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38457.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 67823.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9660.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15183.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3814 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 9688.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10838.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60447.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10749.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12060.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6113.1 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 NPC191444 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
0.9881 High Similarity NPC176858
0.908 High Similarity NPC30445
0.8889 High Similarity NPC108800
0.8652 High Similarity NPC111233
0.8352 Intermediate Similarity NPC173991
0.8132 Intermediate Similarity NPC262295
0.8119 Intermediate Similarity NPC434
0.7889 Intermediate Similarity NPC119677
0.7791 Intermediate Similarity NPC301874
0.7767 Intermediate Similarity NPC79618
0.7738 Intermediate Similarity NPC271732
0.7692 Intermediate Similarity NPC302790
0.76 Intermediate Similarity NPC323726
0.7527 Intermediate Similarity NPC229477
0.7416 Intermediate Similarity NPC325662
0.7416 Intermediate Similarity NPC98269
0.732 Intermediate Similarity NPC78154
0.7282 Intermediate Similarity NPC291610
0.7234 Intermediate Similarity NPC169016
0.7126 Intermediate Similarity NPC219246
0.7126 Intermediate Similarity NPC229235
0.7079 Intermediate Similarity NPC122327
0.7079 Intermediate Similarity NPC112609
0.7079 Intermediate Similarity NPC113000
0.7043 Intermediate Similarity NPC161052
0.7043 Intermediate Similarity NPC258787
0.7033 Intermediate Similarity NPC290638
0.703 Intermediate Similarity NPC329430
0.7024 Intermediate Similarity NPC113670
0.7 Intermediate Similarity NPC276699
0.6983 Remote Similarity NPC475915
0.6981 Remote Similarity NPC38262
0.6964 Remote Similarity NPC205652
0.6947 Remote Similarity NPC134825
0.6944 Remote Similarity NPC172170
0.6923 Remote Similarity NPC132146
0.6907 Remote Similarity NPC258046
0.6903 Remote Similarity NPC317031
0.6889 Remote Similarity NPC66775
0.6875 Remote Similarity NPC314141
0.6875 Remote Similarity NPC187036
0.6814 Remote Similarity NPC470550
0.681 Remote Similarity NPC226143
0.68 Remote Similarity NPC92689
0.6789 Remote Similarity NPC37584
0.6786 Remote Similarity NPC246588
0.6783 Remote Similarity NPC313449
0.6782 Remote Similarity NPC267443
0.6774 Remote Similarity NPC12857
0.675 Remote Similarity NPC474926
0.6744 Remote Similarity NPC291066
0.6739 Remote Similarity NPC139658
0.6737 Remote Similarity NPC307456
0.6733 Remote Similarity NPC470926
0.67 Remote Similarity NPC315403
0.6694 Remote Similarity NPC252794
0.664 Remote Similarity NPC179365
0.6639 Remote Similarity NPC145754
0.6639 Remote Similarity NPC250361
0.6639 Remote Similarity NPC268534
0.6638 Remote Similarity NPC192209
0.663 Remote Similarity NPC98976
0.6629 Remote Similarity NPC246822
0.6629 Remote Similarity NPC213570
0.6629 Remote Similarity NPC473206
0.6629 Remote Similarity NPC139416
0.6609 Remote Similarity NPC288232
0.6598 Remote Similarity NPC15839
0.6598 Remote Similarity NPC104070
0.6581 Remote Similarity NPC264580
0.6579 Remote Similarity NPC296163
0.6577 Remote Similarity NPC164802
0.6574 Remote Similarity NPC178681
0.656 Remote Similarity NPC282398
0.6559 Remote Similarity NPC271642
0.6556 Remote Similarity NPC72670
0.6556 Remote Similarity NPC263385
0.6556 Remote Similarity NPC251490
0.6555 Remote Similarity NPC215519
0.6552 Remote Similarity NPC313673
0.6552 Remote Similarity NPC147957
0.6548 Remote Similarity NPC114327
0.6548 Remote Similarity NPC36357
0.6532 Remote Similarity NPC473762
0.6531 Remote Similarity NPC133162
0.6529 Remote Similarity NPC192533
0.6525 Remote Similarity NPC162689
0.6525 Remote Similarity NPC54102
0.6522 Remote Similarity NPC299134
0.6512 Remote Similarity NPC71009
0.6512 Remote Similarity NPC22786
0.65 Remote Similarity NPC43655
0.6496 Remote Similarity NPC148140
0.6484 Remote Similarity NPC158028
0.6484 Remote Similarity NPC193578
0.6484 Remote Similarity NPC226999
0.6484 Remote Similarity NPC39799
0.6484 Remote Similarity NPC280135
0.6484 Remote Similarity NPC1008
0.6484 Remote Similarity NPC87099
0.6484 Remote Similarity NPC135433
0.6481 Remote Similarity NPC239854
0.648 Remote Similarity NPC473587
0.6475 Remote Similarity NPC122718
0.6471 Remote Similarity NPC317564
0.6452 Remote Similarity NPC328590
0.6442 Remote Similarity NPC476483
0.6442 Remote Similarity NPC322040
0.6441 Remote Similarity NPC81561
0.6436 Remote Similarity NPC297532
0.6429 Remote Similarity NPC22079
0.6429 Remote Similarity NPC475428
0.6422 Remote Similarity NPC474430
0.6413 Remote Similarity NPC1901
0.6413 Remote Similarity NPC244738
0.6395 Remote Similarity NPC135924
0.6381 Remote Similarity NPC108339
0.6378 Remote Similarity NPC475450
0.6373 Remote Similarity NPC240134
0.6373 Remote Similarity NPC107135
0.6364 Remote Similarity NPC328877
0.6344 Remote Similarity NPC258492
0.6344 Remote Similarity NPC96835
0.6337 Remote Similarity NPC60408
0.6333 Remote Similarity NPC179605
0.6333 Remote Similarity NPC279385
0.6328 Remote Similarity NPC473930
0.6322 Remote Similarity NPC200745
0.6322 Remote Similarity NPC29680
0.632 Remote Similarity NPC209389
0.6311 Remote Similarity NPC41174
0.631 Remote Similarity NPC198841
0.6293 Remote Similarity NPC57051
0.6286 Remote Similarity NPC469330
0.6281 Remote Similarity NPC103292
0.6277 Remote Similarity NPC307195
0.625 Remote Similarity NPC88566
0.625 Remote Similarity NPC50266
0.6241 Remote Similarity NPC473429
0.6235 Remote Similarity NPC65873
0.6235 Remote Similarity NPC120441
0.6235 Remote Similarity NPC300345
0.6235 Remote Similarity NPC212114
0.6231 Remote Similarity NPC198988
0.6207 Remote Similarity NPC248705
0.6207 Remote Similarity NPC210849
0.6207 Remote Similarity NPC238023
0.6207 Remote Similarity NPC54368
0.6207 Remote Similarity NPC150196
0.6207 Remote Similarity NPC310758
0.619 Remote Similarity NPC149436
0.6186 Remote Similarity NPC222982
0.6183 Remote Similarity NPC325252
0.618 Remote Similarity NPC155172
0.618 Remote Similarity NPC264470
0.618 Remote Similarity NPC198023
0.618 Remote Similarity NPC32312
0.6161 Remote Similarity NPC474695
0.616 Remote Similarity NPC322433
0.6148 Remote Similarity NPC257490
0.6142 Remote Similarity NPC472245
0.6136 Remote Similarity NPC314102
0.6136 Remote Similarity NPC251722
0.6136 Remote Similarity NPC66517
0.6118 Remote Similarity NPC269586
0.6117 Remote Similarity NPC262393
0.6116 Remote Similarity NPC91958
0.6111 Remote Similarity NPC178527
0.6111 Remote Similarity NPC36440
0.6111 Remote Similarity NPC478079
0.6106 Remote Similarity NPC473498
0.6092 Remote Similarity NPC147062
0.6087 Remote Similarity NPC200936
0.6082 Remote Similarity NPC66270
0.6082 Remote Similarity NPC245896
0.6082 Remote Similarity NPC255345
0.6078 Remote Similarity NPC203076
0.6071 Remote Similarity NPC275467
0.6067 Remote Similarity NPC21211
0.6067 Remote Similarity NPC45756
0.6066 Remote Similarity NPC150323
0.6064 Remote Similarity NPC54269
0.6063 Remote Similarity NPC197680
0.6063 Remote Similarity NPC259098
0.6061 Remote Similarity NPC96102
0.6061 Remote Similarity NPC231986
0.6061 Remote Similarity NPC218268
0.6055 Remote Similarity NPC317642
0.6045 Remote Similarity NPC312092
0.6045 Remote Similarity NPC88097
0.6044 Remote Similarity NPC6107
0.6042 Remote Similarity NPC110264
0.602 Remote Similarity NPC159661
0.6019 Remote Similarity NPC473031
0.6019 Remote Similarity NPC471320
0.6019 Remote Similarity NPC471319
0.6018 Remote Similarity NPC313362
0.6016 Remote Similarity NPC9856
0.6015 Remote Similarity NPC105127
0.6015 Remote Similarity NPC84911

  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 NPC191444 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
0.798 Intermediate Similarity NPD4735 Approved
0.798 Intermediate Similarity NPD4734 Approved
0.7642 Intermediate Similarity NPD2038 Approved
0.7642 Intermediate Similarity NPD2039 Approved
0.7596 Intermediate Similarity NPD6300 Approved
0.7596 Intermediate Similarity NPD6299 Approved
0.75 Intermediate Similarity NPD990 Approved
0.75 Intermediate Similarity NPD993 Approved
0.7477 Intermediate Similarity NPD2999 Approved
0.7477 Intermediate Similarity NPD3001 Approved
0.7453 Intermediate Similarity NPD7633 Discontinued
0.7442 Intermediate Similarity NPD294 Approved
0.7442 Intermediate Similarity NPD292 Approved
0.7333 Intermediate Similarity NPD3546 Approved
0.7333 Intermediate Similarity NPD3545 Approved
0.729 Intermediate Similarity NPD4116 Approved
0.7264 Intermediate Similarity NPD4115 Approved
0.7264 Intermediate Similarity NPD4114 Approved
0.7264 Intermediate Similarity NPD5253 Approved
0.7174 Intermediate Similarity NPD1617 Discontinued
0.7143 Intermediate Similarity NPD9563 Approved
0.7143 Intermediate Similarity NPD79 Approved
0.7143 Intermediate Similarity NPD9564 Approved
0.713 Intermediate Similarity NPD1539 Approved
0.7079 Intermediate Similarity NPD9591 Approved
0.7079 Intermediate Similarity NPD9592 Approved
0.7079 Intermediate Similarity NPD9593 Approved
0.7079 Intermediate Similarity NPD9594 Approved
0.7079 Intermediate Similarity NPD9589 Approved
0.7079 Intermediate Similarity NPD9590 Approved
0.7079 Intermediate Similarity NPD9588 Approved
0.7079 Intermediate Similarity NPD80 Approved
0.7053 Intermediate Similarity NPD9395 Approved
0.703 Intermediate Similarity NPD5554 Approved
0.7027 Intermediate Similarity NPD2913 Approved
0.7027 Intermediate Similarity NPD2914 Approved
0.7024 Intermediate Similarity NPD675 Discontinued
0.6961 Remote Similarity NPD2005 Discontinued
0.6961 Remote Similarity NPD2507 Clinical (unspecified phase)
0.6947 Remote Similarity NPD2001 Discontinued
0.6916 Remote Similarity NPD564 Approved
0.6916 Remote Similarity NPD563 Approved
0.6893 Remote Similarity NPD716 Approved
0.6882 Remote Similarity NPD589 Approved
0.6882 Remote Similarity NPD590 Approved
0.6875 Remote Similarity NPD2539 Approved
0.6875 Remote Similarity NPD2538 Approved
0.687 Remote Similarity NPD1216 Clinical (unspecified phase)
0.6869 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2463 Approved
0.6842 Remote Similarity NPD2464 Approved
0.6842 Remote Similarity NPD2467 Approved
0.6842 Remote Similarity NPD1596 Approved
0.6838 Remote Similarity NPD1236 Phase 3
0.6837 Remote Similarity NPD4145 Approved
0.6837 Remote Similarity NPD4146 Approved
0.6833 Remote Similarity NPD6900 Discontinued
0.6822 Remote Similarity NPD2795 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1108 Approved
0.6818 Remote Similarity NPD1107 Approved
0.6814 Remote Similarity NPD5631 Phase 3
0.6814 Remote Similarity NPD5629 Discontinued
0.6809 Remote Similarity NPD260 Discontinued
0.6807 Remote Similarity NPD1640 Clinical (unspecified phase)
0.6807 Remote Similarity NPD2938 Approved
0.6807 Remote Similarity NPD2940 Approved
0.6803 Remote Similarity NPD2919 Clinical (unspecified phase)
0.6803 Remote Similarity NPD2918 Clinical (unspecified phase)
0.68 Remote Similarity NPD5915 Approved
0.6783 Remote Similarity NPD7481 Approved
0.6783 Remote Similarity NPD7480 Approved
0.6774 Remote Similarity NPD295 Approved
0.6774 Remote Similarity NPD9393 Approved
0.6774 Remote Similarity NPD293 Approved
0.6774 Remote Similarity NPD296 Approved
0.6774 Remote Similarity NPD9397 Approved
0.6765 Remote Similarity NPD464 Approved
0.6765 Remote Similarity NPD463 Approved
0.6765 Remote Similarity NPD462 Approved
0.6762 Remote Similarity NPD1946 Clinical (unspecified phase)
0.6754 Remote Similarity NPD1720 Phase 2
0.6754 Remote Similarity NPD1723 Phase 2
0.675 Remote Similarity NPD1036 Approved
0.6748 Remote Similarity NPD947 Approved
0.6737 Remote Similarity NPD3035 Approved
0.6733 Remote Similarity NPD3000 Approved
0.6733 Remote Similarity NPD2998 Approved
0.6733 Remote Similarity NPD2997 Approved
0.6733 Remote Similarity NPD4543 Discontinued
0.6727 Remote Similarity NPD1721 Clinical (unspecified phase)
0.6726 Remote Similarity NPD5180 Approved
0.6726 Remote Similarity NPD5179 Approved
0.6726 Remote Similarity NPD5181 Approved
0.6703 Remote Similarity NPD505 Clinical (unspecified phase)
0.67 Remote Similarity NPD9108 Approved
0.6698 Remote Similarity NPD1916 Discontinued
0.6696 Remote Similarity NPD6660 Discontinued
0.6694 Remote Similarity NPD1950 Approved
0.6694 Remote Similarity NPD1949 Approved
0.6667 Remote Similarity NPD4170 Approved
0.6667 Remote Similarity NPD4405 Approved
0.6667 Remote Similarity NPD4936 Approved
0.6667 Remote Similarity NPD4408 Approved
0.6667 Remote Similarity NPD4407 Approved
0.6667 Remote Similarity NPD3426 Approved
0.6667 Remote Similarity NPD2002 Discontinued
0.6667 Remote Similarity NPD4169 Approved
0.6667 Remote Similarity NPD3428 Approved
0.6667 Remote Similarity NPD4701 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4937 Approved
0.6638 Remote Similarity NPD299 Phase 3
0.6636 Remote Similarity NPD1417 Approved
0.6636 Remote Similarity NPD1419 Approved
0.6636 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6633 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6320 Approved
0.661 Remote Similarity NPD2338 Clinical (unspecified phase)
0.6609 Remote Similarity NPD224 Phase 2
0.6602 Remote Similarity NPD6549 Approved
0.6602 Remote Similarity NPD4545 Approved
0.6602 Remote Similarity NPD6548 Approved
0.6602 Remote Similarity NPD4542 Approved
0.6598 Remote Similarity NPD262 Approved
0.6598 Remote Similarity NPD263 Approved
0.6587 Remote Similarity NPD5182 Approved
0.6587 Remote Similarity NPD5184 Approved
0.6587 Remote Similarity NPD5185 Approved
0.6581 Remote Similarity NPD922 Approved
0.6577 Remote Similarity NPD477 Phase 1
0.6574 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6531 Remote Similarity NPD3427 Approved
0.6531 Remote Similarity NPD785 Approved
0.6531 Remote Similarity NPD3429 Approved
0.6531 Remote Similarity NPD5178 Approved
0.6525 Remote Similarity NPD3498 Approved
0.6525 Remote Similarity NPD3499 Approved
0.6525 Remote Similarity NPD1479 Clinical (unspecified phase)
0.6518 Remote Similarity NPD3548 Approved
0.6505 Remote Similarity NPD9361 Approved
0.6491 Remote Similarity NPD181 Approved
0.6489 Remote Similarity NPD4147 Approved
0.6489 Remote Similarity NPD603 Approved
0.6489 Remote Similarity NPD4144 Approved
0.648 Remote Similarity NPD3841 Phase 3
0.648 Remote Similarity NPD4866 Approved
0.648 Remote Similarity NPD4867 Approved
0.6475 Remote Similarity NPD4985 Clinical (unspecified phase)
0.6471 Remote Similarity NPD2340 Discontinued
0.6471 Remote Similarity NPD1525 Approved
0.6471 Remote Similarity NPD6892 Discontinued
0.6458 Remote Similarity NPD5372 Approved
0.6458 Remote Similarity NPD5371 Approved
0.6452 Remote Similarity NPD4549 Discontinued
0.6449 Remote Similarity NPD4737 Phase 2
0.6446 Remote Similarity NPD964 Approved
0.6442 Remote Similarity NPD736 Approved
0.6442 Remote Similarity NPD8 Approved
0.6442 Remote Similarity NPD243 Approved
0.6442 Remote Similarity NPD1394 Approved
0.6442 Remote Similarity NPD735 Approved
0.6441 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5675 Discontinued
0.6436 Remote Similarity NPD3345 Approved
0.6435 Remote Similarity NPD1175 Approved
0.6434 Remote Similarity NPD1253 Approved
0.6434 Remote Similarity NPD1256 Approved
0.6434 Remote Similarity NPD1255 Approved
0.6434 Remote Similarity NPD1254 Approved
0.6429 Remote Similarity NPD831 Approved
0.6429 Remote Similarity NPD7156 Discontinued
0.6429 Remote Similarity NPD4635 Approved
0.6429 Remote Similarity NPD830 Approved
0.6417 Remote Similarity NPD1517 Clinical (unspecified phase)
0.6417 Remote Similarity NPD1079 Discontinued
0.6417 Remote Similarity NPD1124 Approved
0.6417 Remote Similarity NPD1123 Approved
0.6415 Remote Similarity NPD9352 Approved
0.6415 Remote Similarity NPD5597 Approved
0.6415 Remote Similarity NPD5598 Approved
0.6413 Remote Similarity NPD9728 Phase 1
0.6412 Remote Similarity NPD2010 Phase 3
0.641 Remote Similarity NPD6070 Approved
0.641 Remote Similarity NPD6069 Approved
0.64 Remote Similarity NPD4636 Approved
0.64 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6396 Remote Similarity NPD1064 Approved
0.6396 Remote Similarity NPD1065 Approved
0.6392 Remote Similarity NPD4027 Approved
0.6392 Remote Similarity NPD4026 Approved
0.6387 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6381 Remote Similarity NPD665 Phase 2
0.6381 Remote Similarity NPD9188 Approved
0.6379 Remote Similarity NPD1813 Discontinued
0.6378 Remote Similarity NPD1251 Discontinued
0.6378 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6371 Remote Similarity NPD1560 Clinical (unspecified phase)
0.6364 Remote Similarity NPD173 Clinical (unspecified phase)
0.6357 Remote Similarity NPD5227 Clinical (unspecified phase)
0.6356 Remote Similarity NPD153 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6499 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