Structure

Physi-Chem Properties

Molecular Weight:  179.07
Volume:  200.276
LogP:  3.292
LogD:  3.121
LogS:  -4.227
# Rotatable Bonds:  0
TPSA:  12.89
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.482
Synthetic Accessibility Score:  1.518
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.43
MDCK Permeability:  2.5003440896398388e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.336
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.992
30% Bioavailability (F30%):  0.784

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.86
Plasma Protein Binding (PPB):  95.26655578613281%
Volume Distribution (VD):  1.485
Pgp-substrate:  3.2265048027038574%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.368
CYP2C19-inhibitor:  0.684
CYP2C19-substrate:  0.254
CYP2C9-inhibitor:  0.249
CYP2C9-substrate:  0.853
CYP2D6-inhibitor:  0.55
CYP2D6-substrate:  0.909
CYP3A4-inhibitor:  0.13
CYP3A4-substrate:  0.179

ADMET: Excretion

Clearance (CL):  4.293
Half-life (T1/2):  0.25

ADMET: Toxicity

hERG Blockers:  0.131
Human Hepatotoxicity (H-HT):  0.377
Drug-inuced Liver Injury (DILI):  0.913
AMES Toxicity:  0.874
Rat Oral Acute Toxicity:  0.431
Maximum Recommended Daily Dose:  0.184
Skin Sensitization:  0.899
Carcinogencity:  0.756
Eye Corrosion:  0.06
Eye Irritation:  0.992
Respiratory Toxicity:  0.978

Download Data

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

  Natural Product: NPC169433

Natural Product ID:  NPC169433
Common Name*:   Benzo[F]Quinoline
IUPAC Name:   benzo[f]quinoline
Synonyms:  
Standard InCHIKey:  HCAUQPZEWLULFJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H9N/c1-2-5-11-10(4-1)7-8-13-12(11)6-3-9-14-13/h1-9H
SMILES:  c1ccc2c(c1)ccc1c2cccn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1565107
PubChem CID:   6796
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001908] Benzoquinolines

*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
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3478 Nelumbo nucifera Species Nelumbonaceae 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
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 31622.8 nM PMID[544735]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 37933.0 nM PMID[544736]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 44565.62 nM PMID[544737]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 75162.29 nM PMID[544737]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 55847.02 nM PMID[544737]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 79250.13 nM PMID[544737]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 85703.78 nM PMID[544737]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 58210.32 nM PMID[544737]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 47097.73 nM PMID[544737]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 58210.32 nM PMID[544737]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 98174.79 nM PMID[544737]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 83752.93 nM PMID[544737]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 85901.35 nM PMID[544737]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[544737]
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency n.a. 74978.0 nM PMID[544735]
NPT103 Individual Protein Nuclear receptor ROR-gamma Homo sapiens Potency n.a. 33491.5 nM PMID[544735]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 158489.3 nM PMID[544738]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 68101.6 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 21689.9 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 8573.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency = 25118.9 nM PMID[544735]
NPT610 Others Molecular identity unknown Potency n.a. 66824.2 nM PMID[544735]
NPT2 Others Unspecified Potency n.a. 61652.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13709.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34436.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38296.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48978.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2153.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21535.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24379.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 304.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12197.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43646.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68101.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10793.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30419.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6069.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43277.1 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 NPC169433 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
0.9185 High Similarity NPC314102
0.9185 High Similarity NPC251722
0.8923 High Similarity NPC46358
0.8881 High Similarity NPC282398
0.8844 High Similarity NPC215584
0.8844 High Similarity NPC44773
0.8712 High Similarity NPC122718
0.855 High Similarity NPC215519
0.8538 High Similarity NPC54102
0.8538 High Similarity NPC91958
0.8538 High Similarity NPC162689
0.8538 High Similarity NPC143603
0.8523 High Similarity NPC56765
0.8389 Intermediate Similarity NPC51054
0.8355 Intermediate Similarity NPC90723
0.8345 Intermediate Similarity NPC86288
0.8278 Intermediate Similarity NPC318065
0.8278 Intermediate Similarity NPC206819
0.8244 Intermediate Similarity NPC148140
0.8212 Intermediate Similarity NPC286427
0.8182 Intermediate Similarity NPC81561
0.8169 Intermediate Similarity NPC261195
0.8169 Intermediate Similarity NPC96102
0.8169 Intermediate Similarity NPC29886
0.8163 Intermediate Similarity NPC63545
0.8158 Intermediate Similarity NPC41257
0.8133 Intermediate Similarity NPC325903
0.8121 Intermediate Similarity NPC40070
0.8112 Intermediate Similarity NPC105127
0.8112 Intermediate Similarity NPC84911
0.8112 Intermediate Similarity NPC150259
0.8108 Intermediate Similarity NPC179787
0.8108 Intermediate Similarity NPC469811
0.8108 Intermediate Similarity NPC470111
0.8108 Intermediate Similarity NPC201380
0.8054 Intermediate Similarity NPC321911
0.8041 Intermediate Similarity NPC288838
0.8014 Intermediate Similarity NPC179365
0.8014 Intermediate Similarity NPC82295
0.8014 Intermediate Similarity NPC256893
0.8013 Intermediate Similarity NPC138842
0.8 Intermediate Similarity NPC110126
0.8 Intermediate Similarity NPC73767
0.8 Intermediate Similarity NPC33421
0.8 Intermediate Similarity NPC312092
0.7945 Intermediate Similarity NPC469768
0.7945 Intermediate Similarity NPC469779
0.7945 Intermediate Similarity NPC469780
0.7945 Intermediate Similarity NPC469783
0.7945 Intermediate Similarity NPC469761
0.7945 Intermediate Similarity NPC279081
0.7945 Intermediate Similarity NPC469767
0.7945 Intermediate Similarity NPC469784
0.7929 Intermediate Similarity NPC473762
0.7911 Intermediate Similarity NPC194411
0.791 Intermediate Similarity NPC297486
0.791 Intermediate Similarity NPC471402
0.791 Intermediate Similarity NPC240136
0.7891 Intermediate Similarity NPC469766
0.7881 Intermediate Similarity NPC53947
0.7872 Intermediate Similarity NPC473587
0.7838 Intermediate Similarity NPC190296
0.7832 Intermediate Similarity NPC473930
0.7829 Intermediate Similarity NPC470233
0.7823 Intermediate Similarity NPC230002
0.7817 Intermediate Similarity NPC475428
0.7806 Intermediate Similarity NPC293487
0.78 Intermediate Similarity NPC143872
0.7786 Intermediate Similarity NPC250361
0.7786 Intermediate Similarity NPC27802
0.7778 Intermediate Similarity NPC237188
0.7771 Intermediate Similarity NPC317105
0.7764 Intermediate Similarity NPC37423
0.7764 Intermediate Similarity NPC275305
0.7762 Intermediate Similarity NPC475450
0.7762 Intermediate Similarity NPC101165
0.7756 Intermediate Similarity NPC122141
0.7755 Intermediate Similarity NPC315348
0.7755 Intermediate Similarity NPC316811
0.7755 Intermediate Similarity NPC32002
0.775 Intermediate Similarity NPC201634
0.7742 Intermediate Similarity NPC236711
0.7742 Intermediate Similarity NPC216643
0.7733 Intermediate Similarity NPC159856
0.7733 Intermediate Similarity NPC314372
0.7733 Intermediate Similarity NPC285731
0.7724 Intermediate Similarity NPC198988
0.7718 Intermediate Similarity NPC20144
0.7714 Intermediate Similarity NPC245244
0.7714 Intermediate Similarity NPC166424
0.7714 Intermediate Similarity NPC146373
0.7707 Intermediate Similarity NPC225018
0.7692 Intermediate Similarity NPC6436
0.7692 Intermediate Similarity NPC69914
0.7692 Intermediate Similarity NPC477591
0.7681 Intermediate Similarity NPC265605
0.7681 Intermediate Similarity NPC182570
0.7681 Intermediate Similarity NPC48564
0.7671 Intermediate Similarity NPC325252
0.7669 Intermediate Similarity NPC68354
0.7658 Intermediate Similarity NPC478182
0.7658 Intermediate Similarity NPC478184
0.7654 Intermediate Similarity NPC297034
0.7643 Intermediate Similarity NPC470204
0.7643 Intermediate Similarity NPC476322
0.7635 Intermediate Similarity NPC88097
0.7635 Intermediate Similarity NPC104483
0.7632 Intermediate Similarity NPC471957
0.7625 Intermediate Similarity NPC70949
0.7622 Intermediate Similarity NPC476131
0.7622 Intermediate Similarity NPC176199
0.7622 Intermediate Similarity NPC215795
0.7595 Intermediate Similarity NPC470203
0.7595 Intermediate Similarity NPC478185
0.758 Intermediate Similarity NPC135141
0.758 Intermediate Similarity NPC92796
0.7571 Intermediate Similarity NPC290094
0.7569 Intermediate Similarity NPC22079
0.7562 Intermediate Similarity NPC478183
0.7562 Intermediate Similarity NPC56233
0.7557 Intermediate Similarity NPC76540
0.7557 Intermediate Similarity NPC231655
0.7535 Intermediate Similarity NPC476140
0.7532 Intermediate Similarity NPC24678
0.7532 Intermediate Similarity NPC105818
0.7518 Intermediate Similarity NPC27740
0.7516 Intermediate Similarity NPC129721
0.7516 Intermediate Similarity NPC21605
0.75 Intermediate Similarity NPC329825
0.75 Intermediate Similarity NPC274229
0.7484 Intermediate Similarity NPC216713
0.7484 Intermediate Similarity NPC470823
0.7469 Intermediate Similarity NPC91895
0.7469 Intermediate Similarity NPC32534
0.7467 Intermediate Similarity NPC59084
0.7467 Intermediate Similarity NPC115611
0.7467 Intermediate Similarity NPC2949
0.7455 Intermediate Similarity NPC157583
0.7452 Intermediate Similarity NPC476464
0.7438 Intermediate Similarity NPC265100
0.7436 Intermediate Similarity NPC259644
0.7436 Intermediate Similarity NPC469765
0.7436 Intermediate Similarity NPC469786
0.7436 Intermediate Similarity NPC141926
0.7436 Intermediate Similarity NPC25008
0.7436 Intermediate Similarity NPC200214
0.7436 Intermediate Similarity NPC469763
0.7436 Intermediate Similarity NPC469760
0.7436 Intermediate Similarity NPC73952
0.7427 Intermediate Similarity NPC95783
0.7417 Intermediate Similarity NPC63157
0.7417 Intermediate Similarity NPC473868
0.7413 Intermediate Similarity NPC169625
0.7413 Intermediate Similarity NPC202957
0.7407 Intermediate Similarity NPC63751
0.7407 Intermediate Similarity NPC201700
0.7405 Intermediate Similarity NPC193740
0.7405 Intermediate Similarity NPC167635
0.7403 Intermediate Similarity NPC477134
0.7394 Intermediate Similarity NPC280852
0.7389 Intermediate Similarity NPC70922
0.7389 Intermediate Similarity NPC211572
0.7389 Intermediate Similarity NPC34844
0.7389 Intermediate Similarity NPC80597
0.7389 Intermediate Similarity NPC75540
0.7389 Intermediate Similarity NPC212376
0.7376 Intermediate Similarity NPC41174
0.7362 Intermediate Similarity NPC97343
0.7358 Intermediate Similarity NPC80681
0.7351 Intermediate Similarity NPC284635
0.7342 Intermediate Similarity NPC469785
0.7338 Intermediate Similarity NPC316069
0.7333 Intermediate Similarity NPC471579
0.7317 Intermediate Similarity NPC82331
0.7315 Intermediate Similarity NPC218268
0.7312 Intermediate Similarity NPC279918
0.731 Intermediate Similarity NPC89490
0.7296 Intermediate Similarity NPC469762
0.729 Intermediate Similarity NPC477974
0.7279 Intermediate Similarity NPC235843
0.7278 Intermediate Similarity NPC476219
0.7273 Intermediate Similarity NPC470440
0.7273 Intermediate Similarity NPC204141
0.7267 Intermediate Similarity NPC282231
0.7267 Intermediate Similarity NPC125746
0.726 Intermediate Similarity NPC329896
0.726 Intermediate Similarity NPC475090
0.726 Intermediate Similarity NPC475105
0.725 Intermediate Similarity NPC230869
0.7246 Intermediate Similarity NPC151939
0.7233 Intermediate Similarity NPC184476
0.7231 Intermediate Similarity NPC83987
0.7229 Intermediate Similarity NPC293216
0.7222 Intermediate Similarity NPC194640
0.7205 Intermediate Similarity NPC131718
0.7202 Intermediate Similarity NPC12649
0.7194 Intermediate Similarity NPC476566
0.719 Intermediate Similarity NPC476454
0.7186 Intermediate Similarity NPC474958
0.7186 Intermediate Similarity NPC150048

  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 NPC169433 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
0.8929 High Similarity NPD1918 Clinical (unspecified phase)
0.8741 High Similarity NPD4547 Phase 3
0.8477 Intermediate Similarity NPD3323 Discontinued
0.8417 Intermediate Similarity NPD3944 Approved
0.8417 Intermediate Similarity NPD3942 Approved
0.8411 Intermediate Similarity NPD5315 Discontinued
0.8382 Intermediate Similarity NPD2118 Approved
0.8382 Intermediate Similarity NPD2119 Approved
0.8286 Intermediate Similarity NPD4030 Approved
0.8286 Intermediate Similarity NPD3385 Approved
0.8286 Intermediate Similarity NPD4028 Approved
0.8286 Intermediate Similarity NPD4029 Approved
0.8264 Intermediate Similarity NPD1722 Approved
0.8248 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.8248 Intermediate Similarity NPD991 Phase 2
0.82 Intermediate Similarity NPD975 Approved
0.82 Intermediate Similarity NPD977 Approved
0.82 Intermediate Similarity NPD976 Approved
0.8194 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD3100 Discontinued
0.8169 Intermediate Similarity NPD1255 Approved
0.8169 Intermediate Similarity NPD1253 Approved
0.8169 Intermediate Similarity NPD1254 Approved
0.8169 Intermediate Similarity NPD1256 Approved
0.8169 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.8163 Intermediate Similarity NPD1683 Approved
0.8129 Intermediate Similarity NPD947 Approved
0.8089 Intermediate Similarity NPD3610 Approved
0.8089 Intermediate Similarity NPD3609 Approved
0.8082 Intermediate Similarity NPD2006 Phase 2
0.8071 Intermediate Similarity NPD715 Phase 3
0.8071 Intermediate Similarity NPD3476 Approved
0.8071 Intermediate Similarity NPD3475 Approved
0.8065 Intermediate Similarity NPD2719 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD2720 Phase 1
0.8054 Intermediate Similarity NPD2430 Phase 2
0.8054 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.8027 Intermediate Similarity NPD5254 Discontinued
0.8026 Intermediate Similarity NPD2748 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD2837 Discontinued
0.8 Intermediate Similarity NPD2172 Phase 1
0.8 Intermediate Similarity NPD786 Approved
0.7986 Intermediate Similarity NPD6554 Approved
0.7986 Intermediate Similarity NPD45 Approved
0.7962 Intermediate Similarity NPD4638 Approved
0.7962 Intermediate Similarity NPD4640 Approved
0.7962 Intermediate Similarity NPD4639 Approved
0.7937 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD9583 Approved
0.7888 Intermediate Similarity NPD4181 Approved
0.7887 Intermediate Similarity NPD1251 Discontinued
0.7838 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD5436 Phase 1
0.777 Intermediate Similarity NPD9357 Approved
0.7764 Intermediate Similarity NPD4128 Approved
0.7755 Intermediate Similarity NPD2070 Approved
0.7755 Intermediate Similarity NPD2073 Approved
0.7755 Intermediate Similarity NPD2071 Approved
0.7755 Intermediate Similarity NPD2072 Approved
0.7755 Intermediate Similarity NPD2069 Approved
0.7755 Intermediate Similarity NPD2074 Approved
0.7755 Intermediate Similarity NPD2075 Approved
0.7755 Intermediate Similarity NPD2068 Approved
0.7748 Intermediate Similarity NPD1661 Suspended
0.7746 Intermediate Similarity NPD3654 Approved
0.7736 Intermediate Similarity NPD2641 Approved
0.7736 Intermediate Similarity NPD2640 Approved
0.7716 Intermediate Similarity NPD4075 Phase 2
0.7703 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD7469 Discontinued
0.7681 Intermediate Similarity NPD271 Approved
0.7681 Intermediate Similarity NPD268 Approved
0.7681 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD3505 Approved
0.7669 Intermediate Similarity NPD3506 Approved
0.7669 Intermediate Similarity NPD7111 Discontinued
0.7667 Intermediate Similarity NPD3401 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD3583 Phase 2
0.7643 Intermediate Similarity NPD1403 Approved
0.7643 Intermediate Similarity NPD1404 Approved
0.764 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD5021 Discontinued
0.7622 Intermediate Similarity NPD4076 Approved
0.7622 Intermediate Similarity NPD4079 Approved
0.7606 Intermediate Similarity NPD1598 Discontinued
0.76 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD1183 Approved
0.7564 Intermediate Similarity NPD2580 Discontinued
0.7561 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD9098 Phase 3
0.7557 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD4509 Discontinued
0.7548 Intermediate Similarity NPD3339 Approved
0.7545 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD5145 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD6281 Approved
0.7516 Intermediate Similarity NPD5862 Discovery
0.7516 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2390 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6497 Approved
0.7515 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1262 Discovery
0.75 Intermediate Similarity NPD2165 Phase 1
0.75 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4298 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD5400 Approved
0.7484 Intermediate Similarity NPD2882 Phase 1
0.747 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD1993 Approved
0.7466 Intermediate Similarity NPD1994 Approved
0.7466 Intermediate Similarity NPD1995 Approved
0.7453 Intermediate Similarity NPD2642 Approved
0.7453 Intermediate Similarity NPD2639 Approved
0.7452 Intermediate Similarity NPD3114 Approved
0.7452 Intermediate Similarity NPD3113 Approved
0.7452 Intermediate Similarity NPD3112 Approved
0.7452 Intermediate Similarity NPD3115 Approved
0.7451 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD5065 Approved
0.7439 Intermediate Similarity NPD3799 Suspended
0.7434 Intermediate Similarity NPD3813 Approved
0.7421 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD7394 Phase 2
0.7407 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD2865 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4703 Approved
0.7403 Intermediate Similarity NPD4702 Approved
0.7391 Intermediate Similarity NPD9392 Approved
0.7391 Intermediate Similarity NPD9396 Approved
0.7372 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD4510 Discontinued
0.7358 Intermediate Similarity NPD3433 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5418 Discontinued
0.7342 Intermediate Similarity NPD2150 Discontinued
0.7337 Intermediate Similarity NPD4957 Phase 2
0.7337 Intermediate Similarity NPD7564 Discontinued
0.7333 Intermediate Similarity NPD3859 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD2960 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD3961 Discontinued
0.7308 Intermediate Similarity NPD2465 Approved
0.7308 Intermediate Similarity NPD2466 Phase 3
0.7308 Intermediate Similarity NPD2462 Phase 3
0.7301 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD4326 Phase 2
0.7294 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD3348 Phase 2
0.7289 Intermediate Similarity NPD5100 Phase 3
0.7279 Intermediate Similarity NPD4824 Approved
0.7279 Intermediate Similarity NPD4823 Approved
0.7278 Intermediate Similarity NPD5105 Approved
0.7278 Intermediate Similarity NPD5106 Approved
0.7278 Intermediate Similarity NPD6285 Phase 2
0.7273 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7216 Approved
0.7273 Intermediate Similarity NPD7217 Approved
0.7267 Intermediate Similarity NPD2385 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4384 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD3262 Approved
0.7261 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD6158 Phase 2
0.7257 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD4902 Discontinued
0.7241 Intermediate Similarity NPD3404 Approved
0.723 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2896 Discontinued
0.7219 Intermediate Similarity NPD5806 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2310 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD8431 Approved
0.7205 Intermediate Similarity NPD112 Approved
0.7205 Intermediate Similarity NPD9705 Discontinued
0.72 Intermediate Similarity NPD792 Discontinued
0.7195 Intermediate Similarity NPD1292 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD2782 Approved
0.7178 Intermediate Similarity NPD2780 Approved
0.7175 Intermediate Similarity NPD6664 Approved
0.7171 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6771 Discontinued
0.716 Intermediate Similarity NPD2481 Approved
0.716 Intermediate Similarity NPD2479 Phase 3
0.7152 Intermediate Similarity NPD4641 Discontinued
0.7143 Intermediate Similarity NPD4047 Discontinued
0.7143 Intermediate Similarity NPD2144 Approved
0.7143 Intermediate Similarity NPD5255 Approved
0.7135 Intermediate Similarity NPD5892 Approved
0.7134 Intermediate Similarity NPD5538 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD3929 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD2140 Approved
0.7133 Intermediate Similarity NPD4880 Discontinued
0.7133 Intermediate Similarity NPD2142 Approved
0.7133 Intermediate Similarity NPD2141 Approved
0.7125 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD1895 Discontinued
0.7118 Intermediate Similarity NPD1707 Approved
0.7118 Intermediate Similarity NPD1708 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