Structure

Physi-Chem Properties

Molecular Weight:  232.1
Volume:  251.968
LogP:  3.939
LogD:  3.606
LogS:  -5.781
# Rotatable Bonds:  0
TPSA:  17.82
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  1.857
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.76
MDCK Permeability:  2.0201103325234726e-05
Pgp-inhibitor:  0.088
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.886
30% Bioavailability (F30%):  0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.944
Plasma Protein Binding (PPB):  97.03168487548828%
Volume Distribution (VD):  0.839
Pgp-substrate:  1.02853524684906%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.557
CYP2C19-inhibitor:  0.813
CYP2C19-substrate:  0.091
CYP2C9-inhibitor:  0.398
CYP2C9-substrate:  0.762
CYP2D6-inhibitor:  0.517
CYP2D6-substrate:  0.888
CYP3A4-inhibitor:  0.374
CYP3A4-substrate:  0.204

ADMET: Excretion

Clearance (CL):  4.835
Half-life (T1/2):  0.156

ADMET: Toxicity

hERG Blockers:  0.121
Human Hepatotoxicity (H-HT):  0.321
Drug-inuced Liver Injury (DILI):  0.278
AMES Toxicity:  0.945
Rat Oral Acute Toxicity:  0.192
Maximum Recommended Daily Dose:  0.774
Skin Sensitization:  0.207
Carcinogencity:  0.869
Eye Corrosion:  0.007
Eye Irritation:  0.983
Respiratory Toxicity:  0.329

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

  Natural Product: NPC288232

Natural Product ID:  NPC288232
Common Name*:   Neocryptolepine
IUPAC Name:   5-methylindolo[2,3-b]quinoline
Synonyms:  
Standard InCHIKey:  PZIIKMBOSNKNFZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12N2/c1-18-15-9-5-2-6-11(15)10-13-12-7-3-4-8-14(12)17-16(13)18/h2-10H,1H3
SMILES:  Cn1c2ccccc2cc2c1nc1c2cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL115585
PubChem CID:   390526
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0001734] Pyrroloquinolines

*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
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. n.a. n.a. PMID[14640526]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. depth of 25 m off the shore of Keomun Island, Korea 2004-AUG PMID[18407691]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[2853205]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9249972]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[9667966]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20299 Strongylophora durissima n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18755 Fumaria judaica Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21890 Epidendrum moseni Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20169 Alseodaphne perakensis Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20989 Calea integrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11155 Ambrosia maritima Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17958 Cryptolepis sanguinolenta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24783 Erysimum diffusum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20912 Wisteria brachybotrys Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20237 Poecillastra wondoensis Species Vulcanellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17131 Yucca periculosa Species Asparagaceae 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
NPT91 Cell Line KB Homo sapiens ID50 = 0.006 uM ml-1 PMID[533108]
NPT171 Cell Line MRC5 Homo sapiens IC50 = 11000.0 nM PMID[533109]
NPT2249 Individual Protein Histidine-rich protein Plasmodium falciparum IC50 = 5.97 milliequivalent PMID[533111]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 4265.8 nM PMID[533114]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 3133.29 nM PMID[533114]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2060.63 nM PMID[533114]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 3349.65 nM PMID[533114]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2600.16 nM PMID[533114]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 3061.96 nM PMID[533114]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 2382.32 nM PMID[533114]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 6823.39 nM PMID[533114]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 3047.89 nM PMID[533114]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 3303.7 nM PMID[533114]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2857.59 nM PMID[533114]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 3411.93 nM PMID[533114]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 5116.82 nM PMID[533114]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 5176.07 nM PMID[533114]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1377.21 nM PMID[533114]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 2766.94 nM PMID[533114]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 4178.3 nM PMID[533114]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 2483.13 nM PMID[533114]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 4111.5 nM PMID[533114]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 5584.7 nM PMID[533114]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 5942.92 nM PMID[533114]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 2197.86 nM PMID[533114]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 7638.36 nM PMID[533114]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 3681.29 nM PMID[533114]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 2070.14 nM PMID[533114]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2182.73 nM PMID[533114]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 2233.57 nM PMID[533114]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 4285.49 nM PMID[533114]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 2449.06 nM PMID[533114]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 3801.89 nM PMID[533114]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 3265.88 nM PMID[533114]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 3191.54 nM PMID[533114]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 3944.57 nM PMID[533114]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 2477.42 nM PMID[533114]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 3380.65 nM PMID[533114]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 3221.07 nM PMID[533114]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1140.25 nM PMID[533114]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1798.87 nM PMID[533114]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 3944.57 nM PMID[533114]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 2275.1 nM PMID[533114]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 3303.7 nM PMID[533114]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2741.57 nM PMID[533114]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 6471.43 nM PMID[533114]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 4808.39 nM PMID[533114]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2382.32 nM PMID[533114]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2600.16 nM PMID[533114]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 3054.92 nM PMID[533114]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 4591.98 nM PMID[533114]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 4197.59 nM PMID[533114]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2703.96 nM PMID[533114]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 4549.88 nM PMID[533114]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 3837.07 nM PMID[533114]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 3908.41 nM PMID[533114]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 3147.75 nM PMID[533114]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2506.11 nM PMID[533114]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 3459.39 nM PMID[533114]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 4875.28 nM PMID[533114]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 3451.44 nM PMID[533114]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 2930.89 nM PMID[533114]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 3194.0 nM PMID[533116]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 3194.0 nM PMID[533117]
NPT35 Others n.a. pKa = 7.24 n.a. PMID[533108]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 250000.0 nM PMID[533108]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 250000.0 nM PMID[533108]
NPT20 Organism Candida albicans Candida albicans MIC = 120000.0 nM PMID[533108]
NPT3173 Organism Arthroderma benhamiae Arthroderma benhamiae MIC = 60000.0 nM PMID[533108]
NPT317 Uncleic Acid Nucleic Acid Delta Tm = 5.2 degrees C PMID[533108]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 27300.0 nM PMID[533109]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 14000.0 nM PMID[533109]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 4000.0 nM PMID[533109]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 4000.0 nM PMID[533109]
NPT317 Uncleic Acid Nucleic Acid IC50 = 92800.0 nM PMID[533109]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.035 ug.mL-1 PMID[533110]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.065 ug.mL-1 PMID[533110]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.051 ug.mL-1 PMID[533110]
NPT2 Others Unspecified Ratio IC50 = 0.4 n.a. PMID[533111]
NPT317 Uncleic Acid Nucleic Acid IC50 = 93000.0 nM PMID[533111]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 27000.0 nM PMID[533111]
NPT27 Others Unspecified IC50 = 11000.0 nM PMID[533111]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 14000.0 nM PMID[533113]
NPT1018 Organism Trypanosoma brucei Trypanosoma brucei IC50 = 4000.0 nM PMID[533113]
NPT2254 Organism Schistosoma mansoni Schistosoma mansoni mortality = 5.0 % PMID[533115]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Ratio IC50 = 1.1 n.a. PMID[533116]
NPT2 Others Unspecified Ratio IC50 = 1.9 n.a. PMID[533116]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 1696.0 nM PMID[533116]
NPT2 Others Unspecified Ratio IC50 = 2.0 n.a. PMID[533116]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1580.0 nM PMID[533116]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Ratio IC50 = 1.07 n.a. PMID[533117]
NPT2 Others Unspecified Ratio IC50 = 1.88 n.a. PMID[533117]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 1696.0 nM PMID[533117]
NPT2 Others Unspecified Ratio IC50 = 2.0 n.a. PMID[533117]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 1580.0 nM PMID[533117]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 0.027 ug.mL-1 PMID[533118]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 0.027 ug.mL-1 PMID[533118]

☑ 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 NPC288232 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
0.8929 High Similarity NPC187036
0.8929 High Similarity NPC296163
0.8783 High Similarity NPC192209
0.8482 Intermediate Similarity NPC164802
0.8151 Intermediate Similarity NPC313449
0.7966 Intermediate Similarity NPC314141
0.7953 Intermediate Similarity NPC9856
0.7923 Intermediate Similarity NPC300299
0.7788 Intermediate Similarity NPC291610
0.7692 Intermediate Similarity NPC302790
0.7642 Intermediate Similarity NPC264580
0.7576 Intermediate Similarity NPC184437
0.748 Intermediate Similarity NPC328683
0.748 Intermediate Similarity NPC283130
0.7385 Intermediate Similarity NPC476950
0.7372 Intermediate Similarity NPC2823
0.7299 Intermediate Similarity NPC207554
0.7246 Intermediate Similarity NPC471574
0.7226 Intermediate Similarity NPC83214
0.7188 Intermediate Similarity NPC257490
0.7167 Intermediate Similarity NPC79618
0.7143 Intermediate Similarity NPC226662
0.7121 Intermediate Similarity NPC478079
0.7092 Intermediate Similarity NPC136002
0.7054 Intermediate Similarity NPC475915
0.7037 Intermediate Similarity NPC207428
0.7031 Intermediate Similarity NPC162689
0.7031 Intermediate Similarity NPC54102
0.7008 Intermediate Similarity NPC148140
0.6993 Remote Similarity NPC469735
0.6978 Remote Similarity NPC125746
0.6975 Remote Similarity NPC474430
0.697 Remote Similarity NPC122718
0.6953 Remote Similarity NPC81561
0.6944 Remote Similarity NPC469740
0.6939 Remote Similarity NPC295021
0.6929 Remote Similarity NPC147957
0.6917 Remote Similarity NPC252794
0.6912 Remote Similarity NPC53044
0.6912 Remote Similarity NPC22079
0.6903 Remote Similarity NPC78154
0.6899 Remote Similarity NPC291962
0.6899 Remote Similarity NPC177684
0.6885 Remote Similarity NPC434
0.6871 Remote Similarity NPC117032
0.6866 Remote Similarity NPC145754
0.6857 Remote Similarity NPC314102
0.6857 Remote Similarity NPC251722
0.6853 Remote Similarity NPC20144
0.6846 Remote Similarity NPC112373
0.6846 Remote Similarity NPC161956
0.6846 Remote Similarity NPC258531
0.6835 Remote Similarity NPC325599
0.6831 Remote Similarity NPC238499
0.6794 Remote Similarity NPC215519
0.6788 Remote Similarity NPC476685
0.6788 Remote Similarity NPC476687
0.6788 Remote Similarity NPC476689
0.6754 Remote Similarity NPC476160
0.6739 Remote Similarity NPC101165
0.6724 Remote Similarity NPC7067
0.6714 Remote Similarity NPC198988
0.6694 Remote Similarity NPC178681
0.6692 Remote Similarity NPC41174
0.6644 Remote Similarity NPC469525
0.6643 Remote Similarity NPC104483
0.6642 Remote Similarity NPC46358
0.6641 Remote Similarity NPC226143
0.6638 Remote Similarity NPC108800
0.662 Remote Similarity NPC150259
0.6619 Remote Similarity NPC475450
0.6618 Remote Similarity NPC250361
0.6609 Remote Similarity NPC191444
0.6607 Remote Similarity NPC229477
0.66 Remote Similarity NPC471132
0.6599 Remote Similarity NPC143872
0.6597 Remote Similarity NPC59084
0.6597 Remote Similarity NPC2949
0.6594 Remote Similarity NPC473587
0.6581 Remote Similarity NPC471130
0.6577 Remote Similarity NPC206592
0.6571 Remote Similarity NPC473930
0.6558 Remote Similarity NPC476231
0.6558 Remote Similarity NPC88970
0.6552 Remote Similarity NPC63157
0.6552 Remote Similarity NPC470926
0.6552 Remote Similarity NPC473868
0.6552 Remote Similarity NPC277157
0.6549 Remote Similarity NPC325252
0.6547 Remote Similarity NPC475428
0.6531 Remote Similarity NPC204141
0.6528 Remote Similarity NPC88097
0.6525 Remote Similarity NPC108339
0.6522 Remote Similarity NPC176858
0.6522 Remote Similarity NPC473762
0.6513 Remote Similarity NPC51054
0.6504 Remote Similarity NPC469974
0.6503 Remote Similarity NPC469560
0.65 Remote Similarity NPC179365
0.6496 Remote Similarity NPC476140
0.6493 Remote Similarity NPC182570
0.6493 Remote Similarity NPC48564
0.6493 Remote Similarity NPC265605
0.6491 Remote Similarity NPC262295
0.6471 Remote Similarity NPC471320
0.6471 Remote Similarity NPC471319
0.6467 Remote Similarity NPC33421
0.6466 Remote Similarity NPC279385
0.6466 Remote Similarity NPC179605
0.6458 Remote Similarity NPC243162
0.6446 Remote Similarity NPC75496
0.6443 Remote Similarity NPC21605
0.6441 Remote Similarity NPC469330
0.6441 Remote Similarity NPC322040
0.6435 Remote Similarity NPC111233
0.6429 Remote Similarity NPC134825
0.6429 Remote Similarity NPC475990
0.6429 Remote Similarity NPC318065
0.6429 Remote Similarity NPC206819
0.6419 Remote Similarity NPC324445
0.6418 Remote Similarity NPC103292
0.6414 Remote Similarity NPC73767
0.6414 Remote Similarity NPC110126
0.6412 Remote Similarity NPC313673
0.6405 Remote Similarity NPC94167
0.6405 Remote Similarity NPC84317
0.6405 Remote Similarity NPC172937
0.6393 Remote Similarity NPC326792
0.6391 Remote Similarity NPC91958
0.6389 Remote Similarity NPC84911
0.6385 Remote Similarity NPC205652
0.6385 Remote Similarity NPC470550
0.6382 Remote Similarity NPC281094
0.6382 Remote Similarity NPC232798
0.6376 Remote Similarity NPC478186
0.637 Remote Similarity NPC39818
0.637 Remote Similarity NPC469761
0.637 Remote Similarity NPC469768
0.637 Remote Similarity NPC469779
0.637 Remote Similarity NPC469767
0.637 Remote Similarity NPC469780
0.637 Remote Similarity NPC469783
0.637 Remote Similarity NPC469784
0.6364 Remote Similarity NPC471123
0.6364 Remote Similarity NPC476566
0.6358 Remote Similarity NPC40070
0.6351 Remote Similarity NPC242556
0.635 Remote Similarity NPC476322
0.6345 Remote Similarity NPC169433
0.6345 Remote Similarity NPC130251
0.6343 Remote Similarity NPC317564
0.634 Remote Similarity NPC476219
0.6338 Remote Similarity NPC313352
0.6335 Remote Similarity NPC475594
0.6333 Remote Similarity NPC114209
0.6333 Remote Similarity NPC321617
0.6331 Remote Similarity NPC150863
0.6329 Remote Similarity NPC49217
0.6327 Remote Similarity NPC469766
0.6319 Remote Similarity NPC29886
0.6319 Remote Similarity NPC218268
0.6319 Remote Similarity NPC261195
0.6319 Remote Similarity NPC96102
0.6316 Remote Similarity NPC471402
0.6316 Remote Similarity NPC297486
0.6316 Remote Similarity NPC240136
0.6316 Remote Similarity NPC228515
0.6312 Remote Similarity NPC282398
0.6309 Remote Similarity NPC470440
0.6304 Remote Similarity NPC250476
0.6301 Remote Similarity NPC301760
0.6301 Remote Similarity NPC22082
0.6301 Remote Similarity NPC186284
0.6301 Remote Similarity NPC312092
0.6296 Remote Similarity NPC98976
0.6296 Remote Similarity NPC475607
0.6293 Remote Similarity NPC30445
0.6291 Remote Similarity NPC37548
0.6286 Remote Similarity NPC473417
0.6283 Remote Similarity NPC104070
0.6282 Remote Similarity NPC122141
0.6276 Remote Similarity NPC105127
0.6269 Remote Similarity NPC143603
0.6268 Remote Similarity NPC471322
0.6268 Remote Similarity NPC82295
0.6267 Remote Similarity NPC288838
0.6265 Remote Similarity NPC21429
0.6259 Remote Similarity NPC115611
0.6259 Remote Similarity NPC284635
0.6258 Remote Similarity NPC474081
0.6258 Remote Similarity NPC104345
0.625 Remote Similarity NPC53947
0.625 Remote Similarity NPC268534
0.6242 Remote Similarity NPC116519
0.6242 Remote Similarity NPC225018
0.6241 Remote Similarity NPC231382
0.6241 Remote Similarity NPC476131
0.6239 Remote Similarity NPC271642
0.6234 Remote Similarity NPC476297
0.6228 Remote Similarity NPC169016

  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 NPC288232 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
0.8667 High Similarity NPD4985 Clinical (unspecified phase)
0.8482 Intermediate Similarity NPD477 Phase 1
0.8403 Intermediate Similarity NPD2340 Discontinued
0.8376 Intermediate Similarity NPD2464 Approved
0.8376 Intermediate Similarity NPD2463 Approved
0.8376 Intermediate Similarity NPD2467 Approved
0.8151 Intermediate Similarity NPD7480 Approved
0.8151 Intermediate Similarity NPD7481 Approved
0.807 Intermediate Similarity NPD6300 Approved
0.807 Intermediate Similarity NPD6299 Approved
0.7857 Intermediate Similarity NPD2840 Approved
0.7826 Intermediate Similarity NPD993 Approved
0.7826 Intermediate Similarity NPD3546 Approved
0.7826 Intermediate Similarity NPD990 Approved
0.7826 Intermediate Similarity NPD3545 Approved
0.7807 Intermediate Similarity NPD1728 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD2143 Discontinued
0.7778 Intermediate Similarity NPD4116 Approved
0.7759 Intermediate Similarity NPD4114 Approved
0.7759 Intermediate Similarity NPD4115 Approved
0.7627 Intermediate Similarity NPD1539 Approved
0.7619 Intermediate Similarity NPD3622 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3623 Clinical (unspecified phase)
0.7615 Intermediate Similarity NPD4866 Approved
0.7615 Intermediate Similarity NPD3841 Phase 3
0.7615 Intermediate Similarity NPD4867 Approved
0.7607 Intermediate Similarity NPD5253 Approved
0.7591 Intermediate Similarity NPD4047 Discontinued
0.7578 Intermediate Similarity NPD6900 Discontinued
0.7557 Intermediate Similarity NPD1919 Approved
0.7557 Intermediate Similarity NPD1920 Approved
0.7521 Intermediate Similarity NPD2914 Approved
0.7521 Intermediate Similarity NPD2913 Approved
0.75 Intermediate Similarity NPD2999 Approved
0.75 Intermediate Similarity NPD3001 Approved
0.748 Intermediate Similarity NPD478 Approved
0.748 Intermediate Similarity NPD6660 Discontinued
0.7479 Intermediate Similarity NPD7633 Discontinued
0.7478 Intermediate Similarity NPD4734 Approved
0.7478 Intermediate Similarity NPD4735 Approved
0.7459 Intermediate Similarity NPD5631 Phase 3
0.7364 Intermediate Similarity NPD1937 Approved
0.7308 Intermediate Similarity NPD1950 Approved
0.7308 Intermediate Similarity NPD1949 Approved
0.7266 Intermediate Similarity NPD6301 Phase 2
0.725 Intermediate Similarity NPD1721 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD6892 Discontinued
0.7236 Intermediate Similarity NPD5181 Approved
0.7236 Intermediate Similarity NPD5180 Approved
0.7236 Intermediate Similarity NPD5179 Approved
0.7218 Intermediate Similarity NPD1001 Discontinued
0.7214 Intermediate Similarity NPD2866 Approved
0.7213 Intermediate Similarity NPD2038 Approved
0.7213 Intermediate Similarity NPD2039 Approved
0.7177 Intermediate Similarity NPD5629 Discontinued
0.7177 Intermediate Similarity NPD1813 Discontinued
0.7153 Intermediate Similarity NPD6575 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3424 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD3385 Approved
0.7123 Intermediate Similarity NPD6285 Phase 2
0.7122 Intermediate Similarity NPD1902 Approved
0.7122 Intermediate Similarity NPD1904 Approved
0.7113 Intermediate Similarity NPD5839 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD986 Discontinued
0.7083 Intermediate Similarity NPD5546 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD7582 Discontinued
0.7059 Intermediate Similarity NPD7200 Approved
0.7049 Intermediate Similarity NPD3548 Approved
0.7031 Intermediate Similarity NPD2212 Approved
0.7031 Intermediate Similarity NPD3498 Approved
0.7031 Intermediate Similarity NPD3499 Approved
0.7031 Intermediate Similarity NPD2210 Approved
0.6993 Remote Similarity NPD3629 Approved
0.6993 Remote Similarity NPD1524 Phase 1
0.6993 Remote Similarity NPD3630 Approved
0.6978 Remote Similarity NPD45 Approved
0.6978 Remote Similarity NPD6554 Approved
0.6972 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6963 Remote Similarity NPD3654 Approved
0.6963 Remote Similarity NPD4300 Clinical (unspecified phase)
0.6953 Remote Similarity NPD5657 Phase 3
0.6953 Remote Similarity NPD1668 Clinical (unspecified phase)
0.6942 Remote Similarity NPD1065 Approved
0.6942 Remote Similarity NPD1064 Approved
0.6929 Remote Similarity NPD6070 Approved
0.6929 Remote Similarity NPD6606 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6069 Approved
0.6894 Remote Similarity NPD2940 Approved
0.6894 Remote Similarity NPD2938 Approved
0.6889 Remote Similarity NPD4019 Clinical (unspecified phase)
0.6875 Remote Similarity NPD153 Clinical (unspecified phase)
0.6871 Remote Similarity NPD3248 Phase 1
0.6861 Remote Similarity NPD1316 Discontinued
0.6853 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6838 Remote Similarity NPD4857 Phase 1
0.6835 Remote Similarity NPD1883 Approved
0.6833 Remote Similarity NPD2244 Clinical (unspecified phase)
0.6833 Remote Similarity NPD1396 Approved
0.6829 Remote Similarity NPD2678 Approved
0.6829 Remote Similarity NPD2679 Approved
0.6822 Remote Similarity NPD1216 Clinical (unspecified phase)
0.6818 Remote Similarity NPD2538 Approved
0.6818 Remote Similarity NPD2539 Approved
0.6806 Remote Similarity NPD5671 Approved
0.6795 Remote Similarity NPD5078 Clinical (unspecified phase)
0.6794 Remote Similarity NPD678 Discontinued
0.6791 Remote Similarity NPD3240 Phase 2
0.6788 Remote Similarity NPD6822 Approved
0.6788 Remote Similarity NPD6820 Approved
0.6786 Remote Similarity NPD4411 Phase 1
0.6786 Remote Similarity NPD3864 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1254 Approved
0.6786 Remote Similarity NPD1253 Approved
0.6786 Remote Similarity NPD1256 Approved
0.6786 Remote Similarity NPD4410 Clinical (unspecified phase)
0.6786 Remote Similarity NPD1255 Approved
0.6781 Remote Similarity NPD5423 Phase 2
0.6774 Remote Similarity NPD1107 Approved
0.6774 Remote Similarity NPD1108 Approved
0.6769 Remote Similarity NPD1306 Clinical (unspecified phase)
0.675 Remote Similarity NPD1417 Approved
0.675 Remote Similarity NPD1419 Approved
0.6742 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6742 Remote Similarity NPD4323 Clinical (unspecified phase)
0.6738 Remote Similarity NPD544 Clinical (unspecified phase)
0.6736 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7091 Discontinued
0.6724 Remote Similarity NPD199 Approved
0.6724 Remote Similarity NPD197 Approved
0.6714 Remote Similarity NPD2140 Approved
0.6714 Remote Similarity NPD2142 Approved
0.6714 Remote Similarity NPD2141 Approved
0.6714 Remote Similarity NPD2292 Approved
0.6713 Remote Similarity NPD3943 Clinical (unspecified phase)
0.6712 Remote Similarity NPD5570 Discontinued
0.6711 Remote Similarity NPD5989 Phase 1
0.6696 Remote Similarity NPD3000 Approved
0.6696 Remote Similarity NPD2998 Approved
0.6696 Remote Similarity NPD2997 Approved
0.6693 Remote Similarity NPD6561 Approved
0.6693 Remote Similarity NPD2658 Approved
0.6693 Remote Similarity NPD3147 Approved
0.6693 Remote Similarity NPD3150 Approved
0.6693 Remote Similarity NPD3149 Approved
0.6693 Remote Similarity NPD2659 Approved
0.6693 Remote Similarity NPD6562 Approved
0.6693 Remote Similarity NPD3148 Approved
0.6692 Remote Similarity NPD1903 Approved
0.6691 Remote Similarity NPD2118 Approved
0.6691 Remote Similarity NPD2119 Approved
0.6691 Remote Similarity NPD1598 Discontinued
0.669 Remote Similarity NPD1870 Approved
0.669 Remote Similarity NPD1866 Approved
0.669 Remote Similarity NPD1864 Clinical (unspecified phase)
0.669 Remote Similarity NPD6017 Discontinued
0.6689 Remote Similarity NPD8355 Approved
0.6689 Remote Similarity NPD8353 Approved
0.6667 Remote Similarity NPD3476 Approved
0.6667 Remote Similarity NPD3475 Approved
0.6643 Remote Similarity NPD4450 Approved
0.6643 Remote Similarity NPD4451 Approved
0.6643 Remote Similarity NPD6821 Approved
0.6643 Remote Similarity NPD679 Approved
0.6643 Remote Similarity NPD6318 Clinical (unspecified phase)
0.6641 Remote Similarity NPD1479 Clinical (unspecified phase)
0.6623 Remote Similarity NPD2150 Discontinued
0.662 Remote Similarity NPD1262 Discovery
0.662 Remote Similarity NPD2733 Approved
0.6619 Remote Similarity NPD3137 Clinical (unspecified phase)
0.6614 Remote Similarity NPD1764 Approved
0.6614 Remote Similarity NPD1762 Approved
0.6613 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6612 Remote Similarity NPD707 Approved
0.6612 Remote Similarity NPD708 Approved
0.66 Remote Similarity NPD8354 Approved
0.66 Remote Similarity NPD1917 Discontinued
0.6596 Remote Similarity NPD407 Approved
0.6596 Remote Similarity NPD406 Approved
0.6596 Remote Similarity NPD1998 Approved
0.6594 Remote Similarity NPD6489 Phase 3
0.6594 Remote Similarity NPD947 Approved
0.6593 Remote Similarity NPD5136 Clinical (unspecified phase)
0.6589 Remote Similarity NPD1723 Phase 2
0.6589 Remote Similarity NPD2622 Approved
0.6589 Remote Similarity NPD1720 Phase 2
0.6585 Remote Similarity NPD1269 Approved
0.6585 Remote Similarity NPD1268 Approved
0.6581 Remote Similarity NPD4550 Clinical (unspecified phase)
0.6579 Remote Similarity NPD2373 Clinical (unspecified phase)
0.6575 Remote Similarity NPD4509 Discontinued
0.6575 Remote Similarity NPD2828 Approved
0.6575 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6575 Remote Similarity NPD5254 Discontinued
0.6573 Remote Similarity NPD2304 Approved
0.6573 Remote Similarity NPD3276 Approved
0.6569 Remote Similarity NPD995 Clinical (unspecified phase)
0.6567 Remote Similarity NPD7461 Approved
0.6565 Remote Similarity NPD18 Approved
0.6558 Remote Similarity NPD5551 Clinical (unspecified phase)
0.6557 Remote Similarity NPD154 Discontinued

  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