Structure

Physi-Chem Properties

Molecular Weight:  232.1
Volume:  251.968
LogP:  4.272
LogD:  3.701
LogS:  -5.977
# 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:  1.914
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.785
MDCK Permeability:  2.6892739697359502e-05
Pgp-inhibitor:  0.045
Pgp-substrate:  0.025
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.936
30% Bioavailability (F30%):  0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.974
Plasma Protein Binding (PPB):  96.30175018310547%
Volume Distribution (VD):  1.772
Pgp-substrate:  1.3179415464401245%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.559
CYP2C19-inhibitor:  0.585
CYP2C19-substrate:  0.194
CYP2C9-inhibitor:  0.338
CYP2C9-substrate:  0.817
CYP2D6-inhibitor:  0.359
CYP2D6-substrate:  0.893
CYP3A4-inhibitor:  0.517
CYP3A4-substrate:  0.187

ADMET: Excretion

Clearance (CL):  7.364
Half-life (T1/2):  0.113

ADMET: Toxicity

hERG Blockers:  0.066
Human Hepatotoxicity (H-HT):  0.419
Drug-inuced Liver Injury (DILI):  0.602
AMES Toxicity:  0.947
Rat Oral Acute Toxicity:  0.157
Maximum Recommended Daily Dose:  0.311
Skin Sensitization:  0.108
Carcinogencity:  0.813
Eye Corrosion:  0.004
Eye Irritation:  0.952
Respiratory Toxicity:  0.495

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

  Natural Product: NPC187036

Natural Product ID:  NPC187036
Common Name*:   Isocryptolepine
IUPAC Name:   5-methylindolo[3,2-c]quinoline
Synonyms:   Isocryptolepine
Standard InCHIKey:  GLYLOCYYFNTVGX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12N2/c1-18-10-13-11-6-2-4-8-14(11)17-16(13)12-7-3-5-9-15(12)18/h2-10H,1H3
SMILES:  Cn1cc2-c(c3ccccc13)nc1ccccc21
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL596333
PubChem CID:   380925
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001253] Quinolines and derivatives
        • [CHEMONTID:0000061] Indoloquinolines

*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]
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]
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[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]
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]
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]

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1566.75 nM PMID[524583]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 2037.04 nM PMID[524583]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 1706.08 nM PMID[524583]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 1506.61 nM PMID[524583]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1914.26 nM PMID[524583]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1399.59 nM PMID[524583]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 2037.04 nM PMID[524583]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 2312.06 nM PMID[524583]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1698.24 nM PMID[524583]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 1721.87 nM PMID[524583]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 2275.1 nM PMID[524583]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 1940.89 nM PMID[524583]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1741.81 nM PMID[524583]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2355.05 nM PMID[524583]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 420.73 nM PMID[524583]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1717.91 nM PMID[524583]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 1592.21 nM PMID[524583]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1595.88 nM PMID[524583]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 2415.46 nM PMID[524583]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 2142.89 nM PMID[524583]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 2349.63 nM PMID[524583]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 2964.83 nM PMID[524583]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 397.19 nM PMID[524583]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 3926.45 nM PMID[524583]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 1122.02 nM PMID[524583]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2079.7 nM PMID[524583]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1406.05 nM PMID[524583]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1625.55 nM PMID[524583]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1534.62 nM PMID[524583]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 1918.67 nM PMID[524583]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1766.04 nM PMID[524583]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 3258.37 nM PMID[524583]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 1914.26 nM PMID[524583]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1603.25 nM PMID[524583]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 2172.7 nM PMID[524583]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 1798.87 nM PMID[524583]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1000.0 nM PMID[524583]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 1967.89 nM PMID[524583]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2333.46 nM PMID[524583]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2673.01 nM PMID[524583]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2517.68 nM PMID[524583]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 1986.09 nM PMID[524583]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 1442.12 nM PMID[524583]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2065.38 nM PMID[524583]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1603.25 nM PMID[524583]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2317.39 nM PMID[524583]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 2779.71 nM PMID[524583]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 2387.81 nM PMID[524583]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1625.55 nM PMID[524583]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 2103.78 nM PMID[524583]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2296.15 nM PMID[524583]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 2306.75 nM PMID[524583]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1448.77 nM PMID[524583]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1288.25 nM PMID[524583]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2382.32 nM PMID[524583]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1462.18 nM PMID[524583]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 1190.0 nM PMID[524584]
NPT171 Cell Line MRC5 Homo sapiens IC50 = 8352.0 nM PMID[524585]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 730.0 nM PMID[524585]
NPT81 Cell Line A549 Homo sapiens IC50 = 1210.0 nM PMID[524585]
NPT65 Cell Line HepG2 Homo sapiens Ratio IC50 = 11.41 n.a. PMID[524585]
NPT793 Cell Line MOLT-3 Homo sapiens Ratio IC50 = 11.41 n.a. PMID[524585]
NPT81 Cell Line A549 Homo sapiens Ratio IC50 = 6.93 n.a. PMID[524585]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 780.0 nM PMID[524584]
NPT2 Others Unspecified Ratio IC50 = 1.5 n.a. PMID[524584]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 778.6 nM PMID[524585]
NPT2 Others Unspecified Ratio IC50 = 10.72 n.a. PMID[524585]
NPT757 Organism Plasmodium falciparum 3D7 Plasmodium falciparum 3D7 IC50 = 585.0 nM PMID[524585]
NPT2 Others Unspecified Ratio IC50 = 14.27 n.a. PMID[524585]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 410.0 nM PMID[524585]
NPT2 Others Unspecified Ratio IC50 = 20.37 n.a. PMID[524585]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 462.8 nM PMID[524585]
NPT2 Others Unspecified Ratio IC50 = 18.04 n.a. PMID[524585]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 1810.0 nM PMID[524585]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 730.0 nM PMID[524585]
NPT2 Others Unspecified Ratio IC50 = 4.62 n.a. PMID[524585]

☑ 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 NPC187036 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
0.9279 High Similarity NPC192209
0.9266 High Similarity NPC296163
0.8929 High Similarity NPC288232
0.8609 High Similarity NPC313449
0.8374 Intermediate Similarity NPC9856
0.8142 Intermediate Similarity NPC302790
0.8067 Intermediate Similarity NPC264580
0.7928 Intermediate Similarity NPC291610
0.7829 Intermediate Similarity NPC184437
0.7797 Intermediate Similarity NPC314141
0.7778 Intermediate Similarity NPC476950
0.7744 Intermediate Similarity NPC471574
0.7672 Intermediate Similarity NPC164802
0.7574 Intermediate Similarity NPC136002
0.75 Intermediate Similarity NPC476160
0.75 Intermediate Similarity NPC478079
0.7463 Intermediate Similarity NPC251722
0.7463 Intermediate Similarity NPC314102
0.7445 Intermediate Similarity NPC20144
0.7419 Intermediate Similarity NPC54102
0.7419 Intermediate Similarity NPC162689
0.741 Intermediate Similarity NPC469740
0.7405 Intermediate Similarity NPC22079
0.7398 Intermediate Similarity NPC148140
0.7344 Intermediate Similarity NPC122718
0.7339 Intermediate Similarity NPC81561
0.7338 Intermediate Similarity NPC469735
0.7313 Intermediate Similarity NPC325599
0.7302 Intermediate Similarity NPC475915
0.7273 Intermediate Similarity NPC53044
0.7214 Intermediate Similarity NPC469525
0.7206 Intermediate Similarity NPC150259
0.7185 Intermediate Similarity NPC198988
0.7165 Intermediate Similarity NPC257490
0.7165 Intermediate Similarity NPC215519
0.7143 Intermediate Similarity NPC79618
0.7132 Intermediate Similarity NPC46358
0.7111 Intermediate Similarity NPC300299
0.7101 Intermediate Similarity NPC104483
0.7095 Intermediate Similarity NPC476231
0.7083 Intermediate Similarity NPC117032
0.708 Intermediate Similarity NPC125746
0.7055 Intermediate Similarity NPC51054
0.705 Intermediate Similarity NPC59084
0.705 Intermediate Similarity NPC2949
0.705 Intermediate Similarity NPC238499
0.704 Intermediate Similarity NPC147957
0.7027 Intermediate Similarity NPC78154
0.7023 Intermediate Similarity NPC252794
0.7007 Intermediate Similarity NPC325252
0.7 Intermediate Similarity NPC63157
0.7 Intermediate Similarity NPC473868
0.6978 Remote Similarity NPC88097
0.6978 Remote Similarity NPC110126
0.6978 Remote Similarity NPC73767
0.697 Remote Similarity NPC145754
0.697 Remote Similarity NPC250361
0.6963 Remote Similarity NPC475450
0.6959 Remote Similarity NPC318065
0.6959 Remote Similarity NPC206819
0.6957 Remote Similarity NPC84911
0.6953 Remote Similarity NPC317564
0.694 Remote Similarity NPC473587
0.6929 Remote Similarity NPC469768
0.6929 Remote Similarity NPC469783
0.6929 Remote Similarity NPC469767
0.6929 Remote Similarity NPC469761
0.6929 Remote Similarity NPC469779
0.6929 Remote Similarity NPC469780
0.6929 Remote Similarity NPC469784
0.6923 Remote Similarity NPC41174
0.6918 Remote Similarity NPC281094
0.6912 Remote Similarity NPC473930
0.6906 Remote Similarity NPC169433
0.6897 Remote Similarity NPC206592
0.6897 Remote Similarity NPC33421
0.6897 Remote Similarity NPC40070
0.6889 Remote Similarity NPC476689
0.6889 Remote Similarity NPC476687
0.6889 Remote Similarity NPC476685
0.6889 Remote Similarity NPC475428
0.6884 Remote Similarity NPC29886
0.6884 Remote Similarity NPC96102
0.6884 Remote Similarity NPC261195
0.6879 Remote Similarity NPC469766
0.6875 Remote Similarity NPC291962
0.6875 Remote Similarity NPC21605
0.6875 Remote Similarity NPC226143
0.6875 Remote Similarity NPC177684
0.6875 Remote Similarity NPC91958
0.6875 Remote Similarity NPC191444
0.6866 Remote Similarity NPC473762
0.686 Remote Similarity NPC434
0.6846 Remote Similarity NPC265605
0.6846 Remote Similarity NPC182570
0.6846 Remote Similarity NPC475990
0.6846 Remote Similarity NPC48564
0.6838 Remote Similarity NPC179365
0.6835 Remote Similarity NPC105127
0.6822 Remote Similarity NPC161956
0.6822 Remote Similarity NPC112373
0.6822 Remote Similarity NPC258531
0.6814 Remote Similarity NPC470926
0.6807 Remote Similarity NPC178681
0.6806 Remote Similarity NPC143872
0.6806 Remote Similarity NPC288838
0.6797 Remote Similarity NPC297486
0.6797 Remote Similarity NPC471402
0.6797 Remote Similarity NPC240136
0.6794 Remote Similarity NPC283130
0.6794 Remote Similarity NPC328683
0.6786 Remote Similarity NPC243162
0.6786 Remote Similarity NPC176858
0.6781 Remote Similarity NPC53947
0.6763 Remote Similarity NPC218268
0.6761 Remote Similarity NPC277157
0.6754 Remote Similarity NPC108800
0.6738 Remote Similarity NPC315348
0.6738 Remote Similarity NPC32002
0.6738 Remote Similarity NPC316811
0.6738 Remote Similarity NPC2823
0.6736 Remote Similarity NPC470440
0.6733 Remote Similarity NPC56765
0.6719 Remote Similarity NPC476566
0.6716 Remote Similarity NPC476140
0.6715 Remote Similarity NPC82295
0.6715 Remote Similarity NPC101165
0.6713 Remote Similarity NPC190296
0.6712 Remote Similarity NPC37548
0.6711 Remote Similarity NPC478182
0.6696 Remote Similarity NPC111233
0.6692 Remote Similarity NPC476322
0.669 Remote Similarity NPC115611
0.669 Remote Similarity NPC478186
0.669 Remote Similarity NPC279081
0.6689 Remote Similarity NPC325903
0.6667 Remote Similarity NPC286427
0.6667 Remote Similarity NPC242556
0.6645 Remote Similarity NPC194411
0.6644 Remote Similarity NPC476219
0.6644 Remote Similarity NPC201380
0.6644 Remote Similarity NPC179787
0.6644 Remote Similarity NPC470111
0.6642 Remote Similarity NPC282398
0.6642 Remote Similarity NPC69914
0.6641 Remote Similarity NPC313673
0.6623 Remote Similarity NPC41257
0.6623 Remote Similarity NPC6436
0.6623 Remote Similarity NPC474880
0.6623 Remote Similarity NPC221786
0.6623 Remote Similarity NPC293487
0.6622 Remote Similarity NPC470233
0.6621 Remote Similarity NPC285731
0.6621 Remote Similarity NPC314372
0.662 Remote Similarity NPC301760
0.662 Remote Similarity NPC312092
0.6617 Remote Similarity NPC290094
0.6615 Remote Similarity NPC143603
0.6614 Remote Similarity NPC470550
0.6614 Remote Similarity NPC205652
0.6607 Remote Similarity NPC262295
0.6599 Remote Similarity NPC187951
0.6599 Remote Similarity NPC321911
0.6596 Remote Similarity NPC469560
0.6596 Remote Similarity NPC83214
0.6594 Remote Similarity NPC256893
0.6579 Remote Similarity NPC229173
0.6579 Remote Similarity NPC44773
0.6579 Remote Similarity NPC215584
0.6577 Remote Similarity NPC229477
0.6575 Remote Similarity NPC63545
0.6573 Remote Similarity NPC284635
0.6573 Remote Similarity NPC230002
0.6571 Remote Similarity NPC98976
0.6569 Remote Similarity NPC476131
0.6556 Remote Similarity NPC129721
0.6556 Remote Similarity NPC216643
0.6554 Remote Similarity NPC24678
0.6554 Remote Similarity NPC148592
0.6554 Remote Similarity NPC105818
0.6552 Remote Similarity NPC116519
0.6549 Remote Similarity NPC130251
0.6549 Remote Similarity NPC207554
0.6549 Remote Similarity NPC30445
0.6547 Remote Similarity NPC313352
0.6545 Remote Similarity NPC134825
0.6544 Remote Similarity NPC150863
0.6541 Remote Similarity NPC329825
0.6538 Remote Similarity NPC65080
0.6533 Remote Similarity NPC476297
0.6533 Remote Similarity NPC38736
0.6533 Remote Similarity NPC470507
0.6531 Remote Similarity NPC469811
0.6531 Remote Similarity NPC471957
0.6531 Remote Similarity NPC477134
0.6529 Remote Similarity NPC474430
0.6519 Remote Similarity NPC275305
0.6519 Remote Similarity NPC245244
0.6519 Remote Similarity NPC146373
0.6519 Remote Similarity NPC37423

  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 NPC187036 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
0.8609 High Similarity NPD7481 Approved
0.8609 High Similarity NPD7480 Approved
0.8545 High Similarity NPD6300 Approved
0.8545 High Similarity NPD6299 Approved
0.8288 Intermediate Similarity NPD990 Approved
0.8288 Intermediate Similarity NPD993 Approved
0.8279 Intermediate Similarity NPD2840 Approved
0.8125 Intermediate Similarity NPD3545 Approved
0.8125 Intermediate Similarity NPD3546 Approved
0.807 Intermediate Similarity NPD4116 Approved
0.8053 Intermediate Similarity NPD4115 Approved
0.8053 Intermediate Similarity NPD4114 Approved
0.8049 Intermediate Similarity NPD4985 Clinical (unspecified phase)
0.7934 Intermediate Similarity NPD2340 Discontinued
0.7903 Intermediate Similarity NPD1937 Approved
0.7797 Intermediate Similarity NPD2913 Approved
0.7797 Intermediate Similarity NPD2914 Approved
0.7778 Intermediate Similarity NPD3001 Approved
0.7778 Intermediate Similarity NPD2999 Approved
0.7768 Intermediate Similarity NPD4735 Approved
0.7768 Intermediate Similarity NPD4734 Approved
0.7759 Intermediate Similarity NPD7633 Discontinued
0.7739 Intermediate Similarity NPD5253 Approved
0.7731 Intermediate Similarity NPD5631 Phase 3
0.7672 Intermediate Similarity NPD477 Phase 1
0.7634 Intermediate Similarity NPD3385 Approved
0.7603 Intermediate Similarity NPD2463 Approved
0.7603 Intermediate Similarity NPD2467 Approved
0.7603 Intermediate Similarity NPD2464 Approved
0.7521 Intermediate Similarity NPD1721 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD2039 Approved
0.7479 Intermediate Similarity NPD2038 Approved
0.7462 Intermediate Similarity NPD3654 Approved
0.7372 Intermediate Similarity NPD6301 Phase 2
0.7355 Intermediate Similarity NPD5179 Approved
0.7355 Intermediate Similarity NPD5181 Approved
0.7355 Intermediate Similarity NPD5180 Approved
0.7328 Intermediate Similarity NPD4866 Approved
0.7328 Intermediate Similarity NPD3841 Phase 3
0.7328 Intermediate Similarity NPD4867 Approved
0.7319 Intermediate Similarity NPD6506 Clinical (unspecified phase)
0.7313 Intermediate Similarity NPD1883 Approved
0.7311 Intermediate Similarity NPD3548 Approved
0.7308 Intermediate Similarity NPD2118 Approved
0.7308 Intermediate Similarity NPD2119 Approved
0.7295 Intermediate Similarity NPD5629 Discontinued
0.7287 Intermediate Similarity NPD6900 Discontinued
0.728 Intermediate Similarity NPD3498 Approved
0.728 Intermediate Similarity NPD3499 Approved
0.7273 Intermediate Similarity NPD3475 Approved
0.7273 Intermediate Similarity NPD3476 Approved
0.7259 Intermediate Similarity NPD3864 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD2143 Discontinued
0.7206 Intermediate Similarity NPD6554 Approved
0.7206 Intermediate Similarity NPD45 Approved
0.72 Intermediate Similarity NPD1668 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1001 Discontinued
0.7197 Intermediate Similarity NPD4300 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD4047 Discontinued
0.7188 Intermediate Similarity NPD3622 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3623 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD2292 Approved
0.7174 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7200 Approved
0.7153 Intermediate Similarity NPD1870 Approved
0.7153 Intermediate Similarity NPD1866 Approved
0.7153 Intermediate Similarity NPD1864 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6822 Approved
0.7143 Intermediate Similarity NPD2210 Approved
0.7143 Intermediate Similarity NPD6820 Approved
0.7143 Intermediate Similarity NPD2212 Approved
0.7132 Intermediate Similarity NPD1255 Approved
0.7132 Intermediate Similarity NPD2938 Approved
0.7132 Intermediate Similarity NPD1254 Approved
0.7132 Intermediate Similarity NPD1253 Approved
0.7132 Intermediate Similarity NPD2940 Approved
0.7132 Intermediate Similarity NPD1256 Approved
0.7111 Intermediate Similarity NPD4029 Approved
0.7111 Intermediate Similarity NPD3944 Approved
0.7111 Intermediate Similarity NPD4028 Approved
0.7111 Intermediate Similarity NPD3942 Approved
0.7111 Intermediate Similarity NPD4030 Approved
0.7101 Intermediate Similarity NPD4451 Approved
0.7101 Intermediate Similarity NPD4450 Approved
0.7094 Intermediate Similarity NPD2244 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3248 Phase 1
0.7083 Intermediate Similarity NPD2679 Approved
0.7083 Intermediate Similarity NPD2678 Approved
0.708 Intermediate Similarity NPD2733 Approved
0.7063 Intermediate Similarity NPD3100 Discontinued
0.7063 Intermediate Similarity NPD5657 Phase 3
0.7063 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1065 Approved
0.7059 Intermediate Similarity NPD1998 Approved
0.7059 Intermediate Similarity NPD1064 Approved
0.704 Intermediate Similarity NPD6069 Approved
0.704 Intermediate Similarity NPD6660 Discontinued
0.704 Intermediate Similarity NPD6070 Approved
0.7034 Intermediate Similarity NPD1728 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD6606 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD2304 Approved
0.7029 Intermediate Similarity NPD3276 Approved
0.7025 Intermediate Similarity NPD1539 Approved
0.7023 Intermediate Similarity NPD1950 Approved
0.7023 Intermediate Similarity NPD1949 Approved
0.7021 Intermediate Similarity NPD3401 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD5254 Discontinued
0.7014 Intermediate Similarity NPD8353 Approved
0.7014 Intermediate Similarity NPD6575 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD8355 Approved
0.7009 Intermediate Similarity NPD1419 Approved
0.7009 Intermediate Similarity NPD1417 Approved
0.7007 Intermediate Similarity NPD4411 Phase 1
0.7007 Intermediate Similarity NPD4410 Clinical (unspecified phase)
0.6993 Remote Similarity NPD4547 Phase 3
0.6992 Remote Similarity NPD4019 Clinical (unspecified phase)
0.6985 Remote Similarity NPD6821 Approved
0.6978 Remote Similarity NPD1953 Discontinued
0.6972 Remote Similarity NPD5839 Clinical (unspecified phase)
0.6964 Remote Similarity NPD2998 Approved
0.6964 Remote Similarity NPD2997 Approved
0.6964 Remote Similarity NPD3000 Approved
0.6953 Remote Similarity NPD6892 Discontinued
0.6953 Remote Similarity NPD1525 Approved
0.6944 Remote Similarity NPD2539 Approved
0.6944 Remote Similarity NPD2538 Approved
0.694 Remote Similarity NPD947 Approved
0.6935 Remote Similarity NPD3149 Approved
0.6935 Remote Similarity NPD2659 Approved
0.6935 Remote Similarity NPD3150 Approved
0.6935 Remote Similarity NPD3147 Approved
0.6935 Remote Similarity NPD3148 Approved
0.6935 Remote Similarity NPD2658 Approved
0.6923 Remote Similarity NPD1683 Approved
0.6918 Remote Similarity NPD8354 Approved
0.6917 Remote Similarity NPD992 Clinical (unspecified phase)
0.6917 Remote Similarity NPD995 Clinical (unspecified phase)
0.6917 Remote Similarity NPD991 Phase 2
0.6901 Remote Similarity NPD4509 Discontinued
0.6894 Remote Similarity NPD3240 Phase 2
0.6885 Remote Similarity NPD1108 Approved
0.6885 Remote Similarity NPD1107 Approved
0.6884 Remote Similarity NPD198 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1306 Clinical (unspecified phase)
0.6871 Remote Similarity NPD6285 Phase 2
0.6864 Remote Similarity NPD708 Approved
0.686 Remote Similarity NPD2243 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1904 Approved
0.6857 Remote Similarity NPD786 Approved
0.6857 Remote Similarity NPD1902 Approved
0.6855 Remote Similarity NPD1762 Approved
0.6855 Remote Similarity NPD1764 Approved
0.6846 Remote Similarity NPD270 Clinical (unspecified phase)
0.6846 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6846 Remote Similarity NPD271 Approved
0.6846 Remote Similarity NPD268 Approved
0.6838 Remote Similarity NPD1251 Discontinued
0.6831 Remote Similarity NPD2006 Phase 2
0.6825 Remote Similarity NPD1720 Phase 2
0.6825 Remote Similarity NPD1723 Phase 2
0.6825 Remote Similarity NPD2622 Approved
0.6815 Remote Similarity NPD4857 Phase 1
0.6815 Remote Similarity NPD6489 Phase 3
0.6806 Remote Similarity NPD1886 Approved
0.6794 Remote Similarity NPD1498 Approved
0.6794 Remote Similarity NPD478 Approved
0.6794 Remote Similarity NPD7461 Approved
0.6786 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6017 Discontinued
0.6765 Remote Similarity NPD1920 Approved
0.6765 Remote Similarity NPD1919 Approved
0.6765 Remote Similarity NPD715 Phase 3
0.6761 Remote Similarity NPD5527 Clinical (unspecified phase)
0.6761 Remote Similarity NPD1722 Approved
0.6761 Remote Similarity NPD5526 Phase 2
0.6746 Remote Similarity NPD1813 Discontinued
0.6739 Remote Similarity NPD6318 Clinical (unspecified phase)
0.6738 Remote Similarity NPD2075 Approved
0.6738 Remote Similarity NPD2070 Approved
0.6738 Remote Similarity NPD2071 Approved
0.6738 Remote Similarity NPD2073 Approved
0.6738 Remote Similarity NPD2074 Approved
0.6738 Remote Similarity NPD2068 Approved
0.6738 Remote Similarity NPD2072 Approved
0.6738 Remote Similarity NPD2069 Approved
0.6735 Remote Similarity NPD2882 Phase 1
0.6721 Remote Similarity NPD458 Approved
0.6716 Remote Similarity NPD9583 Approved
0.6715 Remote Similarity NPD1316 Discontinued
0.6713 Remote Similarity NPD2866 Approved
0.6713 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6712 Remote Similarity NPD5546 Clinical (unspecified phase)
0.6712 Remote Similarity NPD2430 Phase 2
0.6712 Remote Similarity NPD5538 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6549 Approved
0.6696 Remote Similarity NPD3345 Approved
0.6696 Remote Similarity NPD6548 Approved
0.6694 Remote Similarity NPD564 Approved
0.6694 Remote Similarity NPD563 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