NPASS Compound

Structure

CID152620 OpenBabel06191715522D 37 42 0 0 1 0 0 0 0 0999 V2000 -2.5268 1.4590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5888 3.8311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6519 -3.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2329 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4898 1.1528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5271 -1.4588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6851 -1.9452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5387 0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5270 -0.4858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6854 0.9721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8988 1.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 -2.6306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4862 -3.4396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5271 -1.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0740 -0.8035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6672 -1.7171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8424 -1.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3308 -0.1344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6847 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0007 2.5109 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6849 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8423 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8422 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -1.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8425 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9151 -2.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 3.0826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5083 -3.3351 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5273 -0.4868 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -0.6344 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3159 4.0497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6847 0.9728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8891 2.9062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6848 -2.9183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 37 1 0 0 0 0 4 5 2 0 0 0 0 4 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 30 1 0 0 0 0 15 23 1 0 0 0 0 15 31 2 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 26 2 0 0 0 0 18 24 1 0 0 0 0 18 25 2 0 0 0 0 19 32 1 0 0 0 0 20 27 2 0 0 0 0 20 31 1 0 0 0 0 21 25 1 0 0 0 0 21 35 1 0 0 0 0 22 29 1 0 0 0 0 22 36 1 0 0 0 0 23 24 2 0 0 0 0 23 37 1 0 0 0 0 24 27 1 0 0 0 0 25 33 1 0 0 0 0 26 28 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 29 34 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.2
Volume:	503.675
LogP:	4.312
LogD:	3.314
LogS:	-5.792
# Rotatable Bonds:	8
TPSA:	102.12
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	3.523
Fsp3:	0.207
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	8.294457074953243e-06
Pgp-inhibitor:	0.973
Pgp-substrate:	0.316
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	94.96778869628906%
Volume Distribution (VD):	0.708
Pgp-substrate:	4.432173252105713%

ADMET: Metabolism

CYP1A2-inhibitor:	0.966
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.824
CYP2C19-substrate:	0.483
CYP2C9-inhibitor:	0.925
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	3.69
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.855
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.61
Carcinogencity:	0.431
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC152620

Natural Product ID:	NPC152620
*Common Name:**	Picrasidine C
IUPAC Name:	4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-2-methoxy-1-(9H-pyrido[3,4-b]indol-1-yl)butan-1-one
Synonyms:	Picrasidine C
Standard InCHIKey:	FNSOWPJAPJEOEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H26N4O4/c1-35-21-10-6-8-18-24-23(37-3)15-31-20(27(24)33-25(18)21)11-12-22(36-2)29(34)28-26-17(13-14-30-28)16-7-4-5-9-19(16)32-26/h4-10,13-15,22,32-33H,11-12H2,1-3H3
SMILES:	COc1cccc2c3c(cnc(CCC(C(=O)c4c5c(ccn4)c4ccccc4[nH]5)OC)c3[nH]c12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086620
PubChem CID:	5315685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18853	Alstonia scholaris	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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

Activity Type	# Activity
IC50	3
Others	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	89910.0	nM	PMID[458782]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[458782]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	44.1	%	PMID[458783]

☑ 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 NPC152620 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	614
0.1-0.2	3626
0.2-0.3	13457
0.3-0.4	8166
0.4-0.5	12351
0.5-0.6	2261
0.6-0.7	1833
0.7-0.8	359
0.8-0.85	22
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9654	High Similarity	NPC53534
0.8913	High Similarity	NPC469554
0.8729	High Similarity	NPC148889
0.867	High Similarity	NPC101543
0.8648	High Similarity	NPC258048
0.8631	High Similarity	NPC26543
0.8565	High Similarity	NPC101350
0.8523	High Similarity	NPC235685
0.8312	Intermediate Similarity	NPC260434
0.8291	Intermediate Similarity	NPC122436
0.8286	Intermediate Similarity	NPC91868
0.8286	Intermediate Similarity	NPC63971
0.8228	Intermediate Similarity	NPC314954
0.8178	Intermediate Similarity	NPC165964
0.8174	Intermediate Similarity	NPC26679
0.8133	Intermediate Similarity	NPC182222
0.8058	Intermediate Similarity	NPC39370
0.805	Intermediate Similarity	NPC473186
0.8043	Intermediate Similarity	NPC185782
0.7992	Intermediate Similarity	NPC15801
0.7975	Intermediate Similarity	NPC207686
0.7912	Intermediate Similarity	NPC178858
0.7901	Intermediate Similarity	NPC196718
0.7869	Intermediate Similarity	NPC141053
0.7857	Intermediate Similarity	NPC323969
0.7839	Intermediate Similarity	NPC470799
0.7839	Intermediate Similarity	NPC8022
0.7833	Intermediate Similarity	NPC229893
0.7828	Intermediate Similarity	NPC102593
0.7826	Intermediate Similarity	NPC245816
0.7826	Intermediate Similarity	NPC476138
0.7787	Intermediate Similarity	NPC118940
0.7778	Intermediate Similarity	NPC123976
0.7778	Intermediate Similarity	NPC167860
0.7778	Intermediate Similarity	NPC123839
0.7768	Intermediate Similarity	NPC266249
0.7764	Intermediate Similarity	NPC36405
0.7753	Intermediate Similarity	NPC196449
0.7753	Intermediate Similarity	NPC314222
0.7741	Intermediate Similarity	NPC288987
0.7724	Intermediate Similarity	NPC329631
0.7702	Intermediate Similarity	NPC184680
0.7696	Intermediate Similarity	NPC19872
0.7683	Intermediate Similarity	NPC49547
0.7679	Intermediate Similarity	NPC476287
0.7676	Intermediate Similarity	NPC60621
0.7674	Intermediate Similarity	NPC74619
0.7671	Intermediate Similarity	NPC470785
0.7667	Intermediate Similarity	NPC213530
0.7667	Intermediate Similarity	NPC193267
0.7664	Intermediate Similarity	NPC478078
0.7633	Intermediate Similarity	NPC194740
0.7631	Intermediate Similarity	NPC472061
0.76	Intermediate Similarity	NPC470784
0.7592	Intermediate Similarity	NPC74575
0.759	Intermediate Similarity	NPC477549
0.7589	Intermediate Similarity	NPC208522
0.7583	Intermediate Similarity	NPC305984
0.7583	Intermediate Similarity	NPC27041
0.7582	Intermediate Similarity	NPC21638
0.7573	Intermediate Similarity	NPC477979
0.7564	Intermediate Similarity	NPC132539
0.7563	Intermediate Similarity	NPC94157
0.7562	Intermediate Similarity	NPC276657
0.7551	Intermediate Similarity	NPC470018
0.7543	Intermediate Similarity	NPC176538
0.7529	Intermediate Similarity	NPC478083
0.7521	Intermediate Similarity	NPC208084
0.7521	Intermediate Similarity	NPC187501
0.752	Intermediate Similarity	NPC257851
0.751	Intermediate Similarity	NPC473312
0.751	Intermediate Similarity	NPC473800
0.75	Intermediate Similarity	NPC216612
0.749	Intermediate Similarity	NPC240384
0.7479	Intermediate Similarity	NPC5145
0.7469	Intermediate Similarity	NPC148183
0.7469	Intermediate Similarity	NPC152768
0.7469	Intermediate Similarity	NPC322482
0.7458	Intermediate Similarity	NPC39500
0.7458	Intermediate Similarity	NPC221100
0.7458	Intermediate Similarity	NPC234078
0.7449	Intermediate Similarity	NPC157931
0.7447	Intermediate Similarity	NPC475774
0.7438	Intermediate Similarity	NPC312645
0.7436	Intermediate Similarity	NPC232727
0.7432	Intermediate Similarity	NPC270515
0.743	Intermediate Similarity	NPC474688
0.7425	Intermediate Similarity	NPC74413
0.7418	Intermediate Similarity	NPC472099
0.7418	Intermediate Similarity	NPC132642
0.7418	Intermediate Similarity	NPC225279
0.7416	Intermediate Similarity	NPC473639
0.7415	Intermediate Similarity	NPC285558
0.7404	Intermediate Similarity	NPC260900
0.7395	Intermediate Similarity	NPC287208
0.7393	Intermediate Similarity	NPC161801
0.7388	Intermediate Similarity	NPC310118
0.7386	Intermediate Similarity	NPC89508
0.7383	Intermediate Similarity	NPC78609
0.7379	Intermediate Similarity	NPC110151
0.7375	Intermediate Similarity	NPC473188
0.7373	Intermediate Similarity	NPC317701
0.7366	Intermediate Similarity	NPC476041
0.7366	Intermediate Similarity	NPC304926
0.736	Intermediate Similarity	NPC267853
0.7358	Intermediate Similarity	NPC132385
0.7358	Intermediate Similarity	NPC144452
0.7349	Intermediate Similarity	NPC471762
0.7344	Intermediate Similarity	NPC142385
0.7341	Intermediate Similarity	NPC97902
0.7339	Intermediate Similarity	NPC267928
0.7336	Intermediate Similarity	NPC184408
0.7336	Intermediate Similarity	NPC469594
0.7331	Intermediate Similarity	NPC244897
0.7326	Intermediate Similarity	NPC471891
0.7325	Intermediate Similarity	NPC322064
0.7324	Intermediate Similarity	NPC315499
0.7323	Intermediate Similarity	NPC41679
0.7312	Intermediate Similarity	NPC473187
0.7311	Intermediate Similarity	NPC472064
0.7309	Intermediate Similarity	NPC473185
0.7308	Intermediate Similarity	NPC137353
0.7308	Intermediate Similarity	NPC67401
0.7306	Intermediate Similarity	NPC292958
0.7306	Intermediate Similarity	NPC74360
0.7303	Intermediate Similarity	NPC82370
0.7303	Intermediate Similarity	NPC146418
0.7302	Intermediate Similarity	NPC180504
0.7298	Intermediate Similarity	NPC179287
0.7295	Intermediate Similarity	NPC472285
0.7291	Intermediate Similarity	NPC477112
0.7283	Intermediate Similarity	NPC215837
0.7283	Intermediate Similarity	NPC470022
0.728	Intermediate Similarity	NPC274640
0.728	Intermediate Similarity	NPC33949
0.7277	Intermediate Similarity	NPC81535
0.7273	Intermediate Similarity	NPC472098
0.7273	Intermediate Similarity	NPC316411
0.7269	Intermediate Similarity	NPC470500
0.7266	Intermediate Similarity	NPC100734
0.7266	Intermediate Similarity	NPC475844
0.7266	Intermediate Similarity	NPC88923
0.7266	Intermediate Similarity	NPC315634
0.7266	Intermediate Similarity	NPC477066
0.7265	Intermediate Similarity	NPC303658
0.7262	Intermediate Similarity	NPC474192
0.7262	Intermediate Similarity	NPC475720
0.7261	Intermediate Similarity	NPC471304
0.7259	Intermediate Similarity	NPC17437
0.7254	Intermediate Similarity	NPC170114
0.725	Intermediate Similarity	NPC82548
0.7248	Intermediate Similarity	NPC81939
0.7248	Intermediate Similarity	NPC472434
0.7245	Intermediate Similarity	NPC191489
0.7244	Intermediate Similarity	NPC57453
0.7244	Intermediate Similarity	NPC295228
0.7244	Intermediate Similarity	NPC470017
0.7243	Intermediate Similarity	NPC471080
0.7243	Intermediate Similarity	NPC469592
0.7243	Intermediate Similarity	NPC236668
0.7239	Intermediate Similarity	NPC227824
0.7238	Intermediate Similarity	NPC45190
0.7237	Intermediate Similarity	NPC477067
0.7237	Intermediate Similarity	NPC478082
0.7237	Intermediate Similarity	NPC478081
0.7233	Intermediate Similarity	NPC323752
0.7231	Intermediate Similarity	NPC208284
0.7227	Intermediate Similarity	NPC477861
0.7222	Intermediate Similarity	NPC475253
0.7222	Intermediate Similarity	NPC476451
0.722	Intermediate Similarity	NPC475666
0.7216	Intermediate Similarity	NPC184225
0.7213	Intermediate Similarity	NPC470549
0.7213	Intermediate Similarity	NPC146976
0.7211	Intermediate Similarity	NPC66777
0.721	Intermediate Similarity	NPC326422
0.7208	Intermediate Similarity	NPC284685
0.7208	Intermediate Similarity	NPC321428
0.7208	Intermediate Similarity	NPC472436
0.7203	Intermediate Similarity	NPC476167
0.7202	Intermediate Similarity	NPC264176
0.7202	Intermediate Similarity	NPC219087
0.7198	Intermediate Similarity	NPC81175
0.7195	Intermediate Similarity	NPC96321
0.7195	Intermediate Similarity	NPC264285
0.7194	Intermediate Similarity	NPC279189
0.7194	Intermediate Similarity	NPC200553
0.7191	Intermediate Similarity	NPC328928
0.719	Intermediate Similarity	NPC470020
0.719	Intermediate Similarity	NPC199667
0.7188	Intermediate Similarity	NPC474183
0.7186	Intermediate Similarity	NPC329982
0.7183	Intermediate Similarity	NPC326363
0.7183	Intermediate Similarity	NPC24019
0.7171	Intermediate Similarity	NPC72905
0.7171	Intermediate Similarity	NPC171393
0.7171	Intermediate Similarity	NPC192712
0.7171	Intermediate Similarity	NPC124300
0.7171	Intermediate Similarity	NPC295452
0.717	Intermediate Similarity	NPC63109

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 NPC152620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	677
0.2-0.3	988
0.3-0.4	1930
0.4-0.5	2621
0.5-0.6	1755
0.6-0.7	774
0.7-0.8	83
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8554	High Similarity	NPD5482	Discontinued
0.8542	High Similarity	NPD5483	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5450	Discontinued
0.8174	Intermediate Similarity	NPD3006	Discontinued
0.814	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD4429	Discontinued
0.7819	Intermediate Similarity	NPD5022	Discontinued
0.7778	Intermediate Similarity	NPD4558	Phase 2
0.7724	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5479	Discontinued
0.7672	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7645	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6242	Discontinued
0.7633	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7603	Discontinued
0.751	Intermediate Similarity	NPD6531	Approved
0.751	Intermediate Similarity	NPD6530	Approved
0.7472	Intermediate Similarity	NPD7925	Phase 2
0.7472	Intermediate Similarity	NPD7924	Phase 2
0.747	Intermediate Similarity	NPD4885	Approved
0.7462	Intermediate Similarity	NPD6961	Discontinued
0.7429	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5559	Phase 2
0.7403	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3389	Approved
0.7397	Intermediate Similarity	NPD3393	Approved
0.7397	Intermediate Similarity	NPD3394	Approved
0.7333	Intermediate Similarity	NPD6790	Phase 1
0.7322	Intermediate Similarity	NPD2510	Approved
0.7322	Intermediate Similarity	NPD2509	Approved
0.732	Intermediate Similarity	NPD4952	Phase 3
0.7303	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7558	Phase 2
0.7296	Intermediate Similarity	NPD5018	Phase 3
0.7295	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4368	Phase 2
0.7269	Intermediate Similarity	NPD5640	Discontinued
0.7266	Intermediate Similarity	NPD7803	Approved
0.7265	Intermediate Similarity	NPD5632	Approved
0.7259	Intermediate Similarity	NPD8358	Approved
0.7252	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7708	Approved
0.7239	Intermediate Similarity	NPD4442	Phase 2
0.7235	Intermediate Similarity	NPD8091	Phase 3
0.7233	Intermediate Similarity	NPD4373	Phase 2
0.7228	Intermediate Similarity	NPD6456	Discontinued
0.7227	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7955	Approved
0.7208	Intermediate Similarity	NPD7956	Approved
0.7205	Intermediate Similarity	NPD2951	Discontinued
0.7183	Intermediate Similarity	NPD1659	Phase 1
0.7176	Intermediate Similarity	NPD7853	Phase 2
0.7171	Intermediate Similarity	NPD7994	Phase 2
0.7165	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8100	Phase 3
0.7143	Intermediate Similarity	NPD4440	Clinical (unspecified phase)
0.7138	Intermediate Similarity	NPD3343	Phase 3
0.7131	Intermediate Similarity	NPD7426	Phase 1
0.7117	Intermediate Similarity	NPD8349	Phase 1
0.7116	Intermediate Similarity	NPD6228	Discontinued
0.7102	Intermediate Similarity	NPD3945	Discontinued
0.7094	Intermediate Similarity	NPD8246	Approved
0.7094	Intermediate Similarity	NPD8247	Approved
0.7091	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5416	Discontinued
0.7076	Intermediate Similarity	NPD6231	Phase 3
0.7073	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8101	Phase 3
0.7068	Intermediate Similarity	NPD8049	Phase 2
0.7064	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1038	Approved
0.7063	Intermediate Similarity	NPD8289	Discontinued
0.7054	Intermediate Similarity	NPD4795	Phase 2
0.7045	Intermediate Similarity	NPD5612	Discontinued
0.7045	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4454	Phase 2
0.7037	Intermediate Similarity	NPD5658	Approved
0.7034	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6770	Approved
0.7027	Intermediate Similarity	NPD1927	Discontinued
0.7025	Intermediate Similarity	NPD3781	Phase 2
0.702	Intermediate Similarity	NPD7470	Discontinued
0.7012	Intermediate Similarity	NPD1856	Discontinued
0.7012	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5293	Phase 2
0.7	Intermediate Similarity	NPD1996	Discontinued
0.6992	Remote Similarity	NPD8463	Approved
0.6992	Remote Similarity	NPD3746	Discontinued
0.6992	Remote Similarity	NPD1480	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5532	Phase 2
0.6988	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4036	Approved
0.6983	Remote Similarity	NPD4035	Approved
0.6983	Remote Similarity	NPD4039	Approved
0.6983	Remote Similarity	NPD4037	Approved
0.6983	Remote Similarity	NPD4033	Approved
0.6983	Remote Similarity	NPD4122	Approved
0.6983	Remote Similarity	NPD32	Approved
0.6983	Remote Similarity	NPD31	Approved
0.6983	Remote Similarity	NPD4038	Approved
0.6983	Remote Similarity	NPD4034	Approved
0.6973	Remote Similarity	NPD6716	Phase 1
0.6971	Remote Similarity	NPD5459	Phase 2
0.6969	Remote Similarity	NPD3259	Approved
0.696	Remote Similarity	NPD7404	Approved
0.696	Remote Similarity	NPD3402	Phase 1
0.6958	Remote Similarity	NPD1740	Approved
0.6958	Remote Similarity	NPD4500	Approved
0.6958	Remote Similarity	NPD1739	Approved
0.6958	Remote Similarity	NPD4501	Approved
0.6955	Remote Similarity	NPD7859	Phase 2
0.6955	Remote Similarity	NPD7001	Phase 3
0.6952	Remote Similarity	NPD3801	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4502	Phase 2
0.6944	Remote Similarity	NPD8356	Approved
0.6944	Remote Similarity	NPD7176	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3986	Discontinued
0.6938	Remote Similarity	NPD6963	Approved
0.6938	Remote Similarity	NPD6964	Approved
0.6934	Remote Similarity	NPD8363	Approved
0.6934	Remote Similarity	NPD8364	Approved
0.6932	Remote Similarity	NPD6276	Discontinued
0.6929	Remote Similarity	NPD3263	Phase 3
0.6926	Remote Similarity	NPD5116	Phase 1
0.692	Remote Similarity	NPD6568	Discontinued
0.6917	Remote Similarity	NPD3825	Phase 3
0.6917	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5891	Approved
0.6906	Remote Similarity	NPD8465	Approved
0.6906	Remote Similarity	NPD8466	Approved
0.6906	Remote Similarity	NPD8467	Approved
0.6903	Remote Similarity	NPD8442	Discontinued
0.6902	Remote Similarity	NPD8430	Approved
0.6899	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6494	Phase 2
0.6898	Remote Similarity	NPD7666	Phase 3
0.6898	Remote Similarity	NPD7665	Phase 2
0.6897	Remote Similarity	NPD8421	Discontinued
0.6897	Remote Similarity	NPD7885	Phase 2
0.6897	Remote Similarity	NPD7886	Phase 2
0.6894	Remote Similarity	NPD5488	Discontinued
0.6893	Remote Similarity	NPD7416	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD7194	Discontinued
0.6891	Remote Similarity	NPD3811	Discontinued
0.6886	Remote Similarity	NPD8284	Discontinued
0.6885	Remote Similarity	NPD946	Discontinued
0.6884	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5475	Discontinued
0.6882	Remote Similarity	NPD7067	Approved
0.6882	Remote Similarity	NPD7068	Approved
0.688	Remote Similarity	NPD4989	Phase 2
0.6867	Remote Similarity	NPD5903	Approved
0.6867	Remote Similarity	NPD5902	Approved
0.6866	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5850	Phase 3
0.6863	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3477	Phase 2
0.6862	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1392	Approved
0.6857	Remote Similarity	NPD7181	Phase 3
0.6851	Remote Similarity	NPD6745	Discontinued
0.6848	Remote Similarity	NPD5924	Discontinued
0.6848	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3947	Discontinued
0.6836	Remote Similarity	NPD4845	Discontinued
0.6831	Remote Similarity	NPD8525	Approved
0.6824	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6962	Phase 2
0.682	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD484	Approved
0.6816	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3003	Approved
0.6815	Remote Similarity	NPD4131	Phase 3
0.6815	Remote Similarity	NPD5066	Phase 2
0.6815	Remote Similarity	NPD5067	Phase 2
0.6813	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8426	Approved
0.6809	Remote Similarity	NPD8459	Approved
0.6809	Remote Similarity	NPD8425	Approved
0.6809	Remote Similarity	NPD8460	Approved
0.6806	Remote Similarity	NPD7417	Discontinued
0.6805	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6799	Remote Similarity	NPD7053	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7222	Phase 2
0.6787	Remote Similarity	NPD7069	Discontinued
0.6787	Remote Similarity	NPD3816	Phase 1
0.6787	Remote Similarity	NPD3815	Phase 1
0.6786	Remote Similarity	NPD7395	Discontinued
0.6786	Remote Similarity	NPD3217	Phase 2
0.6786	Remote Similarity	NPD8428	Approved
0.6786	Remote Similarity	NPD3354	Phase 2
0.6786	Remote Similarity	NPD8429	Approved
0.6786	Remote Similarity	NPD8427	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