NPASS Compound

Structure

NPC475422 OpenBabel07101719512D 44 53 0 0 1 0 0 0 0 0999 V2000 -0.4537 3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3673 4.2146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4976 1.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3663 -0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1120 0.1505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7244 -1.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9404 1.7834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8719 0.5368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1692 0.0514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5881 -1.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2931 3.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6649 2.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0008 0.5761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4721 3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0883 0.3193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0156 3.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8302 1.8447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2014 2.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8302 3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3760 1.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4675 0.6093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0092 3.2666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7268 2.1251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9976 1.6843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2931 2.3186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0092 2.3186 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1394 2.8692 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3673 1.3707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7356 0.6219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6120 0.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0937 -0.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6512 2.3186 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1494 1.8520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0034 1.7379 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4721 1.8447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2420 1.8382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0341 1.1389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0386 1.5233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6692 0.9174 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6512 3.2666 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.4379 1.1078 0.0000 N 0 0 3 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 -3.9537 3.2790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2487 3.6695 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 22 2 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 24 2 0 0 0 0 8 29 2 0 0 0 0 9 30 2 0 0 0 0 10 31 2 0 0 0 0 11 14 1 0 0 0 0 11 25 1 0 0 0 0 12 16 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 38 1 0 0 0 0 14 40 1 0 0 0 0 15 41 1 0 0 0 0 16 43 1 0 0 0 0 17 26 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 22 1 0 0 0 0 19 40 1 0 0 0 0 20 23 1 0 0 0 0 20 41 1 0 0 0 0 21 28 2 0 0 0 0 21 42 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 0 0 0 0 25 35 2 0 0 0 0 26 28 1 6 0 0 0 27 18 1 6 0 0 0 27 34 1 0 0 0 0 28 36 1 0 0 0 0 29 31 1 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 42 1 0 0 0 0 32 35 1 0 0 0 0 32 40 1 6 0 0 0 33 38 1 1 0 0 0 33 41 1 0 0 0 0 34 36 1 0 0 0 0 34 37 1 0 0 0 0 35 39 1 0 0 0 0 36 44 1 0 0 0 0 37 38 1 0 0 0 0 37 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.33
Volume:	615.442
LogP:	3.697
LogD:	3.552
LogS:	-3.794
# Rotatable Bonds:	2
TPSA:	65.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	10
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	6.452
Fsp3:	0.474
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.388
MDCK Permeability:	2.1712960005970672e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.833
20% Bioavailability (F20%):	0.689
30% Bioavailability (F30%):	0.393

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58
Plasma Protein Binding (PPB):	85.63175201416016%
Volume Distribution (VD):	4.088
Pgp-substrate:	12.941692352294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.862
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.521
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	7.798
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.524
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.399
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.723
Carcinogencity:	0.728
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.996

Download Data

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

Natural Product: NPC475422

Natural Product ID:	NPC475422
*Common Name:**	Tetradehydrolongicaudatine Y
IUPAC Name:	n.a.
Synonyms:	Tetradehydrolongicaudatine Y
Standard InCHIKey:	SAOCQHSCOLQBFR-NMWCRYOMSA-N
Standard InCHI:	InChI=1S/C38H42N4O2/c1-2-22-19-40-14-11-25-24-7-3-5-9-30(24)39-35(25)32(40)17-26(22)28-21-42-31-10-6-4-8-29(31)38-13-15-41-20-23(12-16-43)27(18-33(38)41)34(36(28)44)37(38)42/h2-10,12,21,26-27,32-34,36-37,39,43-44H,11,13-20H2,1H3/b22-2-,23-12-/t26-,27-,32-,33-,34-,36+,37-,38+/m0/s1
SMILES:	OC/C=C1/CN2CC[C@@]34[C@@H]2C[C@@H]1[C@H]1[C@H](O)C(=CN([C@H]31)c1c4cccc1)[C@H]1C[C@@H]2N(C/C/1=C/C)CCc1c2[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505319
PubChem CID:	44559870
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO18713	Strychnos usambarensis	Species	Loganiaceae	Eukaryota	roots	n.a.	n.a.	PMID[10217724]
NPO18713	Strychnos usambarensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO18713	Strychnos usambarensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO18713	Strychnos usambarensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18713	Strychnos usambarensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18713	Strychnos usambarensis	Species	Loganiaceae	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	2
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	958.0	nM	PMID[543780]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1236.0	nM	PMID[543780]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	7970.0	nM	PMID[543780]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	12087.0	nM	PMID[543780]

☑ 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 NPC475422 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	434
0.1-0.2	1795
0.2-0.3	10067
0.3-0.4	21771
0.4-0.5	4271
0.5-0.6	2368
0.6-0.7	1520
0.7-0.8	443
0.8-0.85	22
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC87755
0.9375	High Similarity	NPC126066
0.8564	High Similarity	NPC475602
0.8333	Intermediate Similarity	NPC472123
0.8316	Intermediate Similarity	NPC19679
0.8255	Intermediate Similarity	NPC470126
0.8255	Intermediate Similarity	NPC476492
0.822	Intermediate Similarity	NPC139291
0.822	Intermediate Similarity	NPC472108
0.8213	Intermediate Similarity	NPC183407
0.819	Intermediate Similarity	NPC471506
0.8182	Intermediate Similarity	NPC232130
0.8177	Intermediate Similarity	NPC472294
0.8105	Intermediate Similarity	NPC326575
0.8095	Intermediate Similarity	NPC189812
0.8095	Intermediate Similarity	NPC329688
0.8088	Intermediate Similarity	NPC473362
0.8088	Intermediate Similarity	NPC166492
0.8066	Intermediate Similarity	NPC162748
0.8047	Intermediate Similarity	NPC253580
0.797	Intermediate Similarity	NPC95783
0.797	Intermediate Similarity	NPC469470
0.797	Intermediate Similarity	NPC469501
0.7956	Intermediate Similarity	NPC471564
0.7938	Intermediate Similarity	NPC472110
0.7938	Intermediate Similarity	NPC472109
0.7923	Intermediate Similarity	NPC476116
0.7905	Intermediate Similarity	NPC250835
0.7884	Intermediate Similarity	NPC317430
0.7882	Intermediate Similarity	NPC249040
0.7876	Intermediate Similarity	NPC133261
0.7871	Intermediate Similarity	NPC265576
0.7867	Intermediate Similarity	NPC472027
0.7857	Intermediate Similarity	NPC473757
0.7853	Intermediate Similarity	NPC34508
0.7851	Intermediate Similarity	NPC476493
0.7835	Intermediate Similarity	NPC472105
0.7835	Intermediate Similarity	NPC187827
0.7793	Intermediate Similarity	NPC477714
0.7793	Intermediate Similarity	NPC473310
0.7783	Intermediate Similarity	NPC52557
0.7772	Intermediate Similarity	NPC472122
0.7772	Intermediate Similarity	NPC24594
0.7754	Intermediate Similarity	NPC221786
0.7754	Intermediate Similarity	NPC474880
0.7754	Intermediate Similarity	NPC475990
0.7749	Intermediate Similarity	NPC280548
0.7744	Intermediate Similarity	NPC198339
0.774	Intermediate Similarity	NPC477065
0.772	Intermediate Similarity	NPC475097
0.7713	Intermediate Similarity	NPC229173
0.7707	Intermediate Similarity	NPC79129
0.7707	Intermediate Similarity	NPC249150
0.7707	Intermediate Similarity	NPC49196
0.7707	Intermediate Similarity	NPC195461
0.7707	Intermediate Similarity	NPC313985
0.7707	Intermediate Similarity	NPC81654
0.77	Intermediate Similarity	NPC251936
0.7696	Intermediate Similarity	NPC50503
0.7692	Intermediate Similarity	NPC176199
0.7692	Intermediate Similarity	NPC270009
0.7692	Intermediate Similarity	NPC472443
0.7692	Intermediate Similarity	NPC215795
0.7692	Intermediate Similarity	NPC475288
0.7684	Intermediate Similarity	NPC470508
0.7672	Intermediate Similarity	NPC16667
0.7665	Intermediate Similarity	NPC472444
0.7664	Intermediate Similarity	NPC477715
0.7656	Intermediate Similarity	NPC474897
0.7653	Intermediate Similarity	NPC300688
0.7647	Intermediate Similarity	NPC285469
0.7632	Intermediate Similarity	NPC469734
0.7614	Intermediate Similarity	NPC192270
0.7611	Intermediate Similarity	NPC81175
0.7604	Intermediate Similarity	NPC154293
0.7591	Intermediate Similarity	NPC475258
0.7591	Intermediate Similarity	NPC6215
0.7586	Intermediate Similarity	NPC474177
0.7581	Intermediate Similarity	NPC304926
0.7581	Intermediate Similarity	NPC476041
0.7577	Intermediate Similarity	NPC97525
0.7566	Intermediate Similarity	NPC477861
0.7566	Intermediate Similarity	NPC67056
0.7562	Intermediate Similarity	NPC46413
0.7557	Intermediate Similarity	NPC33949
0.7551	Intermediate Similarity	NPC151939
0.7551	Intermediate Similarity	NPC59269
0.7549	Intermediate Similarity	NPC133366
0.7545	Intermediate Similarity	NPC475338
0.7545	Intermediate Similarity	NPC909
0.7538	Intermediate Similarity	NPC472586
0.7536	Intermediate Similarity	NPC314957
0.7526	Intermediate Similarity	NPC81229
0.7526	Intermediate Similarity	NPC255229
0.7525	Intermediate Similarity	NPC472112
0.7513	Intermediate Similarity	NPC201700
0.75	Intermediate Similarity	NPC470507
0.75	Intermediate Similarity	NPC98371
0.75	Intermediate Similarity	NPC207726
0.75	Intermediate Similarity	NPC313884
0.75	Intermediate Similarity	NPC162860
0.75	Intermediate Similarity	NPC15102
0.7488	Intermediate Similarity	NPC32200
0.7477	Intermediate Similarity	NPC56109
0.7477	Intermediate Similarity	NPC191382
0.7476	Intermediate Similarity	NPC229332
0.7475	Intermediate Similarity	NPC34271
0.7475	Intermediate Similarity	NPC175474
0.7463	Intermediate Similarity	NPC195314
0.7462	Intermediate Similarity	NPC293472
0.7462	Intermediate Similarity	NPC68354
0.7451	Intermediate Similarity	NPC472113
0.745	Intermediate Similarity	NPC165201
0.7449	Intermediate Similarity	NPC275305
0.7449	Intermediate Similarity	NPC37423
0.7448	Intermediate Similarity	NPC472587
0.7446	Intermediate Similarity	NPC471891
0.7442	Intermediate Similarity	NPC469592
0.7442	Intermediate Similarity	NPC471080
0.7438	Intermediate Similarity	NPC206967
0.7432	Intermediate Similarity	NPC476491
0.7427	Intermediate Similarity	NPC205403
0.7427	Intermediate Similarity	NPC231342
0.7426	Intermediate Similarity	NPC119700
0.7424	Intermediate Similarity	NPC6093
0.7423	Intermediate Similarity	NPC63751
0.7418	Intermediate Similarity	NPC223791
0.7418	Intermediate Similarity	NPC107077
0.7416	Intermediate Similarity	NPC475506
0.7411	Intermediate Similarity	NPC476451
0.7409	Intermediate Similarity	NPC155444
0.7407	Intermediate Similarity	NPC38736
0.7406	Intermediate Similarity	NPC54420
0.74	Intermediate Similarity	NPC472104
0.7398	Intermediate Similarity	NPC473880
0.7389	Intermediate Similarity	NPC173028
0.7389	Intermediate Similarity	NPC65215
0.7387	Intermediate Similarity	NPC15840
0.7381	Intermediate Similarity	NPC193761
0.7381	Intermediate Similarity	NPC155143
0.7381	Intermediate Similarity	NPC162730
0.738	Intermediate Similarity	NPC37548
0.7371	Intermediate Similarity	NPC475910
0.7371	Intermediate Similarity	NPC49954
0.7371	Intermediate Similarity	NPC474561
0.7366	Intermediate Similarity	NPC477175
0.7366	Intermediate Similarity	NPC470730
0.7356	Intermediate Similarity	NPC473640
0.7356	Intermediate Similarity	NPC473747
0.735	Intermediate Similarity	NPC302191
0.735	Intermediate Similarity	NPC314394
0.734	Intermediate Similarity	NPC33421
0.734	Intermediate Similarity	NPC317030
0.734	Intermediate Similarity	NPC204565
0.7333	Intermediate Similarity	NPC475969
0.7333	Intermediate Similarity	NPC475859
0.7333	Intermediate Similarity	NPC300183
0.733	Intermediate Similarity	NPC280272
0.7323	Intermediate Similarity	NPC280852
0.7323	Intermediate Similarity	NPC288785
0.7315	Intermediate Similarity	NPC75634
0.731	Intermediate Similarity	NPC314603
0.7306	Intermediate Similarity	NPC469594
0.7301	Intermediate Similarity	NPC165743
0.7299	Intermediate Similarity	NPC474116
0.7296	Intermediate Similarity	NPC194411
0.7293	Intermediate Similarity	NPC41679
0.7291	Intermediate Similarity	NPC474707
0.7287	Intermediate Similarity	NPC187951
0.7286	Intermediate Similarity	NPC294909
0.7286	Intermediate Similarity	NPC128265
0.7286	Intermediate Similarity	NPC254240
0.7286	Intermediate Similarity	NPC312870
0.7286	Intermediate Similarity	NPC199851
0.7285	Intermediate Similarity	NPC474896
0.7282	Intermediate Similarity	NPC54988
0.7282	Intermediate Similarity	NPC160105
0.7277	Intermediate Similarity	NPC184476
0.7273	Intermediate Similarity	NPC171317
0.7269	Intermediate Similarity	NPC250129
0.7268	Intermediate Similarity	NPC329858
0.7268	Intermediate Similarity	NPC314333
0.7264	Intermediate Similarity	NPC233936
0.7264	Intermediate Similarity	NPC98715
0.7264	Intermediate Similarity	NPC477135
0.7257	Intermediate Similarity	NPC478080
0.7256	Intermediate Similarity	NPC271862
0.7252	Intermediate Similarity	NPC31097
0.7246	Intermediate Similarity	NPC473178
0.7241	Intermediate Similarity	NPC473189
0.7241	Intermediate Similarity	NPC476319
0.7238	Intermediate Similarity	NPC100321
0.7236	Intermediate Similarity	NPC203754
0.7236	Intermediate Similarity	NPC150048
0.7233	Intermediate Similarity	NPC243716
0.7231	Intermediate Similarity	NPC475420
0.7222	Intermediate Similarity	NPC475165
0.7222	Intermediate Similarity	NPC234999
0.722	Intermediate Similarity	NPC111602
0.722	Intermediate Similarity	NPC102338

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 NPC475422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	526
0.2-0.3	732
0.3-0.4	1985
0.4-0.5	2827
0.5-0.6	2146
0.6-0.7	627
0.7-0.8	84
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7872	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7824	Approved
0.7738	Intermediate Similarity	NPD7950	Approved
0.7738	Intermediate Similarity	NPD7791	Approved
0.7738	Intermediate Similarity	NPD7953	Approved
0.7738	Intermediate Similarity	NPD7789	Approved
0.7738	Intermediate Similarity	NPD7790	Approved
0.7738	Intermediate Similarity	NPD7951	Approved
0.7738	Intermediate Similarity	NPD7952	Approved
0.7707	Intermediate Similarity	NPD4600	Approved
0.7707	Intermediate Similarity	NPD4601	Approved
0.7677	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7730	Approved
0.7671	Intermediate Similarity	NPD7731	Approved
0.7661	Intermediate Similarity	NPD7271	Approved
0.759	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4076	Approved
0.7513	Intermediate Similarity	NPD4079	Approved
0.7512	Intermediate Similarity	NPD8431	Approved
0.7511	Intermediate Similarity	NPD6978	Phase 2
0.7511	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7781	Approved
0.7477	Intermediate Similarity	NPD7780	Approved
0.7475	Intermediate Similarity	NPD6595	Phase 3
0.7474	Intermediate Similarity	NPD1326	Approved
0.7474	Intermediate Similarity	NPD1325	Approved
0.7462	Intermediate Similarity	NPD3505	Approved
0.7462	Intermediate Similarity	NPD3506	Approved
0.7424	Intermediate Similarity	NPD8386	Phase 2
0.7406	Intermediate Similarity	NPD8322	Phase 2
0.7402	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5065	Approved
0.7358	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7957	Phase 1
0.7356	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8115	Approved
0.7311	Intermediate Similarity	NPD8114	Approved
0.7297	Intermediate Similarity	NPD7716	Approved
0.7297	Intermediate Similarity	NPD7717	Approved
0.7286	Intermediate Similarity	NPD4500	Approved
0.7286	Intermediate Similarity	NPD4501	Approved
0.7268	Intermediate Similarity	NPD4499	Approved
0.7238	Intermediate Similarity	NPD8395	Approved
0.7238	Intermediate Similarity	NPD8396	Approved
0.7228	Intermediate Similarity	NPD5596	Phase 2
0.722	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4181	Approved
0.7184	Intermediate Similarity	NPD6281	Approved
0.7179	Intermediate Similarity	NPD3323	Discontinued
0.7178	Intermediate Similarity	NPD7867	Phase 1
0.7177	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3961	Discontinued
0.7171	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4511	Phase 1
0.7169	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4463	Approved
0.7158	Intermediate Similarity	NPD4462	Approved
0.7157	Intermediate Similarity	NPD4639	Approved
0.7157	Intermediate Similarity	NPD4638	Approved
0.7157	Intermediate Similarity	NPD4640	Approved
0.7156	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2380	Approved
0.715	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5913	Phase 3
0.715	Intermediate Similarity	NPD2381	Approved
0.715	Intermediate Similarity	NPD2382	Approved
0.7149	Intermediate Similarity	NPD8358	Approved
0.7143	Intermediate Similarity	NPD8364	Approved
0.7143	Intermediate Similarity	NPD7948	Phase 1
0.7143	Intermediate Similarity	NPD8363	Approved
0.7136	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7665	Phase 2
0.713	Intermediate Similarity	NPD7666	Phase 3
0.7121	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2882	Phase 1
0.7103	Intermediate Similarity	NPD4886	Phase 2
0.71	Intermediate Similarity	NPD4128	Approved
0.7092	Intermediate Similarity	NPD5140	Approved
0.7092	Intermediate Similarity	NPD5138	Approved
0.7091	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8020	Approved
0.7087	Intermediate Similarity	NPD8021	Approved
0.7087	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD8093	Discontinued
0.7078	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6227	Discontinued
0.7071	Intermediate Similarity	NPD5021	Discontinued
0.7071	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7726	Phase 1
0.7048	Intermediate Similarity	NPD7944	Discontinued
0.7045	Intermediate Similarity	NPD8094	Discontinued
0.7044	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6455	Phase 3
0.7033	Intermediate Similarity	NPD3404	Approved
0.7031	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6158	Phase 2
0.7027	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6492	Phase 2
0.701	Intermediate Similarity	NPD8408	Discontinued
0.7009	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5426	Phase 3
0.6986	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4602	Approved
0.6965	Remote Similarity	NPD7418	Discontinued
0.6955	Remote Similarity	NPD7470	Discontinued
0.695	Remote Similarity	NPD7474	Suspended
0.6947	Remote Similarity	NPD6995	Phase 1
0.6946	Remote Similarity	NPD2144	Approved
0.6946	Remote Similarity	NPD8122	Approved
0.6946	Remote Similarity	NPD8123	Approved
0.6943	Remote Similarity	NPD8402	Approved
0.6943	Remote Similarity	NPD8400	Approved
0.6943	Remote Similarity	NPD8401	Approved
0.6931	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3038	Discontinued
0.6923	Remote Similarity	NPD7455	Approved
0.6923	Remote Similarity	NPD7454	Approved
0.6923	Remote Similarity	NPD3330	Phase 1
0.6923	Remote Similarity	NPD2383	Phase 1
0.692	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5901	Discontinued
0.6912	Remote Similarity	NPD8272	Phase 2
0.6908	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8465	Approved
0.6905	Remote Similarity	NPD8466	Approved
0.6905	Remote Similarity	NPD8467	Approved
0.6897	Remote Similarity	NPD4075	Phase 2
0.6895	Remote Similarity	NPD5254	Discontinued
0.6895	Remote Similarity	NPD2916	Discontinued
0.6893	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7194	Discontinued
0.6887	Remote Similarity	NPD7618	Phase 3
0.6887	Remote Similarity	NPD7619	Phase 3
0.6878	Remote Similarity	NPD5473	Discontinued
0.6875	Remote Similarity	NPD7423	Phase 2
0.6875	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8072	Approved
0.6864	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8063	Discontinued
0.6854	Remote Similarity	NPD7935	Phase 2
0.6849	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7921	Approved
0.6846	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6248	Phase 2
0.6837	Remote Similarity	NPD6249	Phase 2
0.6837	Remote Similarity	NPD6999	Discontinued
0.6837	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8321	Discontinued
0.6827	Remote Similarity	NPD3082	Discontinued
0.6823	Remote Similarity	NPD1683	Approved
0.6823	Remote Similarity	NPD7469	Discontinued
0.6822	Remote Similarity	NPD8016	Phase 3
0.6822	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6664	Approved
0.6822	Remote Similarity	NPD7081	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5100	Phase 3
0.6814	Remote Similarity	NPD5104	Approved
0.6804	Remote Similarity	NPD5530	Phase 1
0.6802	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5936	Approved
0.6802	Remote Similarity	NPD5939	Approved
0.6798	Remote Similarity	NPD7221	Approved
0.6798	Remote Similarity	NPD7219	Approved
0.6797	Remote Similarity	NPD8426	Approved
0.6797	Remote Similarity	NPD8459	Approved
0.6797	Remote Similarity	NPD8425	Approved
0.6797	Remote Similarity	NPD8460	Approved
0.6791	Remote Similarity	NPD53	Approved
0.6791	Remote Similarity	NPD7778	Approved
0.6791	Remote Similarity	NPD7777	Approved
0.6783	Remote Similarity	NPD8289	Discontinued
0.6774	Remote Similarity	NPD7817	Phase 1
0.6772	Remote Similarity	NPD8428	Approved
0.6772	Remote Similarity	NPD8427	Approved
0.6772	Remote Similarity	NPD8429	Approved
0.6769	Remote Similarity	NPD6849	Phase 2
0.6769	Remote Similarity	NPD6850	Phase 2
0.6759	Remote Similarity	NPD3814	Phase 1
0.6758	Remote Similarity	NPD8098	Approved
0.6757	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD7112	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