NPASS Compound

Structure

CID223590 OpenBabel06191716022D 42 48 0 0 1 0 0 0 0 0999 V2000 -1.1242 -2.5913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0094 -3.4939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8339 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4537 -1.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0809 0.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2548 -1.5998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0901 4.9927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0716 4.8013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4336 4.2384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3966 3.8555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5111 -0.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3306 -0.0347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5948 -0.5443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0920 -1.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5335 -0.4435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2296 0.8384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7585 3.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1881 -1.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1483 0.1249 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7400 3.1012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4008 -1.8723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4563 -0.4423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0144 -0.3751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8064 -1.3533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4149 -0.3187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9028 -0.7713 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1020 2.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0489 -1.2025 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0953 -0.1073 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3650 -1.0041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2210 -0.5148 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7547 -1.4202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0650 2.1555 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.4614 -0.9911 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8795 2.7299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3037 -0.6592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7138 -2.4193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2369 -2.8588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4756 -2.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8584 -0.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 1.5927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 40 1 0 0 0 0 5 41 1 0 0 0 0 6 34 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 17 2 0 0 0 0 10 20 2 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 29 1 0 0 0 0 13 19 1 0 0 0 0 14 21 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 15 34 1 0 0 0 0 16 42 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 13 1 1 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 31 1 1 0 0 0 20 33 1 0 0 0 0 21 38 1 6 0 0 0 22 31 1 6 0 0 0 22 39 1 0 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 40 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 1 0 0 0 25 31 1 0 0 0 0 26 32 1 6 0 0 0 26 41 1 0 0 0 0 27 35 2 0 0 0 0 27 42 1 0 0 0 0 28 31 1 0 0 0 0 28 32 1 0 0 0 0 28 34 1 0 0 0 0 29 16 1 1 0 0 0 30 32 1 1 0 0 0 30 36 1 0 0 0 0 32 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.16
Volume:	344.239
LogP:	1.783
LogD:	1.54
LogS:	-2.517
# Rotatable Bonds:	3
TPSA:	58.97
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.775
Synthetic Accessibility Score:	5.527
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.756
MDCK Permeability:	3.169163392158225e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.16
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	44.59526443481445%
Volume Distribution (VD):	2.242
Pgp-substrate:	69.11643981933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.225
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.858
CYP3A4-inhibitor:	0.377
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	10.661
Half-life (T1/2):	0.423

ADMET: Toxicity

hERG Blockers:	0.176
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.346
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.778
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.168
Carcinogencity:	0.217
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC223590

Natural Product ID:	NPC223590
*Common Name:**	Anthranoyllycoctonine
IUPAC Name:	n.a.
Synonyms:	Anthranoyllycoctonine
Standard InCHIKey:	NNDHDYDFEDRMGH-CAEIVAEBSA-N
Standard InCHI:	InChI=1S/C32H46N2O8/c1-6-34-15-29(16-42-27(35)17-9-7-8-10-20(17)33)12-11-22(39-3)31-19-13-18-21(38-2)14-30(36,23(19)24(18)40-4)32(37,28(31)34)26(41-5)25(29)31/h7-10,18-19,21-26,28,36-37H,6,11-16,33H2,1-5H3/t18-,19-,21+,22+,23-,24+,25-,26+,28?,29+,30-,31+,32-/m1/s1
SMILES:	CCN1C[C@@]2(CC[C@@H]([C@@]34[C@@H]5C[C@@H]6[C@H](C[C@@]([C@H]5[C@H]6OC)([C@@]([C@H]([C@H]23)OC)(C14)O)O)OC)OC)COC(=O)c1ccccc1N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451362
PubChem CID:	441708
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid 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
NPO33014	delphinium cashmirianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[541686]
NPO9626	Aconitum finetianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9626	Aconitum finetianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9626	Aconitum finetianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9626	Aconitum finetianum	Species	Ranunculaceae	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
EC50	1
LD50	1
Others	3

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	20.8	mg.kg-1	PMID[556284]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	8.0	bpm	PMID[556285]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[556285]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-5.0	bpm	PMID[556285]
NPT2	Others	Unspecified		EC50	=	12882.5	nM	PMID[556286]

☑ 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 NPC223590 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	346
0.1-0.2	1483
0.2-0.3	3245
0.3-0.4	10067
0.4-0.5	20074
0.5-0.6	5985
0.6-0.7	1364
0.7-0.8	86
0.8-0.85	8
0.85-0.9	25
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9698	High Similarity	NPC473667
0.9594	High Similarity	NPC473837
0.955	High Similarity	NPC106593
0.9353	High Similarity	NPC140311
0.9227	High Similarity	NPC470631
0.9227	High Similarity	NPC35390
0.9227	High Similarity	NPC473781
0.9183	High Similarity	NPC475316
0.9183	High Similarity	NPC473486
0.8622	High Similarity	NPC184195
0.8622	High Similarity	NPC166521
0.8622	High Similarity	NPC205
0.8622	High Similarity	NPC172769
0.8622	High Similarity	NPC281470
0.8622	High Similarity	NPC124690
0.852	High Similarity	NPC40539
0.8477	Intermediate Similarity	NPC108276
0.8477	Intermediate Similarity	NPC163578
0.8048	Intermediate Similarity	NPC476496
0.7952	Intermediate Similarity	NPC326895
0.7933	Intermediate Similarity	NPC475223
0.7915	Intermediate Similarity	NPC106840
0.7915	Intermediate Similarity	NPC94687
0.7915	Intermediate Similarity	NPC476495
0.7895	Intermediate Similarity	NPC246983
0.7895	Intermediate Similarity	NPC475448
0.7596	Intermediate Similarity	NPC198205
0.7596	Intermediate Similarity	NPC21483
0.7524	Intermediate Similarity	NPC198390
0.7488	Intermediate Similarity	NPC311054
0.7488	Intermediate Similarity	NPC112752
0.7465	Intermediate Similarity	NPC176371
0.7465	Intermediate Similarity	NPC136573
0.7453	Intermediate Similarity	NPC107828
0.7453	Intermediate Similarity	NPC90358
0.7183	Intermediate Similarity	NPC259791
0.7183	Intermediate Similarity	NPC476207
0.7183	Intermediate Similarity	NPC476206
0.7183	Intermediate Similarity	NPC476212
0.7183	Intermediate Similarity	NPC476129
0.7183	Intermediate Similarity	NPC476205
0.7183	Intermediate Similarity	NPC476256
0.7183	Intermediate Similarity	NPC476257
0.7179	Intermediate Similarity	NPC313720
0.7179	Intermediate Similarity	NPC17160
0.7174	Intermediate Similarity	NPC473458
0.7155	Intermediate Similarity	NPC475596
0.7155	Intermediate Similarity	NPC316841
0.7155	Intermediate Similarity	NPC475303
0.715	Intermediate Similarity	NPC476218
0.715	Intermediate Similarity	NPC108804
0.7149	Intermediate Similarity	NPC127026
0.7149	Intermediate Similarity	NPC127720
0.7143	Intermediate Similarity	NPC471512
0.7137	Intermediate Similarity	NPC475406
0.713	Intermediate Similarity	NPC476436
0.7124	Intermediate Similarity	NPC476429
0.7124	Intermediate Similarity	NPC30456
0.7118	Intermediate Similarity	NPC471980
0.7106	Intermediate Similarity	NPC38959
0.7106	Intermediate Similarity	NPC327904
0.71	Intermediate Similarity	NPC475600
0.71	Intermediate Similarity	NPC228377
0.71	Intermediate Similarity	NPC476110
0.71	Intermediate Similarity	NPC475631
0.71	Intermediate Similarity	NPC87152
0.71	Intermediate Similarity	NPC328186
0.71	Intermediate Similarity	NPC122968
0.71	Intermediate Similarity	NPC477787
0.7097	Intermediate Similarity	NPC475489
0.7094	Intermediate Similarity	NPC30171
0.7093	Intermediate Similarity	NPC84815
0.7093	Intermediate Similarity	NPC301368
0.7091	Intermediate Similarity	NPC476500
0.7082	Intermediate Similarity	NPC473689
0.7082	Intermediate Similarity	NPC292416
0.7069	Intermediate Similarity	NPC470486
0.7069	Intermediate Similarity	NPC471190
0.7069	Intermediate Similarity	NPC471977
0.7069	Intermediate Similarity	NPC475644
0.7064	Intermediate Similarity	NPC327769
0.7051	Intermediate Similarity	NPC319880
0.7051	Intermediate Similarity	NPC320324
0.7051	Intermediate Similarity	NPC244839
0.7048	Intermediate Similarity	NPC62367
0.7043	Intermediate Similarity	NPC76565
0.7043	Intermediate Similarity	NPC57797
0.7043	Intermediate Similarity	NPC250807
0.7037	Intermediate Similarity	NPC36607
0.7034	Intermediate Similarity	NPC154922
0.703	Intermediate Similarity	NPC253738
0.7029	Intermediate Similarity	NPC113455
0.7028	Intermediate Similarity	NPC327699
0.7026	Intermediate Similarity	NPC471513
0.7026	Intermediate Similarity	NPC146824
0.7023	Intermediate Similarity	NPC221687
0.7021	Intermediate Similarity	NPC237702
0.7018	Intermediate Similarity	NPC216428
0.7018	Intermediate Similarity	NPC288110
0.7013	Intermediate Similarity	NPC475498
0.7013	Intermediate Similarity	NPC473850
0.7013	Intermediate Similarity	NPC475137
0.7012	Intermediate Similarity	NPC120239
0.7004	Intermediate Similarity	NPC6981
0.7004	Intermediate Similarity	NPC471016
0.6996	Remote Similarity	NPC475362
0.6992	Remote Similarity	NPC170751
0.6992	Remote Similarity	NPC160113
0.6992	Remote Similarity	NPC476220
0.6983	Remote Similarity	NPC473506
0.6974	Remote Similarity	NPC212768
0.6974	Remote Similarity	NPC75600
0.6974	Remote Similarity	NPC158020
0.6974	Remote Similarity	NPC473089
0.6974	Remote Similarity	NPC294579
0.6974	Remote Similarity	NPC144779
0.6974	Remote Similarity	NPC473115
0.6974	Remote Similarity	NPC6576
0.6965	Remote Similarity	NPC73644
0.6963	Remote Similarity	NPC25401
0.696	Remote Similarity	NPC477909
0.696	Remote Similarity	NPC42678
0.696	Remote Similarity	NPC470306
0.696	Remote Similarity	NPC477907
0.6958	Remote Similarity	NPC469452
0.6957	Remote Similarity	NPC477912
0.6957	Remote Similarity	NPC475427
0.6953	Remote Similarity	NPC211920
0.6946	Remote Similarity	NPC469450
0.6946	Remote Similarity	NPC476258
0.6946	Remote Similarity	NPC304837
0.694	Remote Similarity	NPC328154
0.694	Remote Similarity	NPC477902
0.693	Remote Similarity	NPC471014
0.693	Remote Similarity	NPC475408
0.6929	Remote Similarity	NPC475648
0.6926	Remote Similarity	NPC477788
0.6916	Remote Similarity	NPC4421
0.6912	Remote Similarity	NPC97100
0.6912	Remote Similarity	NPC473375
0.6911	Remote Similarity	NPC131273
0.6911	Remote Similarity	NPC473441
0.691	Remote Similarity	NPC148860
0.6903	Remote Similarity	NPC472553
0.6901	Remote Similarity	NPC329932
0.6894	Remote Similarity	NPC477397
0.6888	Remote Similarity	NPC469451
0.688	Remote Similarity	NPC124029
0.6875	Remote Similarity	NPC471583
0.6875	Remote Similarity	NPC471782
0.6875	Remote Similarity	NPC253482
0.687	Remote Similarity	NPC472555
0.6869	Remote Similarity	NPC477998
0.6847	Remote Similarity	NPC476750
0.6845	Remote Similarity	NPC476749
0.6837	Remote Similarity	NPC471623
0.6835	Remote Similarity	NPC321072
0.6835	Remote Similarity	NPC215892
0.6835	Remote Similarity	NPC242662
0.6835	Remote Similarity	NPC191193
0.6833	Remote Similarity	NPC278540
0.6828	Remote Similarity	NPC476467
0.6828	Remote Similarity	NPC127996
0.681	Remote Similarity	NPC203005
0.681	Remote Similarity	NPC477903
0.6808	Remote Similarity	NPC52262
0.6806	Remote Similarity	NPC453583
0.6806	Remote Similarity	NPC473400
0.6806	Remote Similarity	NPC471629
0.6806	Remote Similarity	NPC471754
0.6806	Remote Similarity	NPC473300
0.6806	Remote Similarity	NPC206211
0.6806	Remote Similarity	NPC475336
0.6806	Remote Similarity	NPC275170
0.6806	Remote Similarity	NPC317882
0.6806	Remote Similarity	NPC324251
0.6806	Remote Similarity	NPC306001
0.6804	Remote Similarity	NPC208553
0.6804	Remote Similarity	NPC181964
0.6804	Remote Similarity	NPC471606
0.6804	Remote Similarity	NPC90967
0.6795	Remote Similarity	NPC477394
0.6793	Remote Similarity	NPC96801
0.6793	Remote Similarity	NPC477906
0.6793	Remote Similarity	NPC150698
0.6783	Remote Similarity	NPC477908
0.6783	Remote Similarity	NPC206343
0.6782	Remote Similarity	NPC323001
0.6782	Remote Similarity	NPC326235
0.6781	Remote Similarity	NPC477911
0.6778	Remote Similarity	NPC475426
0.6778	Remote Similarity	NPC35208
0.6774	Remote Similarity	NPC67246
0.6774	Remote Similarity	NPC33372
0.6773	Remote Similarity	NPC473490
0.6773	Remote Similarity	NPC473558
0.677	Remote Similarity	NPC472550
0.677	Remote Similarity	NPC304179
0.677	Remote Similarity	NPC48042
0.6769	Remote Similarity	NPC319128

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 NPC223590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	595
0.2-0.3	840
0.3-0.4	2296
0.4-0.5	3698
0.5-0.6	1425
0.6-0.7	100
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD7497	Discontinued
0.7115	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD8361	Approved
0.6837	Remote Similarity	NPD8360	Approved
0.6837	Remote Similarity	NPD8435	Approved
0.6822	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6625	Approved
0.6804	Remote Similarity	NPD8485	Approved
0.6781	Remote Similarity	NPD6997	Phase 2
0.6762	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7962	Phase 2
0.6606	Remote Similarity	NPD5928	Phase 1
0.6599	Remote Similarity	NPD8468	Phase 2
0.6595	Remote Similarity	NPD7047	Phase 3
0.6502	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD8407	Phase 2
0.6484	Remote Similarity	NPD7906	Approved
0.6483	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8146	Phase 2
0.6461	Remote Similarity	NPD6723	Discontinued
0.6435	Remote Similarity	NPD8368	Discontinued
0.6429	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2973	Approved
0.6429	Remote Similarity	NPD2974	Approved
0.6429	Remote Similarity	NPD2975	Approved
0.6429	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4580	Approved
0.6396	Remote Similarity	NPD3170	Approved
0.6393	Remote Similarity	NPD7922	Phase 1
0.639	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD2493	Approved
0.6388	Remote Similarity	NPD3450	Approved
0.6388	Remote Similarity	NPD3452	Approved
0.6388	Remote Similarity	NPD2494	Approved
0.6387	Remote Similarity	NPD7907	Approved
0.6387	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4583	Approved
0.6376	Remote Similarity	NPD4582	Approved
0.6372	Remote Similarity	NPD6874	Approved
0.6368	Remote Similarity	NPD7795	Phase 2
0.6355	Remote Similarity	NPD7528	Approved
0.6346	Remote Similarity	NPD7803	Approved
0.6345	Remote Similarity	NPD3437	Discontinued
0.6339	Remote Similarity	NPD7256	Discontinued
0.6332	Remote Similarity	NPD4004	Approved
0.6332	Remote Similarity	NPD4002	Approved
0.6332	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD2672	Discontinued
0.6329	Remote Similarity	NPD2836	Approved
0.6327	Remote Similarity	NPD4668	Phase 2
0.6326	Remote Similarity	NPD7799	Discontinued
0.6325	Remote Similarity	NPD8462	Phase 1
0.6325	Remote Similarity	NPD7827	Phase 1
0.6323	Remote Similarity	NPD7569	Approved
0.6323	Remote Similarity	NPD7570	Approved
0.6318	Remote Similarity	NPD7708	Approved
0.6316	Remote Similarity	NPD8465	Approved
0.6316	Remote Similarity	NPD8467	Approved
0.6316	Remote Similarity	NPD7476	Discontinued
0.6316	Remote Similarity	NPD8466	Approved
0.6314	Remote Similarity	NPD8149	Discontinued
0.6313	Remote Similarity	NPD1110	Approved
0.6313	Remote Similarity	NPD1109	Approved
0.6311	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5997	Discontinued
0.6304	Remote Similarity	NPD8320	Phase 1
0.6304	Remote Similarity	NPD8319	Approved
0.6303	Remote Similarity	NPD7035	Approved
0.6303	Remote Similarity	NPD5430	Discontinued
0.6303	Remote Similarity	NPD7036	Phase 3
0.6293	Remote Similarity	NPD7606	Phase 3
0.6282	Remote Similarity	NPD1945	Phase 1
0.628	Remote Similarity	NPD5742	Approved
0.628	Remote Similarity	NPD5741	Approved
0.628	Remote Similarity	NPD5743	Approved
0.6279	Remote Similarity	NPD7940	Phase 3
0.6279	Remote Similarity	NPD7955	Approved
0.6279	Remote Similarity	NPD7956	Approved
0.6274	Remote Similarity	NPD8363	Approved
0.6274	Remote Similarity	NPD8364	Approved
0.6266	Remote Similarity	NPD3912	Discontinued
0.6256	Remote Similarity	NPD8281	Discontinued
0.6256	Remote Similarity	NPD8007	Approved
0.6256	Remote Similarity	NPD8008	Approved
0.625	Remote Similarity	NPD7048	Phase 3
0.6244	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5411	Discontinued
0.6234	Remote Similarity	NPD7891	Discontinued
0.6234	Remote Similarity	NPD2899	Discontinued
0.6232	Remote Similarity	NPD4120	Approved
0.6232	Remote Similarity	NPD4121	Phase 3
0.6228	Remote Similarity	NPD5609	Approved
0.6228	Remote Similarity	NPD5608	Approved
0.6227	Remote Similarity	NPD4577	Approved
0.6227	Remote Similarity	NPD4578	Approved
0.6226	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8492	Approved
0.6225	Remote Similarity	NPD1802	Approved
0.6225	Remote Similarity	NPD1801	Approved
0.6223	Remote Similarity	NPD7300	Phase 3
0.6223	Remote Similarity	NPD4082	Approved
0.6223	Remote Similarity	NPD7302	Phase 3
0.6222	Remote Similarity	NPD8459	Approved
0.6222	Remote Similarity	NPD8460	Approved
0.6222	Remote Similarity	NPD8425	Approved
0.6222	Remote Similarity	NPD8426	Approved
0.6221	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8404	Phase 2
0.6217	Remote Similarity	NPD5006	Approved
0.6217	Remote Similarity	NPD5005	Approved
0.6216	Remote Similarity	NPD4663	Approved
0.6214	Remote Similarity	NPD7186	Phase 3
0.621	Remote Similarity	NPD5891	Approved
0.6208	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7295	Approved
0.6207	Remote Similarity	NPD8161	Suspended
0.6207	Remote Similarity	NPD7999	Approved
0.6207	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5466	Approved
0.6204	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4888	Discontinued
0.6195	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD8429	Approved
0.6194	Remote Similarity	NPD8427	Approved
0.6194	Remote Similarity	NPD8428	Approved
0.6193	Remote Similarity	NPD5185	Approved
0.6193	Remote Similarity	NPD5182	Approved
0.6193	Remote Similarity	NPD5184	Approved
0.6184	Remote Similarity	NPD4420	Approved
0.6184	Remote Similarity	NPD7239	Suspended
0.6176	Remote Similarity	NPD7236	Approved
0.6171	Remote Similarity	NPD5036	Approved
0.6167	Remote Similarity	NPD4665	Approved
0.6167	Remote Similarity	NPD4111	Phase 1
0.6158	Remote Similarity	NPD7487	Discontinued
0.6157	Remote Similarity	NPD7854	Phase 2
0.6154	Remote Similarity	NPD7546	Discontinued
0.6154	Remote Similarity	NPD7701	Phase 2
0.6154	Remote Similarity	NPD5086	Approved
0.615	Remote Similarity	NPD5610	Approved
0.6146	Remote Similarity	NPD7478	Approved
0.6144	Remote Similarity	NPD5676	Approved
0.6143	Remote Similarity	NPD5037	Approved
0.6143	Remote Similarity	NPD5038	Approved
0.6137	Remote Similarity	NPD6807	Phase 3
0.6134	Remote Similarity	NPD7930	Approved
0.613	Remote Similarity	NPD4107	Approved
0.6121	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7775	Approved
0.6118	Remote Similarity	NPD7301	Phase 3
0.6114	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7699	Phase 2
0.6114	Remote Similarity	NPD5197	Approved
0.6114	Remote Similarity	NPD5196	Approved
0.6114	Remote Similarity	NPD7700	Phase 2
0.6114	Remote Similarity	NPD5194	Approved
0.6113	Remote Similarity	NPD7688	Phase 1
0.6111	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7583	Approved
0.6111	Remote Similarity	NPD6296	Discontinued
0.6111	Remote Similarity	NPD4596	Phase 1
0.6109	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.61	Remote Similarity	NPD2567	Approved
0.61	Remote Similarity	NPD2569	Approved
0.61	Remote Similarity	NPD6770	Approved
0.6094	Remote Similarity	NPD1294	Discontinued
0.6094	Remote Similarity	NPD4040	Phase 1
0.6094	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD2680	Approved
0.6093	Remote Similarity	NPD2247	Approved
0.6093	Remote Similarity	NPD2249	Approved
0.6093	Remote Similarity	NPD2681	Approved
0.6087	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7585	Approved
0.6083	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD4481	Phase 3
0.6081	Remote Similarity	NPD7310	Approved
0.6081	Remote Similarity	NPD7313	Approved
0.6081	Remote Similarity	NPD7311	Approved
0.6081	Remote Similarity	NPD7312	Approved
0.6079	Remote Similarity	NPD6212	Phase 3
0.6079	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6079	Remote Similarity	NPD6213	Phase 3
0.6078	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3057	Approved
0.6076	Remote Similarity	NPD4493	Discontinued
0.6071	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7683	Discontinued
0.6071	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.607	Remote Similarity	NPD8367	Approved
0.6066	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD3051	Approved
0.6063	Remote Similarity	NPD7038	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