NPASS Compound

Structure

NPC473781 OpenBabel07101718192D 48 55 0 0 1 0 0 0 0 0999 V2000 0.4573 -1.4395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9495 2.4018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2552 3.5505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1781 -1.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1477 -1.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3959 -0.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5287 6.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4774 6.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2656 5.0942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1629 5.5821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9902 3.2052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2907 2.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4314 2.5539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2747 2.0556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3478 0.9951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5171 0.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0893 0.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2134 1.3201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9512 4.3946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.5954 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8633 0.7977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8999 4.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1012 0.9326 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4218 2.0728 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5544 4.0824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4225 2.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9013 0.2760 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4093 0.1509 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4116 0.5950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4219 0.1480 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4251 2.5076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2711 0.3556 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.2648 1.0762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5171 -0.0790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4317 1.0933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4058 0.0211 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5855 3.9390 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0079 4.9506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5453 2.5373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1107 1.8080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6337 -1.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6399 -0.7416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1012 1.9121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2651 2.5711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7789 -0.7562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2275 -0.4092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4765 2.2636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 44 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 47 1 0 0 0 0 6 37 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 19 2 0 0 0 0 10 22 2 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 33 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 16 34 1 0 0 0 0 17 33 1 0 0 0 0 17 37 1 0 0 0 0 18 48 1 0 0 0 0 19 22 1 0 0 0 0 19 31 1 0 0 0 0 20 15 1 1 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 35 1 6 0 0 0 22 38 1 0 0 0 0 23 44 1 6 0 0 0 24 35 1 6 0 0 0 24 45 1 0 0 0 0 25 38 1 0 0 0 0 25 39 2 0 0 0 0 26 38 1 0 0 0 0 26 40 2 0 0 0 0 27 28 1 0 0 0 0 27 34 1 6 0 0 0 28 46 1 6 0 0 0 29 30 1 0 0 0 0 29 33 1 6 0 0 0 29 35 1 0 0 0 0 30 36 1 1 0 0 0 30 47 1 0 0 0 0 31 41 2 0 0 0 0 31 48 1 0 0 0 0 32 35 1 0 0 0 0 32 36 1 0 0 0 0 32 37 1 0 0 0 0 33 18 1 1 0 0 0 34 36 1 1 0 0 0 34 42 1 0 0 0 0 36 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	668.33
Volume:	656.837
LogP:	2.328
LogD:	2.808
LogS:	-4.555
# Rotatable Bonds:	10
TPSA:	152.31
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	7.283
Fsp3:	0.694
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.754
MDCK Permeability:	3.882170494762249e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.976
20% Bioavailability (F20%):	0.133
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	54.33606719970703%
Volume Distribution (VD):	0.754
Pgp-substrate:	36.95014190673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.453
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	3.623
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.359
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.402
Skin Sensitization:	0.188
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC473781

Natural Product ID:	NPC473781
*Common Name:**	Lycaconitine
IUPAC Name:	n.a.
Synonyms:	Lycaconitine
Standard InCHIKey:	KFXVNXQXPRPLQA-CPIHIRBUSA-N
Standard InCHI:	InChI=1S/C36H48N2O10/c1-6-37-17-33(18-48-31(41)19-9-7-8-10-22(19)38-25(39)11-12-26(38)40)14-13-24(45-3)35-21-15-20-23(44-2)16-34(42,27(21)28(20)46-4)36(43,32(35)37)30(47-5)29(33)35/h7-10,20-21,23-24,27-30,32,42-43H,6,11-18H2,1-5H3/t20-,21-,23+,24+,27-,28+,29-,30+,32?,33+,34-,35+,36-/m1/s1
SMILES:	CO[C@H]1[C@@H]2[C@]3(CC[C@@H]([C@@]42C([C@@]1(O)[C@@]1(O)C[C@@H]([C@H]2C[C@@H]4[C@@H]1[C@H]2OC)OC)N(C3)CC)OC)COC(=O)c1ccccc1N1C(=O)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451640
PubChem CID:	441745
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]

☑ 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
Ki	2
LD50	1
Others	7

Activity Type	# Activity
Individual Protein	1
Organism	8
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT414	Individual Protein	Neuronal acetylcholine receptor protein alpha-7 subunit	Rattus norvegicus	Ki	=	80.0	nM	PMID[568748]
NPT32	Organism	Mus musculus	Mus musculus	LD50	=	15.0	mg.kg-1	PMID[568748]
NPT412	Protein Complex	Neuronal acetylcholine receptor; alpha4/beta2	Rattus norvegicus	Ki	=	1000.0	nM	PMID[568748]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-10.0	bpm	PMID[568749]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	0.0	bpm	PMID[568749]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	3.0	bpm	PMID[568749]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[568749]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-5.0	bpm	PMID[568749]
NPT2	Others	Unspecified		EC50	=	14791.08	nM	PMID[568750]

☑ 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 NPC473781 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	394
0.1-0.2	1669
0.2-0.3	3637
0.3-0.4	12191
0.4-0.5	19099
0.5-0.6	4578
0.6-0.7	986
0.7-0.8	104
0.8-0.85	25
0.85-0.9	4
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35390
1.0	High Similarity	NPC470631
0.9951	High Similarity	NPC475316
0.9951	High Similarity	NPC473486
0.9227	High Similarity	NPC223590
0.9095	High Similarity	NPC106593
0.9052	High Similarity	NPC473667
0.891	High Similarity	NPC140311
0.8857	High Similarity	NPC473837
0.8204	Intermediate Similarity	NPC166521
0.8204	Intermediate Similarity	NPC172769
0.8204	Intermediate Similarity	NPC184195
0.8204	Intermediate Similarity	NPC205
0.8204	Intermediate Similarity	NPC124690
0.8204	Intermediate Similarity	NPC281470
0.8107	Intermediate Similarity	NPC40539
0.8068	Intermediate Similarity	NPC163578
0.8068	Intermediate Similarity	NPC108276
0.7731	Intermediate Similarity	NPC475223
0.7696	Intermediate Similarity	NPC246983
0.7696	Intermediate Similarity	NPC475448
0.7682	Intermediate Similarity	NPC476496
0.7639	Intermediate Similarity	NPC475489
0.7591	Intermediate Similarity	NPC326895
0.7557	Intermediate Similarity	NPC476495
0.7557	Intermediate Similarity	NPC94687
0.7557	Intermediate Similarity	NPC106840
0.7457	Intermediate Similarity	NPC473458
0.7443	Intermediate Similarity	NPC471512
0.7356	Intermediate Similarity	NPC475427
0.7327	Intermediate Similarity	NPC198205
0.7327	Intermediate Similarity	NPC221687
0.7327	Intermediate Similarity	NPC21483
0.7308	Intermediate Similarity	NPC471513
0.7304	Intermediate Similarity	NPC288110
0.7288	Intermediate Similarity	NPC475303
0.7288	Intermediate Similarity	NPC475596
0.7269	Intermediate Similarity	NPC170751
0.7269	Intermediate Similarity	NPC476220
0.7269	Intermediate Similarity	NPC160113
0.7265	Intermediate Similarity	NPC476436
0.726	Intermediate Similarity	NPC198390
0.7257	Intermediate Similarity	NPC476429
0.7257	Intermediate Similarity	NPC30456
0.7234	Intermediate Similarity	NPC87152
0.7234	Intermediate Similarity	NPC475600
0.7234	Intermediate Similarity	NPC476110
0.7234	Intermediate Similarity	NPC475631
0.7227	Intermediate Similarity	NPC311054
0.7227	Intermediate Similarity	NPC112752
0.722	Intermediate Similarity	NPC476258
0.722	Intermediate Similarity	NPC304837
0.7215	Intermediate Similarity	NPC473375
0.7215	Intermediate Similarity	NPC97100
0.7215	Intermediate Similarity	NPC316841
0.721	Intermediate Similarity	NPC127026
0.721	Intermediate Similarity	NPC127720
0.7207	Intermediate Similarity	NPC136573
0.7207	Intermediate Similarity	NPC176371
0.7203	Intermediate Similarity	NPC475644
0.7203	Intermediate Similarity	NPC471977
0.7203	Intermediate Similarity	NPC471190
0.7203	Intermediate Similarity	NPC470486
0.7197	Intermediate Similarity	NPC327769
0.7197	Intermediate Similarity	NPC475406
0.7195	Intermediate Similarity	NPC107828
0.7195	Intermediate Similarity	NPC90358
0.7179	Intermediate Similarity	NPC471980
0.7179	Intermediate Similarity	NPC76565
0.7173	Intermediate Similarity	NPC477397
0.7167	Intermediate Similarity	NPC327904
0.7167	Intermediate Similarity	NPC38959
0.7161	Intermediate Similarity	NPC228377
0.7161	Intermediate Similarity	NPC122968
0.7161	Intermediate Similarity	NPC328186
0.7161	Intermediate Similarity	NPC477787
0.7155	Intermediate Similarity	NPC84815
0.7155	Intermediate Similarity	NPC301368
0.7149	Intermediate Similarity	NPC475137
0.7149	Intermediate Similarity	NPC475498
0.7143	Intermediate Similarity	NPC292416
0.7143	Intermediate Similarity	NPC473689
0.7143	Intermediate Similarity	NPC105055
0.7143	Intermediate Similarity	NPC22689
0.7119	Intermediate Similarity	NPC473506
0.7116	Intermediate Similarity	NPC322621
0.7113	Intermediate Similarity	NPC244839
0.7113	Intermediate Similarity	NPC319880
0.7113	Intermediate Similarity	NPC320324
0.7108	Intermediate Similarity	NPC473441
0.7108	Intermediate Similarity	NPC131273
0.7106	Intermediate Similarity	NPC250807
0.7106	Intermediate Similarity	NPC57797
0.7095	Intermediate Similarity	NPC154922
0.709	Intermediate Similarity	NPC113455
0.7089	Intermediate Similarity	NPC146824
0.7083	Intermediate Similarity	NPC237702
0.7078	Intermediate Similarity	NPC471782
0.7078	Intermediate Similarity	NPC471583
0.7076	Intermediate Similarity	NPC473850
0.7076	Intermediate Similarity	NPC477394
0.7073	Intermediate Similarity	NPC120239
0.7069	Intermediate Similarity	NPC6981
0.7069	Intermediate Similarity	NPC471016
0.7059	Intermediate Similarity	NPC475362
0.7039	Intermediate Similarity	NPC75600
0.7039	Intermediate Similarity	NPC294579
0.7039	Intermediate Similarity	NPC62367
0.7039	Intermediate Similarity	NPC144779
0.7039	Intermediate Similarity	NPC473115
0.7039	Intermediate Similarity	NPC212768
0.7039	Intermediate Similarity	NPC6576
0.7039	Intermediate Similarity	NPC158020
0.7039	Intermediate Similarity	NPC473089
0.7037	Intermediate Similarity	NPC278540
0.7027	Intermediate Similarity	NPC36607
0.7026	Intermediate Similarity	NPC470306
0.7025	Intermediate Similarity	NPC17160
0.7025	Intermediate Similarity	NPC313720
0.7017	Intermediate Similarity	NPC211920
0.7009	Intermediate Similarity	NPC216428
0.7009	Intermediate Similarity	NPC222046
0.7004	Intermediate Similarity	NPC477902
0.7004	Intermediate Similarity	NPC328154
0.7004	Intermediate Similarity	NPC476500
0.7	Intermediate Similarity	NPC30171
0.6996	Remote Similarity	NPC471014
0.6996	Remote Similarity	NPC475408
0.6992	Remote Similarity	NPC477788
0.6992	Remote Similarity	NPC475648
0.6983	Remote Similarity	NPC475426
0.6983	Remote Similarity	NPC4421
0.6976	Remote Similarity	NPC477396
0.697	Remote Similarity	NPC127996
0.6964	Remote Similarity	NPC477393
0.6964	Remote Similarity	NPC311451
0.6964	Remote Similarity	NPC329932
0.6963	Remote Similarity	NPC321211
0.6957	Remote Similarity	NPC73644
0.6953	Remote Similarity	NPC42678
0.6953	Remote Similarity	NPC477907
0.6953	Remote Similarity	NPC477909
0.6953	Remote Similarity	NPC234772
0.6951	Remote Similarity	NPC469451
0.6951	Remote Similarity	NPC477395
0.6951	Remote Similarity	NPC469452
0.6951	Remote Similarity	NPC475559
0.6949	Remote Similarity	NPC477912
0.6948	Remote Similarity	NPC129624
0.6946	Remote Similarity	NPC124029
0.6939	Remote Similarity	NPC469450
0.6939	Remote Similarity	NPC253482
0.6938	Remote Similarity	NPC253738
0.6914	Remote Similarity	NPC35208
0.6904	Remote Similarity	NPC148860
0.6897	Remote Similarity	NPC472553
0.6878	Remote Similarity	NPC25401
0.6878	Remote Similarity	NPC477903
0.6875	Remote Similarity	NPC302548
0.6875	Remote Similarity	NPC90967
0.6864	Remote Similarity	NPC472555
0.686	Remote Similarity	NPC477906
0.686	Remote Similarity	NPC96801
0.686	Remote Similarity	NPC150698
0.6857	Remote Similarity	NPC472574
0.684	Remote Similarity	NPC469915
0.6835	Remote Similarity	NPC318525
0.6835	Remote Similarity	NPC10653
0.6833	Remote Similarity	NPC473298
0.6829	Remote Similarity	NPC473565
0.6824	Remote Similarity	NPC476467
0.681	Remote Similarity	NPC313757
0.6805	Remote Similarity	NPC475601
0.6803	Remote Similarity	NPC238278
0.6792	Remote Similarity	NPC477900
0.6792	Remote Similarity	NPC477899
0.6791	Remote Similarity	NPC476441
0.6787	Remote Similarity	NPC477998
0.678	Remote Similarity	NPC206343
0.678	Remote Similarity	NPC477908
0.6778	Remote Similarity	NPC469312
0.6778	Remote Similarity	NPC235364
0.6778	Remote Similarity	NPC41318
0.6778	Remote Similarity	NPC477911
0.6776	Remote Similarity	NPC476425
0.6767	Remote Similarity	NPC304179
0.6767	Remote Similarity	NPC48042
0.6767	Remote Similarity	NPC477160
0.6767	Remote Similarity	NPC472550
0.6766	Remote Similarity	NPC264674
0.6766	Remote Similarity	NPC319128
0.6762	Remote Similarity	NPC469748
0.6761	Remote Similarity	NPC301501
0.6742	Remote Similarity	NPC181928
0.6741	Remote Similarity	NPC470485
0.6739	Remote Similarity	NPC329833
0.6737	Remote Similarity	NPC477910
0.6736	Remote Similarity	NPC285411
0.6736	Remote Similarity	NPC14116
0.6728	Remote Similarity	NPC475094

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 NPC473781 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	620
0.2-0.3	908
0.3-0.4	2512
0.4-0.5	3598
0.5-0.6	1226
0.6-0.7	60
0.7-0.8	3
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
0.7534	Intermediate Similarity	NPD7497	Discontinued
0.7137	Intermediate Similarity	NPD6997	Phase 2
0.7103	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8468	Phase 2
0.6652	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7962	Phase 2
0.6597	Remote Similarity	NPD7047	Phase 3
0.6533	Remote Similarity	NPD8361	Approved
0.6533	Remote Similarity	NPD8435	Approved
0.6533	Remote Similarity	NPD8360	Approved
0.6532	Remote Similarity	NPD6625	Approved
0.6518	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD8485	Approved
0.649	Remote Similarity	NPD7186	Phase 3
0.6488	Remote Similarity	NPD3437	Discontinued
0.6488	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7688	Phase 1
0.6445	Remote Similarity	NPD5741	Approved
0.6445	Remote Similarity	NPD5742	Approved
0.6445	Remote Similarity	NPD5743	Approved
0.6444	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD3912	Discontinued
0.6404	Remote Similarity	NPD8146	Phase 2
0.6404	Remote Similarity	NPD7570	Approved
0.6404	Remote Similarity	NPD7569	Approved
0.64	Remote Similarity	NPD6723	Discontinued
0.6398	Remote Similarity	NPD4120	Approved
0.6398	Remote Similarity	NPD4121	Phase 3
0.6389	Remote Similarity	NPD7048	Phase 3
0.6388	Remote Similarity	NPD5928	Phase 1
0.6379	Remote Similarity	NPD6874	Approved
0.6376	Remote Similarity	NPD7795	Phase 2
0.6372	Remote Similarity	NPD6891	Phase 2
0.636	Remote Similarity	NPD6659	Phase 2
0.6352	Remote Similarity	NPD6805	Discontinued
0.635	Remote Similarity	NPD8459	Approved
0.635	Remote Similarity	NPD8460	Approved
0.6349	Remote Similarity	NPD5891	Approved
0.634	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8466	Approved
0.6324	Remote Similarity	NPD8465	Approved
0.6324	Remote Similarity	NPD8467	Approved
0.6322	Remote Similarity	NPD8149	Discontinued
0.632	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5997	Discontinued
0.6304	Remote Similarity	NPD7921	Approved
0.6303	Remote Similarity	NPD7606	Phase 3
0.6301	Remote Similarity	NPD6995	Phase 1
0.6292	Remote Similarity	NPD7803	Approved
0.6288	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD8364	Approved
0.6283	Remote Similarity	NPD8363	Approved
0.6283	Remote Similarity	NPD8407	Phase 2
0.6275	Remote Similarity	NPD7560	Approved
0.6272	Remote Similarity	NPD7906	Approved
0.627	Remote Similarity	NPD7922	Phase 1
0.6264	Remote Similarity	NPD7708	Approved
0.626	Remote Similarity	NPD7805	Phase 3
0.626	Remote Similarity	NPD7907	Approved
0.6255	Remote Similarity	NPD5025	Approved
0.625	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5411	Discontinued
0.625	Remote Similarity	NPD7487	Discontinued
0.6245	Remote Similarity	NPD2899	Discontinued
0.6239	Remote Similarity	NPD5430	Discontinued
0.6236	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD8425	Approved
0.6232	Remote Similarity	NPD8426	Approved
0.6226	Remote Similarity	NPD6716	Phase 1
0.6226	Remote Similarity	NPD7956	Approved
0.6226	Remote Similarity	NPD7955	Approved
0.6223	Remote Similarity	NPD2974	Approved
0.6223	Remote Similarity	NPD2973	Approved
0.6223	Remote Similarity	NPD2975	Approved
0.622	Remote Similarity	NPD7295	Approved
0.6218	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD4580	Approved
0.6204	Remote Similarity	NPD8429	Approved
0.6204	Remote Similarity	NPD8428	Approved
0.6204	Remote Similarity	NPD8427	Approved
0.6203	Remote Similarity	NPD7205	Discontinued
0.6202	Remote Similarity	NPD2820	Phase 3
0.6196	Remote Similarity	NPD4846	Phase 2
0.6188	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD7417	Discontinued
0.6186	Remote Similarity	NPD3452	Approved
0.6186	Remote Similarity	NPD3450	Approved
0.6186	Remote Similarity	NPD2493	Approved
0.6186	Remote Similarity	NPD2494	Approved
0.6185	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5582	Discontinued
0.6176	Remote Similarity	NPD4583	Approved
0.6176	Remote Similarity	NPD4582	Approved
0.6172	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD7854	Phase 2
0.617	Remote Similarity	NPD5608	Approved
0.617	Remote Similarity	NPD5609	Approved
0.6168	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5086	Approved
0.6167	Remote Similarity	NPD7302	Phase 3
0.6167	Remote Similarity	NPD7300	Phase 3
0.6161	Remote Similarity	NPD7478	Approved
0.6154	Remote Similarity	NPD2365	Approved
0.6154	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.615	Remote Similarity	NPD8368	Discontinued
0.6147	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD7820	Phase 3
0.6138	Remote Similarity	NPD7878	Phase 2
0.6134	Remote Similarity	NPD4004	Approved
0.6134	Remote Similarity	NPD4002	Approved
0.6132	Remote Similarity	NPD7225	Discontinued
0.6132	Remote Similarity	NPD7528	Approved
0.6132	Remote Similarity	NPD8462	Phase 1
0.6128	Remote Similarity	NPD4668	Phase 2
0.6128	Remote Similarity	NPD8461	Discontinued
0.6116	Remote Similarity	NPD7799	Discontinued
0.6116	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2836	Approved
0.6109	Remote Similarity	NPD8320	Phase 1
0.6109	Remote Similarity	NPD6457	Approved
0.6109	Remote Similarity	NPD8319	Approved
0.6109	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD7600	Phase 2
0.6098	Remote Similarity	NPD8404	Phase 2
0.6094	Remote Similarity	NPD5610	Approved
0.6092	Remote Similarity	NPD5006	Approved
0.6092	Remote Similarity	NPD5005	Approved
0.6091	Remote Similarity	NPD1945	Phase 1
0.6083	Remote Similarity	NPD8161	Suspended
0.608	Remote Similarity	NPD7279	Phase 2
0.608	Remote Similarity	NPD7278	Phase 2
0.6078	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5042	Phase 1
0.607	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6445	Discontinued
0.6066	Remote Similarity	NPD7301	Phase 3
0.6064	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD4420	Approved
0.6059	Remote Similarity	NPD5197	Approved
0.6059	Remote Similarity	NPD5196	Approved
0.6059	Remote Similarity	NPD5194	Approved
0.6055	Remote Similarity	NPD7599	Phase 2
0.6053	Remote Similarity	NPD8492	Approved
0.6053	Remote Similarity	NPD8281	Discontinued
0.605	Remote Similarity	NPD6238	Discontinued
0.605	Remote Similarity	NPD6321	Discontinued
0.6049	Remote Similarity	NPD5860	Discontinued
0.6048	Remote Similarity	NPD7082	Approved
0.6048	Remote Similarity	NPD4111	Phase 1
0.6048	Remote Similarity	NPD4665	Approved
0.6048	Remote Similarity	NPD6770	Approved
0.6039	Remote Similarity	NPD2670	Approved
0.6035	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7811	Phase 3
0.6034	Remote Similarity	NPD7810	Phase 3
0.6033	Remote Similarity	NPD4082	Approved
0.6032	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD4578	Approved
0.6026	Remote Similarity	NPD4577	Approved
0.6025	Remote Similarity	NPD5676	Approved
0.6025	Remote Similarity	NPD4493	Discontinued
0.6024	Remote Similarity	NPD4981	Phase 2
0.6019	Remote Similarity	NPD7259	Approved
0.6017	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD4663	Approved
0.6015	Remote Similarity	NPD4946	Phase 2
0.6015	Remote Similarity	NPD8463	Approved
0.6009	Remote Similarity	NPD5186	Approved
0.6009	Remote Similarity	NPD1802	Approved
0.6009	Remote Similarity	NPD1801	Approved
0.6009	Remote Similarity	NPD5183	Approved
0.6009	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD4107	Approved
0.6	Remote Similarity	NPD5466	Approved
0.6	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7827	Phase 1
0.5993	Remote Similarity	NPD8489	Phase 1
0.5992	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD7583	Approved
0.5992	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD7181	Phase 3
0.5984	Remote Similarity	NPD5496	Approved
0.5982	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4888	Discontinued
0.5975	Remote Similarity	NPD1294	Discontinued
0.5975	Remote Similarity	NPD3298	Approved
0.5967	Remote Similarity	NPD2907	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