NPASS Compound

Structure

NPC469451 OpenBabel07101718322D 54 66 0 0 1 0 0 0 0 0999 V2000 -0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 3.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4997 -2.8677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4133 -2.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6907 -2.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5178 -1.4664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2320 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4351 -1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0662 -0.3410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6139 1.1368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6143 -2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6261 -2.0811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7168 -0.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 1.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2599 -3.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3720 -2.3186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5932 -2.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1261 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0098 -1.3962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5950 -2.7440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6408 -3.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7952 -1.2854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7088 -0.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 0.3238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 2.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1261 -0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6409 -1.5860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8566 0.0610 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6261 0.3238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1829 -2.2579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1261 -0.5422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6042 0.1159 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4540 -1.5982 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.8171 -1.4933 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 -0.1221 -3.7817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6261 2.0558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 2.9219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3689 0.7116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 52 1 0 0 0 0 2 53 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 29 2 0 0 0 0 7 30 1 0 0 0 0 8 31 2 0 0 0 0 9 32 2 0 0 0 0 10 14 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 43 1 0 0 0 0 13 17 1 0 0 0 0 14 46 1 0 0 0 0 15 47 1 0 0 0 0 16 46 1 0 0 0 0 17 54 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 21 41 1 0 0 0 0 22 28 1 0 0 0 0 22 40 1 0 0 0 0 23 39 1 0 0 0 0 23 47 1 0 0 0 0 24 39 1 0 0 0 0 24 48 1 0 0 0 0 25 41 1 6 0 0 0 26 44 1 1 0 0 0 27 49 2 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 31 1 0 0 0 0 29 42 1 0 0 0 0 30 33 2 0 0 0 0 30 43 1 0 0 0 0 31 45 1 0 0 0 0 32 33 1 0 0 0 0 32 52 1 0 0 0 0 33 48 1 0 0 0 0 34 42 1 0 0 0 0 34 45 1 0 0 0 0 35 50 2 0 0 0 0 35 53 1 0 0 0 0 36 40 1 6 0 0 0 36 42 1 0 0 0 0 36 47 1 0 0 0 0 37 41 1 1 0 0 0 37 43 1 0 0 0 0 37 46 1 0 0 0 0 38 39 1 1 0 0 0 38 40 1 0 0 0 0 38 54 1 0 0 0 0 39 19 1 1 0 0 0 40 13 1 1 0 0 0 41 20 1 1 0 0 0 42 11 1 6 0 0 0 43 44 1 1 0 0 0 44 48 1 0 0 0 0 44 51 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	730.37
Volume:	731.346
LogP:	3.08
LogD:	2.875
LogS:	-4.287
# Rotatable Bonds:	3
TPSA:	104.14
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	13
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	7.254
Fsp3:	0.659
Lipinski Rule-of-5:	Accepted
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:	-5.581
MDCK Permeability:	1.6560894437134266e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.699
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.783
Plasma Protein Binding (PPB):	61.06353759765625%
Volume Distribution (VD):	3.848
Pgp-substrate:	38.64366149902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.798
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.949
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	5.571
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.988
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.994
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.1
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC469451

Natural Product ID:	NPC469451
*Common Name:**	Vobtusine Lactone
IUPAC Name:	n.a.
Synonyms:	Vobtusine Lactone
Standard InCHIKey:	PWQNZSCRPVJZJK-RBUYCUMVSA-N
Standard InCHI:	InChI=1S/C44H50N4O6/c1-52-32-9-5-7-30-33(32)48-24-39(19-26-20-41-21-27(49)18-25(41)10-14-46-16-12-43(30,37(41)46)44(26,48)51)23-47-15-11-42-29-6-3-4-8-31(29)45-34(42)28(35(50)53-2)22-40(36(42)47)13-17-54-38(39)40/h3-9,25-26,36-38,45,51H,10-24H2,1-2H3/t25-,26-,36+,37+,38+,39+,40+,41+,42+,43-,44-/m1/s1
SMILES:	COC1=CC=CC2=C1N3CC4(CC5C3(C26CCN7C6C8(C5)CC(=O)CC8CC7)O)CN9CCC12C9C3(C4OCC3)CC(=C1NC1=CC=CC=C21)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079129
PubChem CID:	46883152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-type 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
NPO33497	tabernaemontana sphaerocarpa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19711971]
NPO32722	voacanga globosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21546135]

☑ 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	8
MIC	1
Others	1

Activity Type	# Activity
Cell Line	5
Individual Protein	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8000.0	nM	PMID[451026]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	18000.0	nM	PMID[451026]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	=	7600.0	nM	PMID[451026]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	17600.0	nM	PMID[451026]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	22500.0	nM	PMID[451026]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	90000.0	nM	PMID[451027]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	50.0	ug.mL-1	PMID[451027]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	Inhibition	=	13.0	%	PMID[451027]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	18000.0	nM	PMID[451027]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	17988.71	nM	PMID[451027]

☑ 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 NPC469451 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	395
0.1-0.2	1768
0.2-0.3	4803
0.3-0.4	12500
0.4-0.5	16604
0.5-0.6	5784
0.6-0.7	695
0.7-0.8	114
0.8-0.85	17
0.85-0.9	4
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC329932
0.9906	High Similarity	NPC469450
0.9814	High Similarity	NPC469452
0.9583	High Similarity	NPC301501
0.9537	High Similarity	NPC131977
0.9533	High Similarity	NPC139373
0.9531	High Similarity	NPC223242
0.8684	High Similarity	NPC469722
0.8372	Intermediate Similarity	NPC246140
0.8372	Intermediate Similarity	NPC195787
0.7991	Intermediate Similarity	NPC87714
0.7982	Intermediate Similarity	NPC1464
0.7939	Intermediate Similarity	NPC128476
0.7924	Intermediate Similarity	NPC151171
0.792	Intermediate Similarity	NPC195636
0.7913	Intermediate Similarity	NPC19175
0.7885	Intermediate Similarity	NPC77777
0.7839	Intermediate Similarity	NPC154922
0.7832	Intermediate Similarity	NPC189661
0.7817	Intermediate Similarity	NPC476069
0.7797	Intermediate Similarity	NPC234772
0.7692	Intermediate Similarity	NPC471513
0.7682	Intermediate Similarity	NPC231924
0.7676	Intermediate Similarity	NPC113455
0.7654	Intermediate Similarity	NPC120239
0.7647	Intermediate Similarity	NPC160113
0.7647	Intermediate Similarity	NPC476220
0.7636	Intermediate Similarity	NPC132874
0.7636	Intermediate Similarity	NPC218733
0.7636	Intermediate Similarity	NPC138615
0.7636	Intermediate Similarity	NPC265642
0.7617	Intermediate Similarity	NPC473458
0.7615	Intermediate Similarity	NPC291173
0.754	Intermediate Similarity	NPC329982
0.7532	Intermediate Similarity	NPC115588
0.7523	Intermediate Similarity	NPC22476
0.7521	Intermediate Similarity	NPC476258
0.7521	Intermediate Similarity	NPC304837
0.75	Intermediate Similarity	NPC269449
0.7479	Intermediate Similarity	NPC477397
0.7468	Intermediate Similarity	NPC288110
0.7465	Intermediate Similarity	NPC14994
0.7443	Intermediate Similarity	NPC25401
0.7442	Intermediate Similarity	NPC159963
0.7435	Intermediate Similarity	NPC119722
0.7435	Intermediate Similarity	NPC127996
0.7434	Intermediate Similarity	NPC475147
0.7426	Intermediate Similarity	NPC476436
0.7398	Intermediate Similarity	NPC477393
0.7397	Intermediate Similarity	NPC5630
0.7393	Intermediate Similarity	NPC222046
0.738	Intermediate Similarity	NPC475133
0.7378	Intermediate Similarity	NPC232600
0.7368	Intermediate Similarity	NPC478075
0.7364	Intermediate Similarity	NPC203628
0.7362	Intermediate Similarity	NPC318525
0.7362	Intermediate Similarity	NPC10653
0.7344	Intermediate Similarity	NPC476429
0.7339	Intermediate Similarity	NPC477396
0.7327	Intermediate Similarity	NPC97584
0.7317	Intermediate Similarity	NPC477395
0.7309	Intermediate Similarity	NPC303214
0.7302	Intermediate Similarity	NPC99043
0.7302	Intermediate Similarity	NPC218594
0.729	Intermediate Similarity	NPC203202
0.729	Intermediate Similarity	NPC264482
0.7257	Intermediate Similarity	NPC138830
0.7256	Intermediate Similarity	NPC186669
0.7244	Intermediate Similarity	NPC100863
0.7234	Intermediate Similarity	NPC126556
0.7227	Intermediate Similarity	NPC21425
0.7225	Intermediate Similarity	NPC469732
0.7181	Intermediate Similarity	NPC67904
0.716	Intermediate Similarity	NPC469734
0.7143	Intermediate Similarity	NPC470485
0.7143	Intermediate Similarity	NPC6974
0.7124	Intermediate Similarity	NPC90967
0.7095	Intermediate Similarity	NPC477394
0.7095	Intermediate Similarity	NPC122886
0.7083	Intermediate Similarity	NPC471303
0.7082	Intermediate Similarity	NPC477160
0.7072	Intermediate Similarity	NPC181928
0.7064	Intermediate Similarity	NPC159815
0.7056	Intermediate Similarity	NPC329833
0.7056	Intermediate Similarity	NPC470484
0.7054	Intermediate Similarity	NPC470483
0.7043	Intermediate Similarity	NPC473005
0.7034	Intermediate Similarity	NPC473006
0.703	Intermediate Similarity	NPC237901
0.703	Intermediate Similarity	NPC195788
0.7009	Intermediate Similarity	NPC474059
0.7009	Intermediate Similarity	NPC105055
0.7009	Intermediate Similarity	NPC22689
0.6992	Remote Similarity	NPC475720
0.6992	Remote Similarity	NPC474192
0.6974	Remote Similarity	NPC162440
0.6964	Remote Similarity	NPC473105
0.696	Remote Similarity	NPC34717
0.6951	Remote Similarity	NPC470631
0.6951	Remote Similarity	NPC35390
0.6951	Remote Similarity	NPC473781
0.6938	Remote Similarity	NPC478083
0.6926	Remote Similarity	NPC260909
0.6923	Remote Similarity	NPC475316
0.6923	Remote Similarity	NPC473486
0.6917	Remote Similarity	NPC81939
0.6899	Remote Similarity	NPC478080
0.6897	Remote Similarity	NPC474077
0.6892	Remote Similarity	NPC475816
0.689	Remote Similarity	NPC475666
0.6888	Remote Similarity	NPC223590
0.6888	Remote Similarity	NPC219397
0.6886	Remote Similarity	NPC230313
0.6886	Remote Similarity	NPC243626
0.688	Remote Similarity	NPC477161
0.6875	Remote Similarity	NPC473837
0.6863	Remote Similarity	NPC17437
0.6858	Remote Similarity	NPC473298
0.683	Remote Similarity	NPC476095
0.683	Remote Similarity	NPC52262
0.6822	Remote Similarity	NPC248117
0.682	Remote Similarity	NPC223595
0.682	Remote Similarity	NPC167724
0.682	Remote Similarity	NPC224970
0.6816	Remote Similarity	NPC21638
0.681	Remote Similarity	NPC475489
0.6809	Remote Similarity	NPC476500
0.6808	Remote Similarity	NPC61013
0.679	Remote Similarity	NPC472099
0.6781	Remote Similarity	NPC471512
0.6778	Remote Similarity	NPC470481
0.6778	Remote Similarity	NPC470482
0.6776	Remote Similarity	NPC193410
0.6772	Remote Similarity	NPC477067
0.6772	Remote Similarity	NPC478082
0.677	Remote Similarity	NPC285841
0.6765	Remote Similarity	NPC474366
0.6761	Remote Similarity	NPC248903
0.6756	Remote Similarity	NPC284685
0.6756	Remote Similarity	NPC473007
0.6755	Remote Similarity	NPC100734
0.6755	Remote Similarity	NPC88923
0.6755	Remote Similarity	NPC315634
0.6753	Remote Similarity	NPC161804
0.6751	Remote Similarity	NPC329567
0.6751	Remote Similarity	NPC330683
0.675	Remote Similarity	NPC30749
0.6735	Remote Similarity	NPC251071
0.6735	Remote Similarity	NPC71539
0.6735	Remote Similarity	NPC250960
0.6734	Remote Similarity	NPC74216
0.6732	Remote Similarity	NPC477066
0.673	Remote Similarity	NPC191489
0.6725	Remote Similarity	NPC473004
0.6721	Remote Similarity	NPC26928
0.6721	Remote Similarity	NPC266994
0.6713	Remote Similarity	NPC293458
0.6711	Remote Similarity	NPC473008
0.6709	Remote Similarity	NPC212123
0.6709	Remote Similarity	NPC198160
0.6708	Remote Similarity	NPC10732
0.6707	Remote Similarity	NPC473667
0.6706	Remote Similarity	NPC478081
0.6706	Remote Similarity	NPC473540
0.6698	Remote Similarity	NPC36495
0.6695	Remote Similarity	NPC25961
0.6694	Remote Similarity	NPC46259
0.6694	Remote Similarity	NPC470480
0.6681	Remote Similarity	NPC52801
0.668	Remote Similarity	NPC475609
0.6667	Remote Similarity	NPC82541
0.6667	Remote Similarity	NPC148124
0.6667	Remote Similarity	NPC127178
0.6653	Remote Similarity	NPC207971
0.6653	Remote Similarity	NPC176113
0.6653	Remote Similarity	NPC140311
0.6652	Remote Similarity	NPC181138
0.6652	Remote Similarity	NPC204970
0.6652	Remote Similarity	NPC21752
0.6652	Remote Similarity	NPC276993
0.6652	Remote Similarity	NPC210415
0.6652	Remote Similarity	NPC298851
0.6652	Remote Similarity	NPC473880
0.6652	Remote Similarity	NPC293255
0.6651	Remote Similarity	NPC123241
0.6639	Remote Similarity	NPC305542
0.6639	Remote Similarity	NPC116178
0.6638	Remote Similarity	NPC473569
0.6638	Remote Similarity	NPC471489
0.6626	Remote Similarity	NPC99724
0.6624	Remote Similarity	NPC268077
0.6623	Remote Similarity	NPC203972
0.6622	Remote Similarity	NPC469726
0.6622	Remote Similarity	NPC329338
0.6621	Remote Similarity	NPC472115
0.6621	Remote Similarity	NPC472114
0.6612	Remote Similarity	NPC217903
0.6612	Remote Similarity	NPC321166
0.6611	Remote Similarity	NPC471950
0.6611	Remote Similarity	NPC471945

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 NPC469451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	639
0.2-0.3	888
0.3-0.4	2209
0.4-0.5	3247
0.5-0.6	1757
0.6-0.7	188
0.7-0.8	0
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
0.7061	Intermediate Similarity	NPD8363	Approved
0.7061	Intermediate Similarity	NPD8364	Approved
0.703	Intermediate Similarity	NPD8466	Approved
0.703	Intermediate Similarity	NPD8465	Approved
0.703	Intermediate Similarity	NPD8467	Approved
0.7008	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD8425	Approved
0.6926	Remote Similarity	NPD8459	Approved
0.6926	Remote Similarity	NPD8426	Approved
0.6926	Remote Similarity	NPD8460	Approved
0.6911	Remote Similarity	NPD6199	Discontinued
0.691	Remote Similarity	NPD6644	Discontinued
0.6903	Remote Similarity	NPD8429	Approved
0.6903	Remote Similarity	NPD8428	Approved
0.6903	Remote Similarity	NPD8427	Approved
0.6895	Remote Similarity	NPD6625	Approved
0.6894	Remote Similarity	NPD4082	Approved
0.6878	Remote Similarity	NPD4493	Discontinued
0.6875	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8358	Approved
0.6849	Remote Similarity	NPD4492	Approved
0.6849	Remote Similarity	NPD4494	Approved
0.6835	Remote Similarity	NPD5860	Discontinued
0.6795	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4596	Phase 1
0.6756	Remote Similarity	NPD7955	Approved
0.6756	Remote Similarity	NPD7956	Approved
0.6755	Remote Similarity	NPD7803	Approved
0.6751	Remote Similarity	NPD2907	Approved
0.6751	Remote Similarity	NPD2906	Approved
0.673	Remote Similarity	NPD7708	Approved
0.6711	Remote Similarity	NPD5928	Phase 1
0.6696	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6874	Approved
0.6695	Remote Similarity	NPD3893	Discontinued
0.6681	Remote Similarity	NPD4022	Approved
0.6681	Remote Similarity	NPD3472	Approved
0.6681	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4455	Discontinued
0.6667	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1945	Phase 1
0.6655	Remote Similarity	NPD8489	Phase 1
0.6654	Remote Similarity	NPD8461	Discontinued
0.6653	Remote Similarity	NPD3437	Discontinued
0.6652	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7279	Phase 2
0.664	Remote Similarity	NPD3006	Discontinued
0.664	Remote Similarity	NPD7278	Phase 2
0.6639	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3888	Discontinued
0.6638	Remote Similarity	NPD6238	Discontinued
0.6627	Remote Similarity	NPD6723	Discontinued
0.6626	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3372	Discontinued
0.6624	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4859	Phase 1
0.661	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD7186	Phase 3
0.6578	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7820	Phase 3
0.6573	Remote Similarity	NPD3912	Discontinued
0.6567	Remote Similarity	NPD5582	Discontinued
0.6565	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5183	Approved
0.6561	Remote Similarity	NPD5186	Approved
0.6549	Remote Similarity	NPD4846	Phase 2
0.6533	Remote Similarity	NPD7479	Phase 2
0.6527	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7497	Discontinued
0.6512	Remote Similarity	NPD6716	Phase 1
0.6511	Remote Similarity	NPD5071	Phase 2
0.6504	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD7293	Approved
0.6498	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7476	Discontinued
0.6498	Remote Similarity	NPD7560	Approved
0.6496	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8149	Discontinued
0.6489	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4465	Phase 2
0.6485	Remote Similarity	NPD4467	Phase 2
0.6478	Remote Similarity	NPD5496	Approved
0.6473	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD2974	Approved
0.6468	Remote Similarity	NPD2973	Approved
0.6468	Remote Similarity	NPD2975	Approved
0.6466	Remote Similarity	NPD6997	Phase 2
0.6466	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD5676	Approved
0.6458	Remote Similarity	NPD7924	Phase 2
0.6458	Remote Similarity	NPD7925	Phase 2
0.6456	Remote Similarity	NPD4580	Approved
0.6453	Remote Similarity	NPD7256	Discontinued
0.6447	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2247	Approved
0.6441	Remote Similarity	NPD2249	Approved
0.6441	Remote Similarity	NPD2680	Approved
0.6441	Remote Similarity	NPD2681	Approved
0.644	Remote Similarity	NPD7542	Phase 3
0.6434	Remote Similarity	NPD7827	Phase 1
0.6431	Remote Similarity	NPD7922	Phase 1
0.6429	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6321	Discontinued
0.6426	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1769	Discontinued
0.6417	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4040	Phase 1
0.6415	Remote Similarity	NPD8463	Approved
0.6411	Remote Similarity	NPD2899	Discontinued
0.64	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.639	Remote Similarity	NPD6905	Phase 2
0.6378	Remote Similarity	NPD4981	Phase 2
0.6371	Remote Similarity	NPD4420	Approved
0.6368	Remote Similarity	NPD6457	Approved
0.6368	Remote Similarity	NPD7126	Discontinued
0.636	Remote Similarity	NPD2494	Approved
0.636	Remote Similarity	NPD2493	Approved
0.636	Remote Similarity	NPD3450	Approved
0.636	Remote Similarity	NPD3452	Approved
0.636	Remote Similarity	NPD7805	Phase 3
0.6349	Remote Similarity	NPD4583	Approved
0.6349	Remote Similarity	NPD7891	Discontinued
0.6349	Remote Similarity	NPD4582	Approved
0.6348	Remote Similarity	NPD2971	Approved
0.6348	Remote Similarity	NPD2968	Approved
0.6345	Remote Similarity	NPD7811	Phase 3
0.6345	Remote Similarity	NPD7810	Phase 3
0.6344	Remote Similarity	NPD5600	Discontinued
0.6344	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5610	Approved
0.6336	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5005	Approved
0.6333	Remote Similarity	NPD5006	Approved
0.633	Remote Similarity	NPD8492	Approved
0.6327	Remote Similarity	NPD7272	Discontinued
0.6327	Remote Similarity	NPD5938	Phase 3
0.6325	Remote Similarity	NPD2490	Approved
0.6325	Remote Similarity	NPD2488	Approved
0.632	Remote Similarity	NPD6851	Approved
0.632	Remote Similarity	NPD6853	Approved
0.6318	Remote Similarity	NPD4107	Approved
0.6312	Remote Similarity	NPD8359	Phase 2
0.6309	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD8025	Phase 2
0.6307	Remote Similarity	NPD4004	Approved
0.6307	Remote Similarity	NPD4002	Approved
0.6303	Remote Similarity	NPD4668	Phase 2
0.63	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2434	Approved
0.6295	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD3983	Phase 3
0.6295	Remote Similarity	NPD6107	Approved
0.6295	Remote Similarity	NPD7556	Discontinued
0.6287	Remote Similarity	NPD3964	Approved
0.6282	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7262	Phase 1
0.627	Remote Similarity	NPD8027	Approved
0.627	Remote Similarity	NPD2514	Approved
0.6265	Remote Similarity	NPD7797	Approved
0.6265	Remote Similarity	NPD7796	Approved
0.6255	Remote Similarity	NPD8161	Suspended
0.625	Remote Similarity	NPD6519	Phase 2
0.6245	Remote Similarity	NPD8255	Phase 2
0.6245	Remote Similarity	NPD8016	Phase 3
0.6245	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4373	Phase 2
0.6235	Remote Similarity	NPD7301	Phase 3
0.6231	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7048	Phase 3
0.6229	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4482	Phase 3
0.6222	Remote Similarity	NPD8091	Phase 3
0.6221	Remote Similarity	NPD7417	Discontinued
0.6218	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1294	Discontinued
0.6213	Remote Similarity	NPD2843	Phase 2
0.6213	Remote Similarity	NPD2845	Phase 2
0.6208	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD4796	Discontinued
0.6204	Remote Similarity	NPD7300	Phase 3
0.6204	Remote Similarity	NPD7302	Phase 3
0.6202	Remote Similarity	NPD4885	Approved
0.6201	Remote Similarity	NPD5313	Approved
0.6201	Remote Similarity	NPD5312	Approved
0.6198	Remote Similarity	NPD7626	Approved
0.6198	Remote Similarity	NPD3057	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