NPASS Compound

Structure

CID126458 OpenBabel06191715482D 33 37 0 0 1 0 0 0 0 0999 V2000 -2.8180 3.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5446 2.4820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7636 3.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2405 -2.3985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4650 -3.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5078 -3.6489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7671 -2.5144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8528 -2.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1121 -1.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8475 -1.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6957 -0.9796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2391 1.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2388 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6947 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8484 1.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8472 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6965 1.9571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3927 2.9348 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1549 -1.9910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6950 -0.9786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6959 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3924 1.9567 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5440 0.4888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8481 0.4893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4999 -1.2640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5443 1.4673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3655 3.0367 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5427 -1.4677 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8020 -0.3331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 1 1 1 0 0 0 20 25 1 0 0 0 0 20 31 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 6 0 0 0 23 32 1 6 0 0 0 24 12 1 1 0 0 0 24 26 1 0 0 0 0 24 27 1 0 0 0 0 25 30 1 6 0 0 0 26 30 1 6 0 0 0 27 29 1 6 0 0 0 28 32 1 0 0 0 0 28 33 2 0 0 0 0 29 2 1 6 0 0 0 30 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.36
Volume:	504.892
LogP:	6.419
LogD:	4.79
LogS:	-4.589
# Rotatable Bonds:	5
TPSA:	32.34
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	4.268
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.695
MDCK Permeability:	1.7509288227302022e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.72
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.107
30% Bioavailability (F30%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	72.30072784423828%
Volume Distribution (VD):	1.543
Pgp-substrate:	7.946232795715332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.22
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.299
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.791
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.575

ADMET: Excretion

Clearance (CL):	6.106
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.984
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.72
AMES Toxicity:	0.154
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.639
Skin Sensitization:	0.963
Carcinogencity:	0.373
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC126458

Natural Product ID:	NPC126458
*Common Name:**	Hookerianamide I
IUPAC Name:	N-[(3S,5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-17-[(1S)-1-(methylamino)ethyl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]-N-methylbenzamide
Synonyms:	Hookerianamide I
Standard InCHIKey:	NISGMKNSSUMSSN-IBWRYCSWSA-N
Standard InCHI:	InChI=1S/C30H46N2O/c1-20(31-4)25-13-14-26-24-12-11-22-19-23(32(5)28(33)21-9-7-6-8-10-21)15-17-29(22,2)27(24)16-18-30(25,26)3/h6-10,20,22-27,31H,11-19H2,1-5H3/t20-,22-,23-,24-,25+,26-,27-,29-,30+/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C(=O)c1ccccc1)NC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503323
PubChem CID:	44587245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002340] Azasteroids and derivatives

*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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17827771]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18681480]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12560	Cassia leptophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4160	Cephalosporium polyaleurum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11838	Euphorbia regis-jubae	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7351	Uncaria pteropoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18213	Strychnos variabilis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2332	Plantago serraria	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10911	Euphorbia peplis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13128	Crotalaria rosenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9527	Dendrodoa grossularia	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5033	Alpinia galanga	Species	Zingiberaceae	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	1
MIC	3
Others	4

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	8800.0	nM	PMID[456084]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	17.5	mm	PMID[456084]
NPT2921	Organism	Pseudomonas	Pseudomonas	IZ	=	18.5	mm	PMID[456084]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	69400.0	nM	PMID[456084]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	69400.0	nM	PMID[456084]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	18.0	mm	PMID[456084]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	=	8.0	mm	PMID[456084]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	34700.0	nM	PMID[456084]

☑ 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 NPC126458 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	353
0.1-0.2	1512
0.2-0.3	5951
0.3-0.4	21612
0.4-0.5	10832
0.5-0.6	2227
0.6-0.7	190
0.7-0.8	14
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC79698
0.9141	High Similarity	NPC473962
0.8618	High Similarity	NPC473573
0.8537	High Similarity	NPC246904
0.7951	Intermediate Similarity	NPC474695
0.7697	Intermediate Similarity	NPC73644
0.748	Intermediate Similarity	NPC474582
0.7222	Intermediate Similarity	NPC475427
0.7143	Intermediate Similarity	NPC119326
0.7132	Intermediate Similarity	NPC55529
0.702	Intermediate Similarity	NPC313850
0.6977	Remote Similarity	NPC167336
0.6899	Remote Similarity	NPC222029
0.6846	Remote Similarity	NPC473418
0.681	Remote Similarity	NPC475248
0.681	Remote Similarity	NPC63047
0.6803	Remote Similarity	NPC162417
0.6803	Remote Similarity	NPC316104
0.6794	Remote Similarity	NPC472699
0.6794	Remote Similarity	NPC472700
0.6744	Remote Similarity	NPC239854
0.6744	Remote Similarity	NPC58200
0.6742	Remote Similarity	NPC472695
0.6742	Remote Similarity	NPC472696
0.6742	Remote Similarity	NPC472701
0.6742	Remote Similarity	NPC472683
0.6733	Remote Similarity	NPC153007
0.672	Remote Similarity	NPC246757
0.672	Remote Similarity	NPC291070
0.6692	Remote Similarity	NPC471829
0.6692	Remote Similarity	NPC474866
0.6692	Remote Similarity	NPC475939
0.6692	Remote Similarity	NPC472691
0.6689	Remote Similarity	NPC130251
0.6667	Remote Similarity	NPC322433
0.6667	Remote Similarity	NPC329430
0.6667	Remote Similarity	NPC256452
0.6645	Remote Similarity	NPC301760
0.6643	Remote Similarity	NPC226143
0.662	Remote Similarity	NPC109151
0.6614	Remote Similarity	NPC185208
0.6614	Remote Similarity	NPC219573
0.6587	Remote Similarity	NPC476754
0.6582	Remote Similarity	NPC66936
0.6564	Remote Similarity	NPC469741
0.6549	Remote Similarity	NPC71684
0.6541	Remote Similarity	NPC473498
0.6538	Remote Similarity	NPC476993
0.6531	Remote Similarity	NPC179224
0.6522	Remote Similarity	NPC113099
0.6491	Remote Similarity	NPC286994
0.6481	Remote Similarity	NPC104345
0.6479	Remote Similarity	NPC27833
0.6475	Remote Similarity	NPC147513
0.6463	Remote Similarity	NPC282339
0.6463	Remote Similarity	NPC99632
0.6463	Remote Similarity	NPC40488
0.6463	Remote Similarity	NPC476750
0.6456	Remote Similarity	NPC109787
0.6434	Remote Similarity	NPC103292
0.6434	Remote Similarity	NPC239185
0.6429	Remote Similarity	NPC471164
0.6429	Remote Similarity	NPC470926
0.6423	Remote Similarity	NPC157479
0.6414	Remote Similarity	NPC192533
0.6392	Remote Similarity	NPC212799
0.6385	Remote Similarity	NPC134882
0.6382	Remote Similarity	NPC478140
0.6378	Remote Similarity	NPC323420
0.6378	Remote Similarity	NPC476753
0.6378	Remote Similarity	NPC59677
0.6378	Remote Similarity	NPC476752
0.6371	Remote Similarity	NPC43308
0.6371	Remote Similarity	NPC17497
0.6371	Remote Similarity	NPC305602
0.6369	Remote Similarity	NPC476749
0.6364	Remote Similarity	NPC179605
0.6364	Remote Similarity	NPC112373
0.6364	Remote Similarity	NPC161956
0.6364	Remote Similarity	NPC279385
0.6364	Remote Similarity	NPC258531
0.6347	Remote Similarity	NPC279527
0.6347	Remote Similarity	NPC214960
0.6346	Remote Similarity	NPC469537
0.6341	Remote Similarity	NPC276085
0.6335	Remote Similarity	NPC117032
0.6319	Remote Similarity	NPC257490
0.6312	Remote Similarity	NPC473329
0.6309	Remote Similarity	NPC472245
0.6308	Remote Similarity	NPC265220
0.6306	Remote Similarity	NPC311330
0.6303	Remote Similarity	NPC225319
0.6299	Remote Similarity	NPC469560
0.6296	Remote Similarity	NPC45033
0.6294	Remote Similarity	NPC177684
0.6294	Remote Similarity	NPC291962
0.6294	Remote Similarity	NPC242269
0.6289	Remote Similarity	NPC2672
0.6288	Remote Similarity	NPC109514
0.6288	Remote Similarity	NPC472879
0.6286	Remote Similarity	NPC33742
0.6276	Remote Similarity	NPC268534
0.6275	Remote Similarity	NPC471123
0.6269	Remote Similarity	NPC275467
0.626	Remote Similarity	NPC169016
0.626	Remote Similarity	NPC75724
0.625	Remote Similarity	NPC188844
0.625	Remote Similarity	NPC1682
0.625	Remote Similarity	NPC473661
0.625	Remote Similarity	NPC266425
0.6242	Remote Similarity	NPC111428
0.6242	Remote Similarity	NPC473322
0.624	Remote Similarity	NPC60408
0.6225	Remote Similarity	NPC32858
0.6225	Remote Similarity	NPC53044
0.6225	Remote Similarity	NPC40364
0.6225	Remote Similarity	NPC194857
0.6224	Remote Similarity	NPC320656
0.6224	Remote Similarity	NPC472698
0.6224	Remote Similarity	NPC472697
0.6224	Remote Similarity	NPC220698
0.6218	Remote Similarity	NPC186284
0.6218	Remote Similarity	NPC2823
0.6218	Remote Similarity	NPC22082
0.6214	Remote Similarity	NPC276949
0.6214	Remote Similarity	NPC35850
0.621	Remote Similarity	NPC311769
0.621	Remote Similarity	NPC182106
0.6207	Remote Similarity	NPC314192
0.6207	Remote Similarity	NPC477042
0.6205	Remote Similarity	NPC472102
0.6205	Remote Similarity	NPC309531
0.6205	Remote Similarity	NPC248117
0.6204	Remote Similarity	NPC470252
0.6202	Remote Similarity	NPC71140
0.6197	Remote Similarity	NPC239357
0.6194	Remote Similarity	NPC83214
0.619	Remote Similarity	NPC267262
0.619	Remote Similarity	NPC222466
0.619	Remote Similarity	NPC22746
0.6187	Remote Similarity	NPC181390
0.6178	Remote Similarity	NPC471516
0.6174	Remote Similarity	NPC71933
0.6174	Remote Similarity	NPC239990
0.6174	Remote Similarity	NPC105114
0.6174	Remote Similarity	NPC89923
0.6174	Remote Similarity	NPC152850
0.6172	Remote Similarity	NPC284475
0.616	Remote Similarity	NPC258046
0.6159	Remote Similarity	NPC255447
0.6154	Remote Similarity	NPC470545
0.6154	Remote Similarity	NPC260233
0.6154	Remote Similarity	NPC472880
0.6154	Remote Similarity	NPC315051
0.6154	Remote Similarity	NPC150712
0.6149	Remote Similarity	NPC470343
0.6149	Remote Similarity	NPC101719
0.6149	Remote Similarity	NPC472244
0.6148	Remote Similarity	NPC90150
0.6145	Remote Similarity	NPC36495
0.6145	Remote Similarity	NPC193410
0.6144	Remote Similarity	NPC132847
0.6144	Remote Similarity	NPC474473
0.6142	Remote Similarity	NPC113307
0.6142	Remote Similarity	NPC298115
0.6138	Remote Similarity	NPC200964
0.6136	Remote Similarity	NPC49994
0.6133	Remote Similarity	NPC209389
0.6133	Remote Similarity	NPC150863
0.6131	Remote Similarity	NPC189116
0.6129	Remote Similarity	NPC132636
0.6125	Remote Similarity	NPC264589
0.6125	Remote Similarity	NPC473541
0.6124	Remote Similarity	NPC475057
0.6124	Remote Similarity	NPC153885
0.6122	Remote Similarity	NPC254698
0.6121	Remote Similarity	NPC93343
0.6118	Remote Similarity	NPC207428
0.6111	Remote Similarity	NPC470546
0.6107	Remote Similarity	NPC136453
0.6104	Remote Similarity	NPC300299
0.6103	Remote Similarity	NPC476198
0.6099	Remote Similarity	NPC57051
0.6098	Remote Similarity	NPC215474
0.6096	Remote Similarity	NPC475915
0.6095	Remote Similarity	NPC71132
0.6094	Remote Similarity	NPC19256
0.6094	Remote Similarity	NPC58872
0.6093	Remote Similarity	NPC280807
0.6093	Remote Similarity	NPC314431
0.6084	Remote Similarity	NPC61013
0.6084	Remote Similarity	NPC123241
0.6084	Remote Similarity	NPC470544
0.6081	Remote Similarity	NPC285394
0.6077	Remote Similarity	NPC238219
0.6077	Remote Similarity	NPC474974
0.6077	Remote Similarity	NPC289883
0.6076	Remote Similarity	NPC475128
0.6074	Remote Similarity	NPC154602
0.6074	Remote Similarity	NPC243756

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 NPC126458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	588
0.2-0.3	825
0.3-0.4	2445
0.4-0.5	3531
0.5-0.6	1304
0.6-0.7	231
0.7-0.8	19
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD5653	Discontinued
0.7761	Intermediate Similarity	NPD3550	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3547	Approved
0.7761	Intermediate Similarity	NPD3549	Approved
0.7752	Intermediate Similarity	NPD1323	Discontinued
0.7674	Intermediate Similarity	NPD853	Approved
0.7674	Intermediate Similarity	NPD851	Approved
0.7606	Intermediate Similarity	NPD7541	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD813	Approved
0.7557	Intermediate Similarity	NPD7679	Phase 2
0.7552	Intermediate Similarity	NPD7254	Discontinued
0.7483	Intermediate Similarity	NPD4705	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8125	Discontinued
0.7381	Intermediate Similarity	NPD1761	Approved
0.7381	Intermediate Similarity	NPD1766	Approved
0.7381	Intermediate Similarity	NPD1767	Approved
0.7381	Intermediate Similarity	NPD1765	Approved
0.7381	Intermediate Similarity	NPD1763	Approved
0.7329	Intermediate Similarity	NPD2010	Phase 3
0.7319	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2754	Discontinued
0.7292	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4549	Discontinued
0.728	Intermediate Similarity	NPD4803	Discontinued
0.7279	Intermediate Similarity	NPD1123	Approved
0.7279	Intermediate Similarity	NPD6768	Approved
0.7279	Intermediate Similarity	NPD1124	Approved
0.7273	Intermediate Similarity	NPD3551	Approved
0.7266	Intermediate Similarity	NPD1321	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8239	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6806	Phase 1
0.7071	Intermediate Similarity	NPD6792	Phase 3
0.7059	Intermediate Similarity	NPD6345	Approved
0.7059	Intermediate Similarity	NPD6343	Approved
0.7055	Intermediate Similarity	NPD7192	Discontinued
0.7039	Intermediate Similarity	NPD8165	Discontinued
0.702	Intermediate Similarity	NPD7602	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6342	Discontinued
0.7007	Intermediate Similarity	NPD6358	Phase 2
0.6993	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD787	Suspended
0.6978	Remote Similarity	NPD3624	Phase 2
0.6977	Remote Similarity	NPD2192	Approved
0.6977	Remote Similarity	NPD2197	Approved
0.6959	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7949	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5918	Discontinued
0.695	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5554	Approved
0.6933	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5630	Phase 1
0.6923	Remote Similarity	NPD1781	Discontinued
0.6906	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5581	Approved
0.6897	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2508	Discontinued
0.6884	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2196	Discontinued
0.6875	Remote Similarity	NPD6027	Approved
0.6875	Remote Similarity	NPD2193	Phase 2
0.6875	Remote Similarity	NPD2648	Phase 3
0.6875	Remote Similarity	NPD6024	Approved
0.6867	Remote Similarity	NPD7720	Phase 2
0.6861	Remote Similarity	NPD5991	Approved
0.6861	Remote Similarity	NPD5990	Approved
0.6855	Remote Similarity	NPD3982	Approved
0.6855	Remote Similarity	NPD2878	Approved
0.6855	Remote Similarity	NPD3980	Approved
0.6838	Remote Similarity	NPD1025	Discontinued
0.6835	Remote Similarity	NPD5836	Discontinued
0.6831	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4655	Approved
0.6825	Remote Similarity	NPD4657	Approved
0.6825	Remote Similarity	NPD1099	Approved
0.6825	Remote Similarity	NPD1100	Approved
0.6821	Remote Similarity	NPD6566	Discontinued
0.6818	Remote Similarity	NPD8009	Approved
0.6818	Remote Similarity	NPD8010	Approved
0.6818	Remote Similarity	NPD7088	Discontinued
0.6815	Remote Similarity	NPD2790	Discontinued
0.6797	Remote Similarity	NPD7575	Phase 3
0.6788	Remote Similarity	NPD5162	Approved
0.6783	Remote Similarity	NPD3245	Phase 3
0.6783	Remote Similarity	NPD3244	Pre-registration
0.6779	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4214	Discontinued
0.6772	Remote Similarity	NPD7072	Phase 2
0.6768	Remote Similarity	NPD7795	Phase 2
0.6767	Remote Similarity	NPD3581	Discontinued
0.6763	Remote Similarity	NPD5516	Phase 2
0.6763	Remote Similarity	NPD5517	Phase 2
0.6761	Remote Similarity	NPD9539	Approved
0.6761	Remote Similarity	NPD9541	Approved
0.6759	Remote Similarity	NPD3063	Discontinued
0.6755	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7142	Discontinued
0.6719	Remote Similarity	NPD742	Approved
0.6714	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5086	Approved
0.6709	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1050	Approved
0.6689	Remote Similarity	NPD6623	Phase 3
0.6687	Remote Similarity	NPD7854	Phase 2
0.6667	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5009	Approved
0.6667	Remote Similarity	NPD5010	Approved
0.6667	Remote Similarity	NPD9540	Approved
0.6667	Remote Similarity	NPD1302	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2820	Phase 3
0.6667	Remote Similarity	NPD4094	Approved
0.6667	Remote Similarity	NPD6294	Approved
0.6667	Remote Similarity	NPD7082	Approved
0.6667	Remote Similarity	NPD6295	Approved
0.6645	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4677	Discontinued
0.6641	Remote Similarity	NPD4937	Approved
0.6641	Remote Similarity	NPD4936	Approved
0.6641	Remote Similarity	NPD466	Approved
0.6623	Remote Similarity	NPD7487	Discontinued
0.6623	Remote Similarity	NPD7259	Approved
0.6622	Remote Similarity	NPD7578	Phase 2
0.6615	Remote Similarity	NPD2171	Approved
0.6614	Remote Similarity	NPD1738	Approved
0.6614	Remote Similarity	NPD2005	Discontinued
0.6613	Remote Similarity	NPD5915	Approved
0.6601	Remote Similarity	NPD2365	Approved
0.6599	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5578	Approved
0.6591	Remote Similarity	NPD1677	Discontinued
0.6589	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7295	Approved
0.6571	Remote Similarity	NPD5511	Discontinued
0.6562	Remote Similarity	NPD5597	Approved
0.6562	Remote Similarity	NPD7954	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5598	Approved
0.6562	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4543	Discontinued
0.6549	Remote Similarity	NPD1079	Discontinued
0.6538	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1524	Phase 1
0.6533	Remote Similarity	NPD3908	Approved
0.6528	Remote Similarity	NPD7464	Phase 3
0.6522	Remote Similarity	NPD1075	Approved
0.6522	Remote Similarity	NPD1073	Approved
0.6522	Remote Similarity	NPD1074	Approved
0.6522	Remote Similarity	NPD3867	Phase 2
0.6522	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1023	Approved
0.6522	Remote Similarity	NPD1021	Approved
0.6522	Remote Similarity	NPD1022	Approved
0.6522	Remote Similarity	NPD1020	Approved
0.6519	Remote Similarity	NPD6611	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.651	Remote Similarity	NPD941	Approved
0.6503	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7610	Discontinued
0.6497	Remote Similarity	NPD7478	Approved
0.6496	Remote Similarity	NPD480	Approved
0.6486	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD2962	Approved
0.6483	Remote Similarity	NPD2961	Approved
0.6481	Remote Similarity	NPD7011	Discontinued
0.6474	Remote Similarity	NPD5933	Phase 3
0.6474	Remote Similarity	NPD8131	Suspended
0.6474	Remote Similarity	NPD5932	Phase 3
0.6474	Remote Similarity	NPD5931	Phase 3
0.6471	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7683	Discontinued
0.6456	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5181	Approved
0.6449	Remote Similarity	NPD1374	Approved
0.6449	Remote Similarity	NPD1370	Approved
0.6449	Remote Similarity	NPD1373	Approved
0.6449	Remote Similarity	NPD5179	Approved
0.6449	Remote Similarity	NPD5180	Approved
0.6449	Remote Similarity	NPD1371	Approved
0.6439	Remote Similarity	NPD3357	Discontinued
0.6434	Remote Similarity	NPD3495	Discontinued
0.6433	Remote Similarity	NPD3519	Discontinued
0.6429	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4461	Discontinued
0.6423	Remote Similarity	NPD2124	Approved
0.642	Remote Similarity	NPD2000	Phase 3
0.642	Remote Similarity	NPD1999	Phase 3
0.6419	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5748	Phase 2
0.6412	Remote Similarity	NPD1916	Discontinued
0.6407	Remote Similarity	NPD2413	Phase 2

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