NPASS Compound

Structure

CID55462 OpenBabel06191715392D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.0013 -0.7052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8689 -1.9622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6590 -5.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3861 -3.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 -2.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6009 -5.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7772 -3.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5387 -0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6922 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0774 -2.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0771 -1.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6930 -2.9308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5395 -3.4192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3465 -0.3530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0722 -1.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 -4.3950 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5390 -1.4652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2323 -3.4187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3855 -1.9536 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6927 -1.9541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8457 -0.4889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4174 -0.6545 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 3.3858 -2.9303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8462 -1.4657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6917 -0.0007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2035 -4.4967 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2141 -1.6099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 9 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 18 3 1 1 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 8 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 0 0 0 0 21 27 1 6 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 28 1 6 0 0 0 24 26 1 0 0 0 0 24 29 1 6 0 0 0 25 29 2 3 0 0 0 25 31 1 0 0 0 0 26 32 1 6 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.36
Volume:	490.283
LogP:	4.949
LogD:	4.637
LogS:	-4.84
# Rotatable Bonds:	5
TPSA:	52.57
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.83
Fsp3:	0.821
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:	-4.875
MDCK Permeability:	1.0987075256707612e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.602
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.238
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.189
Plasma Protein Binding (PPB):	69.10240936279297%
Volume Distribution (VD):	0.882
Pgp-substrate:	25.31585121154785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.403
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.305
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.409
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	9.012
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.728
Carcinogencity:	0.518
Eye Corrosion:	0.323
Eye Irritation:	0.074
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC55462

Natural Product ID:	NPC55462
*Common Name:**	Hookerianamide J
IUPAC Name:	N-[(3S,4R,5R,8R,9S,10R,13S,14S)-17-[(1S)-1-(dimethylamino)ethyl]-4-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]-3-methylbut-2-enamide
Synonyms:	hookerianamide J
Standard InCHIKey:	UBWMSSICUOCSHT-BJHCZKLTSA-N
Standard InCHI:	InChI=1S/C28H46N2O2/c1-17(2)16-25(31)29-24-13-15-28(5)22-12-14-27(4)20(18(3)30(6)7)10-11-21(27)19(22)8-9-23(28)26(24)32/h10,16,18-19,21-24,26,32H,8-9,11-15H2,1-7H3,(H,29,31)/t18-,19-,21-,22-,23-,24-,26+,27+,28+/m0/s1
SMILES:	CC(=CC(=N[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)C(=CC[C@H]4[C@@H]3CC[C@H]2[C@H]1O)[C@H](C)N(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496487
PubChem CID:	25016666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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.	whole plant	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO6711	Streptomyces mirabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19818612]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
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]
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]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12328	Ampelopsis japonica	Species	Vitaceae	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]

☑ 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	3
MIC	2
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	48500.0	nM	PMID[459759]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	800.0	nM	PMID[459759]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	11300.0	nM	PMID[459759]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	15.0	mm	PMID[459759]
NPT2921	Organism	Pseudomonas	Pseudomonas	IZ	=	12.0	mm	PMID[459759]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	141400.0	nM	PMID[459759]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	70700.0	nM	PMID[459759]

☑ 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 NPC55462 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	92
0.1-0.2	774
0.2-0.3	7754
0.3-0.4	18687
0.4-0.5	10244
0.5-0.6	4469
0.6-0.7	631
0.7-0.8	35
0.8-0.85	5
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9223	High Similarity	NPC472359
0.91	High Similarity	NPC471083
0.9048	High Similarity	NPC469968
0.9048	High Similarity	NPC80834
0.8911	High Similarity	NPC247060
0.8725	High Similarity	NPC50815
0.8571	High Similarity	NPC25340
0.8462	Intermediate Similarity	NPC474583
0.8407	Intermediate Similarity	NPC242692
0.8349	Intermediate Similarity	NPC56796
0.8333	Intermediate Similarity	NPC472458
0.8302	Intermediate Similarity	NPC36497
0.8235	Intermediate Similarity	NPC476903
0.7966	Intermediate Similarity	NPC237286
0.7959	Intermediate Similarity	NPC152684
0.7944	Intermediate Similarity	NPC90538
0.7879	Intermediate Similarity	NPC166458
0.7838	Intermediate Similarity	NPC72753
0.7818	Intermediate Similarity	NPC159367
0.781	Intermediate Similarity	NPC140300
0.7807	Intermediate Similarity	NPC165396
0.7778	Intermediate Similarity	NPC241879
0.7768	Intermediate Similarity	NPC66862
0.7664	Intermediate Similarity	NPC275686
0.7615	Intermediate Similarity	NPC45365
0.7615	Intermediate Similarity	NPC293299
0.7551	Intermediate Similarity	NPC257962
0.7549	Intermediate Similarity	NPC34754
0.7477	Intermediate Similarity	NPC240650
0.7383	Intermediate Similarity	NPC289140
0.7358	Intermediate Similarity	NPC243985
0.7358	Intermediate Similarity	NPC280710
0.729	Intermediate Similarity	NPC272732
0.729	Intermediate Similarity	NPC311164
0.7264	Intermediate Similarity	NPC93027
0.7255	Intermediate Similarity	NPC75810
0.7217	Intermediate Similarity	NPC328052
0.7209	Intermediate Similarity	NPC132847
0.7207	Intermediate Similarity	NPC226509
0.7196	Intermediate Similarity	NPC473314
0.7182	Intermediate Similarity	NPC135799
0.7143	Intermediate Similarity	NPC473254
0.7129	Intermediate Similarity	NPC296701
0.7129	Intermediate Similarity	NPC218616
0.7105	Intermediate Similarity	NPC46981
0.7091	Intermediate Similarity	NPC91604
0.708	Intermediate Similarity	NPC470596
0.7075	Intermediate Similarity	NPC84171
0.7071	Intermediate Similarity	NPC11908
0.7069	Intermediate Similarity	NPC472313
0.7054	Intermediate Similarity	NPC476755
0.7054	Intermediate Similarity	NPC152718
0.7018	Intermediate Similarity	NPC258130
0.7	Intermediate Similarity	NPC474164
0.7	Intermediate Similarity	NPC30986
0.7	Intermediate Similarity	NPC209430
0.697	Remote Similarity	NPC470711
0.697	Remote Similarity	NPC470758
0.6964	Remote Similarity	NPC118275
0.6961	Remote Similarity	NPC39966
0.6961	Remote Similarity	NPC224072
0.6957	Remote Similarity	NPC169375
0.6949	Remote Similarity	NPC474452
0.693	Remote Similarity	NPC119329
0.6907	Remote Similarity	NPC474743
0.6903	Remote Similarity	NPC176012
0.69	Remote Similarity	NPC285761
0.69	Remote Similarity	NPC244385
0.69	Remote Similarity	NPC312328
0.69	Remote Similarity	NPC138621
0.69	Remote Similarity	NPC6978
0.69	Remote Similarity	NPC167037
0.6897	Remote Similarity	NPC470595
0.6893	Remote Similarity	NPC82623
0.6891	Remote Similarity	NPC478137
0.6887	Remote Similarity	NPC324405
0.687	Remote Similarity	NPC477292
0.687	Remote Similarity	NPC86906
0.6869	Remote Similarity	NPC470749
0.6869	Remote Similarity	NPC247325
0.6869	Remote Similarity	NPC237460
0.6869	Remote Similarity	NPC244488
0.6864	Remote Similarity	NPC474459
0.6863	Remote Similarity	NPC109533
0.6855	Remote Similarity	NPC478138
0.6847	Remote Similarity	NPC167419
0.6847	Remote Similarity	NPC4834
0.6832	Remote Similarity	NPC109546
0.6832	Remote Similarity	NPC472463
0.6832	Remote Similarity	NPC84694
0.6832	Remote Similarity	NPC47982
0.6832	Remote Similarity	NPC28862
0.6832	Remote Similarity	NPC143182
0.6832	Remote Similarity	NPC81306
0.6832	Remote Similarity	NPC80530
0.6832	Remote Similarity	NPC273410
0.6807	Remote Similarity	NPC476498
0.68	Remote Similarity	NPC91594
0.6796	Remote Similarity	NPC101462
0.6796	Remote Similarity	NPC248886
0.6796	Remote Similarity	NPC470049
0.6796	Remote Similarity	NPC202389
0.6796	Remote Similarity	NPC49964
0.6796	Remote Similarity	NPC87489
0.6783	Remote Similarity	NPC212874
0.6783	Remote Similarity	NPC469958
0.6783	Remote Similarity	NPC475239
0.6768	Remote Similarity	NPC185536
0.6765	Remote Similarity	NPC322313
0.6765	Remote Similarity	NPC236237
0.6765	Remote Similarity	NPC13554
0.6765	Remote Similarity	NPC234193
0.6765	Remote Similarity	NPC102253
0.6765	Remote Similarity	NPC295131
0.6733	Remote Similarity	NPC474216
0.6733	Remote Similarity	NPC302041
0.6733	Remote Similarity	NPC65897
0.6733	Remote Similarity	NPC85346
0.6731	Remote Similarity	NPC246956
0.6731	Remote Similarity	NPC470558
0.6731	Remote Similarity	NPC317458
0.6731	Remote Similarity	NPC134481
0.6729	Remote Similarity	NPC67872
0.6724	Remote Similarity	NPC230677
0.672	Remote Similarity	NPC469943
0.67	Remote Similarity	NPC189883
0.6699	Remote Similarity	NPC23852
0.6699	Remote Similarity	NPC264245
0.6699	Remote Similarity	NPC209620
0.6698	Remote Similarity	NPC261266
0.6698	Remote Similarity	NPC474458
0.6698	Remote Similarity	NPC157479
0.6698	Remote Similarity	NPC139724
0.6698	Remote Similarity	NPC6391
0.6696	Remote Similarity	NPC292819
0.6694	Remote Similarity	NPC476499
0.6667	Remote Similarity	NPC205845
0.6667	Remote Similarity	NPC474047
0.6667	Remote Similarity	NPC476756
0.6667	Remote Similarity	NPC231310
0.6667	Remote Similarity	NPC476366
0.6667	Remote Similarity	NPC124358
0.6667	Remote Similarity	NPC1319
0.6667	Remote Similarity	NPC470077
0.6667	Remote Similarity	NPC244982
0.6667	Remote Similarity	NPC474493
0.6667	Remote Similarity	NPC185568
0.6667	Remote Similarity	NPC201048
0.6667	Remote Similarity	NPC211322
0.6639	Remote Similarity	NPC28280
0.6639	Remote Similarity	NPC304646
0.6639	Remote Similarity	NPC287764
0.6636	Remote Similarity	NPC470620
0.6635	Remote Similarity	NPC50964
0.6635	Remote Similarity	NPC189972
0.6634	Remote Similarity	NPC331618
0.6634	Remote Similarity	NPC257191
0.6634	Remote Similarity	NPC214570
0.6634	Remote Similarity	NPC119355
0.6634	Remote Similarity	NPC248830
0.6634	Remote Similarity	NPC212241
0.6633	Remote Similarity	NPC265789
0.6613	Remote Similarity	NPC35037
0.6604	Remote Similarity	NPC318390
0.6604	Remote Similarity	NPC266511
0.6604	Remote Similarity	NPC470360
0.6604	Remote Similarity	NPC274448
0.6602	Remote Similarity	NPC241290
0.6602	Remote Similarity	NPC209944
0.6602	Remote Similarity	NPC236112
0.6602	Remote Similarity	NPC164840
0.66	Remote Similarity	NPC471723
0.66	Remote Similarity	NPC257347
0.66	Remote Similarity	NPC141071
0.66	Remote Similarity	NPC32832
0.6583	Remote Similarity	NPC79238
0.6574	Remote Similarity	NPC133588
0.6574	Remote Similarity	NPC471952
0.6571	Remote Similarity	NPC207013
0.6571	Remote Similarity	NPC110778
0.6571	Remote Similarity	NPC474634
0.6571	Remote Similarity	NPC113978
0.6571	Remote Similarity	NPC475789
0.6571	Remote Similarity	NPC477818
0.6571	Remote Similarity	NPC470384
0.6569	Remote Similarity	NPC301707
0.6569	Remote Similarity	NPC473943
0.6569	Remote Similarity	NPC477514
0.6569	Remote Similarity	NPC318136
0.6569	Remote Similarity	NPC472342
0.6569	Remote Similarity	NPC275910
0.6552	Remote Similarity	NPC98765
0.6545	Remote Similarity	NPC110923
0.6545	Remote Similarity	NPC74296
0.6542	Remote Similarity	NPC299068
0.6538	Remote Similarity	NPC474752
0.6538	Remote Similarity	NPC474731
0.6538	Remote Similarity	NPC474683
0.6538	Remote Similarity	NPC192456
0.6538	Remote Similarity	NPC476646

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 NPC55462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	387
0.2-0.3	2545
0.3-0.4	4329
0.4-0.5	1492
0.5-0.6	285
0.6-0.7	18
0.7-0.8	1
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
0.7692	Intermediate Similarity	NPD5771	Approved
0.6765	Remote Similarity	NPD7525	Registered
0.6727	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6640	Phase 3
0.6436	Remote Similarity	NPD6942	Approved
0.6436	Remote Similarity	NPD7339	Approved
0.6371	Remote Similarity	NPD7755	Approved
0.6371	Remote Similarity	NPD7754	Approved
0.6346	Remote Similarity	NPD7645	Phase 2
0.6341	Remote Similarity	NPD8298	Phase 2
0.6303	Remote Similarity	NPD7333	Discontinued
0.6293	Remote Similarity	NPD8418	Phase 2
0.6273	Remote Similarity	NPD4722	Approved
0.6273	Remote Similarity	NPD4723	Approved
0.6261	Remote Similarity	NPD7920	Phase 3
0.6261	Remote Similarity	NPD7919	Phase 3
0.625	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7522	Discontinued
0.6214	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8088	Phase 1
0.619	Remote Similarity	NPD6929	Approved
0.6182	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6926	Approved
0.6176	Remote Similarity	NPD6924	Approved
0.6174	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6404	Discontinued
0.6132	Remote Similarity	NPD7509	Discontinued
0.6132	Remote Similarity	NPD6931	Approved
0.6132	Remote Similarity	NPD7332	Phase 2
0.6132	Remote Similarity	NPD6930	Phase 2
0.6071	Remote Similarity	NPD5328	Approved
0.6058	Remote Similarity	NPD6933	Approved
0.6055	Remote Similarity	NPD4786	Approved
0.6033	Remote Similarity	NPD6920	Discontinued
0.6017	Remote Similarity	NPD7639	Approved
0.6017	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD8077	Approved
0.6	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6914	Discontinued
0.6	Remote Similarity	NPD8078	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD7335	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD7336	Phase 2
0.5984	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7514	Phase 3
0.598	Remote Similarity	NPD4243	Approved
0.5968	Remote Similarity	NPD6420	Discontinued
0.5965	Remote Similarity	NPD6079	Approved
0.5963	Remote Similarity	NPD6695	Phase 3
0.5946	Remote Similarity	NPD3618	Phase 1
0.5943	Remote Similarity	NPD7145	Approved
0.5941	Remote Similarity	NPD6923	Approved
0.5941	Remote Similarity	NPD6922	Approved
0.5935	Remote Similarity	NPD6415	Discontinued
0.5932	Remote Similarity	NPD7638	Approved
0.5926	Remote Similarity	NPD6902	Approved
0.5926	Remote Similarity	NPD6898	Phase 1
0.5913	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7144	Approved
0.5882	Remote Similarity	NPD7143	Approved
0.5878	Remote Similarity	NPD6908	Approved
0.5878	Remote Similarity	NPD6909	Approved
0.5877	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6700	Approved
0.5872	Remote Similarity	NPD3667	Approved
0.5865	Remote Similarity	NPD4785	Approved
0.5865	Remote Similarity	NPD4784	Approved
0.5856	Remote Similarity	NPD6893	Approved
0.5856	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6702	Approved
0.5826	Remote Similarity	NPD6703	Approved
0.5825	Remote Similarity	NPD7152	Approved
0.5825	Remote Similarity	NPD7150	Approved
0.5825	Remote Similarity	NPD7151	Approved
0.581	Remote Similarity	NPD8264	Approved
0.5806	Remote Similarity	NPD8174	Phase 2
0.5782	Remote Similarity	NPD8131	Suspended
0.5776	Remote Similarity	NPD4202	Approved
0.5772	Remote Similarity	NPD5357	Phase 1
0.5766	Remote Similarity	NPD3665	Phase 1
0.5766	Remote Similarity	NPD3133	Approved
0.5766	Remote Similarity	NPD3666	Approved
0.5752	Remote Similarity	NPD7524	Approved
0.5752	Remote Similarity	NPD7750	Discontinued
0.5728	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6939	Phase 2
0.5726	Remote Similarity	NPD5707	Approved
0.5724	Remote Similarity	NPD6789	Approved
0.5714	Remote Similarity	NPD7725	Approved
0.5701	Remote Similarity	NPD6932	Approved
0.569	Remote Similarity	NPD7515	Phase 2
0.5688	Remote Similarity	NPD4748	Discontinued
0.5686	Remote Similarity	NPD6705	Phase 1
0.5674	Remote Similarity	NPD8118	Discontinued
0.5664	Remote Similarity	NPD8308	Discontinued
0.566	Remote Similarity	NPD4190	Phase 3
0.566	Remote Similarity	NPD5275	Approved
0.5656	Remote Similarity	NPD5211	Phase 2
0.5649	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.563	Remote Similarity	NPD5221	Approved
0.563	Remote Similarity	NPD4697	Phase 3
0.563	Remote Similarity	NPD5222	Approved
0.563	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.561	Remote Similarity	NPD7912	Approved
0.561	Remote Similarity	NPD7986	Approved
0.561	Remote Similarity	NPD7911	Approved
0.561	Remote Similarity	NPD7987	Approved
0.5607	Remote Similarity	NPD1346	Approved
0.5603	Remote Similarity	NPD4001	Clinical (unspecified phase)

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