NPASS Compound

Structure

CID252794 OpenBabel06191716052D 26 31 0 0 1 0 0 0 0 0999 V2000 0.2406 2.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8054 -2.3276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5716 -0.1164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2716 -2.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0779 -1.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5177 -0.8319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9788 0.2881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4653 -1.7373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0779 -0.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8711 -1.1430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4652 0.8061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6124 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2715 1.2716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6121 -0.9314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3322 -0.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4653 -0.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2716 -0.3408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2783 -0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9307 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9309 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8063 0.4652 0.0000 C 0 0 1 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 0.4652 0.1247 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6853 -1.1426 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4651 1.7370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8057 -1.3966 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 21 1 1 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 1 0 0 0 20 24 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 1 0 0 0 22 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.22
Volume:	365.898
LogP:	3.131
LogD:	2.665
LogS:	-4.307
# Rotatable Bonds:	0
TPSA:	30.54
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	5.187
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.382
MDCK Permeability:	1.0252233551000245e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.567
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	64.46830749511719%
Volume Distribution (VD):	3.137
Pgp-substrate:	47.06922912597656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.459

ADMET: Excretion

Clearance (CL):	9.368
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.885
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.337
Carcinogencity:	0.692
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC252794

Natural Product ID:	NPC252794
*Common Name:**	Calycanthine
IUPAC Name:	n.a.
Synonyms:	Calycanthine
Standard InCHIKey:	XSYCDVWYEVUDKQ-GXRSIYKFSA-N
Standard InCHI:	InChI=1S/C22H26N4/c1-25-13-11-22-16-8-4-5-9-17(16)23-19(25)21(22)12-14-26(2)20(22)24-18-10-6-3-7-15(18)21/h3-10,19-20,23-24H,11-14H2,1-2H3/t19-,20-,21-,22-/m1/s1
SMILES:	CN1CC[C@]23[C@]4([C@@H]1Nc1c3cccc1)CCN([C@H]2Nc1c4cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464770
PubChem CID:	5392245
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000053] Aminoquinolines 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
NPO13462	Plocamium costatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075796]
NPO40170	Idiospermum australiense	Species	Calycanthaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[7595588]
NPO364	Chimonanthus praecox	Species	Calycanthaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO364	Chimonanthus praecox	Species	Calycanthaceae	Eukaryota	n.a.	fruit	n.a.	Database[Article]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3786	Heliotropium arguzioides	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3312	Alstonia legouixiae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3786	Heliotropium arguzioides	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO364	Chimonanthus praecox	Species	Calycanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8441	Clerodendrum wildii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8237	Litsea acuminatissima	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3120	Swertia randaiensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19713	Phaeanthus macropodus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3786	Heliotropium arguzioides	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25966	Myristica maingayi	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14328	Aconitum ouvrardianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9651	Psidium cattleianum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3312	Alstonia legouixiae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12017	Juniperus mexicana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15298	Epilachna borealis	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9848	Coespeletia timotensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10113	Virola venezuelensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7839	Rosa sericea	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO554	Quercus miyagii	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13462	Plocamium costatum	Species	Plocamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3518	Polytrichum ohioense	Species	Polytrichaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1272	Helichrysum crispum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9208	Volutaria crupinoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO75	Streptomyces fragilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7190	Astragalus ptilodes	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16162	Cyclamen cyprium	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2843	Temnopleurus hardwickii	Species	Temnopleuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	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
Others	1
Potency	7

Activity Type	# Activity
Individual Protein	5
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	5623.4	nM	PMID[463133]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[463133]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[463133]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1258.9	nM	PMID[463133]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[463133]
NPT2	Others	Unspecified		Activity	=	20.4	%	PMID[463132]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	5221.3	nM	PMID[463133]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[463133]

☑ 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 NPC252794 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	760
0.1-0.2	5888
0.2-0.3	18244
0.3-0.4	11663
0.4-0.5	4461
0.5-0.6	1363
0.6-0.7	286
0.7-0.8	26
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8231	Intermediate Similarity	NPC145754
0.8189	Intermediate Similarity	NPC475915
0.7902	Intermediate Similarity	NPC109787
0.7667	Intermediate Similarity	NPC291610
0.7462	Intermediate Similarity	NPC313449
0.744	Intermediate Similarity	NPC302790
0.7376	Intermediate Similarity	NPC471123
0.7248	Intermediate Similarity	NPC473329
0.7222	Intermediate Similarity	NPC79618
0.72	Intermediate Similarity	NPC206592
0.717	Intermediate Similarity	NPC242269
0.7153	Intermediate Similarity	NPC469560
0.7143	Intermediate Similarity	NPC276085
0.7078	Intermediate Similarity	NPC222029
0.7059	Intermediate Similarity	NPC476219
0.7032	Intermediate Similarity	NPC221786
0.7032	Intermediate Similarity	NPC474880
0.7025	Intermediate Similarity	NPC329430
0.7024	Intermediate Similarity	NPC128582
0.7023	Intermediate Similarity	NPC187036
0.7015	Intermediate Similarity	NPC264580
0.6953	Remote Similarity	NPC434
0.694	Remote Similarity	NPC192209
0.6933	Remote Similarity	NPC469735
0.6917	Remote Similarity	NPC288232
0.6894	Remote Similarity	NPC314141
0.6879	Remote Similarity	NPC229173
0.6866	Remote Similarity	NPC313673
0.6832	Remote Similarity	NPC474897
0.6821	Remote Similarity	NPC264589
0.6815	Remote Similarity	NPC475990
0.6797	Remote Similarity	NPC318086
0.6779	Remote Similarity	NPC2949
0.6777	Remote Similarity	NPC470926
0.6767	Remote Similarity	NPC296163
0.6766	Remote Similarity	NPC256288
0.6757	Remote Similarity	NPC130251
0.6753	Remote Similarity	NPC66936
0.675	Remote Similarity	NPC475420
0.6731	Remote Similarity	NPC476297
0.673	Remote Similarity	NPC469741
0.6726	Remote Similarity	NPC2933
0.6713	Remote Similarity	NPC9856
0.6711	Remote Similarity	NPC88097
0.6694	Remote Similarity	NPC191444
0.6689	Remote Similarity	NPC20144
0.6687	Remote Similarity	NPC201634
0.6686	Remote Similarity	NPC259626
0.6667	Remote Similarity	NPC30445
0.6667	Remote Similarity	NPC267508
0.6667	Remote Similarity	NPC469740
0.6647	Remote Similarity	NPC473615
0.6645	Remote Similarity	NPC33421
0.6623	Remote Similarity	NPC21605
0.6621	Remote Similarity	NPC476685
0.6621	Remote Similarity	NPC476687
0.6621	Remote Similarity	NPC476689
0.6618	Remote Similarity	NPC125416
0.6612	Remote Similarity	NPC176858
0.661	Remote Similarity	NPC169016
0.6608	Remote Similarity	NPC229484
0.6603	Remote Similarity	NPC117032
0.6601	Remote Similarity	NPC204141
0.6597	Remote Similarity	NPC473417
0.6585	Remote Similarity	NPC108800
0.6573	Remote Similarity	NPC478079
0.6571	Remote Similarity	NPC268534
0.657	Remote Similarity	NPC292675
0.6562	Remote Similarity	NPC239854
0.6556	Remote Similarity	NPC59084
0.6556	Remote Similarity	NPC477179
0.6555	Remote Similarity	NPC229477
0.6554	Remote Similarity	NPC198988
0.6545	Remote Similarity	NPC473880
0.6541	Remote Similarity	NPC167635
0.6525	Remote Similarity	NPC134825
0.6519	Remote Similarity	NPC477181
0.6519	Remote Similarity	NPC254850
0.6519	Remote Similarity	NPC477180
0.6519	Remote Similarity	NPC477178
0.6513	Remote Similarity	NPC63157
0.6513	Remote Similarity	NPC473868
0.651	Remote Similarity	NPC325252
0.65	Remote Similarity	NPC471122
0.65	Remote Similarity	NPC258046
0.649	Remote Similarity	NPC22082
0.649	Remote Similarity	NPC301760
0.649	Remote Similarity	NPC186284
0.6484	Remote Similarity	NPC470490
0.6471	Remote Similarity	NPC311330
0.6467	Remote Similarity	NPC251722
0.6467	Remote Similarity	NPC280852
0.6467	Remote Similarity	NPC314102
0.646	Remote Similarity	NPC68650
0.6456	Remote Similarity	NPC478076
0.6442	Remote Similarity	NPC195507
0.6442	Remote Similarity	NPC2165
0.6438	Remote Similarity	NPC469428
0.6433	Remote Similarity	NPC475763
0.6413	Remote Similarity	NPC475259
0.6413	Remote Similarity	NPC471945
0.6413	Remote Similarity	NPC471950
0.6407	Remote Similarity	NPC475097
0.6405	Remote Similarity	NPC469537
0.64	Remote Similarity	NPC322040
0.6395	Remote Similarity	NPC53044
0.6393	Remote Similarity	NPC111233
0.6385	Remote Similarity	NPC474430
0.6383	Remote Similarity	NPC257490
0.6382	Remote Similarity	NPC104483
0.6358	Remote Similarity	NPC255229
0.6358	Remote Similarity	NPC81229
0.6357	Remote Similarity	NPC226143
0.6347	Remote Similarity	NPC285622
0.6344	Remote Similarity	NPC475359
0.6344	Remote Similarity	NPC191817
0.6341	Remote Similarity	NPC471124
0.6335	Remote Similarity	NPC193740
0.6319	Remote Similarity	NPC99632
0.6319	Remote Similarity	NPC194881
0.6319	Remote Similarity	NPC282339
0.6312	Remote Similarity	NPC279385
0.6312	Remote Similarity	NPC179605
0.6311	Remote Similarity	NPC262295
0.6309	Remote Similarity	NPC313352
0.6304	Remote Similarity	NPC477173
0.6304	Remote Similarity	NPC477174
0.6301	Remote Similarity	NPC307396
0.6296	Remote Similarity	NPC56765
0.6289	Remote Similarity	NPC470233
0.6288	Remote Similarity	NPC474695
0.6286	Remote Similarity	NPC81561
0.6284	Remote Similarity	NPC22079
0.6276	Remote Similarity	NPC245244
0.6276	Remote Similarity	NPC146373
0.6276	Remote Similarity	NPC166424
0.6275	Remote Similarity	NPC73767
0.627	Remote Similarity	NPC470488
0.6269	Remote Similarity	NPC164802
0.6268	Remote Similarity	NPC103292
0.6265	Remote Similarity	NPC475248
0.6265	Remote Similarity	NPC63047
0.6264	Remote Similarity	NPC17273
0.6264	Remote Similarity	NPC135601
0.6264	Remote Similarity	NPC141612
0.625	Remote Similarity	NPC125746
0.625	Remote Similarity	NPC104070
0.625	Remote Similarity	NPC119677
0.625	Remote Similarity	NPC472123
0.6243	Remote Similarity	NPC472294
0.6242	Remote Similarity	NPC475450
0.6241	Remote Similarity	NPC291962
0.6241	Remote Similarity	NPC162689
0.6241	Remote Similarity	NPC177684
0.6241	Remote Similarity	NPC54102
0.6235	Remote Similarity	NPC286427
0.6235	Remote Similarity	NPC61013
0.6234	Remote Similarity	NPC469779
0.6234	Remote Similarity	NPC469784
0.6234	Remote Similarity	NPC469783
0.6234	Remote Similarity	NPC469768
0.6234	Remote Similarity	NPC469780
0.6234	Remote Similarity	NPC469767
0.6234	Remote Similarity	NPC469761
0.6234	Remote Similarity	NPC115611
0.6233	Remote Similarity	NPC476950
0.622	Remote Similarity	NPC470203
0.622	Remote Similarity	NPC176983
0.6218	Remote Similarity	NPC116519
0.6214	Remote Similarity	NPC148140
0.6207	Remote Similarity	NPC122718
0.6207	Remote Similarity	NPC476095
0.6203	Remote Similarity	NPC471951
0.6203	Remote Similarity	NPC471946
0.6197	Remote Similarity	NPC161956
0.6197	Remote Similarity	NPC112373
0.6197	Remote Similarity	NPC258531
0.6196	Remote Similarity	NPC36495
0.6196	Remote Similarity	NPC41257
0.6196	Remote Similarity	NPC193410
0.6194	Remote Similarity	NPC469766
0.619	Remote Similarity	NPC328590
0.6184	Remote Similarity	NPC218268
0.6182	Remote Similarity	NPC271797
0.6182	Remote Similarity	NPC21174
0.6178	Remote Similarity	NPC470440
0.6174	Remote Similarity	NPC69914
0.6169	Remote Similarity	NPC110126
0.6164	Remote Similarity	NPC2272
0.6159	Remote Similarity	NPC470204
0.6159	Remote Similarity	NPC472102
0.6159	Remote Similarity	NPC248117
0.6159	Remote Similarity	NPC309531
0.6154	Remote Similarity	NPC472103
0.6154	Remote Similarity	NPC314192
0.6154	Remote Similarity	NPC473743
0.6149	Remote Similarity	NPC325903
0.6144	Remote Similarity	NPC84911
0.6139	Remote Similarity	NPC143872
0.6138	Remote Similarity	NPC192533

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 NPC252794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	308
0.1-0.2	669
0.2-0.3	1267
0.3-0.4	1715
0.4-0.5	3216
0.5-0.6	1589
0.6-0.7	345
0.7-0.8	38
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
0.825	Intermediate Similarity	NPD4116	Approved
0.7967	Intermediate Similarity	NPD3001	Approved
0.7967	Intermediate Similarity	NPD2999	Approved
0.7823	Intermediate Similarity	NPD2038	Approved
0.7823	Intermediate Similarity	NPD2039	Approved
0.7805	Intermediate Similarity	NPD7633	Discontinued
0.7698	Intermediate Similarity	NPD2913	Approved
0.7698	Intermediate Similarity	NPD2914	Approved
0.7612	Intermediate Similarity	NPD1949	Approved
0.7612	Intermediate Similarity	NPD1950	Approved
0.7594	Intermediate Similarity	NPD2938	Approved
0.7594	Intermediate Similarity	NPD2940	Approved
0.7581	Intermediate Similarity	NPD1721	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3545	Approved
0.7561	Intermediate Similarity	NPD3546	Approved
0.75	Intermediate Similarity	NPD4114	Approved
0.75	Intermediate Similarity	NPD4115	Approved
0.75	Intermediate Similarity	NPD5629	Discontinued
0.7462	Intermediate Similarity	NPD7481	Approved
0.7462	Intermediate Similarity	NPD7480	Approved
0.7445	Intermediate Similarity	NPD3424	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8128	Discontinued
0.7319	Intermediate Similarity	NPD8263	Discontinued
0.7308	Intermediate Similarity	NPD1723	Phase 2
0.7308	Intermediate Similarity	NPD1720	Phase 2
0.7236	Intermediate Similarity	NPD4735	Approved
0.7236	Intermediate Similarity	NPD4734	Approved
0.7226	Intermediate Similarity	NPD6900	Discontinued
0.7222	Intermediate Similarity	NPD5253	Approved
0.7203	Intermediate Similarity	NPD6358	Phase 2
0.7194	Intermediate Similarity	NPD4019	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5181	Approved
0.7154	Intermediate Similarity	NPD5179	Approved
0.7154	Intermediate Similarity	NPD5180	Approved
0.7143	Intermediate Similarity	NPD4866	Approved
0.7143	Intermediate Similarity	NPD3954	Approved
0.7143	Intermediate Similarity	NPD3841	Phase 3
0.7143	Intermediate Similarity	NPD4867	Approved
0.7132	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2463	Approved
0.7121	Intermediate Similarity	NPD2467	Approved
0.7121	Intermediate Similarity	NPD2464	Approved
0.7111	Intermediate Similarity	NPD4546	Discontinued
0.7107	Intermediate Similarity	NPD2005	Discontinued
0.7101	Intermediate Similarity	NPD2840	Approved
0.7087	Intermediate Similarity	NPD6300	Approved
0.7087	Intermediate Similarity	NPD6299	Approved
0.7037	Intermediate Similarity	NPD3956	Phase 3
0.7037	Intermediate Similarity	NPD3955	Approved
0.7037	Intermediate Similarity	NPD3957	Phase 2
0.7008	Intermediate Similarity	NPD990	Approved
0.7008	Intermediate Similarity	NPD993	Approved
0.7	Intermediate Similarity	NPD3012	Approved
0.7	Intermediate Similarity	NPD3008	Approved
0.7	Intermediate Similarity	NPD3011	Approved
0.697	Remote Similarity	NPD5631	Phase 3
0.6963	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6301	Phase 2
0.6944	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6892	Discontinued
0.6889	Remote Similarity	NPD5657	Phase 3
0.6885	Remote Similarity	NPD5554	Approved
0.6884	Remote Similarity	NPD2964	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7200	Approved
0.6871	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3240	Phase 2
0.6849	Remote Similarity	NPD6342	Discontinued
0.6849	Remote Similarity	NPD5318	Discontinued
0.6846	Remote Similarity	NPD3548	Approved
0.6842	Remote Similarity	NPD1813	Discontinued
0.6838	Remote Similarity	NPD3498	Approved
0.6838	Remote Similarity	NPD3499	Approved
0.68	Remote Similarity	NPD5918	Discontinued
0.68	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2998	Approved
0.6777	Remote Similarity	NPD2997	Approved
0.6777	Remote Similarity	NPD3000	Approved
0.6767	Remote Similarity	NPD6561	Approved
0.6767	Remote Similarity	NPD6562	Approved
0.6765	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3483	Approved
0.6741	Remote Similarity	NPD6660	Discontinued
0.6741	Remote Similarity	NPD3484	Approved
0.6718	Remote Similarity	NPD1539	Approved
0.6716	Remote Similarity	NPD7062	Discontinued
0.6715	Remote Similarity	NPD5517	Phase 2
0.6715	Remote Similarity	NPD5516	Phase 2
0.6689	Remote Similarity	NPD7099	Approved
0.6688	Remote Similarity	NPD6574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2399	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6548	Approved
0.6667	Remote Similarity	NPD2867	Approved
0.6667	Remote Similarity	NPD2143	Discontinued
0.6667	Remote Similarity	NPD6489	Phase 3
0.6667	Remote Similarity	NPD6549	Approved
0.6639	Remote Similarity	NPD4543	Discontinued
0.6639	Remote Similarity	NPD4636	Approved
0.6622	Remote Similarity	NPD4411	Phase 1
0.6622	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5243	Approved
0.6618	Remote Similarity	NPD5245	Approved
0.6618	Remote Similarity	NPD5244	Approved
0.6615	Remote Similarity	NPD1065	Approved
0.6615	Remote Similarity	NPD1064	Approved
0.6614	Remote Similarity	NPD1916	Discontinued
0.6603	Remote Similarity	NPD8401	Approved
0.6603	Remote Similarity	NPD3248	Phase 1
0.6603	Remote Similarity	NPD8400	Approved
0.6603	Remote Similarity	NPD8402	Approved
0.6601	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3625	Discontinued
0.6599	Remote Similarity	NPD3385	Approved
0.6597	Remote Similarity	NPD4489	Approved
0.6597	Remote Similarity	NPD4490	Approved
0.6591	Remote Similarity	NPD1108	Approved
0.6591	Remote Similarity	NPD1107	Approved
0.6582	Remote Similarity	NPD2150	Discontinued
0.6579	Remote Similarity	NPD2866	Approved
0.6575	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1683	Approved
0.6557	Remote Similarity	NPD5915	Approved
0.6549	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD2340	Discontinued
0.6541	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD5933	Phase 3
0.6536	Remote Similarity	NPD5671	Approved
0.6536	Remote Similarity	NPD5932	Phase 3
0.6536	Remote Similarity	NPD5931	Phase 3
0.6531	Remote Similarity	NPD5182	Approved
0.6531	Remote Similarity	NPD5185	Approved
0.6531	Remote Similarity	NPD5184	Approved
0.6528	Remote Similarity	NPD4549	Discontinued
0.6525	Remote Similarity	NPD7461	Approved
0.6503	Remote Similarity	NPD572	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1636	Approved
0.6496	Remote Similarity	NPD6070	Approved
0.6496	Remote Similarity	NPD6069	Approved
0.6493	Remote Similarity	NPD526	Approved
0.649	Remote Similarity	NPD1590	Approved
0.6483	Remote Similarity	NPD4365	Phase 2
0.6479	Remote Similarity	NPD2871	Approved
0.6479	Remote Similarity	NPD2870	Approved
0.6475	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4085	Approved
0.6471	Remote Similarity	NPD2538	Approved
0.6471	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2539	Approved
0.6463	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4936	Approved
0.6462	Remote Similarity	NPD4937	Approved
0.6462	Remote Similarity	NPD1728	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5993	Phase 1
0.6457	Remote Similarity	NPD6499	Approved
0.6457	Remote Similarity	NPD6498	Approved
0.6456	Remote Similarity	NPD4121	Phase 3
0.6456	Remote Similarity	NPD4120	Approved
0.6447	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6768	Approved
0.6446	Remote Similarity	NPD4146	Approved
0.6446	Remote Similarity	NPD4145	Approved
0.6444	Remote Similarity	NPD561	Approved
0.6444	Remote Similarity	NPD560	Approved
0.6439	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8060	Phase 1
0.6438	Remote Similarity	NPD5782	Phase 3
0.6434	Remote Similarity	NPD1937	Approved
0.6415	Remote Similarity	NPD5743	Approved
0.6415	Remote Similarity	NPD5741	Approved
0.6415	Remote Similarity	NPD5742	Approved
0.6414	Remote Similarity	NPD2036	Approved
0.6412	Remote Similarity	NPD233	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3799	Suspended
0.64	Remote Similarity	NPD8	Approved
0.64	Remote Similarity	NPD1255	Approved
0.64	Remote Similarity	NPD3980	Approved
0.64	Remote Similarity	NPD2878	Approved
0.64	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1253	Approved
0.64	Remote Similarity	NPD1256	Approved
0.64	Remote Similarity	NPD243	Approved
0.64	Remote Similarity	NPD1254	Approved
0.64	Remote Similarity	NPD3982	Approved
0.6389	Remote Similarity	NPD3438	Approved
0.6387	Remote Similarity	NPD3630	Approved
0.6387	Remote Similarity	NPD3629	Approved
0.6386	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6828	Phase 2
0.6382	Remote Similarity	NPD1953	Discontinued
0.6378	Remote Similarity	NPD5597	Approved
0.6378	Remote Similarity	NPD5598	Approved
0.6376	Remote Similarity	NPD3942	Approved
0.6376	Remote Similarity	NPD3944	Approved
0.6375	Remote Similarity	NPD2927	Phase 3
0.6375	Remote Similarity	NPD7091	Discontinued
0.637	Remote Similarity	NPD5131	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