NPASS Compound

Structure

CID193198 OpenBabel06191715582D 23 25 0 0 1 0 0 0 0 0999 V2000 4.8968 -1.7938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2642 1.6651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5307 -2.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8530 -2.5462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0047 -0.6998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0810 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5576 0.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 -1.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3106 0.6662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6925 0.0209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4882 0.6265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 14 6 1 6 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 11 1 6 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	341.995
LogP:	4.28
LogD:	3.539
LogS:	-4.183
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.76
Synthetic Accessibility Score:	5.187
Fsp3:	0.55
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:	-4.923
MDCK Permeability:	2.6446228730492294e-05
Pgp-inhibitor:	0.398
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	97.2842025756836%
Volume Distribution (VD):	2.539
Pgp-substrate:	2.656177282333374%

ADMET: Metabolism

CYP1A2-inhibitor:	0.365
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.596
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.825
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	1.058
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.93
Carcinogencity:	0.78
Eye Corrosion:	0.004
Eye Irritation:	0.034
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC193198

Natural Product ID:	NPC193198
*Common Name:**	Cespihypotin R
IUPAC Name:	n.a.
Synonyms:	Cespihypotin R
Standard InCHIKey:	YKYLWLYNDKXVIF-MKLFLIHKSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-12-5-6-14-7-8-16-18(20(14,3)4)17(23-19(16)22)11-13(2)10-15(21)9-12/h10,14,17H,1,5-9,11H2,2-4H3/b13-10+/t14-,17-/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)[C@@H](C/C(=C/C(=O)C1)/C)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509380
PubChem CID:	25178793
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21513294]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25205	Thymus borgiae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24805	Thorecta reticulata	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25343	Tanacetum microphyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23999	Rhipidothuria racowitzai	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23333	Michelia excelsa	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28702	Cyclolepis genistoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11177	0ctiluca scintillans	Species	0ctilucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24616	Ottonia vahlii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5543	Persicaria tomentosa	Species	Polygonaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	55.0	uM	PMID[534778]
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	=	50.0	uM	PMID[534778]

☑ 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 NPC193198 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	200
0.1-0.2	1235
0.2-0.3	5174
0.3-0.4	13714
0.4-0.5	10311
0.5-0.6	6361
0.6-0.7	4565
0.7-0.8	1039
0.8-0.85	70
0.85-0.9	22
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9268	High Similarity	NPC312561
0.9259	High Similarity	NPC189311
0.9103	High Similarity	NPC471220
0.8941	High Similarity	NPC281942
0.8941	High Similarity	NPC232426
0.8929	High Similarity	NPC226863
0.8916	High Similarity	NPC220478
0.8902	High Similarity	NPC30486
0.8837	High Similarity	NPC141831
0.8824	High Similarity	NPC5509
0.878	High Similarity	NPC22611
0.8765	High Similarity	NPC282293
0.875	High Similarity	NPC471299
0.8736	High Similarity	NPC476597
0.8736	High Similarity	NPC476598
0.8736	High Similarity	NPC475657
0.8734	High Similarity	NPC316500
0.8721	High Similarity	NPC469595
0.8721	High Similarity	NPC220454
0.8721	High Similarity	NPC8062
0.8721	High Similarity	NPC212679
0.8706	High Similarity	NPC215831
0.8675	High Similarity	NPC474359
0.8675	High Similarity	NPC475100
0.8675	High Similarity	NPC149869
0.8659	High Similarity	NPC200513
0.8659	High Similarity	NPC268122
0.8642	High Similarity	NPC195424
0.8636	High Similarity	NPC53685
0.8636	High Similarity	NPC476596
0.8608	High Similarity	NPC27205
0.8605	High Similarity	NPC73995
0.8605	High Similarity	NPC284561
0.8554	High Similarity	NPC12283
0.8554	High Similarity	NPC474193
0.8554	High Similarity	NPC118423
0.8539	High Similarity	NPC295347
0.8523	High Similarity	NPC115021
0.8519	High Similarity	NPC150646
0.8506	High Similarity	NPC152467
0.8506	High Similarity	NPC469372
0.85	High Similarity	NPC187568
0.85	High Similarity	NPC41780
0.8488	Intermediate Similarity	NPC477128
0.8488	Intermediate Similarity	NPC472302
0.8434	Intermediate Similarity	NPC178676
0.8434	Intermediate Similarity	NPC186276
0.8434	Intermediate Similarity	NPC471218
0.8427	Intermediate Similarity	NPC38830
0.8427	Intermediate Similarity	NPC477129
0.8427	Intermediate Similarity	NPC84893
0.8427	Intermediate Similarity	NPC470697
0.8427	Intermediate Similarity	NPC477130
0.8395	Intermediate Similarity	NPC128276
0.8395	Intermediate Similarity	NPC184737
0.8375	Intermediate Similarity	NPC473223
0.8353	Intermediate Similarity	NPC323765
0.8353	Intermediate Similarity	NPC177932
0.8353	Intermediate Similarity	NPC110405
0.8353	Intermediate Similarity	NPC86316
0.8353	Intermediate Similarity	NPC65661
0.8353	Intermediate Similarity	NPC106416
0.8352	Intermediate Similarity	NPC38530
0.8352	Intermediate Similarity	NPC84335
0.8352	Intermediate Similarity	NPC53844
0.8352	Intermediate Similarity	NPC208094
0.8333	Intermediate Similarity	NPC473369
0.8333	Intermediate Similarity	NPC222358
0.8313	Intermediate Similarity	NPC475665
0.8313	Intermediate Similarity	NPC471325
0.8295	Intermediate Similarity	NPC51486
0.8295	Intermediate Similarity	NPC471818
0.8293	Intermediate Similarity	NPC178277
0.8293	Intermediate Similarity	NPC469690
0.8272	Intermediate Similarity	NPC472300
0.8272	Intermediate Similarity	NPC57744
0.8256	Intermediate Similarity	NPC195640
0.8256	Intermediate Similarity	NPC168248
0.825	Intermediate Similarity	NPC65650
0.8242	Intermediate Similarity	NPC112654
0.8235	Intermediate Similarity	NPC71626
0.8235	Intermediate Similarity	NPC31086
0.8214	Intermediate Similarity	NPC35556
0.8214	Intermediate Similarity	NPC94200
0.8202	Intermediate Similarity	NPC49420
0.8202	Intermediate Similarity	NPC303697
0.8202	Intermediate Similarity	NPC65513
0.8202	Intermediate Similarity	NPC177037
0.8202	Intermediate Similarity	NPC190442
0.8202	Intermediate Similarity	NPC472814
0.8182	Intermediate Similarity	NPC168131
0.8182	Intermediate Similarity	NPC174342
0.8182	Intermediate Similarity	NPC177141
0.8172	Intermediate Similarity	NPC474012
0.8172	Intermediate Similarity	NPC476299
0.8172	Intermediate Similarity	NPC54705
0.8171	Intermediate Similarity	NPC299235
0.8171	Intermediate Similarity	NPC35574
0.8161	Intermediate Similarity	NPC476600
0.8152	Intermediate Similarity	NPC69385
0.8152	Intermediate Similarity	NPC110937
0.8148	Intermediate Similarity	NPC40353
0.814	Intermediate Similarity	NPC471795
0.814	Intermediate Similarity	NPC476678
0.8132	Intermediate Similarity	NPC183012
0.8132	Intermediate Similarity	NPC33473
0.8132	Intermediate Similarity	NPC209355
0.8118	Intermediate Similarity	NPC470047
0.8118	Intermediate Similarity	NPC470046
0.8118	Intermediate Similarity	NPC472377
0.8111	Intermediate Similarity	NPC229976
0.8111	Intermediate Similarity	NPC139692
0.8111	Intermediate Similarity	NPC471571
0.8101	Intermediate Similarity	NPC257618
0.8095	Intermediate Similarity	NPC325031
0.8095	Intermediate Similarity	NPC42470
0.8095	Intermediate Similarity	NPC38642
0.809	Intermediate Similarity	NPC273199
0.8085	Intermediate Similarity	NPC473384
0.8085	Intermediate Similarity	NPC310981
0.8085	Intermediate Similarity	NPC472643
0.8072	Intermediate Similarity	NPC469620
0.8068	Intermediate Similarity	NPC196407
0.8068	Intermediate Similarity	NPC24816
0.8065	Intermediate Similarity	NPC222303
0.8065	Intermediate Similarity	NPC222011
0.8065	Intermediate Similarity	NPC176845
0.8049	Intermediate Similarity	NPC189206
0.8049	Intermediate Similarity	NPC65603
0.8046	Intermediate Similarity	NPC471219
0.8046	Intermediate Similarity	NPC474045
0.8046	Intermediate Similarity	NPC261253
0.8046	Intermediate Similarity	NPC470051
0.8046	Intermediate Similarity	NPC470050
0.8023	Intermediate Similarity	NPC159635
0.8023	Intermediate Similarity	NPC96055
0.8023	Intermediate Similarity	NPC82297
0.8023	Intermediate Similarity	NPC219011
0.8022	Intermediate Similarity	NPC148463
0.8021	Intermediate Similarity	NPC189616
0.8	Intermediate Similarity	NPC473944
0.8	Intermediate Similarity	NPC186363
0.8	Intermediate Similarity	NPC16349
0.8	Intermediate Similarity	NPC472953
0.8	Intermediate Similarity	NPC222244
0.8	Intermediate Similarity	NPC233345
0.8	Intermediate Similarity	NPC173609
0.7979	Intermediate Similarity	NPC117685
0.7979	Intermediate Similarity	NPC472644
0.7978	Intermediate Similarity	NPC174765
0.7978	Intermediate Similarity	NPC251528
0.7978	Intermediate Similarity	NPC280833
0.7978	Intermediate Similarity	NPC288699
0.7978	Intermediate Similarity	NPC173042
0.7976	Intermediate Similarity	NPC47747
0.7976	Intermediate Similarity	NPC268827
0.7957	Intermediate Similarity	NPC474343
0.7957	Intermediate Similarity	NPC202705
0.7955	Intermediate Similarity	NPC181327
0.7955	Intermediate Similarity	NPC477228
0.7952	Intermediate Similarity	NPC475994
0.7931	Intermediate Similarity	NPC470048
0.7931	Intermediate Similarity	NPC472442
0.7931	Intermediate Similarity	NPC161957
0.7931	Intermediate Similarity	NPC179006
0.7931	Intermediate Similarity	NPC474013
0.7931	Intermediate Similarity	NPC474853
0.7931	Intermediate Similarity	NPC33570
0.7931	Intermediate Similarity	NPC78089
0.7931	Intermediate Similarity	NPC21471
0.7927	Intermediate Similarity	NPC41017
0.7927	Intermediate Similarity	NPC123360
0.7927	Intermediate Similarity	NPC235906
0.7917	Intermediate Similarity	NPC132395
0.7917	Intermediate Similarity	NPC471365
0.7917	Intermediate Similarity	NPC471364
0.7912	Intermediate Similarity	NPC169343
0.7912	Intermediate Similarity	NPC271652
0.7912	Intermediate Similarity	NPC472303
0.7912	Intermediate Similarity	NPC166346
0.7907	Intermediate Similarity	NPC472440
0.7907	Intermediate Similarity	NPC194637
0.7907	Intermediate Similarity	NPC477124
0.7907	Intermediate Similarity	NPC53867
0.7907	Intermediate Similarity	NPC311070
0.7901	Intermediate Similarity	NPC259599
0.7901	Intermediate Similarity	NPC117746
0.7901	Intermediate Similarity	NPC294434
0.7901	Intermediate Similarity	NPC20025
0.7901	Intermediate Similarity	NPC15499
0.7901	Intermediate Similarity	NPC476355
0.7889	Intermediate Similarity	NPC477149
0.7889	Intermediate Similarity	NPC198818
0.7889	Intermediate Similarity	NPC477147
0.7889	Intermediate Similarity	NPC280149
0.7889	Intermediate Similarity	NPC161638
0.7889	Intermediate Similarity	NPC159748
0.7889	Intermediate Similarity	NPC477782
0.7889	Intermediate Similarity	NPC101651
0.7889	Intermediate Similarity	NPC221111

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 NPC193198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1769
0.2-0.3	3786
0.3-0.4	2260
0.4-0.5	697
0.5-0.6	315
0.6-0.7	118
0.7-0.8	16
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD4752	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD1694	Approved
0.8256	Intermediate Similarity	NPD5330	Approved
0.8256	Intermediate Similarity	NPD6409	Approved
0.8256	Intermediate Similarity	NPD7334	Approved
0.8256	Intermediate Similarity	NPD7146	Approved
0.8256	Intermediate Similarity	NPD6684	Approved
0.8256	Intermediate Similarity	NPD7521	Approved
0.8068	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD6903	Approved
0.7865	Intermediate Similarity	NPD5737	Approved
0.7865	Intermediate Similarity	NPD6672	Approved
0.7805	Intermediate Similarity	NPD8039	Approved
0.7802	Intermediate Similarity	NPD5693	Phase 1
0.7527	Intermediate Similarity	NPD6399	Phase 3
0.7473	Intermediate Similarity	NPD5208	Approved
0.7447	Intermediate Similarity	NPD7900	Approved
0.7447	Intermediate Similarity	NPD7748	Approved
0.7447	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3665	Phase 1
0.7416	Intermediate Similarity	NPD3133	Approved
0.7416	Intermediate Similarity	NPD3666	Approved
0.7391	Intermediate Similarity	NPD6673	Approved
0.7391	Intermediate Similarity	NPD6904	Approved
0.7391	Intermediate Similarity	NPD6080	Approved
0.7386	Intermediate Similarity	NPD3667	Approved
0.7386	Intermediate Similarity	NPD5209	Approved
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7363	Intermediate Similarity	NPD3573	Approved
0.732	Intermediate Similarity	NPD7638	Approved
0.7312	Intermediate Similarity	NPD5207	Approved
0.7312	Intermediate Similarity	NPD5785	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7253	Intermediate Similarity	NPD6098	Approved
0.7253	Intermediate Similarity	NPD3618	Phase 1
0.7245	Intermediate Similarity	NPD7639	Approved
0.7245	Intermediate Similarity	NPD7640	Approved
0.7234	Intermediate Similarity	NPD7515	Phase 2
0.7234	Intermediate Similarity	NPD6050	Approved
0.7234	Intermediate Similarity	NPD5694	Approved
0.7222	Intermediate Similarity	NPD3668	Phase 3
0.7222	Intermediate Similarity	NPD4786	Approved
0.7216	Intermediate Similarity	NPD6083	Phase 2
0.7216	Intermediate Similarity	NPD6084	Phase 2
0.7216	Intermediate Similarity	NPD7902	Approved
0.7204	Intermediate Similarity	NPD6051	Approved
0.7188	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7125	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD6001	Approved
0.7065	Intermediate Similarity	NPD4623	Approved
0.7065	Intermediate Similarity	NPD5279	Phase 3
0.7065	Intermediate Similarity	NPD4519	Discontinued
0.7059	Intermediate Similarity	NPD6008	Approved
0.7037	Intermediate Similarity	NPD7115	Discovery
0.7033	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.699	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4137	Phase 3
0.6966	Remote Similarity	NPD4695	Discontinued
0.6947	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD6698	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4747	Approved
0.6905	Remote Similarity	NPD4691	Approved
0.6893	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7128	Approved
0.6893	Remote Similarity	NPD6675	Approved
0.6893	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD6079	Approved
0.6875	Remote Similarity	NPD5281	Approved
0.6875	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6857	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4197	Approved
0.6842	Remote Similarity	NPD4753	Phase 2
0.6842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1695	Approved
0.6837	Remote Similarity	NPD5654	Approved
0.6827	Remote Similarity	NPD5701	Approved
0.6827	Remote Similarity	NPD5697	Approved
0.6822	Remote Similarity	NPD6053	Discontinued
0.6804	Remote Similarity	NPD5778	Approved
0.6804	Remote Similarity	NPD5779	Approved
0.6804	Remote Similarity	NPD4202	Approved
0.6792	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5329	Approved
0.6774	Remote Similarity	NPD5363	Approved
0.6774	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7320	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD6899	Approved
0.6762	Remote Similarity	NPD6011	Approved
0.6742	Remote Similarity	NPD3617	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6739	Remote Similarity	NPD7154	Phase 3
0.6702	Remote Similarity	NPD4138	Approved
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD5959	Approved
0.6698	Remote Similarity	NPD6373	Approved
0.6698	Remote Similarity	NPD6013	Approved
0.6698	Remote Similarity	NPD6014	Approved
0.6698	Remote Similarity	NPD6372	Approved
0.6698	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4058	Approved
0.6636	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.663	Remote Similarity	NPD4269	Approved
0.663	Remote Similarity	NPD4270	Approved
0.6628	Remote Similarity	NPD5276	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7732	Phase 3
0.66	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD1696	Phase 3
0.6582	Remote Similarity	NPD287	Approved
0.6574	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD6847	Approved
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD6650	Approved
0.6566	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6526	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD5369	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD5210	Approved
0.65	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7094	Approved
0.6455	Remote Similarity	NPD6858	Approved
0.6452	Remote Similarity	NPD6435	Approved
0.6444	Remote Similarity	NPD4756	Discovery
0.6442	Remote Similarity	NPD5211	Phase 2
0.6437	Remote Similarity	NPD5777	Approved
0.6429	Remote Similarity	NPD7331	Phase 2
0.6421	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4252	Approved
0.6408	Remote Similarity	NPD6404	Discontinued
0.6408	Remote Similarity	NPD5286	Approved
0.6408	Remote Similarity	NPD4700	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6392	Remote Similarity	NPD4518	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6355	Remote Similarity	NPD6614	Approved
0.6355	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD6274	Approved
0.6339	Remote Similarity	NPD6868	Approved
0.6333	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5141	Approved
0.631	Remote Similarity	NPD7341	Phase 2
0.6306	Remote Similarity	NPD4632	Approved
0.6304	Remote Similarity	NPD4195	Approved
0.6286	Remote Similarity	NPD5225	Approved
0.6286	Remote Similarity	NPD5224	Approved
0.6286	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4633	Approved
0.6283	Remote Similarity	NPD6317	Approved
0.6281	Remote Similarity	NPD7260	Phase 2
0.6275	Remote Similarity	NPD7614	Phase 1
0.6275	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7507	Approved
0.6263	Remote Similarity	NPD7838	Discovery
0.6263	Remote Similarity	NPD4096	Approved
0.6237	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD5368	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