NPASS Compound

Structure

CID202394 OpenBabel06191715592D 23 24 0 0 1 0 0 0 0 0999 V2000 2.9392 -1.5314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6641 1.8787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9071 -0.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3506 -0.7798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8551 -0.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0827 0.7798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 1.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4392 -0.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8551 1.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0827 0.2202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9071 1.8383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0608 0.0123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0116 2.8328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3506 1.7798 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 19 1 0 0 0 0 4 19 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 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 11 17 1 0 0 0 0 14 6 1 1 0 0 0 14 19 1 0 0 0 0 15 20 1 1 0 0 0 16 8 1 1 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.2
Volume:	344.682
LogP:	2.596
LogD:	2.301
LogS:	-2.965
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.549
Synthetic Accessibility Score:	5.517
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.632
MDCK Permeability:	2.8664824640145525e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.559
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.671
Plasma Protein Binding (PPB):	81.68372344970703%
Volume Distribution (VD):	0.896
Pgp-substrate:	28.998037338256836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.686
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.741
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.61
CYP3A4-inhibitor:	0.466
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	7.335
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.07
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.386
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.173
Carcinogencity:	0.813
Eye Corrosion:	0.202
Eye Irritation:	0.455
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC202394

Natural Product ID:	NPC202394
*Common Name:**	Cespitulactone A
IUPAC Name:	(1R,6S,7E,12S)-6-hydroxy-8,14,14-trimethyl-4-methylidene-11-oxabicyclo[10.2.2]hexadec-7-ene-10,13-dione
Synonyms:
Standard InCHIKey:	OFYDSJDWPZLVHN-GVCJHLKLSA-N
Standard InCHI:	InChI=1S/C19H28O4/c1-12-5-6-14-7-8-16(18(22)19(14,3)4)23-17(21)11-13(2)10-15(20)9-12/h10,14-16,20H,1,5-9,11H2,2-4H3/b13-10+/t14-,15+,16+/m1/s1
SMILES:	C=C1CC[C@@H]2CC[C@@H](C(=O)C2(C)C)OC(=O)C/C(=C/[C@H](C1)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383035
PubChem CID:	16083143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16495058]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	Taiwanese soft coral	n.a.	PMID[18052327]
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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3.69	ug.mL-1	PMID[570122]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	9.98	ug.mL-1	PMID[570122]
NPT1184	Cell Line	Daoy	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[570122]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[570122]

☑ 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 NPC202394 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	176
0.1-0.2	1053
0.2-0.3	4073
0.3-0.4	9825
0.4-0.5	13180
0.5-0.6	6681
0.6-0.7	5931
0.7-0.8	1727
0.8-0.85	46
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC222358
0.8636	High Similarity	NPC232202
0.8605	High Similarity	NPC473226
0.8462	Intermediate Similarity	NPC134067
0.8404	Intermediate Similarity	NPC472643
0.837	Intermediate Similarity	NPC184065
0.8298	Intermediate Similarity	NPC472644
0.828	Intermediate Similarity	NPC474343
0.828	Intermediate Similarity	NPC254496
0.8276	Intermediate Similarity	NPC52628
0.8235	Intermediate Similarity	NPC473420
0.8202	Intermediate Similarity	NPC104560
0.8191	Intermediate Similarity	NPC478056
0.8182	Intermediate Similarity	NPC82979
0.8182	Intermediate Similarity	NPC322159
0.8182	Intermediate Similarity	NPC329692
0.8182	Intermediate Similarity	NPC198761
0.8172	Intermediate Similarity	NPC202833
0.8161	Intermediate Similarity	NPC295799
0.8132	Intermediate Similarity	NPC219874
0.8111	Intermediate Similarity	NPC118011
0.8111	Intermediate Similarity	NPC36668
0.8105	Intermediate Similarity	NPC472972
0.8105	Intermediate Similarity	NPC266955
0.8095	Intermediate Similarity	NPC239098
0.809	Intermediate Similarity	NPC312561
0.8085	Intermediate Similarity	NPC69385
0.8085	Intermediate Similarity	NPC285513
0.8085	Intermediate Similarity	NPC471916
0.8085	Intermediate Similarity	NPC208094
0.8081	Intermediate Similarity	NPC322903
0.8046	Intermediate Similarity	NPC105173
0.8046	Intermediate Similarity	NPC470948
0.8043	Intermediate Similarity	NPC109414
0.8043	Intermediate Similarity	NPC139692
0.8023	Intermediate Similarity	NPC14203
0.8023	Intermediate Similarity	NPC229584
0.8022	Intermediate Similarity	NPC46441
0.8022	Intermediate Similarity	NPC232426
0.8022	Intermediate Similarity	NPC281942
0.8021	Intermediate Similarity	NPC81530
0.8021	Intermediate Similarity	NPC115862
0.8021	Intermediate Similarity	NPC115899
0.8	Intermediate Similarity	NPC316598
0.8	Intermediate Similarity	NPC222011
0.8	Intermediate Similarity	NPC308038
0.7979	Intermediate Similarity	NPC134072
0.7979	Intermediate Similarity	NPC234993
0.7979	Intermediate Similarity	NPC242848
0.7978	Intermediate Similarity	NPC73038
0.7978	Intermediate Similarity	NPC325594
0.7978	Intermediate Similarity	NPC6979
0.7976	Intermediate Similarity	NPC74995
0.7957	Intermediate Similarity	NPC470957
0.7957	Intermediate Similarity	NPC470958
0.7957	Intermediate Similarity	NPC53685
0.7955	Intermediate Similarity	NPC474359
0.7955	Intermediate Similarity	NPC102048
0.7938	Intermediate Similarity	NPC136289
0.7935	Intermediate Similarity	NPC141831
0.7935	Intermediate Similarity	NPC474525
0.7935	Intermediate Similarity	NPC198054
0.7931	Intermediate Similarity	NPC48362
0.7931	Intermediate Similarity	NPC73882
0.7931	Intermediate Similarity	NPC93590
0.7917	Intermediate Similarity	NPC327431
0.7917	Intermediate Similarity	NPC306856
0.7917	Intermediate Similarity	NPC476274
0.7912	Intermediate Similarity	NPC474396
0.7912	Intermediate Similarity	NPC5509
0.7912	Intermediate Similarity	NPC281524
0.7912	Intermediate Similarity	NPC50488
0.7907	Intermediate Similarity	NPC306095
0.7907	Intermediate Similarity	NPC148685
0.7907	Intermediate Similarity	NPC104120
0.7907	Intermediate Similarity	NPC157895
0.7895	Intermediate Similarity	NPC170131
0.7895	Intermediate Similarity	NPC253826
0.7889	Intermediate Similarity	NPC477926
0.7882	Intermediate Similarity	NPC297996
0.7882	Intermediate Similarity	NPC475994
0.7882	Intermediate Similarity	NPC247783
0.7882	Intermediate Similarity	NPC269543
0.7879	Intermediate Similarity	NPC472645
0.7872	Intermediate Similarity	NPC295347
0.7872	Intermediate Similarity	NPC53565
0.7872	Intermediate Similarity	NPC477437
0.7872	Intermediate Similarity	NPC477438
0.7872	Intermediate Similarity	NPC183012
0.7865	Intermediate Similarity	NPC79573
0.7865	Intermediate Similarity	NPC476602
0.7857	Intermediate Similarity	NPC90177
0.7857	Intermediate Similarity	NPC95899
0.7857	Intermediate Similarity	NPC131366
0.7857	Intermediate Similarity	NPC61863
0.7849	Intermediate Similarity	NPC476597
0.7849	Intermediate Similarity	NPC477435
0.7849	Intermediate Similarity	NPC477436
0.7849	Intermediate Similarity	NPC476598
0.7843	Intermediate Similarity	NPC317107
0.7841	Intermediate Similarity	NPC312480
0.7835	Intermediate Similarity	NPC476223
0.7835	Intermediate Similarity	NPC97435
0.7835	Intermediate Similarity	NPC303559
0.7835	Intermediate Similarity	NPC207885
0.7835	Intermediate Similarity	NPC224720
0.7835	Intermediate Similarity	NPC476240
0.7826	Intermediate Similarity	NPC48732
0.7826	Intermediate Similarity	NPC474728
0.7826	Intermediate Similarity	NPC51486
0.7822	Intermediate Similarity	NPC141350
0.7816	Intermediate Similarity	NPC470241
0.7816	Intermediate Similarity	NPC327002
0.7816	Intermediate Similarity	NPC170303
0.7816	Intermediate Similarity	NPC159148
0.7802	Intermediate Similarity	NPC53454
0.7802	Intermediate Similarity	NPC473229
0.78	Intermediate Similarity	NPC475176
0.7791	Intermediate Similarity	NPC327674
0.7791	Intermediate Similarity	NPC246458
0.7791	Intermediate Similarity	NPC152061
0.7791	Intermediate Similarity	NPC281138
0.7789	Intermediate Similarity	NPC62516
0.7789	Intermediate Similarity	NPC250757
0.7789	Intermediate Similarity	NPC157113
0.7789	Intermediate Similarity	NPC301534
0.7778	Intermediate Similarity	NPC472986
0.7778	Intermediate Similarity	NPC116575
0.7778	Intermediate Similarity	NPC118911
0.7778	Intermediate Similarity	NPC261721
0.7778	Intermediate Similarity	NPC472985
0.7778	Intermediate Similarity	NPC472974
0.7778	Intermediate Similarity	NPC476104
0.7778	Intermediate Similarity	NPC250981
0.7767	Intermediate Similarity	NPC317687
0.7766	Intermediate Similarity	NPC477439
0.7766	Intermediate Similarity	NPC87095
0.7766	Intermediate Similarity	NPC476596
0.7766	Intermediate Similarity	NPC469406
0.7766	Intermediate Similarity	NPC250075
0.7766	Intermediate Similarity	NPC57117
0.7766	Intermediate Similarity	NPC91010
0.7765	Intermediate Similarity	NPC61952
0.7765	Intermediate Similarity	NPC474433
0.7765	Intermediate Similarity	NPC283619
0.7755	Intermediate Similarity	NPC119601
0.7755	Intermediate Similarity	NPC155332
0.7755	Intermediate Similarity	NPC32577
0.7755	Intermediate Similarity	NPC137430
0.7755	Intermediate Similarity	NPC470840
0.7755	Intermediate Similarity	NPC114540
0.7755	Intermediate Similarity	NPC308726
0.7753	Intermediate Similarity	NPC165064
0.7753	Intermediate Similarity	NPC31086
0.7753	Intermediate Similarity	NPC472326
0.7742	Intermediate Similarity	NPC470590
0.7742	Intermediate Similarity	NPC77099
0.7742	Intermediate Similarity	NPC472814
0.7742	Intermediate Similarity	NPC72845
0.7742	Intermediate Similarity	NPC285184
0.7742	Intermediate Similarity	NPC26888
0.7742	Intermediate Similarity	NPC60755
0.7742	Intermediate Similarity	NPC475972
0.7742	Intermediate Similarity	NPC177037
0.7742	Intermediate Similarity	NPC233345
0.7742	Intermediate Similarity	NPC297265
0.7742	Intermediate Similarity	NPC186363
0.7732	Intermediate Similarity	NPC117685
0.7732	Intermediate Similarity	NPC477521
0.7732	Intermediate Similarity	NPC474012
0.7732	Intermediate Similarity	NPC476299
0.7732	Intermediate Similarity	NPC474718
0.7727	Intermediate Similarity	NPC256112
0.7717	Intermediate Similarity	NPC470588
0.7717	Intermediate Similarity	NPC274330
0.7717	Intermediate Similarity	NPC143232
0.7717	Intermediate Similarity	NPC198664
0.7717	Intermediate Similarity	NPC473100
0.7717	Intermediate Similarity	NPC472983
0.7708	Intermediate Similarity	NPC320306
0.7708	Intermediate Similarity	NPC475894
0.7701	Intermediate Similarity	NPC304795
0.7701	Intermediate Similarity	NPC172013
0.7701	Intermediate Similarity	NPC281880
0.77	Intermediate Similarity	NPC475414
0.77	Intermediate Similarity	NPC173172
0.7692	Intermediate Similarity	NPC473097
0.7692	Intermediate Similarity	NPC471738
0.7692	Intermediate Similarity	NPC472926
0.7692	Intermediate Similarity	NPC181327
0.7692	Intermediate Similarity	NPC472929
0.7692	Intermediate Similarity	NPC128644
0.7684	Intermediate Similarity	NPC272617
0.7684	Intermediate Similarity	NPC470978
0.7684	Intermediate Similarity	NPC266899
0.7684	Intermediate Similarity	NPC209355
0.7684	Intermediate Similarity	NPC469599
0.7684	Intermediate Similarity	NPC470974
0.7677	Intermediate Similarity	NPC478057
0.7677	Intermediate Similarity	NPC476237

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 NPC202394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1501
0.2-0.3	3571
0.3-0.4	2439
0.4-0.5	924
0.5-0.6	309
0.6-0.7	205
0.7-0.8	42
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
0.7674	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5778	Approved
0.766	Intermediate Similarity	NPD6399	Phase 3
0.766	Intermediate Similarity	NPD5779	Approved
0.7579	Intermediate Similarity	NPD7748	Approved
0.7553	Intermediate Similarity	NPD6411	Approved
0.7553	Intermediate Similarity	NPD7515	Phase 2
0.7528	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD6083	Phase 2
0.7525	Intermediate Similarity	NPD6402	Approved
0.7525	Intermediate Similarity	NPD5739	Approved
0.7525	Intermediate Similarity	NPD7128	Approved
0.7525	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7451	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD5701	Approved
0.7449	Intermediate Similarity	NPD4225	Approved
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.7444	Intermediate Similarity	NPD5362	Discontinued
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD5737	Approved
0.7379	Intermediate Similarity	NPD6011	Approved
0.7379	Intermediate Similarity	NPD6881	Approved
0.7379	Intermediate Similarity	NPD6899	Approved
0.7379	Intermediate Similarity	NPD7320	Approved
0.7374	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD7640	Approved
0.7363	Intermediate Similarity	NPD4786	Approved
0.7347	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD6101	Approved
0.734	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4270	Approved
0.7333	Intermediate Similarity	NPD4269	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6012	Approved
0.7308	Intermediate Similarity	NPD6014	Approved
0.7308	Intermediate Similarity	NPD6373	Approved
0.7308	Intermediate Similarity	NPD6372	Approved
0.7308	Intermediate Similarity	NPD6013	Approved
0.7303	Intermediate Similarity	NPD4695	Discontinued
0.7273	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD5696	Approved
0.7263	Intermediate Similarity	NPD5785	Approved
0.7238	Intermediate Similarity	NPD7102	Approved
0.7238	Intermediate Similarity	NPD6883	Approved
0.7238	Intermediate Similarity	NPD7290	Approved
0.7204	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.7204	Intermediate Similarity	NPD5786	Approved
0.7188	Intermediate Similarity	NPD7637	Suspended
0.717	Intermediate Similarity	NPD6649	Approved
0.717	Intermediate Similarity	NPD6869	Approved
0.717	Intermediate Similarity	NPD6617	Approved
0.717	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8130	Phase 1
0.717	Intermediate Similarity	NPD6650	Approved
0.717	Intermediate Similarity	NPD6847	Approved
0.7159	Intermediate Similarity	NPD4756	Discovery
0.7111	Intermediate Similarity	NPD4252	Approved
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD8297	Approved
0.7103	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD1694	Approved
0.7097	Intermediate Similarity	NPD5363	Approved
0.7071	Intermediate Similarity	NPD5221	Approved
0.7071	Intermediate Similarity	NPD4697	Phase 3
0.7071	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7900	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD7521	Approved
0.7021	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD7146	Approved
0.7021	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD6684	Approved
0.7021	Intermediate Similarity	NPD6409	Approved
0.7021	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD3668	Phase 3
0.6989	Remote Similarity	NPD3666	Approved
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD6673	Approved
0.6979	Remote Similarity	NPD5328	Approved
0.6979	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6080	Approved
0.6979	Remote Similarity	NPD4753	Phase 2
0.697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6435	Approved
0.6932	Remote Similarity	NPD8039	Approved
0.6923	Remote Similarity	NPD4821	Approved
0.6923	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD4819	Approved
0.6923	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD1696	Phase 3
0.6915	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6868	Approved
0.6909	Remote Similarity	NPD6274	Approved
0.6907	Remote Similarity	NPD46	Approved
0.6907	Remote Similarity	NPD6698	Approved
0.6907	Remote Similarity	NPD5692	Phase 3
0.6889	Remote Similarity	NPD4268	Approved
0.6889	Remote Similarity	NPD4271	Approved
0.6882	Remote Similarity	NPD5332	Approved
0.6882	Remote Similarity	NPD5331	Approved
0.6875	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD5282	Discontinued
0.6863	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5286	Approved
0.6863	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD4696	Approved
0.6848	Remote Similarity	NPD4790	Discontinued
0.6847	Remote Similarity	NPD6317	Approved
0.6837	Remote Similarity	NPD7983	Approved
0.6837	Remote Similarity	NPD6050	Approved
0.6837	Remote Similarity	NPD8035	Phase 2
0.6837	Remote Similarity	NPD5694	Approved
0.6837	Remote Similarity	NPD8034	Phase 2
0.6837	Remote Similarity	NPD6079	Approved
0.6796	Remote Similarity	NPD5223	Approved
0.6786	Remote Similarity	NPD6314	Approved
0.6786	Remote Similarity	NPD6313	Approved
0.6786	Remote Similarity	NPD6335	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6768	Remote Similarity	NPD4202	Approved
0.6742	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD5368	Approved
0.6733	Remote Similarity	NPD7839	Suspended
0.6731	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD5224	Approved
0.6731	Remote Similarity	NPD5225	Approved
0.6731	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD6686	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD7100	Approved
0.6726	Remote Similarity	NPD7101	Approved
0.6702	Remote Similarity	NPD6695	Phase 3
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5344	Discontinued
0.6634	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD5210	Approved
0.6632	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4197	Approved
0.6609	Remote Similarity	NPD5983	Phase 2
0.6609	Remote Similarity	NPD6908	Approved
0.6609	Remote Similarity	NPD6909	Approved
0.6607	Remote Similarity	NPD2629	Approved
0.6606	Remote Similarity	NPD6371	Approved
0.6598	Remote Similarity	NPD4251	Approved
0.6598	Remote Similarity	NPD4250	Approved
0.6588	Remote Similarity	NPD3704	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5329	Approved
0.6548	Remote Similarity	NPD3197	Phase 1
0.6542	Remote Similarity	NPD4767	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4768	Approved
0.6526	Remote Similarity	NPD6110	Phase 1
0.6522	Remote Similarity	NPD3617	Approved
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.6496	Remote Similarity	NPD7604	Phase 2
0.6496	Remote Similarity	NPD8328	Phase 3
0.6495	Remote Similarity	NPD5280	Approved
0.6495	Remote Similarity	NPD6422	Discontinued
0.6495	Remote Similarity	NPD4694	Approved
0.6495	Remote Similarity	NPD5690	Phase 2
0.6484	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5654	Approved
0.6471	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5370	Suspended
0.6452	Remote Similarity	NPD7645	Phase 2
0.6452	Remote Similarity	NPD6929	Approved
0.6444	Remote Similarity	NPD6926	Approved
0.6444	Remote Similarity	NPD6924	Approved
0.6441	Remote Similarity	NPD7492	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