NPASS Compound

Structure

CID222358 OpenBabel06191716012D 26 27 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 4.4209 1.7065 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 4.7299 0.7555 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 5.7081 0.5475 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 4.0608 0.0123 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 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 15 22 2 0 0 0 0 15 25 1 0 0 0 0 16 7 1 1 0 0 0 16 21 1 0 0 0 0 17 25 1 1 0 0 0 18 9 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	385.428
LogP:	3.048
LogD:	2.49
LogS:	-3.195
# Rotatable Bonds:	2
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	5.436
Fsp3:	0.667
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:	-4.571
MDCK Permeability:	7.213756180135533e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.145

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	81.09583282470703%
Volume Distribution (VD):	1.18
Pgp-substrate:	23.84720802307129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.506
CYP3A4-inhibitor:	0.633
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	4.609
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.767
Drug-inuced Liver Injury (DILI):	0.47
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.149
Carcinogencity:	0.889
Eye Corrosion:	0.397
Eye Irritation:	0.276
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC222358

Natural Product ID:	NPC222358
*Common Name:**	Cespitulactone A Monoacetate
IUPAC Name:	[(1R,6S,7E,12S)-8,14,14-trimethyl-4-methylidene-10,13-dioxo-11-oxabicyclo[10.2.2]hexadec-7-en-6-yl] acetate
Synonyms:	Cespitulactone A Monoacetate
Standard InCHIKey:	BNJSOSQFSVHRRK-PCXFWWQXSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-13-6-7-16-8-9-18(20(24)21(16,4)5)26-19(23)12-14(2)11-17(10-13)25-15(3)22/h11,16-18H,1,6-10,12H2,2-5H3/b14-11+/t16-,17+,18+/m1/s1
SMILES:	C=C1CC[C@@H]2CC[C@@H](C(=O)C2(C)C)OC(=O)C/C(=C/[C@H](C1)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL207878
PubChem CID:	44410615
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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	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	IC50	>	20.0	ug.mL-1	PMID[533101]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[533101]

☑ 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 NPC222358 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	202
0.1-0.2	1244
0.2-0.3	4491
0.3-0.4	12176
0.4-0.5	11414
0.5-0.6	7280
0.6-0.7	4958
0.7-0.8	895
0.8-0.85	33
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC202394
0.8675	High Similarity	NPC474359
0.8523	High Similarity	NPC476597
0.8523	High Similarity	NPC476598
0.8427	Intermediate Similarity	NPC476596
0.8333	Intermediate Similarity	NPC470978
0.8333	Intermediate Similarity	NPC474703
0.8333	Intermediate Similarity	NPC193198
0.8333	Intermediate Similarity	NPC470974
0.8295	Intermediate Similarity	NPC471818
0.828	Intermediate Similarity	NPC472643
0.8276	Intermediate Similarity	NPC477128
0.8261	Intermediate Similarity	NPC264378
0.8256	Intermediate Similarity	NPC220478
0.8222	Intermediate Similarity	NPC148463
0.8222	Intermediate Similarity	NPC38830
0.8222	Intermediate Similarity	NPC470697
0.8202	Intermediate Similarity	NPC473944
0.8182	Intermediate Similarity	NPC280833
0.814	Intermediate Similarity	NPC189311
0.8095	Intermediate Similarity	NPC229584
0.8095	Intermediate Similarity	NPC14203
0.8023	Intermediate Similarity	NPC30486
0.8023	Intermediate Similarity	NPC149869
0.8	Intermediate Similarity	NPC200513
0.8	Intermediate Similarity	NPC178676
0.8	Intermediate Similarity	NPC219874
0.8	Intermediate Similarity	NPC49420
0.7979	Intermediate Similarity	NPC472644
0.7978	Intermediate Similarity	NPC288699
0.7978	Intermediate Similarity	NPC284561
0.7978	Intermediate Similarity	NPC73995
0.7976	Intermediate Similarity	NPC469802
0.7976	Intermediate Similarity	NPC195424
0.7976	Intermediate Similarity	NPC304795
0.7957	Intermediate Similarity	NPC254496
0.7957	Intermediate Similarity	NPC474343
0.7957	Intermediate Similarity	NPC285513
0.7957	Intermediate Similarity	NPC110937
0.7957	Intermediate Similarity	NPC69385
0.7952	Intermediate Similarity	NPC35574
0.7952	Intermediate Similarity	NPC471220
0.7952	Intermediate Similarity	NPC184737
0.7935	Intermediate Similarity	NPC295347
0.7931	Intermediate Similarity	NPC476678
0.7931	Intermediate Similarity	NPC110405
0.7912	Intermediate Similarity	NPC139692
0.7889	Intermediate Similarity	NPC8062
0.7889	Intermediate Similarity	NPC232202
0.7889	Intermediate Similarity	NPC469595
0.7889	Intermediate Similarity	NPC220454
0.7889	Intermediate Similarity	NPC152467
0.7889	Intermediate Similarity	NPC212679
0.7882	Intermediate Similarity	NPC25554
0.7872	Intermediate Similarity	NPC222011
0.7865	Intermediate Similarity	NPC226863
0.7865	Intermediate Similarity	NPC215831
0.7857	Intermediate Similarity	NPC471299
0.7849	Intermediate Similarity	NPC202833
0.7841	Intermediate Similarity	NPC473226
0.7841	Intermediate Similarity	NPC329692
0.7831	Intermediate Similarity	NPC189206
0.7826	Intermediate Similarity	NPC84893
0.7826	Intermediate Similarity	NPC477130
0.7826	Intermediate Similarity	NPC477129
0.7816	Intermediate Similarity	NPC470011
0.7816	Intermediate Similarity	NPC139566
0.7816	Intermediate Similarity	NPC475100
0.7816	Intermediate Similarity	NPC219011
0.7791	Intermediate Similarity	NPC471218
0.7791	Intermediate Similarity	NPC475936
0.7778	Intermediate Similarity	NPC135703
0.7778	Intermediate Similarity	NPC5509
0.7778	Intermediate Similarity	NPC322903
0.7766	Intermediate Similarity	NPC38530
0.7766	Intermediate Similarity	NPC208094
0.7766	Intermediate Similarity	NPC84335
0.7755	Intermediate Similarity	NPC472645
0.7753	Intermediate Similarity	NPC312561
0.7753	Intermediate Similarity	NPC181327
0.7742	Intermediate Similarity	NPC134067
0.7742	Intermediate Similarity	NPC183012
0.7738	Intermediate Similarity	NPC128276
0.7738	Intermediate Similarity	NPC474341
0.7727	Intermediate Similarity	NPC65661
0.7727	Intermediate Similarity	NPC96621
0.7727	Intermediate Similarity	NPC177932
0.7717	Intermediate Similarity	NPC475657
0.7717	Intermediate Similarity	NPC271652
0.7717	Intermediate Similarity	NPC169343
0.7711	Intermediate Similarity	NPC471726
0.7711	Intermediate Similarity	NPC474527
0.7708	Intermediate Similarity	NPC473384
0.7708	Intermediate Similarity	NPC476478
0.7701	Intermediate Similarity	NPC12283
0.7701	Intermediate Similarity	NPC22611
0.7701	Intermediate Similarity	NPC474193
0.7701	Intermediate Similarity	NPC194637
0.7701	Intermediate Similarity	NPC53867
0.7692	Intermediate Similarity	NPC161638
0.7692	Intermediate Similarity	NPC232426
0.7692	Intermediate Similarity	NPC198818
0.7692	Intermediate Similarity	NPC51486
0.7692	Intermediate Similarity	NPC281942
0.7684	Intermediate Similarity	NPC316598
0.7684	Intermediate Similarity	NPC252295
0.7677	Intermediate Similarity	NPC475510
0.7677	Intermediate Similarity	NPC475587
0.7674	Intermediate Similarity	NPC40228
0.7674	Intermediate Similarity	NPC473420
0.7674	Intermediate Similarity	NPC301477
0.7674	Intermediate Similarity	NPC475665
0.7674	Intermediate Similarity	NPC25684
0.7674	Intermediate Similarity	NPC281949
0.7674	Intermediate Similarity	NPC471325
0.7674	Intermediate Similarity	NPC38642
0.7667	Intermediate Similarity	NPC24816
0.7667	Intermediate Similarity	NPC69713
0.766	Intermediate Similarity	NPC234993
0.766	Intermediate Similarity	NPC184065
0.766	Intermediate Similarity	NPC242848
0.766	Intermediate Similarity	NPC134072
0.766	Intermediate Similarity	NPC307164
0.7654	Intermediate Similarity	NPC40327
0.7647	Intermediate Similarity	NPC469620
0.7647	Intermediate Similarity	NPC469690
0.7647	Intermediate Similarity	NPC158565
0.7647	Intermediate Similarity	NPC178277
0.764	Intermediate Similarity	NPC250981
0.764	Intermediate Similarity	NPC474045
0.764	Intermediate Similarity	NPC261253
0.764	Intermediate Similarity	NPC279859
0.764	Intermediate Similarity	NPC38576
0.764	Intermediate Similarity	NPC261721
0.764	Intermediate Similarity	NPC472863
0.7634	Intermediate Similarity	NPC250075
0.7634	Intermediate Similarity	NPC91010
0.7634	Intermediate Similarity	NPC53685
0.7629	Intermediate Similarity	NPC114540
0.7629	Intermediate Similarity	NPC32577
0.7629	Intermediate Similarity	NPC155332
0.7619	Intermediate Similarity	NPC470240
0.7619	Intermediate Similarity	NPC41780
0.7619	Intermediate Similarity	NPC476794
0.7619	Intermediate Similarity	NPC65603
0.7619	Intermediate Similarity	NPC57744
0.7619	Intermediate Similarity	NPC187568
0.7614	Intermediate Similarity	NPC295799
0.7614	Intermediate Similarity	NPC60951
0.7614	Intermediate Similarity	NPC159635
0.7614	Intermediate Similarity	NPC96055
0.7609	Intermediate Similarity	NPC186363
0.7609	Intermediate Similarity	NPC233437
0.7609	Intermediate Similarity	NPC141831
0.7609	Intermediate Similarity	NPC472953
0.7609	Intermediate Similarity	NPC207641
0.7609	Intermediate Similarity	NPC475972
0.7609	Intermediate Similarity	NPC303697
0.7609	Intermediate Similarity	NPC233345
0.7609	Intermediate Similarity	NPC72845
0.7604	Intermediate Similarity	NPC472972
0.7604	Intermediate Similarity	NPC117685
0.7604	Intermediate Similarity	NPC469551
0.7604	Intermediate Similarity	NPC474012
0.7604	Intermediate Similarity	NPC476299
0.76	Intermediate Similarity	NPC473939
0.76	Intermediate Similarity	NPC473595
0.759	Intermediate Similarity	NPC244166
0.759	Intermediate Similarity	NPC228978
0.7586	Intermediate Similarity	NPC123880
0.7586	Intermediate Similarity	NPC471159
0.7586	Intermediate Similarity	NPC35556
0.7586	Intermediate Similarity	NPC226988
0.7582	Intermediate Similarity	NPC50070
0.7582	Intermediate Similarity	NPC36668
0.7582	Intermediate Similarity	NPC118011
0.7582	Intermediate Similarity	NPC50488
0.7582	Intermediate Similarity	NPC474396
0.7579	Intermediate Similarity	NPC253826
0.7579	Intermediate Similarity	NPC2049
0.7576	Intermediate Similarity	NPC173172
0.7576	Intermediate Similarity	NPC475414
0.7561	Intermediate Similarity	NPC470237
0.7558	Intermediate Similarity	NPC268827
0.7558	Intermediate Similarity	NPC233332
0.7556	Intermediate Similarity	NPC478144
0.7556	Intermediate Similarity	NPC175293
0.7556	Intermediate Similarity	NPC102640
0.7556	Intermediate Similarity	NPC162107
0.7556	Intermediate Similarity	NPC46912
0.7553	Intermediate Similarity	NPC209355
0.7553	Intermediate Similarity	NPC33473
0.7551	Intermediate Similarity	NPC19239
0.7551	Intermediate Similarity	NPC474166
0.7551	Intermediate Similarity	NPC471364
0.7551	Intermediate Similarity	NPC132395
0.7551	Intermediate Similarity	NPC471365
0.7551	Intermediate Similarity	NPC194323
0.7549	Intermediate Similarity	NPC317107
0.7531	Intermediate Similarity	NPC469660

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 NPC222358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1625
0.2-0.3	3734
0.3-0.4	2317
0.4-0.5	804
0.5-0.6	318
0.6-0.7	159
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1694	Approved
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.7609	Intermediate Similarity	NPD5693	Phase 1
0.759	Intermediate Similarity	NPD8039	Approved
0.734	Intermediate Similarity	NPD6399	Phase 3
0.7263	Intermediate Similarity	NPD7900	Approved
0.7263	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7748	Approved
0.7253	Intermediate Similarity	NPD6409	Approved
0.7253	Intermediate Similarity	NPD5330	Approved
0.7253	Intermediate Similarity	NPD6684	Approved
0.7253	Intermediate Similarity	NPD7146	Approved
0.7253	Intermediate Similarity	NPD6098	Approved
0.7253	Intermediate Similarity	NPD7334	Approved
0.7253	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD6673	Approved
0.7204	Intermediate Similarity	NPD6904	Approved
0.7204	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7128	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6903	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7128	Approved
0.7059	Intermediate Similarity	NPD5739	Approved
0.7059	Intermediate Similarity	NPD6675	Approved
0.7059	Intermediate Similarity	NPD6402	Approved
0.7053	Intermediate Similarity	NPD6050	Approved
0.7053	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD6411	Approved
0.7053	Intermediate Similarity	NPD5694	Approved
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7041	Intermediate Similarity	NPD7902	Approved
0.7033	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD3667	Approved
0.7	Intermediate Similarity	NPD5209	Approved
0.699	Remote Similarity	NPD5701	Approved
0.699	Remote Similarity	NPD5697	Approved
0.6989	Remote Similarity	NPD3573	Approved
0.6979	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD5778	Approved
0.697	Remote Similarity	NPD5696	Approved
0.6966	Remote Similarity	NPD4695	Discontinued
0.6947	Remote Similarity	NPD5785	Approved
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6899	Approved
0.6857	Remote Similarity	NPD6373	Approved
0.6857	Remote Similarity	NPD6372	Approved
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6848	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7102	Approved
0.6792	Remote Similarity	NPD6883	Approved
0.6792	Remote Similarity	NPD7290	Approved
0.6771	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD46	Approved
0.6739	Remote Similarity	NPD5362	Discontinued
0.6739	Remote Similarity	NPD7154	Phase 3
0.6731	Remote Similarity	NPD6008	Approved
0.6729	Remote Similarity	NPD8130	Phase 1
0.6729	Remote Similarity	NPD6869	Approved
0.6729	Remote Similarity	NPD6649	Approved
0.6729	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD6617	Approved
0.6729	Remote Similarity	NPD6650	Approved
0.6729	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7115	Discovery
0.6707	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4269	Approved
0.663	Remote Similarity	NPD4270	Approved
0.6629	Remote Similarity	NPD4756	Discovery
0.6604	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4697	Phase 3
0.6593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD4755	Approved
0.6535	Remote Similarity	NPD5959	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD8035	Phase 2
0.6531	Remote Similarity	NPD8034	Phase 2
0.6526	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD5369	Approved
0.6509	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD1695	Approved
0.6495	Remote Similarity	NPD4753	Phase 2
0.6495	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6489	Remote Similarity	NPD3666	Approved
0.6486	Remote Similarity	NPD6274	Approved
0.6486	Remote Similarity	NPD6868	Approved
0.6452	Remote Similarity	NPD6435	Approved
0.6449	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5211	Phase 2
0.6442	Remote Similarity	NPD7632	Discontinued
0.6429	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD6317	Approved
0.6421	Remote Similarity	NPD5363	Approved
0.6421	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4252	Approved
0.6408	Remote Similarity	NPD5286	Approved
0.6408	Remote Similarity	NPD4700	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD6001	Approved
0.6389	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6335	Approved
0.6372	Remote Similarity	NPD6313	Approved
0.6372	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD6079	Approved
0.6355	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6422	Discontinued
0.6346	Remote Similarity	NPD5344	Discontinued
0.6346	Remote Similarity	NPD5223	Approved
0.633	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6371	Approved
0.6321	Remote Similarity	NPD5141	Approved
0.6316	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4197	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD7100	Approved
0.6306	Remote Similarity	NPD4632	Approved
0.63	Remote Similarity	NPD4202	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	NPD6009	Approved
0.6275	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD5329	Approved
0.6237	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD5368	Approved
0.6237	Remote Similarity	NPD4822	Approved
0.6237	Remote Similarity	NPD4821	Approved
0.6237	Remote Similarity	NPD4820	Approved
0.6235	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5174	Approved
0.6226	Remote Similarity	NPD4754	Approved
0.6226	Remote Similarity	NPD5175	Approved
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.6207	Remote Similarity	NPD5983	Phase 2
0.6207	Remote Similarity	NPD6908	Approved
0.6207	Remote Similarity	NPD6909	Approved
0.6204	Remote Similarity	NPD6614	Approved
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD5284	Approved
0.62	Remote Similarity	NPD7983	Approved
0.6196	Remote Similarity	NPD4268	Approved
0.6196	Remote Similarity	NPD4271	Approved
0.6196	Remote Similarity	NPD3617	Approved
0.6186	Remote Similarity	NPD4519	Discontinued
0.6186	Remote Similarity	NPD4623	Approved
0.6186	Remote Similarity	NPD5690	Phase 2
0.6186	Remote Similarity	NPD4694	Approved
0.6186	Remote Similarity	NPD5280	Approved
0.6182	Remote Similarity	NPD2067	Discontinued
0.6176	Remote Similarity	NPD4629	Approved
0.6176	Remote Similarity	NPD5210	Approved
0.617	Remote Similarity	NPD4790	Discontinued
0.6126	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7839	Suspended
0.6117	Remote Similarity	NPD7732	Phase 3
0.6111	Remote Similarity	NPD4768	Approved
0.6111	Remote Similarity	NPD4767	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.6105	Remote Similarity	NPD4221	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