NPASS Compound

Structure

CID53685 OpenBabel06191715392D 26 28 0 0 1 0 0 0 0 0999 V2000 2.8774 -0.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6822 -3.1632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5058 -3.6634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 0.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6167 -0.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1110 0.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5170 -0.6990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -1.2827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9758 -1.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 -2.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9288 -0.5587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 -2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4258 -3.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5276 0.2503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7469 -1.6779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1551 -1.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1616 -2.0016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3508 -0.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -2.0096 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4629 -1.0481 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 3.2253 -3.8721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4196 -2.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4115 -0.7314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5464 -2.2787 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 14 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 14 23 2 0 0 0 0 14 26 1 0 0 0 0 15 7 1 6 0 0 0 15 22 1 0 0 0 0 16 26 1 6 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 13 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 24 1 1 0 0 0 21 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	385.377
LogP:	3.68
LogD:	0.951
LogS:	-2.459
# Rotatable Bonds:	2
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	6.012
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.539
MDCK Permeability:	1.8802649719873443e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.929
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.257
Plasma Protein Binding (PPB):	69.14735412597656%
Volume Distribution (VD):	1.482
Pgp-substrate:	31.682945251464844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.592
CYP2C9-inhibitor:	0.048
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	8.677
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.691
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.066
Carcinogencity:	0.371
Eye Corrosion:	0.753
Eye Irritation:	0.079
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC53685

Natural Product ID:	NPC53685
*Common Name:**	Cespitularin J
IUPAC Name:	n.a.
Synonyms:	6-O-Acetylcespitularin F; Cespitularin J
Standard InCHIKey:	DRTGEVIELDJQLH-ASBCJFQQSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-12-6-7-15-8-9-17-19(22(15,4)5)21(25)18(20(17)24)13(2)11-16(10-12)26-14(3)23/h11,15-16,18,20,24H,1,6-10H2,2-5H3/b13-11+/t15-,16+,18+,20+/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C(=O)[C@@H](/C(=C/[C@H](C1)OC(=O)C)/C)[C@H]3O)C2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL382420
PubChem CID:	16083136
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols 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
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]
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[HerDing]
NPO25548	Balanophora indica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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[TCM_Taiwan]
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]
NPO20428	Debregeasia salicifolia	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25485	Agathosma lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25061	Lactarius glyciosmus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19210	Quercus lusitanica	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5278	Acacia cyperophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11177	0ctiluca scintillans	Species	0ctilucaceae	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]
NPO3706	Hedypnois rhagadioloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25205	Thymus borgiae	Species	Lamiaceae	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]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25684	Fagus dombeyi	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24435	Beschorneria bracteata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25631	Picris kamtschatica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25606	Aster patagonicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25314	Usnea ceratina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25655	Pseudocyphellaria granulata	Species	Lobariaceae	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]
NPO2404	Heterophragma quadriloculare	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6639	Flagelloscypha pilatii	Species	Tricholomataceae	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]

☑ 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[496042]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[496042]

☑ 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 NPC53685 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	192
0.1-0.2	1049
0.2-0.3	4332
0.3-0.4	9703
0.4-0.5	13518
0.5-0.6	6647
0.6-0.7	5254
0.7-0.8	1878
0.8-0.85	109
0.85-0.9	9
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC312561
0.908	High Similarity	NPC179006
0.908	High Similarity	NPC474853
0.9	High Similarity	NPC232426
0.9	High Similarity	NPC281942
0.8901	High Similarity	NPC141831
0.883	High Similarity	NPC53844
0.8804	High Similarity	NPC115021
0.8681	High Similarity	NPC5509
0.8636	High Similarity	NPC193198
0.8632	High Similarity	NPC69385
0.86	High Similarity	NPC220155
0.8587	High Similarity	NPC51486
0.8571	High Similarity	NPC474854
0.8542	High Similarity	NPC222011
0.8542	High Similarity	NPC316598
0.85	High Similarity	NPC91034
0.8495	Intermediate Similarity	NPC472814
0.8495	Intermediate Similarity	NPC177037
0.8454	Intermediate Similarity	NPC474012
0.8454	Intermediate Similarity	NPC476299
0.8438	Intermediate Similarity	NPC208094
0.8431	Intermediate Similarity	NPC29133
0.8421	Intermediate Similarity	NPC209355
0.8387	Intermediate Similarity	NPC477147
0.8387	Intermediate Similarity	NPC477149
0.8367	Intermediate Similarity	NPC244456
0.8367	Intermediate Similarity	NPC469657
0.8352	Intermediate Similarity	NPC194417
0.835	Intermediate Similarity	NPC470961
0.8333	Intermediate Similarity	NPC31086
0.8333	Intermediate Similarity	NPC242848
0.8333	Intermediate Similarity	NPC184065
0.828	Intermediate Similarity	NPC168131
0.828	Intermediate Similarity	NPC214387
0.8269	Intermediate Similarity	NPC191620
0.8265	Intermediate Similarity	NPC54705
0.8265	Intermediate Similarity	NPC117685
0.8247	Intermediate Similarity	NPC474343
0.8247	Intermediate Similarity	NPC475709
0.8242	Intermediate Similarity	NPC189311
0.8229	Intermediate Similarity	NPC295347
0.8229	Intermediate Similarity	NPC183012
0.8211	Intermediate Similarity	NPC271652
0.8211	Intermediate Similarity	NPC109414
0.8182	Intermediate Similarity	NPC99411
0.8173	Intermediate Similarity	NPC474315
0.8163	Intermediate Similarity	NPC471717
0.8163	Intermediate Similarity	NPC23364
0.8163	Intermediate Similarity	NPC235464
0.8163	Intermediate Similarity	NPC197386
0.8163	Intermediate Similarity	NPC141191
0.8163	Intermediate Similarity	NPC166745
0.8152	Intermediate Similarity	NPC261721
0.8152	Intermediate Similarity	NPC220478
0.8144	Intermediate Similarity	NPC328371
0.8144	Intermediate Similarity	NPC17578
0.8144	Intermediate Similarity	NPC470801
0.8144	Intermediate Similarity	NPC240673
0.8144	Intermediate Similarity	NPC476797
0.8125	Intermediate Similarity	NPC470697
0.8125	Intermediate Similarity	NPC474555
0.8125	Intermediate Similarity	NPC167219
0.8119	Intermediate Similarity	NPC472868
0.81	Intermediate Similarity	NPC476890
0.8085	Intermediate Similarity	NPC174342
0.8081	Intermediate Similarity	NPC472644
0.8081	Intermediate Similarity	NPC476274
0.8081	Intermediate Similarity	NPC306856
0.8068	Intermediate Similarity	NPC475994
0.8061	Intermediate Similarity	NPC202705
0.8061	Intermediate Similarity	NPC475894
0.8061	Intermediate Similarity	NPC476253
0.8061	Intermediate Similarity	NPC253826
0.8061	Intermediate Similarity	NPC477949
0.8061	Intermediate Similarity	NPC169205
0.8043	Intermediate Similarity	NPC86316
0.8043	Intermediate Similarity	NPC106416
0.8043	Intermediate Similarity	NPC65661
0.8043	Intermediate Similarity	NPC261380
0.8041	Intermediate Similarity	NPC476487
0.8041	Intermediate Similarity	NPC173875
0.8041	Intermediate Similarity	NPC318282
0.8041	Intermediate Similarity	NPC476488
0.8041	Intermediate Similarity	NPC469995
0.8041	Intermediate Similarity	NPC174948
0.8022	Intermediate Similarity	NPC472377
0.8021	Intermediate Similarity	NPC139692
0.8021	Intermediate Similarity	NPC472871
0.802	Intermediate Similarity	NPC95899
0.802	Intermediate Similarity	NPC476889
0.802	Intermediate Similarity	NPC236390
0.8019	Intermediate Similarity	NPC122056
0.8	Intermediate Similarity	NPC145666
0.8	Intermediate Similarity	NPC324683
0.8	Intermediate Similarity	NPC472643
0.8	Intermediate Similarity	NPC469595
0.8	Intermediate Similarity	NPC77337
0.8	Intermediate Similarity	NPC93744
0.8	Intermediate Similarity	NPC8062
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC476888
0.8	Intermediate Similarity	NPC476223
0.8	Intermediate Similarity	NPC472924
0.8	Intermediate Similarity	NPC476240
0.8	Intermediate Similarity	NPC212679
0.8	Intermediate Similarity	NPC220454
0.8	Intermediate Similarity	NPC477782
0.8	Intermediate Similarity	NPC475099
0.8	Intermediate Similarity	NPC282293
0.798	Intermediate Similarity	NPC98868
0.798	Intermediate Similarity	NPC478056
0.798	Intermediate Similarity	NPC222303
0.7979	Intermediate Similarity	NPC226863
0.7979	Intermediate Similarity	NPC472378
0.7979	Intermediate Similarity	NPC472870
0.7963	Intermediate Similarity	NPC312824
0.7963	Intermediate Similarity	NPC470493
0.7963	Intermediate Similarity	NPC183580
0.7961	Intermediate Similarity	NPC475294
0.7959	Intermediate Similarity	NPC134072
0.7959	Intermediate Similarity	NPC472941
0.7959	Intermediate Similarity	NPC456
0.7959	Intermediate Similarity	NPC185553
0.7959	Intermediate Similarity	NPC29152
0.7959	Intermediate Similarity	NPC202833
0.7959	Intermediate Similarity	NPC234993
0.7957	Intermediate Similarity	NPC322159
0.7957	Intermediate Similarity	NPC473226
0.7957	Intermediate Similarity	NPC202394
0.7957	Intermediate Similarity	NPC476043
0.7957	Intermediate Similarity	NPC198761
0.7944	Intermediate Similarity	NPC67259
0.7944	Intermediate Similarity	NPC147912
0.7941	Intermediate Similarity	NPC294259
0.7941	Intermediate Similarity	NPC309190
0.7941	Intermediate Similarity	NPC146731
0.7941	Intermediate Similarity	NPC296950
0.7938	Intermediate Similarity	NPC148463
0.7938	Intermediate Similarity	NPC474554
0.7938	Intermediate Similarity	NPC84893
0.7938	Intermediate Similarity	NPC184870
0.7935	Intermediate Similarity	NPC474359
0.7935	Intermediate Similarity	NPC475100
0.7935	Intermediate Similarity	NPC472865
0.7935	Intermediate Similarity	NPC165064
0.7925	Intermediate Similarity	NPC69291
0.7921	Intermediate Similarity	NPC195290
0.7921	Intermediate Similarity	NPC137430
0.7921	Intermediate Similarity	NPC469606
0.7921	Intermediate Similarity	NPC273005
0.7921	Intermediate Similarity	NPC31058
0.7921	Intermediate Similarity	NPC40918
0.7921	Intermediate Similarity	NPC32577
0.7921	Intermediate Similarity	NPC155332
0.7921	Intermediate Similarity	NPC114540
0.7921	Intermediate Similarity	NPC136289
0.7921	Intermediate Similarity	NPC204450
0.7921	Intermediate Similarity	NPC475320
0.7917	Intermediate Similarity	NPC303697
0.7917	Intermediate Similarity	NPC261607
0.7917	Intermediate Similarity	NPC186363
0.7917	Intermediate Similarity	NPC300312
0.7917	Intermediate Similarity	NPC111114
0.7917	Intermediate Similarity	NPC233345
0.7917	Intermediate Similarity	NPC477783
0.7905	Intermediate Similarity	NPC37116
0.7905	Intermediate Similarity	NPC206595
0.7905	Intermediate Similarity	NPC179642
0.79	Intermediate Similarity	NPC266955
0.79	Intermediate Similarity	NPC241221
0.79	Intermediate Similarity	NPC174314
0.79	Intermediate Similarity	NPC469864
0.79	Intermediate Similarity	NPC477521
0.79	Intermediate Similarity	NPC469872
0.7895	Intermediate Similarity	NPC206001
0.7895	Intermediate Similarity	NPC470734
0.7895	Intermediate Similarity	NPC472970
0.7895	Intermediate Similarity	NPC474396
0.7895	Intermediate Similarity	NPC36668
0.7895	Intermediate Similarity	NPC472971
0.7895	Intermediate Similarity	NPC118011
0.7895	Intermediate Similarity	NPC284561
0.7895	Intermediate Similarity	NPC50488
0.7895	Intermediate Similarity	NPC474570
0.7895	Intermediate Similarity	NPC218927
0.7889	Intermediate Similarity	NPC45495
0.7889	Intermediate Similarity	NPC271104
0.7885	Intermediate Similarity	NPC151393
0.7885	Intermediate Similarity	NPC322903
0.7879	Intermediate Similarity	NPC18319
0.7879	Intermediate Similarity	NPC156546
0.7879	Intermediate Similarity	NPC107243
0.7879	Intermediate Similarity	NPC254496
0.7879	Intermediate Similarity	NPC320306
0.7872	Intermediate Similarity	NPC171722
0.7872	Intermediate Similarity	NPC96496
0.787	Intermediate Similarity	NPC64318
0.7865	Intermediate Similarity	NPC471220

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 NPC53685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1596
0.2-0.3	3541
0.3-0.4	2481
0.4-0.5	852
0.5-0.6	329
0.6-0.7	156
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8191	Intermediate Similarity	NPD5785	Approved
0.7857	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4225	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7736	Intermediate Similarity	NPD6371	Approved
0.7717	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6083	Phase 2
0.77	Intermediate Similarity	NPD6084	Phase 2
0.7677	Intermediate Similarity	NPD5695	Phase 3
0.766	Intermediate Similarity	NPD5363	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7634	Intermediate Similarity	NPD5362	Discontinued
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD3665	Phase 1
0.7553	Intermediate Similarity	NPD3666	Approved
0.7553	Intermediate Similarity	NPD3133	Approved
0.7551	Intermediate Similarity	NPD5693	Phase 1
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7527	Intermediate Similarity	NPD5209	Approved
0.7527	Intermediate Similarity	NPD4270	Approved
0.7527	Intermediate Similarity	NPD4269	Approved
0.7475	Intermediate Similarity	NPD5779	Approved
0.7475	Intermediate Similarity	NPD5778	Approved
0.7474	Intermediate Similarity	NPD1694	Approved
0.7473	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7638	Approved
0.7451	Intermediate Similarity	NPD5696	Approved
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.74	Intermediate Similarity	NPD7748	Approved
0.7396	Intermediate Similarity	NPD5786	Approved
0.7374	Intermediate Similarity	NPD7515	Phase 2
0.7374	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD4786	Approved
0.7358	Intermediate Similarity	NPD6675	Approved
0.7358	Intermediate Similarity	NPD6402	Approved
0.7358	Intermediate Similarity	NPD7128	Approved
0.7358	Intermediate Similarity	NPD5739	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.734	Intermediate Similarity	NPD3667	Approved
0.7312	Intermediate Similarity	NPD4252	Approved
0.729	Intermediate Similarity	NPD5697	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD6053	Discontinued
0.7263	Intermediate Similarity	NPD7154	Phase 3
0.7234	Intermediate Similarity	NPD5369	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD7320	Approved
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.7216	Intermediate Similarity	NPD4623	Approved
0.7216	Intermediate Similarity	NPD4519	Discontinued
0.7216	Intermediate Similarity	NPD5279	Phase 3
0.72	Intermediate Similarity	NPD5281	Approved
0.72	Intermediate Similarity	NPD7637	Suspended
0.72	Intermediate Similarity	NPD5284	Approved
0.7188	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7902	Approved
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6101	Approved
0.7172	Intermediate Similarity	NPD6904	Approved
0.7172	Intermediate Similarity	NPD6673	Approved
0.7172	Intermediate Similarity	NPD5328	Approved
0.7172	Intermediate Similarity	NPD6080	Approved
0.7158	Intermediate Similarity	NPD4223	Phase 3
0.7158	Intermediate Similarity	NPD4221	Approved
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6373	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.7156	Intermediate Similarity	NPD6372	Approved
0.7129	Intermediate Similarity	NPD4202	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.71	Intermediate Similarity	NPD6698	Approved
0.71	Intermediate Similarity	NPD46	Approved
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7075	Intermediate Similarity	NPD5211	Phase 2
0.7071	Intermediate Similarity	NPD5208	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD5282	Discontinued
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5694	Approved
0.703	Intermediate Similarity	NPD6079	Approved
0.703	Intermediate Similarity	NPD6050	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6869	Approved
0.7019	Intermediate Similarity	NPD4755	Approved
0.701	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.6972	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6957	Remote Similarity	NPD8039	Approved
0.6947	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4695	Discontinued
0.6944	Remote Similarity	NPD5141	Approved
0.6939	Remote Similarity	NPD1696	Phase 3
0.6939	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5329	Approved
0.6931	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5222	Approved
0.6916	Remote Similarity	NPD7632	Discontinued
0.6907	Remote Similarity	NPD5331	Approved
0.6907	Remote Similarity	NPD5332	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4700	Approved
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6881	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD4790	Discontinued
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6869	Remote Similarity	NPD4690	Approved
0.6869	Remote Similarity	NPD4693	Phase 3
0.6869	Remote Similarity	NPD5690	Phase 2
0.6869	Remote Similarity	NPD5205	Approved
0.6869	Remote Similarity	NPD4138	Approved
0.6869	Remote Similarity	NPD6098	Approved
0.6869	Remote Similarity	NPD4689	Approved
0.6869	Remote Similarity	NPD4688	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6832	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5223	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD6435	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6771	Remote Similarity	NPD4819	Approved
0.6771	Remote Similarity	NPD4821	Approved
0.6771	Remote Similarity	NPD4820	Approved
0.6771	Remote Similarity	NPD4822	Approved
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6737	Remote Similarity	NPD4271	Approved
0.6737	Remote Similarity	NPD4268	Approved
0.6731	Remote Similarity	NPD6001	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6699	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7983	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5370	Suspended
0.6667	Remote Similarity	NPD5654	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3573	Approved
0.6632	Remote Similarity	NPD4756	Discovery
0.6612	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD7100	Approved
0.6604	Remote Similarity	NPD7839	Suspended
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5368	Approved
0.6581	Remote Similarity	NPD6009	Approved
0.6577	Remote Similarity	NPD4767	Approved
0.6577	Remote Similarity	NPD4768	Approved
0.6574	Remote Similarity	NPD6404	Discontinued
0.6569	Remote Similarity	NPD4518	Approved
0.6566	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD3617	Approved
0.6557	Remote Similarity	NPD7507	Approved
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6542	Remote Similarity	NPD5959	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