NPASS Compound

Structure

CID141831 OpenBabel06191715502D 25 27 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 1.1284 1.6223 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 1 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 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 0.9945 -0.1045 0.0000 C 0 0 1 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 1.5600 0.7203 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 13 2 0 0 0 0 2 14 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 24 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 15 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 15 7 1 6 0 0 0 15 20 1 0 0 0 0 16 22 1 1 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	370.718
LogP:	3.959
LogD:	3.701
LogS:	-4.257
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	5.859
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:	-4.733
MDCK Permeability:	2.0430763470358215e-05
Pgp-inhibitor:	0.931
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.73
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.74
Plasma Protein Binding (PPB):	83.18132019042969%
Volume Distribution (VD):	1.25
Pgp-substrate:	10.1603422164917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.503
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.201
CYP2D6-inhibitor:	0.127
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.514

ADMET: Excretion

Clearance (CL):	10.289
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.446
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.656
Carcinogencity:	0.626
Eye Corrosion:	0.004
Eye Irritation:	0.048
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC141831

Natural Product ID:	NPC141831
*Common Name:**	Cespitulactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PEIJBVSHZDEKRL-ZEJWHYPOSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-13-6-7-15-8-9-17-18(20(15,3)4)21(24-5,25-19(17)23)12-14(2)11-16(22)10-13/h11,15-16,22H,1,6-10,12H2,2-5H3/b14-11+/t15-,16+,21-/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)[C@](C/C(=C/[C@H](C1)O)/C)(OC)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL383410
PubChem CID:	16083142
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0001656] Acetals [CHEMONTID:0004472] Ketals

*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]
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]
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]
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]
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]
NPO25427	Solanum vespertilio	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24482	Phyllanthus oxyphyllus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25516	Dahlia sherffii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25452	Crucigenia apiculata	Species	Scenedesmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25548	Balanophora indica	Species	Balanophoraceae	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]

☑ 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[536691]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[536691]

☑ 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 NPC141831 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	1048
0.2-0.3	4376
0.3-0.4	10569
0.4-0.5	12801
0.5-0.6	6762
0.6-0.7	5460
0.7-0.8	1377
0.8-0.85	91
0.85-0.9	15
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC232426
0.9882	High Similarity	NPC281942
0.9529	High Similarity	NPC312561
0.8977	High Similarity	NPC472378
0.8901	High Similarity	NPC474554
0.8901	High Similarity	NPC53685
0.8876	High Similarity	NPC5509
0.8837	High Similarity	NPC193198
0.8791	High Similarity	NPC115021
0.8778	High Similarity	NPC477782
0.871	High Similarity	NPC17578
0.871	High Similarity	NPC240673
0.8681	High Similarity	NPC477783
0.8667	High Similarity	NPC470734
0.8632	High Similarity	NPC472644
0.8617	High Similarity	NPC53844
0.8617	High Similarity	NPC208094
0.8617	High Similarity	NPC475709
0.8587	High Similarity	NPC472303
0.8542	High Similarity	NPC472643
0.8539	High Similarity	NPC474062
0.8523	High Similarity	NPC31086
0.8511	High Similarity	NPC470801
0.8495	Intermediate Similarity	NPC298973
0.8495	Intermediate Similarity	NPC474555
0.8495	Intermediate Similarity	NPC104925
0.8478	Intermediate Similarity	NPC289479
0.8478	Intermediate Similarity	NPC177037
0.8478	Intermediate Similarity	NPC472814
0.8462	Intermediate Similarity	NPC168131
0.8462	Intermediate Similarity	NPC174342
0.8462	Intermediate Similarity	NPC251528
0.8438	Intermediate Similarity	NPC477720
0.8438	Intermediate Similarity	NPC476299
0.8438	Intermediate Similarity	NPC476767
0.8438	Intermediate Similarity	NPC474012
0.8427	Intermediate Similarity	NPC189311
0.8427	Intermediate Similarity	NPC42586
0.8427	Intermediate Similarity	NPC471300
0.8427	Intermediate Similarity	NPC65661
0.8427	Intermediate Similarity	NPC473251
0.8427	Intermediate Similarity	NPC86316
0.8427	Intermediate Similarity	NPC106416
0.8427	Intermediate Similarity	NPC474860
0.8409	Intermediate Similarity	NPC472377
0.8404	Intermediate Similarity	NPC295347
0.8404	Intermediate Similarity	NPC183012
0.8387	Intermediate Similarity	NPC166346
0.8387	Intermediate Similarity	NPC242069
0.8387	Intermediate Similarity	NPC139692
0.837	Intermediate Similarity	NPC51486
0.8352	Intermediate Similarity	NPC472809
0.8352	Intermediate Similarity	NPC226863
0.8352	Intermediate Similarity	NPC472810
0.8333	Intermediate Similarity	NPC222303
0.8333	Intermediate Similarity	NPC23364
0.8316	Intermediate Similarity	NPC134072
0.8316	Intermediate Similarity	NPC242848
0.8316	Intermediate Similarity	NPC112654
0.8316	Intermediate Similarity	NPC234993
0.8315	Intermediate Similarity	NPC71626
0.8298	Intermediate Similarity	NPC475572
0.8298	Intermediate Similarity	NPC469697
0.8295	Intermediate Similarity	NPC471298
0.828	Intermediate Similarity	NPC179517
0.828	Intermediate Similarity	NPC65513
0.828	Intermediate Similarity	NPC472811
0.828	Intermediate Similarity	NPC165904
0.8265	Intermediate Similarity	NPC134077
0.8242	Intermediate Similarity	NPC475678
0.8229	Intermediate Similarity	NPC69385
0.8229	Intermediate Similarity	NPC476253
0.8229	Intermediate Similarity	NPC474343
0.8222	Intermediate Similarity	NPC471795
0.8211	Intermediate Similarity	NPC473369
0.8211	Intermediate Similarity	NPC209355
0.8202	Intermediate Similarity	NPC471297
0.8202	Intermediate Similarity	NPC311070
0.8202	Intermediate Similarity	NPC474809
0.8191	Intermediate Similarity	NPC472812
0.8191	Intermediate Similarity	NPC475657
0.8191	Intermediate Similarity	NPC469939
0.8182	Intermediate Similarity	NPC475944
0.8182	Intermediate Similarity	NPC471208
0.8182	Intermediate Similarity	NPC325031
0.8172	Intermediate Similarity	NPC469595
0.8172	Intermediate Similarity	NPC78973
0.8172	Intermediate Similarity	NPC220454
0.8172	Intermediate Similarity	NPC212679
0.8172	Intermediate Similarity	NPC477149
0.8172	Intermediate Similarity	NPC477147
0.8163	Intermediate Similarity	NPC303559
0.8163	Intermediate Similarity	NPC469657
0.8163	Intermediate Similarity	NPC63249
0.8163	Intermediate Similarity	NPC244456
0.8163	Intermediate Similarity	NPC471075
0.8152	Intermediate Similarity	NPC474629
0.8144	Intermediate Similarity	NPC222011
0.8144	Intermediate Similarity	NPC316598
0.8132	Intermediate Similarity	NPC220478
0.8132	Intermediate Similarity	NPC473226
0.8125	Intermediate Similarity	NPC162346
0.8125	Intermediate Similarity	NPC165632
0.8111	Intermediate Similarity	NPC82297
0.8111	Intermediate Similarity	NPC471301
0.8111	Intermediate Similarity	NPC474865
0.8105	Intermediate Similarity	NPC470255
0.809	Intermediate Similarity	NPC471296
0.809	Intermediate Similarity	NPC200513
0.809	Intermediate Similarity	NPC323251
0.8085	Intermediate Similarity	NPC303697
0.8085	Intermediate Similarity	NPC329842
0.8085	Intermediate Similarity	NPC477122
0.8085	Intermediate Similarity	NPC186363
0.8085	Intermediate Similarity	NPC233345
0.8081	Intermediate Similarity	NPC273005
0.8081	Intermediate Similarity	NPC58329
0.8081	Intermediate Similarity	NPC476081
0.8081	Intermediate Similarity	NPC31058
0.8081	Intermediate Similarity	NPC469606
0.8081	Intermediate Similarity	NPC476769
0.8068	Intermediate Similarity	NPC271104
0.8065	Intermediate Similarity	NPC50488
0.8065	Intermediate Similarity	NPC474396
0.8065	Intermediate Similarity	NPC206001
0.8065	Intermediate Similarity	NPC218927
0.8065	Intermediate Similarity	NPC214387
0.8061	Intermediate Similarity	NPC54705
0.8061	Intermediate Similarity	NPC117685
0.8046	Intermediate Similarity	NPC471220
0.8046	Intermediate Similarity	NPC475994
0.8046	Intermediate Similarity	NPC209135
0.8046	Intermediate Similarity	NPC474816
0.8041	Intermediate Similarity	NPC151681
0.8041	Intermediate Similarity	NPC121402
0.8041	Intermediate Similarity	NPC224356
0.8041	Intermediate Similarity	NPC253826
0.8041	Intermediate Similarity	NPC132753
0.8041	Intermediate Similarity	NPC175351
0.8041	Intermediate Similarity	NPC202705
0.8022	Intermediate Similarity	NPC179006
0.8022	Intermediate Similarity	NPC52628
0.8022	Intermediate Similarity	NPC472442
0.8022	Intermediate Similarity	NPC474853
0.8022	Intermediate Similarity	NPC163606
0.8021	Intermediate Similarity	NPC472441
0.8021	Intermediate Similarity	NPC476487
0.8021	Intermediate Similarity	NPC476488
0.802	Intermediate Similarity	NPC472645
0.802	Intermediate Similarity	NPC153095
0.802	Intermediate Similarity	NPC127609
0.8	Intermediate Similarity	NPC12283
0.8	Intermediate Similarity	NPC472440
0.8	Intermediate Similarity	NPC471571
0.8	Intermediate Similarity	NPC476598
0.8	Intermediate Similarity	NPC474193
0.8	Intermediate Similarity	NPC120321
0.8	Intermediate Similarity	NPC22611
0.8	Intermediate Similarity	NPC42476
0.8	Intermediate Similarity	NPC476597
0.798	Intermediate Similarity	NPC473384
0.798	Intermediate Similarity	NPC471412
0.7979	Intermediate Similarity	NPC469368
0.7979	Intermediate Similarity	NPC182136
0.7979	Intermediate Similarity	NPC469372
0.7979	Intermediate Similarity	NPC221111
0.7979	Intermediate Similarity	NPC280149
0.7978	Intermediate Similarity	NPC229584
0.7978	Intermediate Similarity	NPC40228
0.7978	Intermediate Similarity	NPC14203
0.7961	Intermediate Similarity	NPC137911
0.7961	Intermediate Similarity	NPC228477
0.7959	Intermediate Similarity	NPC478056
0.7959	Intermediate Similarity	NPC98868
0.7959	Intermediate Similarity	NPC471610
0.7959	Intermediate Similarity	NPC241657
0.7959	Intermediate Similarity	NPC473154
0.7959	Intermediate Similarity	NPC474440
0.7957	Intermediate Similarity	NPC477128
0.7957	Intermediate Similarity	NPC196407
0.7957	Intermediate Similarity	NPC472302
0.7957	Intermediate Similarity	NPC136879
0.7957	Intermediate Similarity	NPC477302
0.7957	Intermediate Similarity	NPC24816
0.7955	Intermediate Similarity	NPC242767
0.7955	Intermediate Similarity	NPC471299
0.7941	Intermediate Similarity	NPC91034
0.7941	Intermediate Similarity	NPC67321
0.7941	Intermediate Similarity	NPC187435
0.7938	Intermediate Similarity	NPC154526
0.7938	Intermediate Similarity	NPC472363
0.7938	Intermediate Similarity	NPC202833
0.7938	Intermediate Similarity	NPC472362
0.7938	Intermediate Similarity	NPC328371
0.7935	Intermediate Similarity	NPC82979
0.7935	Intermediate Similarity	NPC322159
0.7935	Intermediate Similarity	NPC329692
0.7935	Intermediate Similarity	NPC202394
0.7935	Intermediate Similarity	NPC305475
0.7935	Intermediate Similarity	NPC131813

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 NPC141831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1591
0.2-0.3	3583
0.3-0.4	2504
0.4-0.5	812
0.5-0.6	334
0.6-0.7	142
0.7-0.8	17
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
0.809	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD6686	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7604	Intermediate Similarity	NPD5785	Approved
0.76	Intermediate Similarity	NPD4225	Approved
0.76	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD6399	Phase 3
0.7447	Intermediate Similarity	NPD1694	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD7515	Phase 2
0.734	Intermediate Similarity	NPD3665	Phase 1
0.734	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD3133	Approved
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD3667	Approved
0.73	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7253	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD46	Approved
0.7245	Intermediate Similarity	NPD6698	Approved
0.7234	Intermediate Similarity	NPD5362	Discontinued
0.7234	Intermediate Similarity	NPD7154	Phase 3
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD6672	Approved
0.7216	Intermediate Similarity	NPD5737	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3618	Phase 1
0.7172	Intermediate Similarity	NPD6411	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7158	Intermediate Similarity	NPD4786	Approved
0.7157	Intermediate Similarity	NPD7902	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8039	Approved
0.7103	Intermediate Similarity	NPD6412	Phase 2
0.7091	Intermediate Similarity	NPD6882	Approved
0.7091	Intermediate Similarity	NPD6053	Discontinued
0.7087	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD5363	Approved
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.701	Intermediate Similarity	NPD4519	Discontinued
0.701	Intermediate Similarity	NPD5279	Phase 3
0.701	Intermediate Similarity	NPD4623	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5328	Approved
0.697	Remote Similarity	NPD6101	Approved
0.697	Remote Similarity	NPD4753	Phase 2
0.6949	Remote Similarity	NPD7507	Approved
0.6947	Remote Similarity	NPD4269	Approved
0.6947	Remote Similarity	NPD4270	Approved
0.6944	Remote Similarity	NPD5701	Approved
0.6944	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4695	Discontinued
0.6909	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6371	Approved
0.6881	Remote Similarity	NPD6011	Approved
0.6881	Remote Similarity	NPD6899	Approved
0.6881	Remote Similarity	NPD7320	Approved
0.6881	Remote Similarity	NPD6881	Approved
0.6863	Remote Similarity	NPD7900	Approved
0.6863	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5786	Approved
0.6832	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD7637	Suspended
0.6832	Remote Similarity	NPD6079	Approved
0.6832	Remote Similarity	NPD5284	Approved
0.6818	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6013	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.6818	Remote Similarity	NPD6012	Approved
0.6818	Remote Similarity	NPD6373	Approved
0.6804	Remote Similarity	NPD3668	Phase 3
0.68	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD6904	Approved
0.68	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7319	Approved
0.6771	Remote Similarity	NPD5209	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD4202	Approved
0.6757	Remote Similarity	NPD6883	Approved
0.6757	Remote Similarity	NPD7290	Approved
0.6757	Remote Similarity	NPD7102	Approved
0.6737	Remote Similarity	NPD4819	Approved
0.6737	Remote Similarity	NPD4821	Approved
0.6737	Remote Similarity	NPD4252	Approved
0.6737	Remote Similarity	NPD4822	Approved
0.6737	Remote Similarity	NPD4820	Approved
0.6735	Remote Similarity	NPD1696	Phase 3
0.6735	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5692	Phase 3
0.6731	Remote Similarity	NPD4697	Phase 3
0.6731	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5221	Approved
0.6731	Remote Similarity	NPD7839	Suspended
0.6729	Remote Similarity	NPD5211	Phase 2
0.6702	Remote Similarity	NPD4271	Approved
0.6702	Remote Similarity	NPD4268	Approved
0.6701	Remote Similarity	NPD5331	Approved
0.6701	Remote Similarity	NPD5332	Approved
0.67	Remote Similarity	NPD5208	Approved
0.6696	Remote Similarity	NPD6847	Approved
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6617	Approved
0.6696	Remote Similarity	NPD6869	Approved
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8130	Phase 1
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.6637	Remote Similarity	NPD8297	Approved
0.6636	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6635	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4197	Approved
0.661	Remote Similarity	NPD8033	Approved
0.6606	Remote Similarity	NPD5141	Approved
0.66	Remote Similarity	NPD3573	Approved
0.6598	Remote Similarity	NPD6435	Approved
0.6596	Remote Similarity	NPD4756	Discovery
0.6581	Remote Similarity	NPD7516	Approved
0.6569	Remote Similarity	NPD5207	Approved
0.6569	Remote Similarity	NPD7838	Discovery
0.6566	Remote Similarity	NPD5329	Approved
0.6566	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4700	Approved
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD6404	Discontinued
0.6542	Remote Similarity	NPD5285	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD5282	Discontinued
0.6526	Remote Similarity	NPD3617	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.6505	Remote Similarity	NPD8034	Phase 2
0.6505	Remote Similarity	NPD8035	Phase 2
0.6505	Remote Similarity	NPD7983	Approved
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD5280	Approved
0.65	Remote Similarity	NPD4694	Approved
0.65	Remote Similarity	NPD4693	Phase 3
0.65	Remote Similarity	NPD4249	Approved
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD5690	Phase 2
0.65	Remote Similarity	NPD6098	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD4138	Approved
0.65	Remote Similarity	NPD4690	Approved
0.6489	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5344	Discontinued
0.6481	Remote Similarity	NPD5223	Approved
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8380	Approved
0.6471	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD6274	Approved
0.6466	Remote Similarity	NPD6868	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD4251	Approved
0.6435	Remote Similarity	NPD4632	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