NPASS Compound

Structure

CID325594 OpenBabel06191716182D 35 37 0 0 1 0 0 0 0 0999 V2000 8.6318 4.2944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1383 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6659 4.5532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5105 2.1730 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 6.7693 1.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2176 2.8801 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 6.0622 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 8.1835 2.6213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9588 3.8461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 21 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 2 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 10 35 1 0 0 0 0 11 13 1 0 0 0 0 11 22 2 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 19 1 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 19 32 1 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 31 1 6 0 0 0 25 31 1 6 0 0 0 26 32 1 6 0 0 0 27 30 1 0 0 0 0 27 32 1 6 0 0 0 28 30 1 0 0 0 0 28 33 1 6 0 0 0 29 34 2 0 0 0 0 29 35 1 0 0 0 0 31 8 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.39
Volume:	552.183
LogP:	7.004
LogD:	5.394
LogS:	-5.968
# Rotatable Bonds:	9
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	4.885
Fsp3:	0.781
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.645
MDCK Permeability:	1.6322857845807448e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	92.13690948486328%
Volume Distribution (VD):	0.862
Pgp-substrate:	2.7962584495544434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.107
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.76
CYP2C9-inhibitor:	0.523
CYP2C9-substrate:	0.168
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.668
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	10.074
Half-life (T1/2):	0.021

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.252
Carcinogencity:	0.044
Eye Corrosion:	0.018
Eye Irritation:	0.038
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC325594

Natural Product ID:	NPC325594
*Common Name:**	Ethyl Lansiolate
IUPAC Name:	ethyl 3-[(1S,2S,6S)-2-[2-[(1S,4aR,6S,8aR)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-1,3-dimethyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]propanoate
Synonyms:	Ethyl Lansiolate
Standard InCHIKey:	MBFTWDFKACXAAV-XXYMEPQGSA-N
Standard InCHI:	InChI=1S/C32H52O3/c1-10-35-29(34)18-20-31(8)24(21(2)3)13-11-22(4)25(31)14-15-26-23(5)12-16-27-30(6,7)28(33)17-19-32(26,27)9/h11,24-28,33H,2,5,10,12-20H2,1,3-4,6-9H3/t24-,25-,26-,27-,28-,31-,32+/m0/s1
SMILES:	CCOC(=O)CC[C@]1(C)[C@@H](CC[C@H]2C(=C)CC[C@@H]3[C@]2(C)CC[C@@H](C3(C)C)O)C(=CC[C@H]1C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782136
PubChem CID:	53262848
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	exocarp	n.a.	DOI[10.1021/jo00172a004]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444710]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[19299148]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Mengla County, Yunnan Province, China	2005-AUG	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[30335380]
NPO20633	Lansium domesticum	Species	Meliaceae	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
MIC	11
Others	1

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[453199]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[453199]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[453199]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[453199]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[453199]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[453199]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[453199]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[453199]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[453199]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[453199]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[453199]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	7.9	%	PMID[453200]

☑ 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 NPC325594 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	179
0.1-0.2	1067
0.2-0.3	4461
0.3-0.4	12838
0.4-0.5	9858
0.5-0.6	6121
0.6-0.7	4846
0.7-0.8	2826
0.8-0.85	397
0.85-0.9	98
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC73038
0.9302	High Similarity	NPC86368
0.9294	High Similarity	NPC471896
0.9294	High Similarity	NPC113989
0.9294	High Similarity	NPC120840
0.9286	High Similarity	NPC246708
0.9286	High Similarity	NPC40552
0.9186	High Similarity	NPC77099
0.9186	High Similarity	NPC60755
0.9186	High Similarity	NPC285184
0.9186	High Similarity	NPC470590
0.9176	High Similarity	NPC470588
0.9176	High Similarity	NPC30522
0.9167	High Similarity	NPC88716
0.9167	High Similarity	NPC142361
0.9167	High Similarity	NPC68160
0.9167	High Similarity	NPC102683
0.9167	High Similarity	NPC51700
0.9167	High Similarity	NPC242468
0.9167	High Similarity	NPC130577
0.9167	High Similarity	NPC18064
0.9167	High Similarity	NPC98442
0.9167	High Similarity	NPC171203
0.9167	High Similarity	NPC307426
0.9167	High Similarity	NPC474684
0.9167	High Similarity	NPC142415
0.9167	High Similarity	NPC293564
0.9136	High Similarity	NPC473420
0.9091	High Similarity	NPC474727
0.908	High Similarity	NPC49776
0.908	High Similarity	NPC474436
0.908	High Similarity	NPC470224
0.908	High Similarity	NPC63118
0.907	High Similarity	NPC175628
0.907	High Similarity	NPC474728
0.907	High Similarity	NPC148414
0.907	High Similarity	NPC111585
0.9059	High Similarity	NPC474512
0.9059	High Similarity	NPC17733
0.9059	High Similarity	NPC52169
0.9059	High Similarity	NPC470629
0.9059	High Similarity	NPC290690
0.9059	High Similarity	NPC182797
0.9059	High Similarity	NPC181225
0.9059	High Similarity	NPC473242
0.9048	High Similarity	NPC72638
0.9048	High Similarity	NPC91525
0.9048	High Similarity	NPC10005
0.9048	High Similarity	NPC9892
0.9048	High Similarity	NPC329943
0.8989	High Similarity	NPC327179
0.8989	High Similarity	NPC230151
0.8977	High Similarity	NPC184006
0.8977	High Similarity	NPC159410
0.8977	High Similarity	NPC23621
0.8977	High Similarity	NPC74751
0.8977	High Similarity	NPC78580
0.8977	High Similarity	NPC296164
0.8966	High Similarity	NPC26888
0.8953	High Similarity	NPC290972
0.8953	High Similarity	NPC234346
0.8953	High Similarity	NPC143232
0.8953	High Similarity	NPC127689
0.8953	High Similarity	NPC61543
0.8953	High Similarity	NPC475921
0.8953	High Similarity	NPC64872
0.8953	High Similarity	NPC270768
0.8953	High Similarity	NPC121798
0.8953	High Similarity	NPC263393
0.8953	High Similarity	NPC59263
0.8953	High Similarity	NPC198664
0.8953	High Similarity	NPC293048
0.8953	High Similarity	NPC474972
0.8953	High Similarity	NPC225585
0.8953	High Similarity	NPC474889
0.8953	High Similarity	NPC25906
0.8953	High Similarity	NPC274330
0.8953	High Similarity	NPC95246
0.8953	High Similarity	NPC474704
0.8953	High Similarity	NPC161751
0.8953	High Similarity	NPC130520
0.8941	High Similarity	NPC159046
0.8941	High Similarity	NPC71507
0.8941	High Similarity	NPC233836
0.8941	High Similarity	NPC187376
0.8941	High Similarity	NPC162107
0.8941	High Similarity	NPC46912
0.8929	High Similarity	NPC191965
0.8902	High Similarity	NPC142163
0.8902	High Similarity	NPC327002
0.8889	High Similarity	NPC476878
0.8889	High Similarity	NPC476879
0.8889	High Similarity	NPC327674
0.8876	High Similarity	NPC23241
0.8876	High Similarity	NPC279974
0.8876	High Similarity	NPC195715
0.8864	High Similarity	NPC141497
0.8864	High Similarity	NPC136313
0.8864	High Similarity	NPC272075
0.8864	High Similarity	NPC307335
0.8864	High Similarity	NPC295643
0.8864	High Similarity	NPC214756
0.8864	High Similarity	NPC107674
0.8864	High Similarity	NPC170220
0.8864	High Similarity	NPC74855
0.8851	High Similarity	NPC172361
0.8851	High Similarity	NPC290614
0.8851	High Similarity	NPC291028
0.8851	High Similarity	NPC18872
0.8851	High Similarity	NPC130278
0.8851	High Similarity	NPC210037
0.8851	High Similarity	NPC470589
0.8851	High Similarity	NPC120968
0.8851	High Similarity	NPC111110
0.8851	High Similarity	NPC273621
0.8851	High Similarity	NPC126369
0.8851	High Similarity	NPC227467
0.8851	High Similarity	NPC477872
0.8851	High Similarity	NPC7260
0.8851	High Similarity	NPC86372
0.8837	High Similarity	NPC224145
0.8824	High Similarity	NPC55309
0.8824	High Similarity	NPC155011
0.8824	High Similarity	NPC28252
0.8824	High Similarity	NPC322159
0.8824	High Similarity	NPC6979
0.8824	High Similarity	NPC84121
0.8824	High Similarity	NPC82979
0.8824	High Similarity	NPC137306
0.881	High Similarity	NPC171789
0.8795	High Similarity	NPC73882
0.8795	High Similarity	NPC48362
0.8791	High Similarity	NPC58942
0.8791	High Similarity	NPC260149
0.8791	High Similarity	NPC471966
0.8764	High Similarity	NPC91010
0.875	High Similarity	NPC71074
0.875	High Similarity	NPC212301
0.875	High Similarity	NPC324341
0.875	High Similarity	NPC105189
0.875	High Similarity	NPC52021
0.875	High Similarity	NPC282616
0.875	High Similarity	NPC233455
0.875	High Similarity	NPC110657
0.875	High Similarity	NPC235884
0.875	High Similarity	NPC301244
0.875	High Similarity	NPC472149
0.875	High Similarity	NPC65120
0.875	High Similarity	NPC84319
0.875	High Similarity	NPC966
0.875	High Similarity	NPC189520
0.875	High Similarity	NPC86266
0.875	High Similarity	NPC4036
0.875	High Similarity	NPC145067
0.875	High Similarity	NPC25299
0.875	High Similarity	NPC228784
0.875	High Similarity	NPC297265
0.875	High Similarity	NPC288833
0.875	High Similarity	NPC187722
0.875	High Similarity	NPC158030
0.875	High Similarity	NPC300351
0.875	High Similarity	NPC306541
0.875	High Similarity	NPC474525
0.875	High Similarity	NPC155120
0.8736	High Similarity	NPC475049
0.8736	High Similarity	NPC474686
0.8736	High Similarity	NPC84271
0.8736	High Similarity	NPC102414
0.8736	High Similarity	NPC77168
0.8721	High Similarity	NPC477926
0.8706	High Similarity	NPC133954
0.869	High Similarity	NPC470948
0.869	High Similarity	NPC474789
0.869	High Similarity	NPC52108
0.8681	High Similarity	NPC26413
0.8681	High Similarity	NPC158347
0.8667	High Similarity	NPC69548
0.8667	High Similarity	NPC184848
0.8659	High Similarity	NPC100906
0.8652	High Similarity	NPC470376
0.8652	High Similarity	NPC275809
0.8652	High Similarity	NPC474806
0.8652	High Similarity	NPC118519
0.8652	High Similarity	NPC229281
0.8652	High Similarity	NPC158059
0.8652	High Similarity	NPC202728
0.8652	High Similarity	NPC298554
0.8652	High Similarity	NPC470375
0.8652	High Similarity	NPC133579
0.8636	High Similarity	NPC46441
0.8636	High Similarity	NPC193750
0.8636	High Similarity	NPC49320
0.8621	High Similarity	NPC242864
0.8621	High Similarity	NPC24816
0.8605	High Similarity	NPC264127
0.8605	High Similarity	NPC235341
0.8605	High Similarity	NPC475862
0.8605	High Similarity	NPC473226
0.8605	High Similarity	NPC95594
0.8605	High Similarity	NPC74363

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 NPC325594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1438
0.2-0.3	3752
0.3-0.4	2506
0.4-0.5	744
0.5-0.6	244
0.6-0.7	187
0.7-0.8	107
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD7748	Approved
0.875	High Similarity	NPD7515	Phase 2
0.8681	High Similarity	NPD7902	Approved
0.8444	Intermediate Similarity	NPD6399	Phase 3
0.8391	Intermediate Similarity	NPD3618	Phase 1
0.8372	Intermediate Similarity	NPD4786	Approved
0.8353	Intermediate Similarity	NPD3667	Approved
0.8352	Intermediate Similarity	NPD7900	Approved
0.8352	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD5328	Approved
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7521	Approved
0.8182	Intermediate Similarity	NPD6684	Approved
0.8182	Intermediate Similarity	NPD6409	Approved
0.8182	Intermediate Similarity	NPD5330	Approved
0.8182	Intermediate Similarity	NPD7146	Approved
0.8182	Intermediate Similarity	NPD7334	Approved
0.8132	Intermediate Similarity	NPD8034	Phase 2
0.8132	Intermediate Similarity	NPD6079	Approved
0.8132	Intermediate Similarity	NPD8035	Phase 2
0.8061	Intermediate Similarity	NPD6402	Approved
0.8061	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD7128	Approved
0.8061	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD6903	Approved
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7645	Phase 2
0.7955	Intermediate Similarity	NPD3665	Phase 1
0.7955	Intermediate Similarity	NPD3666	Approved
0.7955	Intermediate Similarity	NPD3133	Approved
0.7935	Intermediate Similarity	NPD6411	Approved
0.7917	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD7640	Approved
0.79	Intermediate Similarity	NPD6881	Approved
0.79	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6899	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7889	Intermediate Similarity	NPD3573	Approved
0.7849	Intermediate Similarity	NPD4202	Approved
0.7843	Intermediate Similarity	NPD8130	Phase 1
0.7822	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD6373	Approved
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.78	Intermediate Similarity	NPD5701	Approved
0.78	Intermediate Similarity	NPD5697	Approved
0.7767	Intermediate Similarity	NPD8297	Approved
0.7745	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD7290	Approved
0.7745	Intermediate Similarity	NPD6883	Approved
0.7723	Intermediate Similarity	NPD6011	Approved
0.7717	Intermediate Similarity	NPD6101	Approved
0.7717	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6869	Approved
0.767	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6649	Approved
0.767	Intermediate Similarity	NPD6847	Approved
0.767	Intermediate Similarity	NPD6617	Approved
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.7604	Intermediate Similarity	NPD4697	Phase 3
0.7604	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5222	Approved
0.7604	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD6882	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7529	Intermediate Similarity	NPD7339	Approved
0.7529	Intermediate Similarity	NPD6942	Approved
0.7526	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7476	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5696	Approved
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6117	Approved
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5279	Phase 3
0.7383	Intermediate Similarity	NPD6868	Approved
0.7374	Intermediate Similarity	NPD5286	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7374	Intermediate Similarity	NPD4696	Approved
0.7374	Intermediate Similarity	NPD5285	Approved
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.734	Intermediate Similarity	NPD4753	Phase 2
0.7333	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7303	Intermediate Similarity	NPD4695	Discontinued
0.73	Intermediate Similarity	NPD5223	Approved
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7283	Intermediate Similarity	NPD5329	Approved
0.7283	Intermediate Similarity	NPD1694	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7248	Intermediate Similarity	NPD6335	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD5226	Approved
0.7228	Intermediate Similarity	NPD5224	Approved
0.7228	Intermediate Similarity	NPD4633	Approved
0.7228	Intermediate Similarity	NPD5225	Approved
0.7228	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD6274	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7204	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4632	Approved
0.7184	Intermediate Similarity	NPD6008	Approved
0.7182	Intermediate Similarity	NPD7100	Approved
0.7182	Intermediate Similarity	NPD7101	Approved
0.7174	Intermediate Similarity	NPD4197	Approved
0.7157	Intermediate Similarity	NPD5175	Approved
0.7157	Intermediate Similarity	NPD5174	Approved
0.7157	Intermediate Similarity	NPD4754	Approved
0.7156	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8039	Approved
0.7115	Intermediate Similarity	NPD6412	Phase 2
0.7091	Intermediate Similarity	NPD6314	Approved
0.7091	Intermediate Similarity	NPD6313	Approved
0.7087	Intermediate Similarity	NPD5141	Approved
0.708	Intermediate Similarity	NPD8328	Phase 3
0.7079	Intermediate Similarity	NPD3617	Approved
0.7065	Intermediate Similarity	NPD4788	Approved
0.7054	Intermediate Similarity	NPD6908	Approved
0.7054	Intermediate Similarity	NPD6909	Approved
0.7048	Intermediate Similarity	NPD6686	Approved
0.7021	Intermediate Similarity	NPD4519	Discontinued
0.7021	Intermediate Similarity	NPD4693	Phase 3
0.7021	Intermediate Similarity	NPD4690	Approved
0.7021	Intermediate Similarity	NPD4138	Approved
0.7021	Intermediate Similarity	NPD4688	Approved
0.7021	Intermediate Similarity	NPD5205	Approved
0.7021	Intermediate Similarity	NPD4689	Approved
0.7021	Intermediate Similarity	NPD4623	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.7019	Intermediate Similarity	NPD4767	Approved
0.701	Intermediate Similarity	NPD5693	Phase 1
0.701	Intermediate Similarity	NPD5284	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6051	Approved
0.6977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD5210	Approved
0.6964	Remote Similarity	NPD6319	Approved
0.6941	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8264	Approved
0.693	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD5692	Phase 3
0.6903	Remote Similarity	NPD5983	Phase 2
0.6903	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7614	Phase 1
0.69	Remote Similarity	NPD7732	Phase 3
0.6897	Remote Similarity	NPD8293	Discontinued
0.6889	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4729	Approved
0.6887	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5168	Approved
0.6887	Remote Similarity	NPD5128	Approved
0.6887	Remote Similarity	NPD4730	Approved
0.687	Remote Similarity	NPD7492	Approved
0.6842	Remote Similarity	NPD5690	Phase 2
0.6842	Remote Similarity	NPD5280	Approved
0.6842	Remote Similarity	NPD4694	Approved
0.6838	Remote Similarity	NPD7736	Approved
0.6837	Remote Similarity	NPD5694	Approved
0.6837	Remote Similarity	NPD7637	Suspended
0.6818	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6814	Remote Similarity	NPD6054	Approved
0.6814	Remote Similarity	NPD6059	Approved
0.681	Remote Similarity	NPD6616	Approved
0.681	Remote Similarity	NPD6336	Discontinued
0.6782	Remote Similarity	NPD5777	Approved
0.6782	Remote Similarity	NPD4243	Approved
0.6774	Remote Similarity	NPD6435	Approved
0.6759	Remote Similarity	NPD5249	Phase 3

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