NPASS Compound

Structure

CID73038 OpenBabel06191715412D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 1.0000 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 -6.5622 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0622 2.5000 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 -4.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6962 3.5981 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 0.0000 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 -4.3301 -0.5000 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 -6.9282 1.0000 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 -3.6962 1.8660 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 -4.6962 1.8660 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 -6.0622 -0.5000 0.0000 C 0 0 0 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 -5.1962 0.0000 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 -6.0622 1.5000 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 -3.1962 2.7321 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 2.5000 0.0000 C 0 0 0 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 -5.1962 1.0000 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 -3.6962 3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1962 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 21 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 9 35 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 21 2 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 30 1 6 0 0 0 23 31 1 1 0 0 0 24 28 1 0 0 0 0 24 30 1 6 0 0 0 25 29 1 0 0 0 0 25 31 1 1 0 0 0 26 28 1 0 0 0 0 26 32 1 6 0 0 0 27 33 2 0 0 0 0 27 35 1 0 0 0 0 29 34 1 0 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	546.314
LogP:	5.9
LogD:	5.107
LogS:	-5.041
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	4.939
Fsp3:	0.839
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:	-4.712
MDCK Permeability:	1.888934821181465e-05
Pgp-inhibitor:	0.909
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	0.613

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	90.07649993896484%
Volume Distribution (VD):	0.707
Pgp-substrate:	2.582662582397461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.18
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.453
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.571
CYP3A4-inhibitor:	0.51
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	6.01
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.22
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.353
Carcinogencity:	0.012
Eye Corrosion:	0.01
Eye Irritation:	0.076
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC73038

Natural Product ID:	NPC73038
*Common Name:**	Lamesticumin B
IUPAC Name:	methyl 3-[(1R,2S,6R)-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]-6-(2-hydroxypropan-2-yl)-1,3-dimethylcyclohex-3-en-1-yl]propanoate
Synonyms:	Lamesticumin B
Standard InCHIKey:	KYHATJJXUGJUJJ-LUFVGXTESA-N
Standard InCHI:	InChI=1S/C31H52O4/c1-20-10-14-24-28(3,4)26(32)16-18-30(24,7)22(20)12-13-23-21(2)11-15-25(29(5,6)34)31(23,8)19-17-27(33)35-9/h11,22-26,32,34H,1,10,12-19H2,2-9H3/t22-,23-,24-,25-,26-,30+,31+/m0/s1
SMILES:	COC(=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(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782130
PubChem CID:	53262847
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

Activity Type	# Activity
Organism	11

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[543805]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[543805]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.12	ug.mL-1	PMID[543805]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[543805]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[543805]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[543805]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[543805]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[543805]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[543805]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[543805]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[543805]

☑ 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 NPC73038 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	178
0.1-0.2	1052
0.2-0.3	4381
0.3-0.4	12427
0.4-0.5	10161
0.5-0.6	6095
0.6-0.7	4825
0.7-0.8	2967
0.8-0.85	467
0.85-0.9	133
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC325594
0.9286	High Similarity	NPC246708
0.9286	High Similarity	NPC52169
0.9286	High Similarity	NPC182797
0.9286	High Similarity	NPC40552
0.9176	High Similarity	NPC121798
0.9176	High Similarity	NPC263393
0.9176	High Similarity	NPC274330
0.9176	High Similarity	NPC127689
0.9176	High Similarity	NPC470588
0.9176	High Similarity	NPC143232
0.9176	High Similarity	NPC474704
0.9176	High Similarity	NPC25906
0.9176	High Similarity	NPC61543
0.9176	High Similarity	NPC293048
0.9176	High Similarity	NPC225585
0.9176	High Similarity	NPC234346
0.9176	High Similarity	NPC130520
0.9176	High Similarity	NPC290972
0.9176	High Similarity	NPC59263
0.9176	High Similarity	NPC270768
0.9176	High Similarity	NPC198664
0.9176	High Similarity	NPC64872
0.9176	High Similarity	NPC475921
0.9167	High Similarity	NPC88716
0.9167	High Similarity	NPC142361
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
0.9167	High Similarity	NPC68160
0.9136	High Similarity	NPC473420
0.908	High Similarity	NPC86368
0.908	High Similarity	NPC118519
0.908	High Similarity	NPC307335
0.908	High Similarity	NPC170220
0.908	High Similarity	NPC74855
0.908	High Similarity	NPC272075
0.908	High Similarity	NPC295643
0.908	High Similarity	NPC141497
0.908	High Similarity	NPC136313
0.908	High Similarity	NPC275809
0.908	High Similarity	NPC202728
0.908	High Similarity	NPC158059
0.908	High Similarity	NPC214756
0.908	High Similarity	NPC107674
0.907	High Similarity	NPC290614
0.907	High Similarity	NPC111110
0.907	High Similarity	NPC130278
0.907	High Similarity	NPC227467
0.907	High Similarity	NPC18872
0.907	High Similarity	NPC291028
0.907	High Similarity	NPC120968
0.907	High Similarity	NPC470589
0.907	High Similarity	NPC477872
0.907	High Similarity	NPC471896
0.907	High Similarity	NPC474728
0.907	High Similarity	NPC273621
0.907	High Similarity	NPC7260
0.907	High Similarity	NPC113989
0.907	High Similarity	NPC210037
0.907	High Similarity	NPC120840
0.907	High Similarity	NPC126369
0.9059	High Similarity	NPC17733
0.9059	High Similarity	NPC470629
0.9059	High Similarity	NPC474512
0.9059	High Similarity	NPC290690
0.9059	High Similarity	NPC181225
0.9059	High Similarity	NPC473242
0.9048	High Similarity	NPC72638
0.9048	High Similarity	NPC324063
0.9048	High Similarity	NPC322159
0.9	High Similarity	NPC321514
0.8989	High Similarity	NPC327179
0.8977	High Similarity	NPC6818
0.8977	High Similarity	NPC191412
0.8977	High Similarity	NPC91010
0.8977	High Similarity	NPC114159
0.8966	High Similarity	NPC25299
0.8966	High Similarity	NPC300351
0.8966	High Similarity	NPC77099
0.8966	High Similarity	NPC65120
0.8966	High Similarity	NPC84319
0.8966	High Similarity	NPC472149
0.8966	High Similarity	NPC966
0.8966	High Similarity	NPC235884
0.8966	High Similarity	NPC155120
0.8966	High Similarity	NPC105189
0.8966	High Similarity	NPC60755
0.8966	High Similarity	NPC324341
0.8966	High Similarity	NPC145067
0.8966	High Similarity	NPC306541
0.8966	High Similarity	NPC212301
0.8966	High Similarity	NPC474525
0.8966	High Similarity	NPC228784
0.8966	High Similarity	NPC470590
0.8966	High Similarity	NPC282616
0.8966	High Similarity	NPC158030
0.8966	High Similarity	NPC86266
0.8966	High Similarity	NPC71074
0.8966	High Similarity	NPC187722
0.8966	High Similarity	NPC52021
0.8966	High Similarity	NPC4036
0.8966	High Similarity	NPC110657
0.8966	High Similarity	NPC288833
0.8966	High Similarity	NPC189520
0.8966	High Similarity	NPC233455
0.8966	High Similarity	NPC297265
0.8966	High Similarity	NPC285184
0.8953	High Similarity	NPC474972
0.8953	High Similarity	NPC95246
0.8953	High Similarity	NPC30522
0.8953	High Similarity	NPC161751
0.8941	High Similarity	NPC71507
0.8941	High Similarity	NPC477926
0.8941	High Similarity	NPC233836
0.8941	High Similarity	NPC187376
0.8941	High Similarity	NPC159046
0.8902	High Similarity	NPC327002
0.8889	High Similarity	NPC259788
0.8889	High Similarity	NPC255589
0.8876	High Similarity	NPC474727
0.8876	High Similarity	NPC279974
0.8876	High Similarity	NPC53565
0.8864	High Similarity	NPC470375
0.8864	High Similarity	NPC229281
0.8864	High Similarity	NPC63118
0.8864	High Similarity	NPC470376
0.8864	High Similarity	NPC298554
0.8864	High Similarity	NPC133579
0.8864	High Similarity	NPC474806
0.8864	High Similarity	NPC118490
0.8864	High Similarity	NPC49776
0.8864	High Similarity	NPC474436
0.8864	High Similarity	NPC470224
0.8851	High Similarity	NPC49320
0.8851	High Similarity	NPC172361
0.8851	High Similarity	NPC111585
0.8851	High Similarity	NPC175628
0.8851	High Similarity	NPC469400
0.8851	High Similarity	NPC148414
0.8851	High Similarity	NPC46441
0.8851	High Similarity	NPC193750
0.8851	High Similarity	NPC86372
0.8837	High Similarity	NPC242864
0.8824	High Similarity	NPC55309
0.8824	High Similarity	NPC82979
0.8824	High Similarity	NPC155011
0.8824	High Similarity	NPC473226
0.8824	High Similarity	NPC28252
0.881	High Similarity	NPC171789
0.8795	High Similarity	NPC48362
0.8795	High Similarity	NPC73882
0.878	High Similarity	NPC37038
0.878	High Similarity	NPC104545
0.8778	High Similarity	NPC116457
0.8778	High Similarity	NPC259733
0.8778	High Similarity	NPC207922
0.8778	High Similarity	NPC158371
0.8778	High Similarity	NPC98874
0.8778	High Similarity	NPC230151
0.8778	High Similarity	NPC62516
0.8778	High Similarity	NPC157113
0.8778	High Similarity	NPC132824
0.8764	High Similarity	NPC222047
0.8764	High Similarity	NPC159410
0.8764	High Similarity	NPC32407
0.8764	High Similarity	NPC299996
0.8764	High Similarity	NPC74751
0.8764	High Similarity	NPC231063
0.8764	High Similarity	NPC78580
0.8764	High Similarity	NPC145667
0.8764	High Similarity	NPC296164
0.8764	High Similarity	NPC49670
0.8764	High Similarity	NPC80365
0.8764	High Similarity	NPC23621
0.8764	High Similarity	NPC282395
0.8764	High Similarity	NPC20235
0.8764	High Similarity	NPC474529
0.8764	High Similarity	NPC209868
0.8764	High Similarity	NPC263548
0.8764	High Similarity	NPC88116
0.8764	High Similarity	NPC159365
0.8764	High Similarity	NPC184006
0.8764	High Similarity	NPC60692
0.875	High Similarity	NPC26888
0.875	High Similarity	NPC6255
0.875	High Similarity	NPC471588
0.875	High Similarity	NPC475708
0.875	High Similarity	NPC38754
0.875	High Similarity	NPC301244
0.8736	High Similarity	NPC77168
0.8736	High Similarity	NPC474686

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 NPC73038 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1437
0.2-0.3	3710
0.3-0.4	2503
0.4-0.5	800
0.5-0.6	227
0.6-0.7	171
0.7-0.8	135
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
0.8966	High Similarity	NPD7515	Phase 2
0.8764	High Similarity	NPD7748	Approved
0.8478	Intermediate 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
0.8315	Intermediate Similarity	NPD5328	Approved
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD5739	Approved
0.8247	Intermediate Similarity	NPD6675	Approved
0.8247	Intermediate Similarity	NPD7128	Approved
0.8247	Intermediate Similarity	NPD6402	Approved
0.8152	Intermediate Similarity	NPD7900	Approved
0.8152	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD6079	Approved
0.8085	Intermediate Similarity	NPD6083	Phase 2
0.8085	Intermediate Similarity	NPD6084	Phase 2
0.8081	Intermediate Similarity	NPD6881	Approved
0.8081	Intermediate Similarity	NPD6899	Approved
0.8081	Intermediate Similarity	NPD7320	Approved
0.8043	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD6373	Approved
0.798	Intermediate Similarity	NPD5701	Approved
0.798	Intermediate Similarity	NPD5697	Approved
0.7978	Intermediate Similarity	NPD7146	Approved
0.7978	Intermediate Similarity	NPD7521	Approved
0.7978	Intermediate Similarity	NPD7334	Approved
0.7978	Intermediate Similarity	NPD6409	Approved
0.7978	Intermediate Similarity	NPD6684	Approved
0.7978	Intermediate Similarity	NPD5330	Approved
0.7955	Intermediate Similarity	NPD3665	Phase 1
0.7955	Intermediate Similarity	NPD3666	Approved
0.7955	Intermediate Similarity	NPD3133	Approved
0.7935	Intermediate Similarity	NPD8035	Phase 2
0.7935	Intermediate Similarity	NPD8034	Phase 2
0.7935	Intermediate Similarity	NPD6411	Approved
0.7921	Intermediate Similarity	NPD6883	Approved
0.7921	Intermediate Similarity	NPD7290	Approved
0.7921	Intermediate Similarity	NPD7102	Approved
0.7917	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD7640	Approved
0.7907	Intermediate Similarity	NPD7525	Registered
0.79	Intermediate Similarity	NPD6011	Approved
0.7895	Intermediate Similarity	NPD4755	Approved
0.7889	Intermediate Similarity	NPD3573	Approved
0.7843	Intermediate Similarity	NPD6649	Approved
0.7843	Intermediate Similarity	NPD6650	Approved
0.7843	Intermediate Similarity	NPD6847	Approved
0.7843	Intermediate Similarity	NPD6617	Approved
0.7843	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6869	Approved
0.7843	Intermediate Similarity	NPD8130	Phase 1
0.7822	Intermediate Similarity	NPD6012	Approved
0.7822	Intermediate Similarity	NPD6014	Approved
0.7822	Intermediate Similarity	NPD6013	Approved
0.7802	Intermediate Similarity	NPD6903	Approved
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.7802	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5222	Approved
0.7789	Intermediate Similarity	NPD4697	Phase 3
0.7789	Intermediate Similarity	NPD5221	Approved
0.7767	Intermediate Similarity	NPD6882	Approved
0.7767	Intermediate Similarity	NPD8297	Approved
0.7753	Intermediate Similarity	NPD3668	Phase 3
0.7732	Intermediate Similarity	NPD4700	Approved
0.7732	Intermediate Similarity	NPD4696	Approved
0.7732	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD5286	Approved
0.7717	Intermediate Similarity	NPD4753	Phase 2
0.7717	Intermediate Similarity	NPD6101	Approved
0.7717	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5173	Approved
0.7684	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5695	Phase 3
0.7653	Intermediate Similarity	NPD5223	Approved
0.7647	Intermediate Similarity	NPD6117	Approved
0.7629	Intermediate Similarity	NPD5696	Approved
0.7582	Intermediate Similarity	NPD6098	Approved
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5225	Approved
0.7576	Intermediate Similarity	NPD5226	Approved
0.7576	Intermediate Similarity	NPD5224	Approved
0.7576	Intermediate Similarity	NPD4633	Approved
0.7576	Intermediate Similarity	NPD5211	Phase 2
0.7558	Intermediate Similarity	NPD6116	Phase 1
0.7529	Intermediate Similarity	NPD7339	Approved
0.7529	Intermediate Similarity	NPD6942	Approved
0.7528	Intermediate Similarity	NPD4223	Phase 3
0.7528	Intermediate Similarity	NPD4221	Approved
0.7527	Intermediate Similarity	NPD6673	Approved
0.7527	Intermediate Similarity	NPD6080	Approved
0.7527	Intermediate Similarity	NPD6904	Approved
0.7527	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7473	Intermediate Similarity	NPD5329	Approved
0.7471	Intermediate Similarity	NPD6115	Approved
0.7471	Intermediate Similarity	NPD6118	Approved
0.7471	Intermediate Similarity	NPD6697	Approved
0.7471	Intermediate Similarity	NPD6114	Approved
0.7442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5141	Approved
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6335	Approved
0.7391	Intermediate Similarity	NPD5279	Phase 3
0.7383	Intermediate Similarity	NPD6868	Approved
0.7383	Intermediate Similarity	NPD6274	Approved
0.7368	Intermediate Similarity	NPD5281	Approved
0.7368	Intermediate Similarity	NPD5284	Approved
0.7363	Intermediate Similarity	NPD4197	Approved
0.7353	Intermediate Similarity	NPD4768	Approved
0.7353	Intermediate Similarity	NPD4767	Approved
0.7353	Intermediate Similarity	NPD6008	Approved
0.7339	Intermediate Similarity	NPD7100	Approved
0.7339	Intermediate Similarity	NPD7101	Approved
0.7333	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD5210	Approved
0.732	Intermediate Similarity	NPD4629	Approved
0.7315	Intermediate Similarity	NPD6009	Approved
0.7315	Intermediate Similarity	NPD6317	Approved
0.7308	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5779	Approved
0.7292	Intermediate Similarity	NPD5778	Approved
0.7273	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD4788	Approved
0.7248	Intermediate Similarity	NPD6313	Approved
0.7248	Intermediate Similarity	NPD6314	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7216	Intermediate Similarity	NPD6001	Approved
0.7212	Intermediate Similarity	NPD5128	Approved
0.7212	Intermediate Similarity	NPD4730	Approved
0.7212	Intermediate Similarity	NPD4729	Approved
0.7207	Intermediate Similarity	NPD6909	Approved
0.7207	Intermediate Similarity	NPD6908	Approved
0.7204	Intermediate Similarity	NPD4690	Approved
0.7204	Intermediate Similarity	NPD4693	Phase 3
0.7204	Intermediate Similarity	NPD5205	Approved
0.7204	Intermediate Similarity	NPD4138	Approved
0.7204	Intermediate Similarity	NPD4689	Approved
0.7204	Intermediate Similarity	NPD4623	Approved
0.7204	Intermediate Similarity	NPD4688	Approved
0.7204	Intermediate Similarity	NPD4519	Discontinued
0.7188	Intermediate Similarity	NPD5693	Phase 1
0.7188	Intermediate Similarity	NPD6050	Approved
0.7158	Intermediate Similarity	NPD6051	Approved
0.7117	Intermediate Similarity	NPD6319	Approved
0.7115	Intermediate Similarity	NPD6412	Phase 2
0.7097	Intermediate Similarity	NPD1694	Approved
0.7083	Intermediate Similarity	NPD5692	Phase 3
0.708	Intermediate Similarity	NPD7604	Phase 2
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3617	Approved
0.7075	Intermediate Similarity	NPD5251	Approved
0.7075	Intermediate Similarity	NPD4634	Approved
0.7075	Intermediate Similarity	NPD5250	Approved
0.7075	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5135	Approved
0.7075	Intermediate Similarity	NPD5248	Approved
0.7075	Intermediate Similarity	NPD5249	Phase 3
0.7075	Intermediate Similarity	NPD5169	Approved
0.7075	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5247	Approved
0.7071	Intermediate Similarity	NPD7614	Phase 1
0.7054	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7048	Intermediate Similarity	NPD6686	Approved
0.7048	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5168	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.7021	Intermediate Similarity	NPD4694	Approved
0.7021	Intermediate Similarity	NPD5280	Approved
0.7021	Intermediate Similarity	NPD5690	Phase 2
0.7018	Intermediate Similarity	NPD7492	Approved
0.7011	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6924	Approved
0.701	Intermediate Similarity	NPD5694	Approved
0.7009	Intermediate Similarity	NPD5215	Approved
0.7009	Intermediate Similarity	NPD5127	Approved
0.7009	Intermediate Similarity	NPD5217	Approved
0.7009	Intermediate Similarity	NPD5216	Approved
0.6977	Remote Similarity	NPD4243	Approved
0.6977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6059	Approved
0.6964	Remote Similarity	NPD6054	Approved
0.6957	Remote Similarity	NPD6336	Discontinued
0.6957	Remote Similarity	NPD6616	Approved
0.6941	Remote Similarity	NPD3699	Clinical (unspecified phase)

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