NPASS Compound

Structure

CID327674 OpenBabel06191716192D 36 37 0 0 1 0 0 0 0 0999 V2000 2.5696 3.7944 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 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6037 4.0532 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 0.0000 -2.0000 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 0.8660 -1.5000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 0.7071 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -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 -3.4641 -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 -4.8301 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 2.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8301 -3.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1213 2.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8966 3.3461 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 2 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 24 2 0 0 0 0 10 36 1 0 0 0 0 11 13 1 0 0 0 0 11 23 2 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 20 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 31 1 6 0 0 0 26 32 1 6 0 0 0 27 31 1 6 0 0 0 28 32 1 6 0 0 0 29 33 2 0 0 0 0 29 34 1 0 0 0 0 30 35 2 0 0 0 0 30 36 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:	498.37
Volume:	564.257
LogP:	6.949
LogD:	4.739
LogS:	-5.411
# Rotatable Bonds:	13
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.217
Synthetic Accessibility Score:	4.985
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.1
MDCK Permeability:	1.5087407518876716e-05
Pgp-inhibitor:	0.446
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.067

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	88.47452545166016%
Volume Distribution (VD):	0.668
Pgp-substrate:	5.323213577270508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.425
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.345
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	12.516
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.369
Maximum Recommended Daily Dose:	0.608
Skin Sensitization:	0.21
Carcinogencity:	0.365
Eye Corrosion:	0.036
Eye Irritation:	0.013
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC327674

Natural Product ID:	NPC327674
*Common Name:**	Lansic Accid 3-Ethyl Ester
IUPAC Name:	3-[(1S,2S,6S)-2-[2-[(1S,2S,3S)-2-(3-ethoxy-3-oxopropyl)-2-methyl-6-methylidene-3-prop-1-en-2-ylcyclohexyl]ethyl]-1,3-dimethyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]propanoic acid
Synonyms:	Lansic Acid 3-Ethyl Ester
Standard InCHIKey:	ZLSDLEGKMGQSFU-BFIHGEENSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-10-36-30(35)18-20-32(9)26(22(4)5)14-12-24(7)28(32)16-15-27-23(6)11-13-25(21(2)3)31(27,8)19-17-29(33)34/h11,25-28H,2,4,7,10,12-20H2,1,3,5-6,8-9H3,(H,33,34)/t25-,26-,27-,28-,31-,32-/m0/s1
SMILES:	CCOC(=O)CCC1(C(CCC(=C)C1CCC2C(=CCC(C2(C)CCC(=O)O)C(=C)C)C)C(=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782135
PubChem CID:	53355791
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane 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	=	50.0	ug.mL-1	PMID[496707]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[496707]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[496707]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[496707]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[496707]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[496707]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[496707]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[496707]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[496707]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[496707]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[496707]

☑ 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 NPC327674 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	155
0.1-0.2	1027
0.2-0.3	5036
0.3-0.4	14883
0.4-0.5	8499
0.5-0.6	6512
0.6-0.7	4900
0.7-0.8	1548
0.8-0.85	116
0.85-0.9	17
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC327002
0.9333	High Similarity	NPC321514
0.9091	High Similarity	NPC104545
0.9091	High Similarity	NPC477057
0.9041	High Similarity	NPC160817
0.8987	High Similarity	NPC200752
0.8974	High Similarity	NPC14203
0.8974	High Similarity	NPC229584
0.8889	High Similarity	NPC325594
0.8831	High Similarity	NPC110094
0.8831	High Similarity	NPC4827
0.8831	High Similarity	NPC260385
0.8831	High Similarity	NPC280654
0.8795	High Similarity	NPC474570
0.878	High Similarity	NPC167877
0.8765	High Similarity	NPC76333
0.8718	High Similarity	NPC199595
0.8701	High Similarity	NPC107039
0.8701	High Similarity	NPC471897
0.8701	High Similarity	NPC471899
0.869	High Similarity	NPC471896
0.869	High Similarity	NPC111585
0.869	High Similarity	NPC113989
0.869	High Similarity	NPC120840
0.869	High Similarity	NPC148414
0.869	High Similarity	NPC175628
0.8684	High Similarity	NPC192540
0.8684	High Similarity	NPC279666
0.8659	High Similarity	NPC73038
0.8659	High Similarity	NPC324063
0.8642	High Similarity	NPC156981
0.8625	High Similarity	NPC296367
0.8625	High Similarity	NPC15910
0.8608	High Similarity	NPC37038
0.859	High Similarity	NPC239098
0.859	High Similarity	NPC179028
0.8588	High Similarity	NPC77099
0.8588	High Similarity	NPC26888
0.8588	High Similarity	NPC60755
0.8588	High Similarity	NPC285184
0.8588	High Similarity	NPC470590
0.8571	High Similarity	NPC89294
0.8571	High Similarity	NPC474700
0.8571	High Similarity	NPC30522
0.8571	High Similarity	NPC69143
0.8571	High Similarity	NPC309399
0.8571	High Similarity	NPC180886
0.8571	High Similarity	NPC474889
0.8571	High Similarity	NPC899
0.8553	High Similarity	NPC251970
0.8553	High Similarity	NPC241854
0.8553	High Similarity	NPC283908
0.8553	High Similarity	NPC306928
0.8553	High Similarity	NPC161923
0.8553	High Similarity	NPC301065
0.8553	High Similarity	NPC476046
0.8553	High Similarity	NPC103958
0.8553	High Similarity	NPC183503
0.8553	High Similarity	NPC166797
0.85	High Similarity	NPC221647
0.85	High Similarity	NPC40228
0.85	High Similarity	NPC278459
0.85	High Similarity	NPC473420
0.8488	Intermediate Similarity	NPC86368
0.8488	Intermediate Similarity	NPC169343
0.8481	Intermediate Similarity	NPC16394
0.8481	Intermediate Similarity	NPC231431
0.8481	Intermediate Similarity	NPC477371
0.8471	Intermediate Similarity	NPC474728
0.8452	Intermediate Similarity	NPC24816
0.8442	Intermediate Similarity	NPC476844
0.8442	Intermediate Similarity	NPC476795
0.8434	Intermediate Similarity	NPC322159
0.8434	Intermediate Similarity	NPC262085
0.8415	Intermediate Similarity	NPC165064
0.8415	Intermediate Similarity	NPC312660
0.8415	Intermediate Similarity	NPC100391
0.84	Intermediate Similarity	NPC91369
0.8395	Intermediate Similarity	NPC133391
0.8395	Intermediate Similarity	NPC240302
0.8391	Intermediate Similarity	NPC23621
0.8391	Intermediate Similarity	NPC159410
0.8391	Intermediate Similarity	NPC296164
0.8391	Intermediate Similarity	NPC74751
0.8391	Intermediate Similarity	NPC78580
0.8391	Intermediate Similarity	NPC184006
0.8378	Intermediate Similarity	NPC290445
0.8378	Intermediate Similarity	NPC36616
0.8372	Intermediate Similarity	NPC470113
0.8354	Intermediate Similarity	NPC59436
0.8354	Intermediate Similarity	NPC74410
0.8353	Intermediate Similarity	NPC5509
0.8353	Intermediate Similarity	NPC174342
0.8333	Intermediate Similarity	NPC41017
0.8333	Intermediate Similarity	NPC162107
0.8333	Intermediate Similarity	NPC476601
0.8333	Intermediate Similarity	NPC158141
0.8333	Intermediate Similarity	NPC46912
0.8333	Intermediate Similarity	NPC96496
0.8333	Intermediate Similarity	NPC173089
0.8313	Intermediate Similarity	NPC65661
0.8313	Intermediate Similarity	NPC283733
0.8313	Intermediate Similarity	NPC329738
0.8313	Intermediate Similarity	NPC2709
0.8312	Intermediate Similarity	NPC237591
0.8312	Intermediate Similarity	NPC3753
0.8295	Intermediate Similarity	NPC474727
0.8295	Intermediate Similarity	NPC195715
0.8295	Intermediate Similarity	NPC23241
0.8293	Intermediate Similarity	NPC97913
0.8293	Intermediate Similarity	NPC470948
0.8293	Intermediate Similarity	NPC477373
0.8289	Intermediate Similarity	NPC72343
0.8276	Intermediate Similarity	NPC151722
0.8272	Intermediate Similarity	NPC477372
0.8272	Intermediate Similarity	NPC474955
0.8272	Intermediate Similarity	NPC162632
0.8272	Intermediate Similarity	NPC274050
0.8272	Intermediate Similarity	NPC147066
0.8272	Intermediate Similarity	NPC263272
0.8272	Intermediate Similarity	NPC90055
0.8272	Intermediate Similarity	NPC201912
0.8272	Intermediate Similarity	NPC267691
0.8272	Intermediate Similarity	NPC142244
0.8272	Intermediate Similarity	NPC471898
0.8272	Intermediate Similarity	NPC38350
0.8256	Intermediate Similarity	NPC198818
0.825	Intermediate Similarity	NPC158846
0.825	Intermediate Similarity	NPC196827
0.825	Intermediate Similarity	NPC274996
0.8235	Intermediate Similarity	NPC40552
0.8235	Intermediate Similarity	NPC52169
0.8235	Intermediate Similarity	NPC294480
0.8235	Intermediate Similarity	NPC183546
0.8235	Intermediate Similarity	NPC246708
0.8235	Intermediate Similarity	NPC1753
0.8235	Intermediate Similarity	NPC474474
0.8235	Intermediate Similarity	NPC474511
0.8235	Intermediate Similarity	NPC182797
0.8228	Intermediate Similarity	NPC472300
0.8228	Intermediate Similarity	NPC61952
0.8228	Intermediate Similarity	NPC165711
0.8214	Intermediate Similarity	NPC6979
0.8214	Intermediate Similarity	NPC329943
0.8214	Intermediate Similarity	NPC10005
0.8214	Intermediate Similarity	NPC9892
0.8214	Intermediate Similarity	NPC264127
0.8214	Intermediate Similarity	NPC91525
0.8214	Intermediate Similarity	NPC155011
0.8214	Intermediate Similarity	NPC473226
0.8202	Intermediate Similarity	NPC327179
0.8202	Intermediate Similarity	NPC230151
0.8193	Intermediate Similarity	NPC476038
0.8193	Intermediate Similarity	NPC96095
0.8193	Intermediate Similarity	NPC164577
0.8193	Intermediate Similarity	NPC472865
0.8193	Intermediate Similarity	NPC194937
0.8182	Intermediate Similarity	NPC35656
0.8182	Intermediate Similarity	NPC474963
0.8171	Intermediate Similarity	NPC73882
0.8171	Intermediate Similarity	NPC69101
0.8171	Intermediate Similarity	NPC251779
0.8171	Intermediate Similarity	NPC260956
0.8161	Intermediate Similarity	NPC154101
0.8161	Intermediate Similarity	NPC179517
0.8161	Intermediate Similarity	NPC297265
0.8161	Intermediate Similarity	NPC165904
0.8148	Intermediate Similarity	NPC267517
0.8148	Intermediate Similarity	NPC2482
0.8148	Intermediate Similarity	NPC195424
0.814	Intermediate Similarity	NPC64872
0.814	Intermediate Similarity	NPC474704
0.814	Intermediate Similarity	NPC281524
0.814	Intermediate Similarity	NPC263393
0.814	Intermediate Similarity	NPC130520
0.814	Intermediate Similarity	NPC25906
0.814	Intermediate Similarity	NPC59263
0.814	Intermediate Similarity	NPC127689
0.814	Intermediate Similarity	NPC215029
0.814	Intermediate Similarity	NPC198664
0.814	Intermediate Similarity	NPC121798
0.814	Intermediate Similarity	NPC274330
0.814	Intermediate Similarity	NPC476733
0.814	Intermediate Similarity	NPC469866
0.814	Intermediate Similarity	NPC477973
0.814	Intermediate Similarity	NPC470588
0.814	Intermediate Similarity	NPC143232
0.814	Intermediate Similarity	NPC475049
0.814	Intermediate Similarity	NPC290972
0.814	Intermediate Similarity	NPC234346
0.814	Intermediate Similarity	NPC475921
0.814	Intermediate Similarity	NPC168131
0.814	Intermediate Similarity	NPC61543
0.814	Intermediate Similarity	NPC293048
0.814	Intermediate Similarity	NPC270768
0.814	Intermediate Similarity	NPC225585
0.814	Intermediate Similarity	NPC471342
0.8125	Intermediate Similarity	NPC198240
0.8125	Intermediate Similarity	NPC35574
0.8118	Intermediate Similarity	NPC51700

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 NPC327674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1502
0.2-0.3	3851
0.3-0.4	2388
0.4-0.5	718
0.5-0.6	321
0.6-0.7	190
0.7-0.8	42
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8391	Intermediate Similarity	NPD7748	Approved
0.8276	Intermediate Similarity	NPD6399	Phase 3
0.8111	Intermediate Similarity	NPD7902	Approved
0.8023	Intermediate Similarity	NPD6672	Approved
0.8023	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD7521	Approved
0.8	Intermediate Similarity	NPD7146	Approved
0.8	Intermediate Similarity	NPD6684	Approved
0.8	Intermediate Similarity	NPD5330	Approved
0.8	Intermediate Similarity	NPD6409	Approved
0.8	Intermediate Similarity	NPD7334	Approved
0.7955	Intermediate Similarity	NPD7515	Phase 2
0.7952	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD6083	Phase 2
0.7912	Intermediate Similarity	NPD6084	Phase 2
0.7889	Intermediate Similarity	NPD5695	Phase 3
0.7816	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7900	Approved
0.7765	Intermediate Similarity	NPD4786	Approved
0.7753	Intermediate Similarity	NPD6411	Approved
0.775	Intermediate Similarity	NPD8039	Approved
0.7738	Intermediate Similarity	NPD3667	Approved
0.7634	Intermediate Similarity	NPD5696	Approved
0.7586	Intermediate Similarity	NPD6098	Approved
0.7558	Intermediate Similarity	NPD3665	Phase 1
0.7558	Intermediate Similarity	NPD3666	Approved
0.7558	Intermediate Similarity	NPD3133	Approved
0.7556	Intermediate Similarity	NPD8035	Phase 2
0.7556	Intermediate Similarity	NPD8034	Phase 2
0.7528	Intermediate Similarity	NPD6101	Approved
0.7528	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6673	Approved
0.7528	Intermediate Similarity	NPD6080	Approved
0.7528	Intermediate Similarity	NPD6904	Approved
0.7528	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7386	Intermediate Similarity	NPD3618	Phase 1
0.7363	Intermediate Similarity	NPD5284	Approved
0.7363	Intermediate Similarity	NPD6050	Approved
0.7363	Intermediate Similarity	NPD5281	Approved
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.7347	Intermediate Similarity	NPD6675	Approved
0.7347	Intermediate Similarity	NPD6402	Approved
0.7347	Intermediate Similarity	NPD7128	Approved
0.7347	Intermediate Similarity	NPD5739	Approved
0.7333	Intermediate Similarity	NPD5328	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7326	Intermediate Similarity	NPD4223	Phase 3
0.7326	Intermediate Similarity	NPD4221	Approved
0.7312	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3573	Approved
0.7283	Intermediate Similarity	NPD5778	Approved
0.7283	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7638	Approved
0.7253	Intermediate Similarity	NPD5692	Phase 3
0.7222	Intermediate Similarity	NPD5208	Approved
0.72	Intermediate Similarity	NPD6881	Approved
0.72	Intermediate Similarity	NPD7320	Approved
0.72	Intermediate Similarity	NPD6899	Approved
0.7191	Intermediate Similarity	NPD5279	Phase 3
0.7188	Intermediate Similarity	NPD7640	Approved
0.7188	Intermediate Similarity	NPD7639	Approved
0.7174	Intermediate Similarity	NPD5694	Approved
0.7174	Intermediate Similarity	NPD6079	Approved
0.7174	Intermediate Similarity	NPD5693	Phase 1
0.7159	Intermediate Similarity	NPD4197	Approved
0.7157	Intermediate Similarity	NPD8130	Phase 1
0.7129	Intermediate Similarity	NPD6373	Approved
0.7129	Intermediate Similarity	NPD6372	Approved
0.71	Intermediate Similarity	NPD5701	Approved
0.71	Intermediate Similarity	NPD5697	Approved
0.7087	Intermediate Similarity	NPD8297	Approved
0.7079	Intermediate Similarity	NPD1694	Approved
0.7065	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7290	Approved
0.7059	Intermediate Similarity	NPD7102	Approved
0.7059	Intermediate Similarity	NPD3617	Approved
0.7059	Intermediate Similarity	NPD6883	Approved
0.7053	Intermediate Similarity	NPD7732	Phase 3
0.7053	Intermediate Similarity	NPD7614	Phase 1
0.703	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD4690	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD5280	Approved
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD4694	Approved
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD4623	Approved
0.7	Intermediate Similarity	NPD4689	Approved
0.699	Remote Similarity	NPD6617	Approved
0.699	Remote Similarity	NPD6869	Approved
0.699	Remote Similarity	NPD6847	Approved
0.699	Remote Similarity	NPD6650	Approved
0.699	Remote Similarity	NPD6649	Approved
0.699	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7645	Phase 2
0.6961	Remote Similarity	NPD6012	Approved
0.6961	Remote Similarity	NPD6013	Approved
0.6961	Remote Similarity	NPD6014	Approved
0.6957	Remote Similarity	NPD6051	Approved
0.6947	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD4629	Approved
0.6932	Remote Similarity	NPD6435	Approved
0.6931	Remote Similarity	NPD6412	Phase 2
0.6923	Remote Similarity	NPD6882	Approved
0.6915	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD7339	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6875	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5221	Approved
0.6875	Remote Similarity	NPD4697	Phase 3
0.6875	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6686	Approved
0.6854	Remote Similarity	NPD7154	Phase 3
0.6854	Remote Similarity	NPD4788	Approved
0.6854	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD6001	Approved
0.6837	Remote Similarity	NPD6404	Discontinued
0.6824	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4139	Approved
0.6818	Remote Similarity	NPD5369	Approved
0.6818	Remote Similarity	NPD4692	Approved
0.6813	Remote Similarity	NPD6422	Discontinued
0.6809	Remote Similarity	NPD7637	Suspended
0.6804	Remote Similarity	NPD5173	Approved
0.6804	Remote Similarity	NPD4755	Approved
0.6796	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5654	Approved
0.675	Remote Similarity	NPD7331	Phase 2
0.6747	Remote Similarity	NPD4243	Approved
0.6735	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD6868	Approved
0.6707	Remote Similarity	NPD4137	Phase 3
0.6706	Remote Similarity	NPD3702	Approved
0.6705	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD7525	Registered
0.6705	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6634	Remote Similarity	NPD6052	Approved
0.6633	Remote Similarity	NPD5959	Approved
0.6628	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD4747	Approved
0.6627	Remote Similarity	NPD4691	Approved
0.6625	Remote Similarity	NPD7341	Phase 2
0.6622	Remote Similarity	NPD4266	Approved
0.6622	Remote Similarity	NPD3196	Approved
0.6622	Remote Similarity	NPD3195	Phase 2
0.6622	Remote Similarity	NPD3194	Approved
0.6606	Remote Similarity	NPD6335	Approved
0.66	Remote Similarity	NPD5223	Approved
0.6591	Remote Similarity	NPD4195	Approved
0.6588	Remote Similarity	NPD4785	Approved
0.6588	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5733	Approved
0.6588	Remote Similarity	NPD4784	Approved
0.6588	Remote Similarity	NPD6926	Approved
0.6588	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6274	Approved
0.6556	Remote Similarity	NPD4270	Approved
0.6556	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD6116	Phase 1
0.6548	Remote Similarity	NPD5777	Approved
0.6548	Remote Similarity	NPD6081	Approved
0.6545	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD7101	Approved
0.6543	Remote Similarity	NPD4224	Phase 2
0.6542	Remote Similarity	NPD4632	Approved
0.6535	Remote Similarity	NPD5224	Approved
0.6535	Remote Similarity	NPD5225	Approved
0.6535	Remote Similarity	NPD5226	Approved
0.6535	Remote Similarity	NPD4633	Approved
0.6535	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD5211	Phase 2
0.6531	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD4096	Approved
0.6526	Remote Similarity	NPD5785	Approved
0.6526	Remote Similarity	NPD6698	Approved
0.6526	Remote Similarity	NPD46	Approved
0.6517	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6317	Approved
0.6512	Remote Similarity	NPD8264	Approved
0.65	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3172	Approved
0.6484	Remote Similarity	NPD6695	Phase 3
0.6477	Remote Similarity	NPD6697	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