NPASS Compound

Structure

CID327002 OpenBabel06191716192D 37 38 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 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 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 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 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 -0.8660 1.5000 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 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 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 -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 -1.7321 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 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 -1.7321 -1.0000 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 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 37 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 31 1 0 0 0 0 20 32 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 33 2 0 0 0 0 28 34 1 0 0 0 0 29 35 2 0 0 0 0 29 37 1 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:	516.38
Volume:	575.684
LogP:	6.091
LogD:	4.608
LogS:	-4.997
# Rotatable Bonds:	13
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.207
Synthetic Accessibility Score:	5.017
Fsp3:	0.75
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.137
MDCK Permeability:	1.3260576452012174e-05
Pgp-inhibitor:	0.703
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.914
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	90.43897247314453%
Volume Distribution (VD):	0.498
Pgp-substrate:	4.80349588394165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.357
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	5.196
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.864
Skin Sensitization:	0.232
Carcinogencity:	0.128
Eye Corrosion:	0.013
Eye Irritation:	0.082
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC327002

Natural Product ID:	NPC327002
*Common Name:**	3-((1S,2S,6S)-2-(2-((1S,2R,3R)-2-(3-Ethoxy-3-Oxopropyl)-3-(2-Hydroxypropan-2-Yl)-2-Methyl-6-Methylenecyclohexyl)Ethyl)-1,3-Dimethyl-6-(Prop-1-En-2-Yl)Cyclohex-3-Enyl)Propanoic Acid
IUPAC Name:	3-[(1S,2S,6S)-2-[2-[(1S,2R,3R)-2-(3-ethoxy-3-oxopropyl)-3-(2-hydroxypropan-2-yl)-2-methyl-6-methylidenecyclohexyl]ethyl]-1,3-dimethyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]propanoic acid
Synonyms:
Standard InCHIKey:	JYNTZOBOTQIVKY-GIRUYCOHSA-N
Standard InCHI:	InChI=1S/C32H52O5/c1-10-37-29(35)18-20-32(9)26(23(5)12-16-27(32)30(6,7)36)15-14-25-22(4)11-13-24(21(2)3)31(25,8)19-17-28(33)34/h11,24-27,36H,2,5,10,12-20H2,1,3-4,6-9H3,(H,33,34)/t24-,25-,26-,27-,31-,32+/m0/s1
SMILES:	CCOC(=O)CC[C@]1(C)[C@@H](CC[C@H]2C(=CC[C@H]([C@]2(C)CCC(=O)O)C(=C)C)C)C(=C)CC[C@H]1C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782103
PubChem CID:	53355685
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[506809]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	12.5	ug.mL-1	PMID[506809]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[506809]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[506809]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[506809]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[506809]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[506809]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[506809]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[506809]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[506809]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[506809]

☑ 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 NPC327002 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	165
0.1-0.2	1018
0.2-0.3	4744
0.3-0.4	14277
0.4-0.5	8781
0.5-0.6	6449
0.6-0.7	5298
0.7-0.8	1814
0.8-0.85	135
0.85-0.9	13
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC327674
0.96	High Similarity	NPC321514
0.8902	High Similarity	NPC324063
0.8902	High Similarity	NPC73038
0.8902	High Similarity	NPC325594
0.8889	High Similarity	NPC156981
0.8861	High Similarity	NPC477057
0.8861	High Similarity	NPC37038
0.8861	High Similarity	NPC104545
0.8846	High Similarity	NPC179028
0.881	High Similarity	NPC474570
0.88	High Similarity	NPC160817
0.8795	High Similarity	NPC167877
0.8765	High Similarity	NPC200752
0.875	High Similarity	NPC14203
0.875	High Similarity	NPC229584
0.8734	High Similarity	NPC231431
0.8706	High Similarity	NPC471896
0.8706	High Similarity	NPC111585
0.8706	High Similarity	NPC113989
0.8706	High Similarity	NPC120840
0.8706	High Similarity	NPC175628
0.8706	High Similarity	NPC148414
0.8675	High Similarity	NPC262085
0.8608	High Similarity	NPC280654
0.8608	High Similarity	NPC260385
0.8608	High Similarity	NPC4827
0.8608	High Similarity	NPC110094
0.8605	High Similarity	NPC60755
0.8605	High Similarity	NPC470590
0.8605	High Similarity	NPC285184
0.8605	High Similarity	NPC77099
0.8605	High Similarity	NPC26888
0.859	High Similarity	NPC180886
0.8588	High Similarity	NPC474889
0.8588	High Similarity	NPC474700
0.8588	High Similarity	NPC30522
0.8554	High Similarity	NPC76333
0.8537	High Similarity	NPC477373
0.8519	High Similarity	NPC278459
0.8519	High Similarity	NPC142244
0.8519	High Similarity	NPC473420
0.8506	High Similarity	NPC86368
0.8506	High Similarity	NPC169343
0.85	High Similarity	NPC199595
0.85	High Similarity	NPC477371
0.8488	Intermediate Similarity	NPC474728
0.8481	Intermediate Similarity	NPC471897
0.8481	Intermediate Similarity	NPC471899
0.8481	Intermediate Similarity	NPC107039
0.8471	Intermediate Similarity	NPC24816
0.8462	Intermediate Similarity	NPC279666
0.8462	Intermediate Similarity	NPC192540
0.8452	Intermediate Similarity	NPC322159
0.8434	Intermediate Similarity	NPC100391
0.8434	Intermediate Similarity	NPC165064
0.8434	Intermediate Similarity	NPC312660
0.8427	Intermediate Similarity	NPC327179
0.8415	Intermediate Similarity	NPC15910
0.8415	Intermediate Similarity	NPC296367
0.8415	Intermediate Similarity	NPC133391
0.8415	Intermediate Similarity	NPC240302
0.8409	Intermediate Similarity	NPC296164
0.8409	Intermediate Similarity	NPC184006
0.8409	Intermediate Similarity	NPC23621
0.8409	Intermediate Similarity	NPC159410
0.8409	Intermediate Similarity	NPC74751
0.8409	Intermediate Similarity	NPC78580
0.8375	Intermediate Similarity	NPC239098
0.8375	Intermediate Similarity	NPC74410
0.8372	Intermediate Similarity	NPC476733
0.8372	Intermediate Similarity	NPC215029
0.8372	Intermediate Similarity	NPC471342
0.8372	Intermediate Similarity	NPC5509
0.8372	Intermediate Similarity	NPC469866
0.8354	Intermediate Similarity	NPC69143
0.8354	Intermediate Similarity	NPC899
0.8354	Intermediate Similarity	NPC89294
0.8354	Intermediate Similarity	NPC309399
0.8353	Intermediate Similarity	NPC128644
0.8353	Intermediate Similarity	NPC173089
0.8353	Intermediate Similarity	NPC162107
0.8353	Intermediate Similarity	NPC158141
0.8353	Intermediate Similarity	NPC46912
0.8353	Intermediate Similarity	NPC96496
0.8353	Intermediate Similarity	NPC171722
0.8333	Intermediate Similarity	NPC241854
0.8333	Intermediate Similarity	NPC103958
0.8333	Intermediate Similarity	NPC306928
0.8333	Intermediate Similarity	NPC166797
0.8333	Intermediate Similarity	NPC283908
0.8333	Intermediate Similarity	NPC183503
0.8333	Intermediate Similarity	NPC476046
0.8333	Intermediate Similarity	NPC329738
0.8333	Intermediate Similarity	NPC251970
0.8333	Intermediate Similarity	NPC301065
0.8333	Intermediate Similarity	NPC161923
0.8315	Intermediate Similarity	NPC195715
0.8315	Intermediate Similarity	NPC474727
0.8315	Intermediate Similarity	NPC279974
0.8315	Intermediate Similarity	NPC23241
0.8315	Intermediate Similarity	NPC134067
0.8313	Intermediate Similarity	NPC470948
0.8313	Intermediate Similarity	NPC476100
0.8295	Intermediate Similarity	NPC476416
0.8293	Intermediate Similarity	NPC38350
0.8293	Intermediate Similarity	NPC474955
0.8293	Intermediate Similarity	NPC477372
0.8293	Intermediate Similarity	NPC90055
0.8293	Intermediate Similarity	NPC263272
0.8293	Intermediate Similarity	NPC274050
0.8293	Intermediate Similarity	NPC162632
0.8293	Intermediate Similarity	NPC476988
0.8293	Intermediate Similarity	NPC40228
0.8293	Intermediate Similarity	NPC14044
0.8293	Intermediate Similarity	NPC147066
0.8293	Intermediate Similarity	NPC221647
0.8293	Intermediate Similarity	NPC172309
0.8293	Intermediate Similarity	NPC267691
0.8293	Intermediate Similarity	NPC117960
0.8293	Intermediate Similarity	NPC201912
0.8293	Intermediate Similarity	NPC471898
0.8276	Intermediate Similarity	NPC198818
0.8272	Intermediate Similarity	NPC16394
0.8256	Intermediate Similarity	NPC182797
0.8256	Intermediate Similarity	NPC40552
0.8256	Intermediate Similarity	NPC183546
0.8256	Intermediate Similarity	NPC52169
0.8256	Intermediate Similarity	NPC294480
0.8256	Intermediate Similarity	NPC1753
0.8256	Intermediate Similarity	NPC246708
0.8256	Intermediate Similarity	NPC474474
0.8256	Intermediate Similarity	NPC474511
0.8256	Intermediate Similarity	NPC472870
0.825	Intermediate Similarity	NPC325946
0.825	Intermediate Similarity	NPC472300
0.825	Intermediate Similarity	NPC283619
0.825	Intermediate Similarity	NPC165711
0.8235	Intermediate Similarity	NPC476104
0.8235	Intermediate Similarity	NPC9892
0.8235	Intermediate Similarity	NPC264127
0.8235	Intermediate Similarity	NPC91525
0.8235	Intermediate Similarity	NPC155011
0.8235	Intermediate Similarity	NPC473226
0.8235	Intermediate Similarity	NPC10005
0.8235	Intermediate Similarity	NPC6979
0.8235	Intermediate Similarity	NPC329943
0.8228	Intermediate Similarity	NPC476795
0.8228	Intermediate Similarity	NPC476844
0.8222	Intermediate Similarity	NPC230151
0.8214	Intermediate Similarity	NPC96095
0.8202	Intermediate Similarity	NPC476415
0.8202	Intermediate Similarity	NPC474963
0.8193	Intermediate Similarity	NPC251779
0.8193	Intermediate Similarity	NPC260956
0.8193	Intermediate Similarity	NPC69101
0.8193	Intermediate Similarity	NPC73882
0.8182	Intermediate Similarity	NPC154101
0.8182	Intermediate Similarity	NPC91369
0.8182	Intermediate Similarity	NPC297265
0.8182	Intermediate Similarity	NPC470113
0.8171	Intermediate Similarity	NPC267517
0.8171	Intermediate Similarity	NPC2482
0.8161	Intermediate Similarity	NPC121798
0.8161	Intermediate Similarity	NPC274330
0.8161	Intermediate Similarity	NPC263393
0.8161	Intermediate Similarity	NPC130520
0.8161	Intermediate Similarity	NPC36668
0.8161	Intermediate Similarity	NPC143232
0.8161	Intermediate Similarity	NPC290972
0.8161	Intermediate Similarity	NPC474704
0.8161	Intermediate Similarity	NPC281524
0.8161	Intermediate Similarity	NPC25906
0.8161	Intermediate Similarity	NPC61543
0.8161	Intermediate Similarity	NPC118011
0.8161	Intermediate Similarity	NPC293048
0.8161	Intermediate Similarity	NPC225585
0.8161	Intermediate Similarity	NPC198664
0.8161	Intermediate Similarity	NPC174342
0.8161	Intermediate Similarity	NPC59263
0.8161	Intermediate Similarity	NPC475049
0.8161	Intermediate Similarity	NPC470588
0.8161	Intermediate Similarity	NPC270768
0.8161	Intermediate Similarity	NPC234346
0.8161	Intermediate Similarity	NPC127689
0.8161	Intermediate Similarity	NPC64872
0.8161	Intermediate Similarity	NPC477973
0.8161	Intermediate Similarity	NPC475921
0.8158	Intermediate Similarity	NPC36616
0.8158	Intermediate Similarity	NPC290445
0.8152	Intermediate Similarity	NPC167974
0.8148	Intermediate Similarity	NPC59436
0.8148	Intermediate Similarity	NPC275494
0.8148	Intermediate Similarity	NPC471409
0.8148	Intermediate Similarity	NPC35574
0.814	Intermediate Similarity	NPC102683
0.814	Intermediate Similarity	NPC474684
0.814	Intermediate Similarity	NPC136948
0.814	Intermediate Similarity	NPC18064
0.814	Intermediate Similarity	NPC68160

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 NPC327002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1469
0.2-0.3	3805
0.3-0.4	2430
0.4-0.5	737
0.5-0.6	305
0.6-0.7	200
0.7-0.8	61
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
0.8409	Intermediate Similarity	NPD7748	Approved
0.8295	Intermediate Similarity	NPD6399	Phase 3
0.8132	Intermediate Similarity	NPD7902	Approved
0.8132	Intermediate Similarity	NPD6083	Phase 2
0.8132	Intermediate Similarity	NPD6084	Phase 2
0.8111	Intermediate Similarity	NPD5695	Phase 3
0.8046	Intermediate Similarity	NPD6672	Approved
0.8046	Intermediate Similarity	NPD5737	Approved
0.8023	Intermediate Similarity	NPD6684	Approved
0.8023	Intermediate Similarity	NPD7334	Approved
0.8023	Intermediate Similarity	NPD7521	Approved
0.8023	Intermediate Similarity	NPD7146	Approved
0.8023	Intermediate Similarity	NPD6409	Approved
0.8023	Intermediate Similarity	NPD5330	Approved
0.7978	Intermediate Similarity	NPD7515	Phase 2
0.7849	Intermediate Similarity	NPD5696	Approved
0.7841	Intermediate Similarity	NPD6903	Approved
0.7841	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6098	Approved
0.7802	Intermediate Similarity	NPD7900	Approved
0.7802	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4786	Approved
0.7778	Intermediate Similarity	NPD6411	Approved
0.7765	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3667	Approved
0.7753	Intermediate Similarity	NPD6904	Approved
0.7753	Intermediate Similarity	NPD6673	Approved
0.7753	Intermediate Similarity	NPD6080	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD5284	Approved
0.7582	Intermediate Similarity	NPD6050	Approved
0.7582	Intermediate Similarity	NPD5281	Approved
0.7582	Intermediate Similarity	NPD8035	Phase 2
0.7582	Intermediate Similarity	NPD8034	Phase 2
0.7561	Intermediate Similarity	NPD8039	Approved
0.7558	Intermediate Similarity	NPD4223	Phase 3
0.7558	Intermediate Similarity	NPD4221	Approved
0.7556	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4753	Phase 2
0.7556	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6101	Approved
0.7551	Intermediate Similarity	NPD6402	Approved
0.7551	Intermediate Similarity	NPD7128	Approved
0.7551	Intermediate Similarity	NPD5739	Approved
0.7551	Intermediate Similarity	NPD6675	Approved
0.7529	Intermediate Similarity	NPD4695	Discontinued
0.7528	Intermediate Similarity	NPD3573	Approved
0.7527	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5329	Approved
0.7473	Intermediate Similarity	NPD5692	Phase 3
0.7444	Intermediate Similarity	NPD5208	Approved
0.7416	Intermediate Similarity	NPD3618	Phase 1
0.74	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD5693	Phase 1
0.7391	Intermediate Similarity	NPD5694	Approved
0.7386	Intermediate Similarity	NPD4197	Approved
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7363	Intermediate Similarity	NPD5328	Approved
0.7353	Intermediate Similarity	NPD8130	Phase 1
0.7327	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6373	Approved
0.7312	Intermediate Similarity	NPD5779	Approved
0.7312	Intermediate Similarity	NPD5778	Approved
0.7303	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5701	Approved
0.73	Intermediate Similarity	NPD5697	Approved
0.7292	Intermediate Similarity	NPD7638	Approved
0.7283	Intermediate Similarity	NPD5207	Approved
0.7282	Intermediate Similarity	NPD8297	Approved
0.7255	Intermediate Similarity	NPD7102	Approved
0.7255	Intermediate Similarity	NPD7290	Approved
0.7255	Intermediate Similarity	NPD6883	Approved
0.7228	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7222	Intermediate Similarity	NPD4689	Approved
0.7222	Intermediate Similarity	NPD4623	Approved
0.7222	Intermediate Similarity	NPD4688	Approved
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7222	Intermediate Similarity	NPD4519	Discontinued
0.7222	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4694	Approved
0.7222	Intermediate Similarity	NPD4138	Approved
0.7222	Intermediate Similarity	NPD5280	Approved
0.7222	Intermediate Similarity	NPD4690	Approved
0.7222	Intermediate Similarity	NPD5205	Approved
0.7222	Intermediate Similarity	NPD4693	Phase 3
0.7216	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD7640	Approved
0.7204	Intermediate Similarity	NPD6079	Approved
0.7184	Intermediate Similarity	NPD6649	Approved
0.7184	Intermediate Similarity	NPD6617	Approved
0.7184	Intermediate Similarity	NPD6847	Approved
0.7184	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6869	Approved
0.7174	Intermediate Similarity	NPD6051	Approved
0.7158	Intermediate Similarity	NPD5210	Approved
0.7158	Intermediate Similarity	NPD4629	Approved
0.7157	Intermediate Similarity	NPD6013	Approved
0.7157	Intermediate Similarity	NPD6014	Approved
0.7157	Intermediate Similarity	NPD6012	Approved
0.7128	Intermediate Similarity	NPD4202	Approved
0.7115	Intermediate Similarity	NPD6882	Approved
0.7111	Intermediate Similarity	NPD1694	Approved
0.7093	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3617	Approved
0.7083	Intermediate Similarity	NPD7732	Phase 3
0.7083	Intermediate Similarity	NPD7614	Phase 1
0.7079	Intermediate Similarity	NPD4788	Approved
0.7053	Intermediate Similarity	NPD6001	Approved
0.7045	Intermediate Similarity	NPD4692	Approved
0.7045	Intermediate Similarity	NPD5369	Approved
0.7045	Intermediate Similarity	NPD4139	Approved
0.7011	Intermediate Similarity	NPD7645	Phase 2
0.701	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD7331	Phase 2
0.6988	Remote Similarity	NPD4243	Approved
0.6979	Remote Similarity	NPD5654	Approved
0.6966	Remote Similarity	NPD6435	Approved
0.6961	Remote Similarity	NPD6412	Phase 2
0.6941	Remote Similarity	NPD3702	Approved
0.6941	Remote Similarity	NPD6942	Approved
0.6941	Remote Similarity	NPD7339	Approved
0.6932	Remote Similarity	NPD7525	Registered
0.6907	Remote Similarity	NPD5221	Approved
0.6907	Remote Similarity	NPD5222	Approved
0.6907	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4697	Phase 3
0.6893	Remote Similarity	NPD6686	Approved
0.6889	Remote Similarity	NPD7154	Phase 3
0.6889	Remote Similarity	NPD5362	Discontinued
0.6875	Remote Similarity	NPD7341	Phase 2
0.6869	Remote Similarity	NPD5285	Approved
0.6869	Remote Similarity	NPD5286	Approved
0.6869	Remote Similarity	NPD4700	Approved
0.6869	Remote Similarity	NPD4696	Approved
0.6863	Remote Similarity	NPD6008	Approved
0.686	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7115	Discovery
0.6848	Remote Similarity	NPD6422	Discontinued
0.6842	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD5173	Approved
0.6837	Remote Similarity	NPD5959	Approved
0.6832	Remote Similarity	NPD6052	Approved
0.6827	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6924	Approved
0.6824	Remote Similarity	NPD4785	Approved
0.6824	Remote Similarity	NPD4784	Approved
0.6824	Remote Similarity	NPD6926	Approved
0.6818	Remote Similarity	NPD4195	Approved
0.68	Remote Similarity	NPD5223	Approved
0.6789	Remote Similarity	NPD6335	Approved
0.6768	Remote Similarity	NPD4225	Approved
0.6759	Remote Similarity	NPD6274	Approved
0.6759	Remote Similarity	NPD6868	Approved
0.6747	Remote Similarity	NPD4137	Phase 3
0.6742	Remote Similarity	NPD5368	Approved
0.6742	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4096	Approved
0.6733	Remote Similarity	NPD4633	Approved
0.6733	Remote Similarity	NPD5224	Approved
0.6733	Remote Similarity	NPD5211	Phase 2
0.6733	Remote Similarity	NPD5225	Approved
0.6733	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD4632	Approved
0.6727	Remote Similarity	NPD7100	Approved
0.6727	Remote Similarity	NPD7101	Approved
0.6703	Remote Similarity	NPD6695	Phase 3
0.67	Remote Similarity	NPD6404	Discontinued
0.6697	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4691	Approved
0.6636	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD6314	Approved
0.6636	Remote Similarity	NPD6313	Approved
0.6635	Remote Similarity	NPD6614	Approved
0.663	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5733	Approved
0.6628	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6908	Approved
0.6607	Remote Similarity	NPD6909	Approved
0.6604	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5141	Approved
0.6598	Remote Similarity	NPD5133	Approved
0.6596	Remote Similarity	NPD7750	Discontinued
0.6593	Remote Similarity	NPD4270	Approved
0.6593	Remote Similarity	NPD4269	Approved
0.6591	Remote Similarity	NPD6116	Phase 1
0.6588	Remote Similarity	NPD5777	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