NPASS Compound

Structure

NPC472814 OpenBabel07101719152D 23 25 0 0 1 0 0 0 0 0999 V2000 3.3147 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7788 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2788 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -0.6636 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 3.3147 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4487 0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9128 0.8364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4487 1.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 1 0 0 0 16 21 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	4.347
LogD:	3.927
LogS:	-3.977
# Rotatable Bonds:	3
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.378
Fsp3:	0.7
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:	-4.651
MDCK Permeability:	2.0383240553201176e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.934
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.79
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	90.1852035522461%
Volume Distribution (VD):	1.633
Pgp-substrate:	11.359946250915527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.569
CYP2C9-inhibitor:	0.435
CYP2C9-substrate:	0.638
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.664
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	13.896
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.378
Carcinogencity:	0.922
Eye Corrosion:	0.008
Eye Irritation:	0.08
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472814

Natural Product ID:	NPC472814
*Common Name:**	(12S)-12-Hydroxylabda-8(17),13-Dien-15-16-Olide
IUPAC Name:	4-[(1S)-2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	NNNUJNWMFLYQTF-OGNFBWPZSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-7-17-19(2,3)9-5-10-20(17,4)15(13)12-16(21)14-8-11-23-18(14)22/h8,15-17,21H,1,5-7,9-12H2,2-4H3/t15-,16-,17-,20+/m0/s1
SMILES:	C=C1CC[C@@H]2[C@]([C@H]1C[C@@H](C1=CCOC1=O)O)(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586267
PubChem CID:	16081511
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO32474	vitex vestita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26034885]

☑ 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	46
Others	4

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3
Organism	43

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	GI	=	71.0	%	PMID[506198]
NPT171	Cell Line	MRC5	Homo sapiens	GI	=	0.0	%	PMID[506198]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	69.0	%	PMID[506198]
NPT393	Cell Line	HCT-116	Homo sapiens	GI	=	0.0	%	PMID[506198]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	25000.0	nM	PMID[506198]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	50000.0	nM	PMID[506198]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	=	25000.0	nM	PMID[506198]
NPT4843	Organism	Corynebacterium striatum	Corynebacterium striatum	MIC	=	50000.0	nM	PMID[506198]
NPT4075	Organism	Enterococcus avium	Enterococcus avium	MIC	>	79000.0	nM	PMID[506198]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	79000.0	nM	PMID[506198]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	50000.0	nM	PMID[506198]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	79000.0	nM	PMID[506198]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	79000.0	nM	PMID[506198]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	50000.0	nM	PMID[506198]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	>	79000.0	nM	PMID[506198]
NPT4844	Organism	Enterococcus gallinarum	Enterococcus gallinarum	MIC	=	50000.0	nM	PMID[506198]
NPT3721	Organism	Enterococcus hirae	Enterococcus hirae	MIC	>	79000.0	nM	PMID[506198]
NPT4845	Organism	Listeria innocua	Listeria innocua	MIC	=	50000.0	nM	PMID[506198]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	>	79000.0	nM	PMID[506198]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	MIC	=	50000.0	nM	PMID[506198]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	79000.0	nM	PMID[506198]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50000.0	nM	PMID[506198]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	50000.0	nM	PMID[506198]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	79000.0	nM	PMID[506198]
NPT4839	Organism	Staphylococcus intermedius	Staphylococcus intermedius	MIC	=	50000.0	nM	PMID[506198]
NPT4840	Organism	Staphylococcus lugdunensis	Staphylococcus lugdunensis	MIC	=	79000.0	nM	PMID[506198]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	>	79000.0	nM	PMID[506198]
NPT4428	Organism	Staphylococcus sciuri	Staphylococcus sciuri	MIC	>	79000.0	nM	PMID[506198]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	50000.0	nM	PMID[506198]

☑ 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 NPC472814 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	182
0.1-0.2	1005
0.2-0.3	3915
0.3-0.4	8372
0.4-0.5	13486
0.5-0.6	6734
0.6-0.7	6479
0.7-0.8	2297
0.8-0.85	179
0.85-0.9	32
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177037
0.9655	High Similarity	NPC115021
0.9551	High Similarity	NPC242848
0.9444	High Similarity	NPC475709
0.9425	High Similarity	NPC51486
0.9294	High Similarity	NPC106416
0.9294	High Similarity	NPC86316
0.9213	High Similarity	NPC139692
0.9121	High Similarity	NPC134072
0.9121	High Similarity	NPC234993
0.9091	High Similarity	NPC174342
0.907	High Similarity	NPC65661
0.9059	High Similarity	NPC311070
0.9011	High Similarity	NPC209355
0.8889	High Similarity	NPC477783
0.8876	High Similarity	NPC5509
0.8876	High Similarity	NPC251528
0.8864	High Similarity	NPC312561
0.883	High Similarity	NPC476299
0.883	High Similarity	NPC474012
0.8778	High Similarity	NPC477782
0.8723	High Similarity	NPC316598
0.8721	High Similarity	NPC200513
0.8667	High Similarity	NPC50488
0.8667	High Similarity	NPC474396
0.8632	High Similarity	NPC117685
0.8617	High Similarity	NPC474343
0.8617	High Similarity	NPC53844
0.8571	High Similarity	NPC281942
0.8571	High Similarity	NPC8062
0.8571	High Similarity	NPC182136
0.8571	High Similarity	NPC232426
0.8556	High Similarity	NPC104560
0.8556	High Similarity	NPC472810
0.8556	High Similarity	NPC472809
0.8539	High Similarity	NPC131813
0.8526	High Similarity	NPC124512
0.8526	High Similarity	NPC159763
0.8526	High Similarity	NPC278386
0.8511	High Similarity	NPC240673
0.8511	High Similarity	NPC17578
0.8495	Intermediate Similarity	NPC474555
0.8495	Intermediate Similarity	NPC53685
0.8478	Intermediate Similarity	NPC141831
0.8478	Intermediate Similarity	NPC72845
0.8462	Intermediate Similarity	NPC79027
0.8438	Intermediate Similarity	NPC201406
0.8427	Intermediate Similarity	NPC189311
0.8421	Intermediate Similarity	NPC253826
0.8421	Intermediate Similarity	NPC73911
0.8409	Intermediate Similarity	NPC42476
0.8391	Intermediate Similarity	NPC229584
0.8391	Intermediate Similarity	NPC40228
0.8391	Intermediate Similarity	NPC14203
0.8387	Intermediate Similarity	NPC162615
0.8387	Intermediate Similarity	NPC152778
0.8387	Intermediate Similarity	NPC472303
0.8387	Intermediate Similarity	NPC205034
0.837	Intermediate Similarity	NPC310479
0.837	Intermediate Similarity	NPC78973
0.8367	Intermediate Similarity	NPC476889
0.8367	Intermediate Similarity	NPC112009
0.8352	Intermediate Similarity	NPC226863
0.8351	Intermediate Similarity	NPC303559
0.8351	Intermediate Similarity	NPC471412
0.8351	Intermediate Similarity	NPC471075
0.8333	Intermediate Similarity	NPC329692
0.8333	Intermediate Similarity	NPC194417
0.8316	Intermediate Similarity	NPC202833
0.8316	Intermediate Similarity	NPC29952
0.8316	Intermediate Similarity	NPC184065
0.83	Intermediate Similarity	NPC91034
0.8298	Intermediate Similarity	NPC474554
0.8298	Intermediate Similarity	NPC57117
0.8298	Intermediate Similarity	NPC84893
0.828	Intermediate Similarity	NPC303697
0.828	Intermediate Similarity	NPC289479
0.8265	Intermediate Similarity	NPC40918
0.8265	Intermediate Similarity	NPC476081
0.8265	Intermediate Similarity	NPC476890
0.8261	Intermediate Similarity	NPC470734
0.8261	Intermediate Similarity	NPC168131
0.8256	Intermediate Similarity	NPC239098
0.8256	Intermediate Similarity	NPC198240
0.8247	Intermediate Similarity	NPC54705
0.8247	Intermediate Similarity	NPC476767
0.8247	Intermediate Similarity	NPC471413
0.8242	Intermediate Similarity	NPC171722
0.8229	Intermediate Similarity	NPC208094
0.8229	Intermediate Similarity	NPC156546
0.8222	Intermediate Similarity	NPC30984
0.8222	Intermediate Similarity	NPC52628
0.8218	Intermediate Similarity	NPC476765
0.8218	Intermediate Similarity	NPC220155
0.8211	Intermediate Similarity	NPC183012
0.8211	Intermediate Similarity	NPC293052
0.8202	Intermediate Similarity	NPC472377
0.8202	Intermediate Similarity	NPC193198
0.8191	Intermediate Similarity	NPC472812
0.8191	Intermediate Similarity	NPC472871
0.8182	Intermediate Similarity	NPC329345
0.8182	Intermediate Similarity	NPC475526
0.8182	Intermediate Similarity	NPC72151
0.8182	Intermediate Similarity	NPC325031
0.8182	Intermediate Similarity	NPC282293
0.8182	Intermediate Similarity	NPC120321
0.8182	Intermediate Similarity	NPC473283
0.8182	Intermediate Similarity	NPC471938
0.8182	Intermediate Similarity	NPC180204
0.8172	Intermediate Similarity	NPC221111
0.8172	Intermediate Similarity	NPC280149
0.8163	Intermediate Similarity	NPC476888
0.8163	Intermediate Similarity	NPC469657
0.8163	Intermediate Similarity	NPC93744
0.8163	Intermediate Similarity	NPC244456
0.8163	Intermediate Similarity	NPC282524
0.8161	Intermediate Similarity	NPC150646
0.8155	Intermediate Similarity	NPC474315
0.8152	Intermediate Similarity	NPC472870
0.8144	Intermediate Similarity	NPC108368
0.8144	Intermediate Similarity	NPC57079
0.8144	Intermediate Similarity	NPC98868
0.8144	Intermediate Similarity	NPC23364
0.814	Intermediate Similarity	NPC61952
0.8132	Intermediate Similarity	NPC261721
0.8132	Intermediate Similarity	NPC474062
0.8125	Intermediate Similarity	NPC473153
0.8125	Intermediate Similarity	NPC16967
0.8125	Intermediate Similarity	NPC476797
0.8125	Intermediate Similarity	NPC29152
0.8119	Intermediate Similarity	NPC67321
0.8119	Intermediate Similarity	NPC187435
0.8111	Intermediate Similarity	NPC30486
0.8111	Intermediate Similarity	NPC475100
0.8111	Intermediate Similarity	NPC31086
0.8111	Intermediate Similarity	NPC149869
0.8105	Intermediate Similarity	NPC469697
0.8105	Intermediate Similarity	NPC476415
0.8105	Intermediate Similarity	NPC470697
0.8105	Intermediate Similarity	NPC191521
0.81	Intermediate Similarity	NPC296950
0.81	Intermediate Similarity	NPC146731
0.81	Intermediate Similarity	NPC471937
0.8085	Intermediate Similarity	NPC470113
0.8085	Intermediate Similarity	NPC186363
0.8085	Intermediate Similarity	NPC472811
0.8085	Intermediate Similarity	NPC233345
0.8081	Intermediate Similarity	NPC471914
0.8081	Intermediate Similarity	NPC114540
0.8081	Intermediate Similarity	NPC320447
0.8081	Intermediate Similarity	NPC155332
0.8081	Intermediate Similarity	NPC162973
0.8081	Intermediate Similarity	NPC32577
0.8068	Intermediate Similarity	NPC271104
0.8061	Intermediate Similarity	NPC477720
0.8061	Intermediate Similarity	NPC47024
0.8061	Intermediate Similarity	NPC472644
0.8061	Intermediate Similarity	NPC174314
0.8061	Intermediate Similarity	NPC306856
0.8061	Intermediate Similarity	NPC477521
0.8058	Intermediate Similarity	NPC29133
0.8058	Intermediate Similarity	NPC476766
0.8058	Intermediate Similarity	NPC179642
0.8046	Intermediate Similarity	NPC59436
0.8043	Intermediate Similarity	NPC181103
0.8041	Intermediate Similarity	NPC287668
0.8041	Intermediate Similarity	NPC2049
0.8039	Intermediate Similarity	NPC177524
0.8039	Intermediate Similarity	NPC306265
0.8039	Intermediate Similarity	NPC219900
0.8039	Intermediate Similarity	NPC392
0.8022	Intermediate Similarity	NPC473251
0.8022	Intermediate Similarity	NPC261380
0.8022	Intermediate Similarity	NPC42586
0.8022	Intermediate Similarity	NPC471795
0.8021	Intermediate Similarity	NPC295347
0.8021	Intermediate Similarity	NPC476174
0.802	Intermediate Similarity	NPC266570
0.802	Intermediate Similarity	NPC34768
0.802	Intermediate Similarity	NPC1679
0.8	Intermediate Similarity	NPC166346
0.8	Intermediate Similarity	NPC476416
0.8	Intermediate Similarity	NPC159533
0.8	Intermediate Similarity	NPC95899
0.8	Intermediate Similarity	NPC122056
0.8	Intermediate Similarity	NPC476237
0.8	Intermediate Similarity	NPC475657
0.8	Intermediate Similarity	NPC53555
0.8	Intermediate Similarity	NPC215893
0.8	Intermediate Similarity	NPC79945
0.8	Intermediate Similarity	NPC22611
0.7981	Intermediate Similarity	NPC470961
0.798	Intermediate Similarity	NPC475099
0.798	Intermediate Similarity	NPC472643
0.798	Intermediate Similarity	NPC115899
0.7979	Intermediate Similarity	NPC473448
0.7979	Intermediate Similarity	NPC472866
0.7979	Intermediate Similarity	NPC469368
0.7979	Intermediate Similarity	NPC476437
0.7979	Intermediate Similarity	NPC232202

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 NPC472814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1325
0.2-0.3	3444
0.3-0.4	2724
0.4-0.5	963
0.5-0.6	239
0.6-0.7	235
0.7-0.8	60
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8721	High Similarity	NPD4752	Clinical (unspecified phase)
0.8526	High Similarity	NPD4225	Approved
0.8039	Intermediate Similarity	NPD6686	Approved
0.7879	Intermediate Similarity	NPD7640	Approved
0.7879	Intermediate Similarity	NPD7639	Approved
0.7789	Intermediate Similarity	NPD5785	Approved
0.7778	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD7638	Approved
0.7653	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1694	Approved
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7527	Intermediate Similarity	NPD3666	Approved
0.7527	Intermediate Similarity	NPD3665	Phase 1
0.7527	Intermediate Similarity	NPD3133	Approved
0.7526	Intermediate Similarity	NPD7637	Suspended
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD5779	Approved
0.7449	Intermediate Similarity	NPD5778	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6903	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD3618	Phase 1
0.7347	Intermediate Similarity	NPD7515	Phase 2
0.7347	Intermediate Similarity	NPD6411	Approved
0.734	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3667	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7264	Intermediate Similarity	NPD5697	Approved
0.7263	Intermediate Similarity	NPD5363	Approved
0.7255	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD6371	Approved
0.7216	Intermediate Similarity	NPD6672	Approved
0.7216	Intermediate Similarity	NPD5737	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7196	Intermediate Similarity	NPD6899	Approved
0.7196	Intermediate Similarity	NPD6881	Approved
0.7188	Intermediate Similarity	NPD4623	Approved
0.7188	Intermediate Similarity	NPD4519	Discontinued
0.7188	Intermediate Similarity	NPD5279	Phase 3
0.7172	Intermediate Similarity	NPD6079	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.717	Intermediate Similarity	NPD6675	Approved
0.717	Intermediate Similarity	NPD7128	Approved
0.717	Intermediate Similarity	NPD6402	Approved
0.717	Intermediate Similarity	NPD5739	Approved
0.7158	Intermediate Similarity	NPD4786	Approved
0.7157	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.7128	Intermediate Similarity	NPD5209	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7071	Intermediate Similarity	NPD46	Approved
0.7071	Intermediate Similarity	NPD6698	Approved
0.7065	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD6883	Approved
0.7053	Intermediate Similarity	NPD7154	Phase 3
0.7048	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD7320	Approved
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6373	Approved
0.6972	Remote Similarity	NPD6372	Approved
0.6961	Remote Similarity	NPD4629	Approved
0.6961	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4269	Approved
0.6947	Remote Similarity	NPD4221	Approved
0.6947	Remote Similarity	NPD4270	Approved
0.6939	Remote Similarity	NPD3573	Approved
0.6937	Remote Similarity	NPD8297	Approved
0.6937	Remote Similarity	NPD6882	Approved
0.6931	Remote Similarity	NPD4202	Approved
0.6923	Remote Similarity	NPD8039	Approved
0.6917	Remote Similarity	NPD7319	Approved
0.6916	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5221	Approved
0.6893	Remote Similarity	NPD5222	Approved
0.6875	Remote Similarity	NPD5362	Discontinued
0.6869	Remote Similarity	NPD5208	Approved
0.6863	Remote Similarity	NPD7900	Approved
0.6863	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5285	Approved
0.6857	Remote Similarity	NPD5286	Approved
0.6857	Remote Similarity	NPD4696	Approved
0.6837	Remote Similarity	NPD5786	Approved
0.6827	Remote Similarity	NPD5173	Approved
0.6827	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6804	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD6051	Approved
0.68	Remote Similarity	NPD6080	Approved
0.68	Remote Similarity	NPD6673	Approved
0.68	Remote Similarity	NPD6904	Approved
0.6789	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6053	Discontinued
0.6754	Remote Similarity	NPD6274	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4252	Approved
0.6735	Remote Similarity	NPD5329	Approved
0.6731	Remote Similarity	NPD4697	Phase 3
0.6729	Remote Similarity	NPD5226	Approved
0.6729	Remote Similarity	NPD5225	Approved
0.6729	Remote Similarity	NPD4633	Approved
0.6729	Remote Similarity	NPD5224	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6701	Remote Similarity	NPD6695	Phase 3
0.6701	Remote Similarity	NPD4788	Approved
0.6699	Remote Similarity	NPD5282	Discontinued
0.6698	Remote Similarity	NPD6404	Discontinued
0.6698	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3668	Phase 3
0.6633	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6929	Approved
0.6609	Remote Similarity	NPD6868	Approved
0.6607	Remote Similarity	NPD4634	Approved
0.6598	Remote Similarity	NPD6435	Approved
0.6583	Remote Similarity	NPD7492	Approved
0.6581	Remote Similarity	NPD7100	Approved
0.6581	Remote Similarity	NPD7101	Approved
0.6579	Remote Similarity	NPD4632	Approved
0.6577	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7839	Suspended
0.6569	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD5207	Approved
0.6569	Remote Similarity	NPD5692	Phase 3
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4821	Approved
0.6562	Remote Similarity	NPD4822	Approved
0.6562	Remote Similarity	NPD4819	Approved
0.6562	Remote Similarity	NPD4820	Approved
0.6562	Remote Similarity	NPD6930	Phase 2
0.6562	Remote Similarity	NPD6931	Approved
0.6552	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD6001	Approved
0.6529	Remote Similarity	NPD6616	Approved
0.6526	Remote Similarity	NPD4271	Approved
0.6526	Remote Similarity	NPD4268	Approved
0.6525	Remote Similarity	NPD6054	Approved
0.6505	Remote Similarity	NPD5694	Approved
0.6505	Remote Similarity	NPD6050	Approved
0.65	Remote Similarity	NPD5280	Approved
0.65	Remote Similarity	NPD4694	Approved
0.6496	Remote Similarity	NPD6335	Approved
0.6496	Remote Similarity	NPD6313	Approved
0.6496	Remote Similarity	NPD7328	Approved
0.6496	Remote Similarity	NPD7327	Approved
0.6496	Remote Similarity	NPD6314	Approved
0.6489	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4691	Approved
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7078	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