NPASS Compound

Structure

NPC475414 OpenBabel07101718322D 44 47 0 0 1 0 0 0 0 0999 V2000 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6986 -0.8560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6805 0.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 5.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 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 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9761 -1.0371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 -1.1303 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 3.8601 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7851 -0.4493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4533 -0.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0625 -0.6303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 2 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 -2.3660 4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 O 0 0 0 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 1 11 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 34 1 0 0 0 0 6 34 1 0 0 0 0 10 42 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 2 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 35 1 0 0 0 0 17 36 1 0 0 0 0 18 22 2 0 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 20 30 1 0 0 0 0 21 24 1 0 0 0 0 21 43 1 0 0 0 0 23 4 1 1 0 0 0 23 32 1 0 0 0 0 24 19 1 1 0 0 0 24 26 1 0 0 0 0 25 18 1 6 0 0 0 25 43 1 0 0 0 0 26 35 1 6 0 0 0 27 35 1 0 0 0 0 27 37 1 0 0 0 0 28 36 1 1 0 0 0 28 37 1 0 0 0 0 29 34 1 0 0 0 0 29 36 1 6 0 0 0 30 37 1 6 0 0 0 30 44 1 0 0 0 0 31 38 2 0 0 0 0 31 42 1 0 0 0 0 32 33 1 0 0 0 0 32 39 1 6 0 0 0 33 40 2 0 0 0 0 33 44 1 0 0 0 0 34 41 1 0 0 0 0 35 7 1 6 0 0 0 36 8 1 1 0 0 0 37 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.43
Volume:	665.268
LogP:	5.555
LogD:	3.773
LogS:	-4.361
# Rotatable Bonds:	12
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	5.704
Fsp3:	0.838
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.725
MDCK Permeability:	1.6194613635889255e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.834
30% Bioavailability (F30%):	0.307

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	97.2172622680664%
Volume Distribution (VD):	2.094
Pgp-substrate:	3.857003927230835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.884
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	7.496
Half-life (T1/2):	0.499

ADMET: Toxicity

hERG Blockers:	0.45
Human Hepatotoxicity (H-HT):	0.769
Drug-inuced Liver Injury (DILI):	0.293
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.928
Carcinogencity:	0.106
Eye Corrosion:	0.005
Eye Irritation:	0.02
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC475414

Natural Product ID:	NPC475414
*Common Name:**	Argentinic Acid A Methyl Ester
IUPAC Name:	[(3S,3aS,5aR,6R,7S,9R,9aR)-7-(2-hydroxypropan-2-yl)-6-(3-methoxy-3-oxopropyl)-3a,6,9a-trimethyl-3-[(3S,5S)-5-(2-methylprop-1-enyl)oxolan-3-yl]-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-9-yl] (2R,3R)-2-hydroxy-3-methylpentanoate
Synonyms:	Argentinic Acid A Methyl Ester
Standard InCHIKey:	SCOHMQDRAZPUAU-ZCAFCYEMSA-N
Standard InCHI:	InChI=1S/C37H60O7/c1-11-23(4)32(39)33(40)44-30-20-29(34(5,6)41)36(8,17-15-31(38)42-10)28-14-16-35(7)26(12-13-27(35)37(28,30)9)24-19-25(43-21-24)18-22(2)3/h13,18,23-26,28-30,32,39,41H,11-12,14-17,19-21H2,1-10H3/t23-,24-,25-,26+,28-,29-,30-,32-,35+,36-,37+/m1/s1
SMILES:	COC(=O)CC[C@@]1(C)[C@H](C[C@H]([C@@]2([C@@H]1CC[C@@]1(C2=CC[C@H]1[C@H]1CO[C@@H](C1)C=C(C)C)C)C)OC(=O)[C@@H]([C@@H](CC)C)O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505139
PubChem CID:	44566303
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32953	aaglaia argentea	Species	n.a.	n.a.	bark	n.a.	n.a.	PMID[10395505]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[524835]

☑ 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 NPC475414 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	195
0.1-0.2	1104
0.2-0.3	3822
0.3-0.4	8649
0.4-0.5	12727
0.5-0.6	5975
0.6-0.7	6796
0.7-0.8	3272
0.8-0.85	137
0.85-0.9	12
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC173172
0.9898	High Similarity	NPC475176
0.9604	High Similarity	NPC475134
0.9604	High Similarity	NPC475563
0.951	High Similarity	NPC473921
0.951	High Similarity	NPC475480
0.951	High Similarity	NPC475668
0.9118	High Similarity	NPC131665
0.9118	High Similarity	NPC255387
0.8762	High Similarity	NPC5475
0.8762	High Similarity	NPC173905
0.8762	High Similarity	NPC472216
0.8762	High Similarity	NPC284828
0.8692	High Similarity	NPC470063
0.8529	High Similarity	NPC473510
0.8462	Intermediate Similarity	NPC476237
0.8462	Intermediate Similarity	NPC324001
0.8462	Intermediate Similarity	NPC36688
0.8411	Intermediate Similarity	NPC475065
0.8396	Intermediate Similarity	NPC67321
0.8396	Intermediate Similarity	NPC187435
0.835	Intermediate Similarity	NPC230546
0.835	Intermediate Similarity	NPC476303
0.8333	Intermediate Similarity	NPC210337
0.8318	Intermediate Similarity	NPC472218
0.8318	Intermediate Similarity	NPC318363
0.8318	Intermediate Similarity	NPC473482
0.8318	Intermediate Similarity	NPC472219
0.8318	Intermediate Similarity	NPC472217
0.8318	Intermediate Similarity	NPC475418
0.8317	Intermediate Similarity	NPC37787
0.8317	Intermediate Similarity	NPC469329
0.8317	Intermediate Similarity	NPC473415
0.8317	Intermediate Similarity	NPC180557
0.8317	Intermediate Similarity	NPC30677
0.8302	Intermediate Similarity	NPC477125
0.8302	Intermediate Similarity	NPC472655
0.8286	Intermediate Similarity	NPC112009
0.8286	Intermediate Similarity	NPC180204
0.8269	Intermediate Similarity	NPC303559
0.8241	Intermediate Similarity	NPC218853
0.8241	Intermediate Similarity	NPC42662
0.8235	Intermediate Similarity	NPC88009
0.823	Intermediate Similarity	NPC477071
0.8224	Intermediate Similarity	NPC473173
0.8224	Intermediate Similarity	NPC329048
0.8224	Intermediate Similarity	NPC330011
0.8224	Intermediate Similarity	NPC475294
0.8224	Intermediate Similarity	NPC301666
0.8224	Intermediate Similarity	NPC469318
0.8214	Intermediate Similarity	NPC473590
0.8214	Intermediate Similarity	NPC284068
0.8208	Intermediate Similarity	NPC258532
0.8208	Intermediate Similarity	NPC471293
0.819	Intermediate Similarity	NPC469316
0.819	Intermediate Similarity	NPC155332
0.819	Intermediate Similarity	NPC114540
0.819	Intermediate Similarity	NPC476081
0.819	Intermediate Similarity	NPC32577
0.8173	Intermediate Similarity	NPC201406
0.8173	Intermediate Similarity	NPC473176
0.8165	Intermediate Similarity	NPC472215
0.8165	Intermediate Similarity	NPC472214
0.8165	Intermediate Similarity	NPC101450
0.8165	Intermediate Similarity	NPC5284
0.8155	Intermediate Similarity	NPC254496
0.8155	Intermediate Similarity	NPC285513
0.8148	Intermediate Similarity	NPC306265
0.8148	Intermediate Similarity	NPC258323
0.8142	Intermediate Similarity	NPC311554
0.8142	Intermediate Similarity	NPC257457
0.8137	Intermediate Similarity	NPC53565
0.8137	Intermediate Similarity	NPC279974
0.8131	Intermediate Similarity	NPC475494
0.812	Intermediate Similarity	NPC15095
0.8119	Intermediate Similarity	NPC470224
0.8119	Intermediate Similarity	NPC472871
0.8119	Intermediate Similarity	NPC53555
0.8113	Intermediate Similarity	NPC474124
0.8113	Intermediate Similarity	NPC176883
0.8113	Intermediate Similarity	NPC474775
0.8113	Intermediate Similarity	NPC194323
0.81	Intermediate Similarity	NPC471896
0.8095	Intermediate Similarity	NPC476897
0.8095	Intermediate Similarity	NPC54909
0.8095	Intermediate Similarity	NPC475617
0.8095	Intermediate Similarity	NPC233012
0.8077	Intermediate Similarity	NPC471784
0.8077	Intermediate Similarity	NPC303777
0.8073	Intermediate Similarity	NPC141350
0.8073	Intermediate Similarity	NPC41405
0.807	Intermediate Similarity	NPC469380
0.8058	Intermediate Similarity	NPC307164
0.8058	Intermediate Similarity	NPC235053
0.8058	Intermediate Similarity	NPC471777
0.8056	Intermediate Similarity	NPC473284
0.8056	Intermediate Similarity	NPC144459
0.8056	Intermediate Similarity	NPC59530
0.8053	Intermediate Similarity	NPC475323
0.8053	Intermediate Similarity	NPC470493
0.8053	Intermediate Similarity	NPC183580
0.8053	Intermediate Similarity	NPC473656
0.8053	Intermediate Similarity	NPC312824
0.8039	Intermediate Similarity	NPC240617
0.8039	Intermediate Similarity	NPC159410
0.8039	Intermediate Similarity	NPC471720
0.8037	Intermediate Similarity	NPC473175
0.8037	Intermediate Similarity	NPC474550
0.8037	Intermediate Similarity	NPC475585
0.8037	Intermediate Similarity	NPC473577
0.8037	Intermediate Similarity	NPC473543
0.8036	Intermediate Similarity	NPC178289
0.802	Intermediate Similarity	NPC471747
0.802	Intermediate Similarity	NPC26888
0.802	Intermediate Similarity	NPC233345
0.802	Intermediate Similarity	NPC186363
0.802	Intermediate Similarity	NPC473166
0.802	Intermediate Similarity	NPC189520
0.8019	Intermediate Similarity	NPC476471
0.8019	Intermediate Similarity	NPC475344
0.8018	Intermediate Similarity	NPC473877
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC6206
0.8	Intermediate Similarity	NPC167974
0.8	Intermediate Similarity	NPC470074
0.8	Intermediate Similarity	NPC241935
0.8	Intermediate Similarity	NPC266955
0.8	Intermediate Similarity	NPC250956
0.8	Intermediate Similarity	NPC269267
0.8	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC279478
0.7982	Intermediate Similarity	NPC709
0.7982	Intermediate Similarity	NPC88701
0.7982	Intermediate Similarity	NPC50774
0.7981	Intermediate Similarity	NPC73911
0.7981	Intermediate Similarity	NPC291634
0.798	Intermediate Similarity	NPC166857
0.7965	Intermediate Similarity	NPC474046
0.7965	Intermediate Similarity	NPC470628
0.7965	Intermediate Similarity	NPC259306
0.7965	Intermediate Similarity	NPC474734
0.7963	Intermediate Similarity	NPC475290
0.7963	Intermediate Similarity	NPC470055
0.7963	Intermediate Similarity	NPC127609
0.7963	Intermediate Similarity	NPC470056
0.7961	Intermediate Similarity	NPC134067
0.7961	Intermediate Similarity	NPC183012
0.7949	Intermediate Similarity	NPC41129
0.7946	Intermediate Similarity	NPC469496
0.7946	Intermediate Similarity	NPC469463
0.7946	Intermediate Similarity	NPC477126
0.7946	Intermediate Similarity	NPC469454
0.7944	Intermediate Similarity	NPC473523
0.7944	Intermediate Similarity	NPC222153
0.7944	Intermediate Similarity	NPC120321
0.7941	Intermediate Similarity	NPC139692
0.7941	Intermediate Similarity	NPC141497
0.7941	Intermediate Similarity	NPC170220
0.7941	Intermediate Similarity	NPC107674
0.7934	Intermediate Similarity	NPC34963
0.7925	Intermediate Similarity	NPC471412
0.7925	Intermediate Similarity	NPC115899
0.7925	Intermediate Similarity	NPC235142
0.7921	Intermediate Similarity	NPC175628
0.7921	Intermediate Similarity	NPC472307
0.7921	Intermediate Similarity	NPC111585
0.7921	Intermediate Similarity	NPC148414
0.7917	Intermediate Similarity	NPC35109
0.7913	Intermediate Similarity	NPC476529
0.7913	Intermediate Similarity	NPC475775
0.7913	Intermediate Similarity	NPC9674
0.7913	Intermediate Similarity	NPC19028
0.7913	Intermediate Similarity	NPC475041
0.7909	Intermediate Similarity	NPC10064
0.7909	Intermediate Similarity	NPC170221
0.7905	Intermediate Similarity	NPC57079
0.7905	Intermediate Similarity	NPC218107
0.7905	Intermediate Similarity	NPC124512
0.7905	Intermediate Similarity	NPC252295
0.7905	Intermediate Similarity	NPC119036
0.7905	Intermediate Similarity	NPC159763
0.7905	Intermediate Similarity	NPC124703
0.7905	Intermediate Similarity	NPC470068
0.7905	Intermediate Similarity	NPC470066
0.7905	Intermediate Similarity	NPC316598
0.7905	Intermediate Similarity	NPC234617
0.7905	Intermediate Similarity	NPC278386
0.7905	Intermediate Similarity	NPC470067
0.7905	Intermediate Similarity	NPC473155
0.7905	Intermediate Similarity	NPC108368
0.79	Intermediate Similarity	NPC255176
0.79	Intermediate Similarity	NPC250687
0.79	Intermediate Similarity	NPC477128
0.79	Intermediate Similarity	NPC48824
0.79	Intermediate Similarity	NPC229407
0.79	Intermediate Similarity	NPC254572
0.7899	Intermediate Similarity	NPC298841
0.7895	Intermediate Similarity	NPC140055
0.7895	Intermediate Similarity	NPC286528
0.7895	Intermediate Similarity	NPC167606

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 NPC475414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1329
0.2-0.3	3611
0.3-0.4	2587
0.4-0.5	876
0.5-0.6	273
0.6-0.7	199
0.7-0.8	110
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
0.7905	Intermediate Similarity	NPD4225	Approved
0.7895	Intermediate Similarity	NPD7115	Discovery
0.7857	Intermediate Similarity	NPD8297	Approved
0.7818	Intermediate Similarity	NPD7320	Approved
0.7798	Intermediate Similarity	NPD5739	Approved
0.7798	Intermediate Similarity	NPD6675	Approved
0.7798	Intermediate Similarity	NPD6402	Approved
0.7798	Intermediate Similarity	NPD7128	Approved
0.7767	Intermediate Similarity	NPD6399	Phase 3
0.7736	Intermediate Similarity	NPD7638	Approved
0.7664	Intermediate Similarity	NPD7640	Approved
0.7664	Intermediate Similarity	NPD7639	Approved
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7611	Intermediate Similarity	NPD8130	Phase 1
0.7589	Intermediate Similarity	NPD6373	Approved
0.7589	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD5701	Approved
0.7568	Intermediate Similarity	NPD5697	Approved
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD7290	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.7521	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.7478	Intermediate Similarity	NPD4632	Approved
0.7477	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD6083	Phase 2
0.7456	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD6650	Approved
0.7456	Intermediate Similarity	NPD6869	Approved
0.7456	Intermediate Similarity	NPD6649	Approved
0.7456	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD6014	Approved
0.7434	Intermediate Similarity	NPD6012	Approved
0.7434	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD7748	Approved
0.7345	Intermediate Similarity	NPD6686	Approved
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD8033	Approved
0.7327	Intermediate Similarity	NPD4786	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7315	Intermediate Similarity	NPD4755	Approved
0.7315	Intermediate Similarity	NPD7902	Approved
0.7295	Intermediate Similarity	NPD7492	Approved
0.7258	Intermediate Similarity	NPD7736	Approved
0.7255	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8377	Approved
0.725	Intermediate Similarity	NPD6054	Approved
0.725	Intermediate Similarity	NPD8294	Approved
0.725	Intermediate Similarity	NPD6059	Approved
0.725	Intermediate Similarity	NPD6319	Approved
0.7236	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD7328	Approved
0.7212	Intermediate Similarity	NPD6672	Approved
0.7212	Intermediate Similarity	NPD5737	Approved
0.7207	Intermediate Similarity	NPD5211	Phase 2
0.719	Intermediate Similarity	NPD8380	Approved
0.719	Intermediate Similarity	NPD8379	Approved
0.719	Intermediate Similarity	NPD8378	Approved
0.719	Intermediate Similarity	NPD8335	Approved
0.719	Intermediate Similarity	NPD8296	Approved
0.7182	Intermediate Similarity	NPD5286	Approved
0.7182	Intermediate Similarity	NPD5285	Approved
0.7182	Intermediate Similarity	NPD4700	Approved
0.7182	Intermediate Similarity	NPD4696	Approved
0.7179	Intermediate Similarity	NPD8133	Approved
0.7177	Intermediate Similarity	NPD7078	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD5693	Phase 1
0.7168	Intermediate Similarity	NPD6008	Approved
0.7167	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7131	Intermediate Similarity	NPD6370	Approved
0.713	Intermediate Similarity	NPD5695	Phase 3
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3667	Approved
0.7117	Intermediate Similarity	NPD5223	Approved
0.7103	Intermediate Similarity	NPD4202	Approved
0.71	Intermediate Similarity	NPD7525	Registered
0.7091	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD6335	Approved
0.708	Intermediate Similarity	NPD5141	Approved
0.7073	Intermediate Similarity	NPD7604	Phase 2
0.7069	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD4697	Phase 3
0.7064	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD5362	Discontinued
0.7059	Intermediate Similarity	NPD6274	Approved
0.7054	Intermediate Similarity	NPD5225	Approved
0.7054	Intermediate Similarity	NPD5226	Approved
0.7054	Intermediate Similarity	NPD4633	Approved
0.7054	Intermediate Similarity	NPD5224	Approved
0.7054	Intermediate Similarity	NPD7632	Discontinued
0.7049	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6015	Approved
0.7049	Intermediate Similarity	NPD6016	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7019	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6992	Remote Similarity	NPD5988	Approved
0.6991	Remote Similarity	NPD4754	Approved
0.6991	Remote Similarity	NPD5174	Approved
0.6991	Remote Similarity	NPD5175	Approved
0.6981	Remote Similarity	NPD6904	Approved
0.6981	Remote Similarity	NPD6051	Approved
0.6981	Remote Similarity	NPD4753	Phase 2
0.6981	Remote Similarity	NPD6080	Approved
0.6981	Remote Similarity	NPD6673	Approved
0.696	Remote Similarity	NPD6336	Discontinued
0.6949	Remote Similarity	NPD6053	Discontinued
0.6942	Remote Similarity	NPD6314	Approved
0.6942	Remote Similarity	NPD6313	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6923	Remote Similarity	NPD1694	Approved
0.6917	Remote Similarity	NPD6868	Approved
0.6916	Remote Similarity	NPD6698	Approved
0.6916	Remote Similarity	NPD46	Approved
0.6911	Remote Similarity	NPD6909	Approved
0.6911	Remote Similarity	NPD6908	Approved
0.6887	Remote Similarity	NPD6903	Approved
0.687	Remote Similarity	NPD4767	Approved
0.687	Remote Similarity	NPD4768	Approved
0.686	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD7521	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.685	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5344	Discontinued
0.681	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6412	Phase 2
0.68	Remote Similarity	NPD6116	Phase 1
0.68	Remote Similarity	NPD8328	Phase 3
0.6792	Remote Similarity	NPD7524	Approved
0.6774	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD8515	Approved
0.6762	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4730	Approved
0.6752	Remote Similarity	NPD4729	Approved
0.6752	Remote Similarity	NPD5128	Approved
0.6733	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7154	Phase 3
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6001	Approved
0.67	Remote Similarity	NPD6117	Approved
0.67	Remote Similarity	NPD6933	Approved
0.6698	Remote Similarity	NPD5279	Phase 3
0.6697	Remote Similarity	NPD6050	Approved
0.6697	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD3665	Phase 1
0.664	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD5135	Approved
0.6639	Remote Similarity	NPD5250	Approved
0.6639	Remote Similarity	NPD5248	Approved
0.6639	Remote Similarity	NPD5169	Approved
0.6639	Remote Similarity	NPD5249	Phase 3
0.6639	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD5251	Approved
0.6639	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD5692	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data