NPASS Compound

Structure

CID46912 OpenBabel06191715382D 37 41 0 0 1 0 0 0 0 0999 V2000 -5.0724 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 4.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0481 4.2621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0243 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0481 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3816 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 1 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 2.5362 1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9178 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 28 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 7 31 1 0 0 0 0 9 36 1 0 0 0 0 10 11 1 0 0 0 0 10 22 2 0 0 0 0 11 25 1 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 30 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 18 33 1 0 0 0 0 19 33 1 0 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 34 2 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 33 1 6 0 0 0 24 29 1 0 0 0 0 24 30 1 1 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 37 1 1 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 30 6 1 1 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 33 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	793.44
Volume:	813.838
LogP:	3.128
LogD:	2.313
LogS:	-3.517
# Rotatable Bonds:	13
TPSA:	238.86
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	5.328
Fsp3:	0.537
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:	-6.647
MDCK Permeability:	5.273851911624661e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.856
20% Bioavailability (F20%):	0.762
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	62.44409942626953%
Volume Distribution (VD):	0.332
Pgp-substrate:	16.572269439697266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.598
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.093
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	1.354
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.119
Carcinogencity:	0.05
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.435

Download Data

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

Natural Product: NPC46912

Natural Product ID:	NPC46912
*Common Name:**	3-Beta-Acetylolean-12-En-28-Methyl Ester
IUPAC Name:	methyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:
Standard InCHIKey:	VTZCFEUQVQTSSV-LVNUYWAMSA-N
Standard InCHI:	InChI=1S/C33H52O4/c1-21(34)37-26-13-14-30(6)24(29(26,4)5)12-15-32(8)25(30)11-10-22-23-20-28(2,3)16-18-33(23,27(35)36-9)19-17-31(22,32)7/h10,23-26H,11-20H2,1-9H3/t23-,24-,25+,26-,30-,31+,32+,33-/m0/s1
SMILES:	COC(=O)[C@@]12CCC(C[C@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)OC(=O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380326
PubChem CID:	10255859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[12350142]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	Indo-Pacific	n.a.	PMID[15387674]
NPO33322	caesalpinia volkensii	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[23562058]
NPO28722	Radermachera xylocarpa	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2117	Plakortis nigra	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24317	Primula integrifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22067	Pogostemon stellatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2543	Anthopleura pacifica	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13905	Galaxaura filamentosa	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28655	Perovskia angustifolia	Species	Lamiaceae	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
IC50	9
Others	7

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	15.68	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	72.47	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	9.43	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	2.41	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	28.8	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	15.9	%	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	Activity	=	55.29	%	PMID[454581]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	=	34300.0	nM	PMID[454581]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16700.0	nM	PMID[454581]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	26700.0	nM	PMID[454581]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	26100.0	nM	PMID[454581]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	8600.0	nM	PMID[454581]
NPT1215	Cell Line	8505C	Homo sapiens	IC50	=	20500.0	nM	PMID[454581]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	24440.0	nM	PMID[454580]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	18690.0	nM	PMID[454580]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	34100.0	nM	PMID[454581]

☑ 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 NPC46912 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	235
0.1-0.2	1518
0.2-0.3	5404
0.3-0.4	15430
0.4-0.5	7926
0.5-0.6	5279
0.6-0.7	4940
0.7-0.8	1513
0.8-0.85	181
0.85-0.9	149
0.9-0.95	101
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162107
0.9877	High Similarity	NPC10005
0.9877	High Similarity	NPC329943
0.9877	High Similarity	NPC9892
0.9877	High Similarity	NPC91525
0.9759	High Similarity	NPC475049
0.9643	High Similarity	NPC113989
0.9643	High Similarity	NPC120840
0.9639	High Similarity	NPC224145
0.9529	High Similarity	NPC285184
0.9529	High Similarity	NPC60755
0.9529	High Similarity	NPC470590
0.9529	High Similarity	NPC77099
0.9524	High Similarity	NPC30522
0.9419	High Similarity	NPC86368
0.9412	High Similarity	NPC474728
0.9383	High Similarity	NPC286786
0.931	High Similarity	NPC296164
0.931	High Similarity	NPC78580
0.931	High Similarity	NPC74751
0.931	High Similarity	NPC23621
0.931	High Similarity	NPC184006
0.9268	High Similarity	NPC132386
0.9259	High Similarity	NPC195334
0.9259	High Similarity	NPC290495
0.9205	High Similarity	NPC195715
0.9205	High Similarity	NPC474727
0.9205	High Similarity	NPC23241
0.9176	High Similarity	NPC52169
0.9176	High Similarity	NPC474845
0.9176	High Similarity	NPC40552
0.9176	High Similarity	NPC182797
0.9176	High Similarity	NPC246708
0.9157	High Similarity	NPC312660
0.9146	High Similarity	NPC163236
0.9101	High Similarity	NPC230151
0.9101	High Similarity	NPC327179
0.907	High Similarity	NPC234346
0.907	High Similarity	NPC198664
0.907	High Similarity	NPC293048
0.907	High Similarity	NPC270768
0.907	High Similarity	NPC274330
0.907	High Similarity	NPC263393
0.907	High Similarity	NPC25906
0.907	High Similarity	NPC290972
0.907	High Similarity	NPC61543
0.907	High Similarity	NPC225585
0.907	High Similarity	NPC64872
0.907	High Similarity	NPC121798
0.907	High Similarity	NPC130520
0.907	High Similarity	NPC59263
0.907	High Similarity	NPC127689
0.907	High Similarity	NPC470588
0.907	High Similarity	NPC143232
0.9059	High Similarity	NPC130577
0.9059	High Similarity	NPC51700
0.9059	High Similarity	NPC102683
0.9059	High Similarity	NPC88716
0.9059	High Similarity	NPC68160
0.9059	High Similarity	NPC293564
0.9059	High Similarity	NPC142415
0.9059	High Similarity	NPC242468
0.9059	High Similarity	NPC18064
0.9059	High Similarity	NPC307426
0.9059	High Similarity	NPC98442
0.9059	High Similarity	NPC171203
0.9024	High Similarity	NPC108476
0.9	High Similarity	NPC476879
0.9	High Similarity	NPC158347
0.9	High Similarity	NPC476878
0.9	High Similarity	NPC26413
0.8977	High Similarity	NPC272075
0.8977	High Similarity	NPC307335
0.8977	High Similarity	NPC295643
0.8977	High Similarity	NPC474436
0.8977	High Similarity	NPC214756
0.8977	High Similarity	NPC74855
0.8977	High Similarity	NPC49776
0.8977	High Similarity	NPC63118
0.8977	High Similarity	NPC136313
0.8966	High Similarity	NPC470589
0.8966	High Similarity	NPC227467
0.8966	High Similarity	NPC477872
0.8966	High Similarity	NPC111110
0.8966	High Similarity	NPC7260
0.8966	High Similarity	NPC126369
0.8966	High Similarity	NPC18872
0.8966	High Similarity	NPC273621
0.8966	High Similarity	NPC290614
0.8966	High Similarity	NPC291028
0.8966	High Similarity	NPC120968
0.8966	High Similarity	NPC210037
0.8966	High Similarity	NPC130278
0.8953	High Similarity	NPC470629
0.8953	High Similarity	NPC290690
0.8953	High Similarity	NPC473242
0.8953	High Similarity	NPC17733
0.8953	High Similarity	NPC181225
0.8953	High Similarity	NPC474512
0.8941	High Similarity	NPC72638
0.8941	High Similarity	NPC325594
0.8902	High Similarity	NPC267517
0.8901	High Similarity	NPC260149
0.8901	High Similarity	NPC58942
0.8901	High Similarity	NPC471966
0.8876	High Similarity	NPC91010
0.8864	High Similarity	NPC474525
0.8864	High Similarity	NPC233455
0.8864	High Similarity	NPC966
0.8864	High Similarity	NPC52021
0.8864	High Similarity	NPC4036
0.8864	High Similarity	NPC235884
0.8864	High Similarity	NPC300351
0.8864	High Similarity	NPC65120
0.8864	High Similarity	NPC145067
0.8864	High Similarity	NPC228784
0.8864	High Similarity	NPC282616
0.8864	High Similarity	NPC158030
0.8864	High Similarity	NPC155120
0.8864	High Similarity	NPC105189
0.8864	High Similarity	NPC71074
0.8864	High Similarity	NPC187722
0.8864	High Similarity	NPC25299
0.8864	High Similarity	NPC288833
0.8864	High Similarity	NPC324341
0.8864	High Similarity	NPC306541
0.8864	High Similarity	NPC84319
0.8864	High Similarity	NPC472149
0.8851	High Similarity	NPC474972
0.8851	High Similarity	NPC161751
0.8851	High Similarity	NPC95246
0.8824	High Similarity	NPC191965
0.8824	High Similarity	NPC98270
0.881	High Similarity	NPC200752
0.8764	High Similarity	NPC275809
0.8764	High Similarity	NPC298554
0.8764	High Similarity	NPC158059
0.8764	High Similarity	NPC169343
0.8764	High Similarity	NPC229281
0.8764	High Similarity	NPC118519
0.8764	High Similarity	NPC202728
0.875	High Similarity	NPC46441
0.875	High Similarity	NPC172361
0.875	High Similarity	NPC193750
0.875	High Similarity	NPC49320
0.875	High Similarity	NPC86372
0.875	High Similarity	NPC471896
0.875	High Similarity	NPC328141
0.8721	High Similarity	NPC73038
0.8721	High Similarity	NPC84121
0.8721	High Similarity	NPC137306
0.871	High Similarity	NPC54909
0.871	High Similarity	NPC233012
0.8706	High Similarity	NPC475509
0.8696	High Similarity	NPC164349
0.8681	High Similarity	NPC98874
0.8667	High Similarity	NPC231063
0.8667	High Similarity	NPC145667
0.8667	High Similarity	NPC474963
0.8667	High Similarity	NPC209868
0.8667	High Similarity	NPC32407
0.8667	High Similarity	NPC282395
0.8667	High Similarity	NPC269729
0.8667	High Similarity	NPC474529
0.8667	High Similarity	NPC20235
0.8667	High Similarity	NPC159365
0.8667	High Similarity	NPC299996
0.8667	High Similarity	NPC6818
0.8667	High Similarity	NPC191412
0.8667	High Similarity	NPC114159
0.8667	High Similarity	NPC263548
0.8667	High Similarity	NPC88116
0.8667	High Similarity	NPC222047
0.8652	High Similarity	NPC6255
0.8652	High Similarity	NPC471588
0.8652	High Similarity	NPC38754
0.8652	High Similarity	NPC475708
0.8636	High Similarity	NPC474700
0.8636	High Similarity	NPC474686
0.8621	High Similarity	NPC71507
0.8605	High Similarity	NPC133954
0.8602	High Similarity	NPC475156
0.8602	High Similarity	NPC473576
0.8587	High Similarity	NPC255589
0.8587	High Similarity	NPC10057
0.8587	High Similarity	NPC259788
0.8571	High Similarity	NPC198245
0.8571	High Similarity	NPC96916
0.8571	High Similarity	NPC473240
0.8571	High Similarity	NPC148523
0.8571	High Similarity	NPC139570
0.8571	High Similarity	NPC274417
0.8556	High Similarity	NPC133579
0.8556	High Similarity	NPC474806
0.8556	High Similarity	NPC118490
0.8539	High Similarity	NPC175628
0.8539	High Similarity	NPC198818
0.8539	High Similarity	NPC111585
0.8539	High Similarity	NPC148414
0.8537	High Similarity	NPC84868

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 NPC46912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1779
0.2-0.3	4024
0.3-0.4	2090
0.4-0.5	617
0.5-0.6	209
0.6-0.7	180
0.7-0.8	33
0.8-0.85	4
0.85-0.9	1
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD7748	Approved
0.931	High Similarity	NPD7900	Approved
0.931	High Similarity	NPD7901	Clinical (unspecified phase)
0.9	High Similarity	NPD7902	Approved
0.8864	High Similarity	NPD7515	Phase 2
0.8315	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD8034	Phase 2
0.8242	Intermediate Similarity	NPD8035	Phase 2
0.809	Intermediate Similarity	NPD6684	Approved
0.809	Intermediate Similarity	NPD7146	Approved
0.809	Intermediate Similarity	NPD7521	Approved
0.809	Intermediate Similarity	NPD6409	Approved
0.809	Intermediate Similarity	NPD7334	Approved
0.809	Intermediate Similarity	NPD5330	Approved
0.8	Intermediate Similarity	NPD3573	Approved
0.7978	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD6399	Phase 3
0.7912	Intermediate Similarity	NPD6672	Approved
0.7912	Intermediate Similarity	NPD5737	Approved
0.7912	Intermediate Similarity	NPD6903	Approved
0.7907	Intermediate Similarity	NPD7645	Phase 2
0.7604	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7638	Approved
0.7526	Intermediate Similarity	NPD7732	Phase 3
0.75	Intermediate Similarity	NPD6098	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7473	Intermediate Similarity	NPD4786	Approved
0.7473	Intermediate Similarity	NPD3668	Phase 3
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7447	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD6080	Approved
0.7447	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6904	Approved
0.7444	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3667	Approved
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7292	Intermediate Similarity	NPD6079	Approved
0.7292	Intermediate Similarity	NPD6411	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7238	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7204	Intermediate Similarity	NPD1694	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD8328	Phase 3
0.7158	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7113	Intermediate Similarity	NPD5693	Phase 1
0.7113	Intermediate Similarity	NPD6050	Approved
0.7103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD3133	Approved
0.7097	Intermediate Similarity	NPD3666	Approved
0.7097	Intermediate Similarity	NPD3665	Phase 1
0.7091	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7071	Intermediate Similarity	NPD5695	Phase 3
0.7045	Intermediate Similarity	NPD8039	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD6882	Approved
0.7033	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD5696	Approved
0.701	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD7614	Phase 1
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4697	Phase 3
0.6966	Remote Similarity	NPD6117	Approved
0.6939	Remote Similarity	NPD5694	Approved
0.6937	Remote Similarity	NPD7115	Discovery
0.6931	Remote Similarity	NPD5173	Approved
0.6931	Remote Similarity	NPD4755	Approved
0.6897	Remote Similarity	NPD5777	Approved
0.6889	Remote Similarity	NPD6116	Phase 1
0.6848	Remote Similarity	NPD4695	Discontinued
0.6847	Remote Similarity	NPD6868	Approved
0.6837	Remote Similarity	NPD5207	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.6796	Remote Similarity	NPD5286	Approved
0.6796	Remote Similarity	NPD5285	Approved
0.6796	Remote Similarity	NPD4700	Approved
0.6796	Remote Similarity	NPD4696	Approved
0.6771	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4753	Phase 2
0.6731	Remote Similarity	NPD5223	Approved
0.6729	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6412	Phase 2
0.6726	Remote Similarity	NPD6335	Approved
0.6702	Remote Similarity	NPD4221	Approved
0.6702	Remote Similarity	NPD4223	Phase 3
0.67	Remote Similarity	NPD5779	Approved
0.67	Remote Similarity	NPD5778	Approved
0.6699	Remote Similarity	NPD4225	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6637	Remote Similarity	NPD6317	Approved
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5175	Approved
0.6604	Remote Similarity	NPD6052	Approved
0.6604	Remote Similarity	NPD5174	Approved
0.6604	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5281	Approved
0.66	Remote Similarity	NPD5284	Approved
0.6598	Remote Similarity	NPD5279	Phase 3
0.6596	Remote Similarity	NPD8028	Phase 2
0.6593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4691	Approved
0.6591	Remote Similarity	NPD4747	Approved
0.6579	Remote Similarity	NPD6314	Approved
0.6579	Remote Similarity	NPD6313	Approved
0.6569	Remote Similarity	NPD5654	Approved
0.6562	Remote Similarity	NPD4197	Approved
0.6552	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6909	Approved
0.6552	Remote Similarity	NPD6908	Approved
0.6545	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5141	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.6491	Remote Similarity	NPD6009	Approved
0.6481	Remote Similarity	NPD4768	Approved
0.6481	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD7507	Approved
0.6466	Remote Similarity	NPD6319	Approved
0.6458	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD3617	Approved
0.6442	Remote Similarity	NPD5959	Approved
0.6441	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD4693	Phase 3
0.6429	Remote Similarity	NPD4689	Approved
0.6429	Remote Similarity	NPD4688	Approved
0.6429	Remote Similarity	NPD5205	Approved
0.6429	Remote Similarity	NPD4623	Approved
0.6429	Remote Similarity	NPD4519	Discontinued
0.6429	Remote Similarity	NPD6422	Discontinued
0.6429	Remote Similarity	NPD4690	Approved
0.6429	Remote Similarity	NPD4138	Approved
0.6422	Remote Similarity	NPD6614	Approved
0.6417	Remote Similarity	NPD8293	Discontinued
0.641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD5210	Approved
0.6408	Remote Similarity	NPD4629	Approved
0.6387	Remote Similarity	NPD7492	Approved
0.6374	Remote Similarity	NPD4058	Approved
0.6374	Remote Similarity	NPD5733	Approved
0.6364	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD4730	Approved
0.6364	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5168	Approved
0.6333	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4809	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data