NPASS Compound

Structure

NPC469546 OpenBabel07101718222D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.5259 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8540 -3.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8818 -3.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 -2.4306 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 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 2.5259 -1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.9722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 32 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 28 2 0 0 0 0 16 17 1 0 0 0 0 16 29 2 0 0 0 0 17 18 1 0 0 0 0 18 26 1 6 0 0 0 19 24 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 21 25 1 6 0 0 0 21 27 1 0 0 0 0 22 26 1 0 0 0 0 22 30 2 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 27 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.27
Volume:	472.091
LogP:	3.01
LogD:	2.899
LogS:	-4.305
# Rotatable Bonds:	4
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	5.166
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.882
MDCK Permeability:	1.9647026419988833e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.743

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	46.970497131347656%
Volume Distribution (VD):	1.283
Pgp-substrate:	56.693138122558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.677
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.261
CYP3A4-inhibitor:	0.852
CYP3A4-substrate:	0.532

ADMET: Excretion

Clearance (CL):	14.473
Half-life (T1/2):	0.237

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.202
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.616
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.926
Carcinogencity:	0.46
Eye Corrosion:	0.987
Eye Irritation:	0.724
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC469546

Natural Product ID:	NPC469546
*Common Name:**	24-Methyl-12,24,25-Trioxoscalar-16-En-22-Oate
IUPAC Name:	methyl (4aR,4bS,6aS,7S,10aS,10bS,12aS)-8-acetyl-7-formyl-1,1,6a,10b-tetramethyl-6-oxo-3,4,4b,5,7,10,10a,11,12,12a-decahydro-2H-chrysene-4a-carboxylate
Synonyms:
Standard InCHIKey:	FSJDOSKYUBIXLN-OIQDPBBISA-N
Standard InCHI:	InChI=1S/C27H38O5/c1-16(29)17-8-9-20-25(4)13-10-19-24(2,3)11-7-12-27(19,23(31)32-6)21(25)14-22(30)26(20,5)18(17)15-28/h8,15,18-21H,7,9-14H2,1-6H3/t18-,19-,20-,21-,25-,26+,27+/m0/s1
SMILES:	CC(=O)C1=CCC2C3(CCC4C(CCCC4(C3CC(=O)C2(C1C=O)C)C(=O)OC)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086909
PubChem CID:	46881366
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17958396]
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18989978]

☑ 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	14

Activity Type	# Activity
Cell Line	8
PROTEIN FAMILY	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1900.0	nM	PMID[495162]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	2000.0	nM	PMID[495162]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	5500.0	nM	PMID[495162]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6100.0	nM	PMID[495162]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	6400.0	nM	PMID[495162]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6800.0	nM	PMID[495162]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	10200.0	nM	PMID[495162]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	10800.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1000.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	2700.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	7700.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	9000.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	23000.0	nM	PMID[495162]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	30000.0	nM	PMID[495162]

☑ 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 NPC469546 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	228
0.1-0.2	1559
0.2-0.3	6326
0.3-0.4	14392
0.4-0.5	8488
0.5-0.6	6453
0.6-0.7	4196
0.7-0.8	980
0.8-0.85	59
0.85-0.9	12
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC230064
0.908	High Similarity	NPC184663
0.9059	High Similarity	NPC2709
0.9	High Similarity	NPC274417
0.8889	High Similarity	NPC269729
0.8764	High Similarity	NPC101651
0.8764	High Similarity	NPC159748
0.8764	High Similarity	NPC328141
0.8675	High Similarity	NPC115515
0.8652	High Similarity	NPC477973
0.8617	High Similarity	NPC475202
0.8617	High Similarity	NPC475385
0.8617	High Similarity	NPC475392
0.8571	High Similarity	NPC151722
0.8554	High Similarity	NPC472300
0.8488	Intermediate Similarity	NPC142683
0.8471	Intermediate Similarity	NPC267517
0.8471	Intermediate Similarity	NPC474956
0.8427	Intermediate Similarity	NPC477228
0.8391	Intermediate Similarity	NPC307258
0.8372	Intermediate Similarity	NPC278459
0.8372	Intermediate Similarity	NPC90055
0.8372	Intermediate Similarity	NPC471898
0.8352	Intermediate Similarity	NPC476369
0.8352	Intermediate Similarity	NPC476437
0.8352	Intermediate Similarity	NPC252737
0.8351	Intermediate Similarity	NPC95585
0.8351	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC474474
0.8295	Intermediate Similarity	NPC96095
0.8295	Intermediate Similarity	NPC312660
0.8276	Intermediate Similarity	NPC302661
0.8276	Intermediate Similarity	NPC238991
0.8261	Intermediate Similarity	NPC218301
0.8256	Intermediate Similarity	NPC104545
0.8222	Intermediate Similarity	NPC476409
0.8211	Intermediate Similarity	NPC226986
0.8211	Intermediate Similarity	NPC473456
0.8202	Intermediate Similarity	NPC474537
0.8193	Intermediate Similarity	NPC211641
0.8182	Intermediate Similarity	NPC271784
0.8182	Intermediate Similarity	NPC102197
0.8172	Intermediate Similarity	NPC295643
0.8172	Intermediate Similarity	NPC474185
0.8172	Intermediate Similarity	NPC272075
0.8172	Intermediate Similarity	NPC214756
0.8172	Intermediate Similarity	NPC476416
0.8161	Intermediate Similarity	NPC221647
0.8144	Intermediate Similarity	NPC310981
0.814	Intermediate Similarity	NPC28319
0.8132	Intermediate Similarity	NPC224145
0.8125	Intermediate Similarity	NPC471966
0.8111	Intermediate Similarity	NPC195640
0.8111	Intermediate Similarity	NPC324063
0.8105	Intermediate Similarity	NPC111684
0.8105	Intermediate Similarity	NPC471039
0.8105	Intermediate Similarity	NPC5532
0.8105	Intermediate Similarity	NPC61369
0.8105	Intermediate Similarity	NPC471775
0.8105	Intermediate Similarity	NPC469545
0.8105	Intermediate Similarity	NPC58052
0.809	Intermediate Similarity	NPC320801
0.8085	Intermediate Similarity	NPC74751
0.8085	Intermediate Similarity	NPC471040
0.8085	Intermediate Similarity	NPC476415
0.8068	Intermediate Similarity	NPC100297
0.8068	Intermediate Similarity	NPC470813
0.8065	Intermediate Similarity	NPC233455
0.8065	Intermediate Similarity	NPC145067
0.8065	Intermediate Similarity	NPC158030
0.8065	Intermediate Similarity	NPC4036
0.8065	Intermediate Similarity	NPC65120
0.8046	Intermediate Similarity	NPC477057
0.8046	Intermediate Similarity	NPC37038
0.8043	Intermediate Similarity	NPC474700
0.8023	Intermediate Similarity	NPC280654
0.8023	Intermediate Similarity	NPC59436
0.8023	Intermediate Similarity	NPC110094
0.8023	Intermediate Similarity	NPC260385
0.8022	Intermediate Similarity	NPC158141
0.8022	Intermediate Similarity	NPC173089
0.8022	Intermediate Similarity	NPC30421
0.8022	Intermediate Similarity	NPC46912
0.8022	Intermediate Similarity	NPC162107
0.8021	Intermediate Similarity	NPC476768
0.8021	Intermediate Similarity	NPC23680
0.8	Intermediate Similarity	NPC323765
0.8	Intermediate Similarity	NPC474680
0.8	Intermediate Similarity	NPC139570
0.8	Intermediate Similarity	NPC139459
0.8	Intermediate Similarity	NPC189311
0.7979	Intermediate Similarity	NPC263780
0.7979	Intermediate Similarity	NPC79117
0.7978	Intermediate Similarity	NPC200752
0.7978	Intermediate Similarity	NPC469561
0.7976	Intermediate Similarity	NPC166797
0.7976	Intermediate Similarity	NPC219232
0.7976	Intermediate Similarity	NPC128346
0.7957	Intermediate Similarity	NPC198818
0.7955	Intermediate Similarity	NPC162632
0.7955	Intermediate Similarity	NPC274050
0.7955	Intermediate Similarity	NPC267691
0.7955	Intermediate Similarity	NPC474955
0.7955	Intermediate Similarity	NPC263272
0.7952	Intermediate Similarity	NPC474562
0.7938	Intermediate Similarity	NPC194196
0.7935	Intermediate Similarity	NPC474925
0.7935	Intermediate Similarity	NPC1753
0.7935	Intermediate Similarity	NPC206060
0.7935	Intermediate Similarity	NPC474511
0.7935	Intermediate Similarity	NPC474845
0.7931	Intermediate Similarity	NPC476177
0.7931	Intermediate Similarity	NPC231431
0.7931	Intermediate Similarity	NPC199595
0.7931	Intermediate Similarity	NPC471475
0.7917	Intermediate Similarity	NPC98874
0.7912	Intermediate Similarity	NPC9892
0.7912	Intermediate Similarity	NPC220478
0.7912	Intermediate Similarity	NPC10005
0.7912	Intermediate Similarity	NPC329943
0.7912	Intermediate Similarity	NPC91525
0.7912	Intermediate Similarity	NPC158393
0.7907	Intermediate Similarity	NPC471897
0.7907	Intermediate Similarity	NPC165711
0.7907	Intermediate Similarity	NPC107039
0.7907	Intermediate Similarity	NPC471899
0.7895	Intermediate Similarity	NPC294266
0.7895	Intermediate Similarity	NPC84893
0.7889	Intermediate Similarity	NPC149869
0.7889	Intermediate Similarity	NPC156981
0.7872	Intermediate Similarity	NPC470036
0.7872	Intermediate Similarity	NPC174167
0.7865	Intermediate Similarity	NPC321289
0.7865	Intermediate Similarity	NPC69101
0.7865	Intermediate Similarity	NPC251779
0.7865	Intermediate Similarity	NPC327969
0.7865	Intermediate Similarity	NPC163236
0.7865	Intermediate Similarity	NPC240302
0.7849	Intermediate Similarity	NPC475049
0.7849	Intermediate Similarity	NPC281524
0.7849	Intermediate Similarity	NPC284561
0.7841	Intermediate Similarity	NPC26139
0.7841	Intermediate Similarity	NPC474509
0.7841	Intermediate Similarity	NPC2482
0.7835	Intermediate Similarity	NPC89225
0.7835	Intermediate Similarity	NPC170131
0.7835	Intermediate Similarity	NPC26413
0.7826	Intermediate Similarity	NPC93778
0.7822	Intermediate Similarity	NPC470267
0.7816	Intermediate Similarity	NPC321514
0.7816	Intermediate Similarity	NPC74410
0.7816	Intermediate Similarity	NPC4827
0.7812	Intermediate Similarity	NPC148523
0.7802	Intermediate Similarity	NPC470223
0.7802	Intermediate Similarity	NPC29447
0.7802	Intermediate Similarity	NPC133652
0.7802	Intermediate Similarity	NPC473038
0.78	Intermediate Similarity	NPC179208
0.7791	Intermediate Similarity	NPC89294
0.7791	Intermediate Similarity	NPC180886
0.7791	Intermediate Similarity	NPC899
0.7789	Intermediate Similarity	NPC169343
0.7789	Intermediate Similarity	NPC298554
0.7778	Intermediate Similarity	NPC105803
0.7778	Intermediate Similarity	NPC70834
0.7766	Intermediate Similarity	NPC120840
0.7766	Intermediate Similarity	NPC46441
0.7766	Intermediate Similarity	NPC193750
0.7766	Intermediate Similarity	NPC291028
0.7766	Intermediate Similarity	NPC474728
0.7766	Intermediate Similarity	NPC113989
0.7766	Intermediate Similarity	NPC474842
0.7766	Intermediate Similarity	NPC475965
0.7755	Intermediate Similarity	NPC478056
0.7753	Intermediate Similarity	NPC3915
0.7753	Intermediate Similarity	NPC149237
0.7753	Intermediate Similarity	NPC142244
0.7753	Intermediate Similarity	NPC327002
0.7742	Intermediate Similarity	NPC473229
0.7742	Intermediate Similarity	NPC40552
0.7742	Intermediate Similarity	NPC182797
0.7742	Intermediate Similarity	NPC52169
0.7742	Intermediate Similarity	NPC246708
0.7732	Intermediate Similarity	NPC122324
0.7732	Intermediate Similarity	NPC106425
0.7732	Intermediate Similarity	NPC472806
0.7732	Intermediate Similarity	NPC472941
0.7732	Intermediate Similarity	NPC456
0.7732	Intermediate Similarity	NPC167193
0.7732	Intermediate Similarity	NPC151725
0.7727	Intermediate Similarity	NPC16394
0.7727	Intermediate Similarity	NPC327674
0.7727	Intermediate Similarity	NPC90965
0.7717	Intermediate Similarity	NPC322159
0.7717	Intermediate Similarity	NPC229717
0.7717	Intermediate Similarity	NPC73038
0.7717	Intermediate Similarity	NPC471042
0.7708	Intermediate Similarity	NPC209868
0.7708	Intermediate Similarity	NPC474529
0.7708	Intermediate Similarity	NPC56525

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 NPC469546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1829
0.2-0.3	4051
0.3-0.4	2093
0.4-0.5	570
0.5-0.6	190
0.6-0.7	166
0.7-0.8	36
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7732	Phase 3
0.828	Intermediate Similarity	NPD7900	Approved
0.828	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD6672	Approved
0.8132	Intermediate Similarity	NPD5737	Approved
0.8111	Intermediate Similarity	NPD7521	Approved
0.8111	Intermediate Similarity	NPD6409	Approved
0.8111	Intermediate Similarity	NPD5330	Approved
0.8111	Intermediate Similarity	NPD7334	Approved
0.8111	Intermediate Similarity	NPD6684	Approved
0.8111	Intermediate Similarity	NPD7146	Approved
0.8085	Intermediate Similarity	NPD7748	Approved
0.8065	Intermediate Similarity	NPD7515	Phase 2
0.8022	Intermediate Similarity	NPD3573	Approved
0.8021	Intermediate Similarity	NPD7902	Approved
0.7935	Intermediate Similarity	NPD6903	Approved
0.7917	Intermediate Similarity	NPD7614	Phase 1
0.7667	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6080	Approved
0.766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD6673	Approved
0.766	Intermediate Similarity	NPD6904	Approved
0.7604	Intermediate Similarity	NPD6399	Phase 3
0.7576	Intermediate Similarity	NPD5696	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7449	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4695	Discontinued
0.7374	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD5208	Approved
0.734	Intermediate Similarity	NPD6098	Approved
0.732	Intermediate Similarity	NPD6050	Approved
0.732	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD5693	Phase 1
0.7312	Intermediate Similarity	NPD3666	Approved
0.7312	Intermediate Similarity	NPD3665	Phase 1
0.7312	Intermediate Similarity	NPD3133	Approved
0.7292	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD4629	Approved
0.7273	Intermediate Similarity	NPD5210	Approved
0.7273	Intermediate Similarity	NPD5695	Phase 3
0.7216	Intermediate Similarity	NPD5692	Phase 3
0.7209	Intermediate Similarity	NPD4691	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.7158	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7143	Intermediate Similarity	NPD5694	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.7128	Intermediate Similarity	NPD4786	Approved
0.7128	Intermediate Similarity	NPD3668	Phase 3
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.7097	Intermediate Similarity	NPD4223	Phase 3
0.7097	Intermediate Similarity	NPD4221	Approved
0.7097	Intermediate Similarity	NPD3667	Approved
0.7093	Intermediate Similarity	NPD4137	Phase 3
0.7075	Intermediate Similarity	NPD6614	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7053	Intermediate Similarity	NPD5329	Approved
0.7053	Intermediate Similarity	NPD1694	Approved
0.7041	Intermediate Similarity	NPD5207	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.703	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5221	Approved
0.703	Intermediate Similarity	NPD5222	Approved
0.7011	Intermediate Similarity	NPD4747	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD6001	Approved
0.6981	Remote Similarity	NPD6008	Approved
0.6979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6617	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.697	Remote Similarity	NPD8034	Phase 2
0.697	Remote Similarity	NPD8035	Phase 2
0.6966	Remote Similarity	NPD4058	Approved
0.6961	Remote Similarity	NPD5173	Approved
0.6947	Remote Similarity	NPD4197	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6909	Remote Similarity	NPD8297	Approved
0.6893	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3617	Approved
0.6842	Remote Similarity	NPD4788	Approved
0.6827	Remote Similarity	NPD4696	Approved
0.6827	Remote Similarity	NPD5285	Approved
0.6827	Remote Similarity	NPD7640	Approved
0.6827	Remote Similarity	NPD5286	Approved
0.6827	Remote Similarity	NPD7639	Approved
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8028	Phase 2
0.6804	Remote Similarity	NPD4138	Approved
0.6804	Remote Similarity	NPD4688	Approved
0.6804	Remote Similarity	NPD5690	Phase 2
0.6804	Remote Similarity	NPD4689	Approved
0.6804	Remote Similarity	NPD5279	Phase 3
0.6804	Remote Similarity	NPD4519	Discontinued
0.6804	Remote Similarity	NPD4693	Phase 3
0.6804	Remote Similarity	NPD4623	Approved
0.6804	Remote Similarity	NPD4690	Approved
0.6804	Remote Similarity	NPD5205	Approved
0.68	Remote Similarity	NPD6411	Approved
0.6796	Remote Similarity	NPD4755	Approved
0.6792	Remote Similarity	NPD6052	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6765	Remote Similarity	NPD5654	Approved
0.6762	Remote Similarity	NPD5223	Approved
0.6759	Remote Similarity	NPD6412	Phase 2
0.6733	Remote Similarity	NPD4202	Approved
0.6726	Remote Similarity	NPD6868	Approved
0.6698	Remote Similarity	NPD5225	Approved
0.6698	Remote Similarity	NPD5211	Phase 2
0.6698	Remote Similarity	NPD4633	Approved
0.6698	Remote Similarity	NPD5226	Approved
0.6698	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD7094	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD5175	Approved
0.6635	Remote Similarity	NPD5959	Approved
0.6633	Remote Similarity	NPD4694	Approved
0.6633	Remote Similarity	NPD5280	Approved
0.6609	Remote Similarity	NPD6335	Approved
0.66	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4195	Approved
0.6596	Remote Similarity	NPD7645	Phase 2
0.6593	Remote Similarity	NPD4687	Approved
0.6591	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6274	Approved
0.6574	Remote Similarity	NPD5141	Approved
0.6556	Remote Similarity	NPD5777	Approved
0.6556	Remote Similarity	NPD6081	Approved
0.6556	Remote Similarity	NPD5276	Approved
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6542	Remote Similarity	NPD5091	Approved
0.6522	Remote Similarity	NPD8039	Approved
0.6522	Remote Similarity	NPD6009	Approved
0.6522	Remote Similarity	NPD6317	Approved
0.6481	Remote Similarity	NPD4754	Approved
0.6471	Remote Similarity	NPD8328	Phase 3
0.6466	Remote Similarity	NPD6314	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6396	Remote Similarity	NPD4729	Approved
0.6396	Remote Similarity	NPD5128	Approved
0.6396	Remote Similarity	NPD5168	Approved
0.6396	Remote Similarity	NPD4730	Approved
0.6393	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD7331	Phase 2
0.6364	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6355	Remote Similarity	NPD6404	Discontinued
0.6339	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7604	Phase 2
0.6306	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5983	Phase 2
0.6303	Remote Similarity	NPD6909	Approved
0.6303	Remote Similarity	NPD6908	Approved
0.6283	Remote Similarity	NPD5135	Approved
0.6283	Remote Similarity	NPD5247	Approved
0.6283	Remote Similarity	NPD5249	Phase 3
0.6283	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4634	Approved
0.6283	Remote Similarity	NPD5250	Approved
0.6283	Remote Similarity	NPD5169	Approved
0.6283	Remote Similarity	NPD5248	Approved
0.6283	Remote Similarity	NPD5251	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6262	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD7632	Discontinued
0.623	Remote Similarity	NPD6616	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