NPASS Compound

Structure

NPC204054 OpenBabel07101718322D 35 39 0 0 1 0 0 0 0 0999 V2000 3.2709 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3685 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 33 1 0 0 0 0 17 30 2 0 0 0 0 17 33 1 0 0 0 0 18 31 2 0 0 0 0 18 34 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 1 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 0 0 0 0 23 28 1 1 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 34 1 6 0 0 0 25 35 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	509.553
LogP:	4.958
LogD:	4.071
LogS:	-5.19
# Rotatable Bonds:	5
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	5.138
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.832
MDCK Permeability:	3.279453085269779e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.651
Plasma Protein Binding (PPB):	66.39253234863281%
Volume Distribution (VD):	1.531
Pgp-substrate:	28.533092498779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.48
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	3.598
Half-life (T1/2):	0.055

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.225
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.448
Maximum Recommended Daily Dose:	0.814
Skin Sensitization:	0.695
Carcinogencity:	0.222
Eye Corrosion:	0.893
Eye Irritation:	0.368
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC204054

Natural Product ID:	NPC204054
*Common Name:**	12-Deacetoxy-23-Acetoxyscalarin
IUPAC Name:	[(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-acetyloxy-5b,8,8,13a-tetramethyl-3-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-11a-yl]methyl acetate
Synonyms:
Standard InCHIKey:	HTBVRXFAQQUUQL-OFFJBMDCSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-17(30)33-16-29-13-7-12-26(3,4)20(29)10-14-27(5)21-9-8-19-23(28(21,6)15-11-22(27)29)25(34-18(2)31)35-24(19)32/h8,20-23,25H,7,9-16H2,1-6H3/t20-,21-,22-,23+,25+,27-,28-,29+/m0/s1
SMILES:	CC(=O)OC[C@@]12CCCC([C@@H]2CC[C@@]2([C@@H]1CC[C@]1([C@H]2CC=C2[C@@H]1[C@H](OC(=O)C)OC2=O)C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573356
PubChem CID:	11443149
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
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497955]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252912]
NPO32965	smenospongia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18973387]

☑ 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
MIC	6
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	11.2	ug.mL-1	PMID[544348]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	4.9	ug.mL-1	PMID[544349]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	>	100.0	ug.mL-1	PMID[544349]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[544349]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[544349]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[544349]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[544349]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	>	100.0	ug.mL-1	PMID[544349]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[544349]

☑ 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 NPC204054 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	232
0.1-0.2	1408
0.2-0.3	5026
0.3-0.4	12231
0.4-0.5	9650
0.5-0.6	6629
0.6-0.7	6048
0.7-0.8	1407
0.8-0.85	48
0.85-0.9	12
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257726
0.9574	High Similarity	NPC134077
0.9468	High Similarity	NPC63249
0.9444	High Similarity	NPC65513
0.9	High Similarity	NPC112457
0.8842	High Similarity	NPC112654
0.8842	High Similarity	NPC325960
0.8842	High Similarity	NPC319692
0.8723	High Similarity	NPC166346
0.871	High Similarity	NPC101651
0.871	High Similarity	NPC159748
0.8681	High Similarity	NPC118266
0.8654	High Similarity	NPC157441
0.8617	High Similarity	NPC179517
0.8617	High Similarity	NPC165904
0.8602	High Similarity	NPC293044
0.8558	High Similarity	NPC194951
0.8558	High Similarity	NPC12046
0.8557	High Similarity	NPC76266
0.8556	High Similarity	NPC469
0.8556	High Similarity	NPC22611
0.8515	High Similarity	NPC127790
0.85	High Similarity	NPC254202
0.8462	Intermediate Similarity	NPC71626
0.8384	Intermediate Similarity	NPC477720
0.8352	Intermediate Similarity	NPC472440
0.8351	Intermediate Similarity	NPC473369
0.8333	Intermediate Similarity	NPC267266
0.8333	Intermediate Similarity	NPC277721
0.8317	Intermediate Similarity	NPC471364
0.8317	Intermediate Similarity	NPC132395
0.8317	Intermediate Similarity	NPC471365
0.8316	Intermediate Similarity	NPC220454
0.8316	Intermediate Similarity	NPC469595
0.8316	Intermediate Similarity	NPC212679
0.8298	Intermediate Similarity	NPC226863
0.8283	Intermediate Similarity	NPC473154
0.8265	Intermediate Similarity	NPC94905
0.8265	Intermediate Similarity	NPC8954
0.8265	Intermediate Similarity	NPC73858
0.8265	Intermediate Similarity	NPC311166
0.8247	Intermediate Similarity	NPC477130
0.8247	Intermediate Similarity	NPC477129
0.8242	Intermediate Similarity	NPC200513
0.8242	Intermediate Similarity	NPC186276
0.8235	Intermediate Similarity	NPC476763
0.8235	Intermediate Similarity	NPC476764
0.8229	Intermediate Similarity	NPC477783
0.8222	Intermediate Similarity	NPC195424
0.8211	Intermediate Similarity	NPC251528
0.8211	Intermediate Similarity	NPC168131
0.8191	Intermediate Similarity	NPC477228
0.8182	Intermediate Similarity	NPC476768
0.8173	Intermediate Similarity	NPC189075
0.8173	Intermediate Similarity	NPC275539
0.8172	Intermediate Similarity	NPC189311
0.8172	Intermediate Similarity	NPC472442
0.8155	Intermediate Similarity	NPC476760
0.8155	Intermediate Similarity	NPC476761
0.8155	Intermediate Similarity	NPC476762
0.8144	Intermediate Similarity	NPC471571
0.8144	Intermediate Similarity	NPC475657
0.8144	Intermediate Similarity	NPC151722
0.8144	Intermediate Similarity	NPC470656
0.8125	Intermediate Similarity	NPC477782
0.8119	Intermediate Similarity	NPC473384
0.8105	Intermediate Similarity	NPC477128
0.8085	Intermediate Similarity	NPC244174
0.8085	Intermediate Similarity	NPC173917
0.8077	Intermediate Similarity	NPC110496
0.8061	Intermediate Similarity	NPC477722
0.8061	Intermediate Similarity	NPC88507
0.8061	Intermediate Similarity	NPC476415
0.8058	Intermediate Similarity	NPC222161
0.8021	Intermediate Similarity	NPC174342
0.8021	Intermediate Similarity	NPC284561
0.8	Intermediate Similarity	NPC325054
0.8	Intermediate Similarity	NPC132753
0.8	Intermediate Similarity	NPC10057
0.8	Intermediate Similarity	NPC121402
0.8	Intermediate Similarity	NPC151681
0.8	Intermediate Similarity	NPC175351
0.8	Intermediate Similarity	NPC224356
0.798	Intermediate Similarity	NPC33473
0.7979	Intermediate Similarity	NPC65661
0.7979	Intermediate Similarity	NPC217394
0.7979	Intermediate Similarity	NPC2709
0.7961	Intermediate Similarity	NPC471208
0.7959	Intermediate Similarity	NPC472303
0.7941	Intermediate Similarity	NPC471075
0.7941	Intermediate Similarity	NPC310981
0.7938	Intermediate Similarity	NPC469372
0.7935	Intermediate Similarity	NPC149237
0.7928	Intermediate Similarity	NPC474179
0.7928	Intermediate Similarity	NPC475834
0.7925	Intermediate Similarity	NPC476759
0.7921	Intermediate Similarity	NPC176845
0.7917	Intermediate Similarity	NPC196407
0.7917	Intermediate Similarity	NPC215831
0.7917	Intermediate Similarity	NPC472302
0.79	Intermediate Similarity	NPC164750
0.79	Intermediate Similarity	NPC472362
0.79	Intermediate Similarity	NPC472363
0.79	Intermediate Similarity	NPC154526
0.7895	Intermediate Similarity	NPC220478
0.7864	Intermediate Similarity	NPC476769
0.7857	Intermediate Similarity	NPC141831
0.7857	Intermediate Similarity	NPC289479
0.7857	Intermediate Similarity	NPC49420
0.7849	Intermediate Similarity	NPC178676
0.7843	Intermediate Similarity	NPC219285
0.7843	Intermediate Similarity	NPC477968
0.7843	Intermediate Similarity	NPC470761
0.7843	Intermediate Similarity	NPC477971
0.7843	Intermediate Similarity	NPC473219
0.7843	Intermediate Similarity	NPC20113
0.7843	Intermediate Similarity	NPC477972
0.7843	Intermediate Similarity	NPC161527
0.7843	Intermediate Similarity	NPC228251
0.7838	Intermediate Similarity	NPC475913
0.7835	Intermediate Similarity	NPC73995
0.7835	Intermediate Similarity	NPC477973
0.7835	Intermediate Similarity	NPC177141
0.7835	Intermediate Similarity	NPC5509
0.7835	Intermediate Similarity	NPC174765
0.783	Intermediate Similarity	NPC177524
0.783	Intermediate Similarity	NPC61411
0.783	Intermediate Similarity	NPC90946
0.783	Intermediate Similarity	NPC300614
0.783	Intermediate Similarity	NPC392
0.783	Intermediate Similarity	NPC219900
0.7826	Intermediate Similarity	NPC473685
0.7822	Intermediate Similarity	NPC475709
0.7822	Intermediate Similarity	NPC84335
0.7822	Intermediate Similarity	NPC170131
0.7822	Intermediate Similarity	NPC472188
0.7822	Intermediate Similarity	NPC38530
0.7812	Intermediate Similarity	NPC288952
0.78	Intermediate Similarity	NPC183012
0.7789	Intermediate Similarity	NPC86316
0.7789	Intermediate Similarity	NPC106416
0.7789	Intermediate Similarity	NPC30984
0.7789	Intermediate Similarity	NPC300985
0.7788	Intermediate Similarity	NPC476770
0.7778	Intermediate Similarity	NPC474185
0.7778	Intermediate Similarity	NPC169343
0.7778	Intermediate Similarity	NPC476416
0.7766	Intermediate Similarity	NPC193198
0.7757	Intermediate Similarity	NPC31522
0.7755	Intermediate Similarity	NPC152467
0.7755	Intermediate Similarity	NPC76286
0.7755	Intermediate Similarity	NPC198818
0.7755	Intermediate Similarity	NPC273199
0.7755	Intermediate Similarity	NPC281942
0.7755	Intermediate Similarity	NPC8062
0.7755	Intermediate Similarity	NPC232426
0.7745	Intermediate Similarity	NPC318917
0.7745	Intermediate Similarity	NPC472186
0.7745	Intermediate Similarity	NPC98868
0.7745	Intermediate Similarity	NPC252295
0.7745	Intermediate Similarity	NPC478056
0.7745	Intermediate Similarity	NPC476800
0.7745	Intermediate Similarity	NPC471366
0.7742	Intermediate Similarity	NPC40228
0.7742	Intermediate Similarity	NPC229584
0.7742	Intermediate Similarity	NPC14203
0.7732	Intermediate Similarity	NPC474845
0.7723	Intermediate Similarity	NPC307164
0.7714	Intermediate Similarity	NPC189616
0.7708	Intermediate Similarity	NPC474062
0.7706	Intermediate Similarity	NPC222834
0.77	Intermediate Similarity	NPC104925
0.77	Intermediate Similarity	NPC84893
0.77	Intermediate Similarity	NPC469697
0.77	Intermediate Similarity	NPC269729
0.77	Intermediate Similarity	NPC324078
0.77	Intermediate Similarity	NPC298973
0.77	Intermediate Similarity	NPC470697
0.77	Intermediate Similarity	NPC474554
0.7692	Intermediate Similarity	NPC469606
0.7692	Intermediate Similarity	NPC31058
0.7692	Intermediate Similarity	NPC165250
0.7692	Intermediate Similarity	NPC40918
0.7692	Intermediate Similarity	NPC316500
0.7692	Intermediate Similarity	NPC273005
0.7685	Intermediate Similarity	NPC235014
0.7685	Intermediate Similarity	NPC476766
0.7684	Intermediate Similarity	NPC318515
0.7684	Intermediate Similarity	NPC312660
0.7677	Intermediate Similarity	NPC233345
0.7677	Intermediate Similarity	NPC474631
0.7677	Intermediate Similarity	NPC186363
0.767	Intermediate Similarity	NPC477716
0.767	Intermediate Similarity	NPC473204
0.767	Intermediate Similarity	NPC476767
0.767	Intermediate Similarity	NPC472187
0.767	Intermediate Similarity	NPC470906
0.767	Intermediate Similarity	NPC477721
0.767	Intermediate Similarity	NPC473545
0.7664	Intermediate Similarity	NPC473483

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 NPC204054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1554
0.2-0.3	3854
0.3-0.4	2384
0.4-0.5	714
0.5-0.6	231
0.6-0.7	187
0.7-0.8	35
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD6686	Approved
0.7732	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7900	Approved
0.77	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD1694	Approved
0.7551	Intermediate Similarity	NPD6672	Approved
0.7551	Intermediate Similarity	NPD5737	Approved
0.7526	Intermediate Similarity	NPD7334	Approved
0.7526	Intermediate Similarity	NPD5330	Approved
0.7526	Intermediate Similarity	NPD6684	Approved
0.7526	Intermediate Similarity	NPD7521	Approved
0.7526	Intermediate Similarity	NPD6409	Approved
0.7526	Intermediate Similarity	NPD7146	Approved
0.7476	Intermediate Similarity	NPD7902	Approved
0.7426	Intermediate Similarity	NPD6399	Phase 3
0.7374	Intermediate Similarity	NPD6903	Approved
0.7353	Intermediate Similarity	NPD7748	Approved
0.7327	Intermediate Similarity	NPD5693	Phase 1
0.7282	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6412	Phase 2
0.7238	Intermediate Similarity	NPD7638	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.713	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD6904	Approved
0.7129	Intermediate Similarity	NPD6080	Approved
0.7129	Intermediate Similarity	NPD6673	Approved
0.71	Intermediate Similarity	NPD3573	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7075	Intermediate Similarity	NPD4225	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6981	Remote Similarity	NPD6083	Phase 2
0.6981	Remote Similarity	NPD6084	Phase 2
0.6961	Remote Similarity	NPD6051	Approved
0.6961	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6882	Approved
0.6916	Remote Similarity	NPD5696	Approved
0.6915	Remote Similarity	NPD8039	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6893	Remote Similarity	NPD5207	Approved
0.6887	Remote Similarity	NPD7732	Phase 3
0.6863	Remote Similarity	NPD5208	Approved
0.6857	Remote Similarity	NPD6001	Approved
0.6832	Remote Similarity	NPD6098	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD6050	Approved
0.6827	Remote Similarity	NPD8035	Phase 2
0.6827	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5695	Phase 3
0.6786	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7327	Approved
0.678	Remote Similarity	NPD7328	Approved
0.6777	Remote Similarity	NPD8328	Phase 3
0.675	Remote Similarity	NPD8033	Approved
0.675	Remote Similarity	NPD7503	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.6731	Remote Similarity	NPD5692	Phase 3
0.6726	Remote Similarity	NPD6881	Approved
0.6726	Remote Similarity	NPD6899	Approved
0.6724	Remote Similarity	NPD8133	Approved
0.6723	Remote Similarity	NPD7516	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3665	Phase 1
0.6634	Remote Similarity	NPD4786	Approved
0.6634	Remote Similarity	NPD3666	Approved
0.6634	Remote Similarity	NPD3133	Approved
0.6634	Remote Similarity	NPD3668	Phase 3
0.6612	Remote Similarity	NPD8378	Approved
0.6612	Remote Similarity	NPD8380	Approved
0.6612	Remote Similarity	NPD8296	Approved
0.6612	Remote Similarity	NPD8379	Approved
0.6612	Remote Similarity	NPD8335	Approved
0.6609	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD7290	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.66	Remote Similarity	NPD3667	Approved
0.6579	Remote Similarity	NPD6011	Approved
0.6579	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6574	Remote Similarity	NPD7614	Phase 1
0.6571	Remote Similarity	NPD5785	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6847	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6013	Approved
0.6509	Remote Similarity	NPD6079	Approved
0.6505	Remote Similarity	NPD4623	Approved
0.6505	Remote Similarity	NPD4519	Discontinued
0.6505	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6053	Discontinued
0.6496	Remote Similarity	NPD8297	Approved
0.6491	Remote Similarity	NPD6614	Approved
0.6491	Remote Similarity	NPD5701	Approved
0.6489	Remote Similarity	NPD4691	Approved
0.6481	Remote Similarity	NPD5210	Approved
0.6481	Remote Similarity	NPD4629	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD5328	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6475	Remote Similarity	NPD8515	Approved
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6452	Remote Similarity	NPD7492	Approved
0.6436	Remote Similarity	NPD4223	Phase 3
0.6436	Remote Similarity	NPD4221	Approved
0.6417	Remote Similarity	NPD6009	Approved
0.641	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5329	Approved
0.6408	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6616	Approved
0.6396	Remote Similarity	NPD6404	Discontinued
0.6393	Remote Similarity	NPD6054	Approved
0.6383	Remote Similarity	NPD4137	Phase 3
0.6371	Remote Similarity	NPD6067	Discontinued
0.6355	Remote Similarity	NPD6411	Approved
0.6349	Remote Similarity	NPD7078	Approved
0.633	Remote Similarity	NPD5654	Approved
0.6321	Remote Similarity	NPD1695	Approved
0.6316	Remote Similarity	NPD4747	Approved
0.6311	Remote Similarity	NPD4197	Approved
0.6308	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6858	Approved
0.6303	Remote Similarity	NPD7094	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6289	Remote Similarity	NPD4058	Approved
0.6283	Remote Similarity	NPD5211	Phase 2
0.6275	Remote Similarity	NPD5209	Approved
0.6273	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4697	Phase 3
0.6273	Remote Similarity	NPD5221	Approved
0.6273	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5222	Approved
0.6262	Remote Similarity	NPD46	Approved
0.6262	Remote Similarity	NPD6698	Approved
0.626	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4696	Approved
0.623	Remote Similarity	NPD6335	Approved
0.6216	Remote Similarity	NPD5959	Approved
0.6216	Remote Similarity	NPD5173	Approved
0.6216	Remote Similarity	NPD4755	Approved
0.6214	Remote Similarity	NPD4788	Approved
0.621	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6015	Approved
0.621	Remote Similarity	NPD6016	Approved
0.6207	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.62	Remote Similarity	NPD3617	Approved
0.6198	Remote Similarity	NPD6274	Approved
0.6198	Remote Similarity	NPD6868	Approved
0.6195	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD4138	Approved
0.619	Remote Similarity	NPD5690	Phase 2
0.619	Remote Similarity	NPD5205	Approved
0.619	Remote Similarity	NPD4690	Approved
0.619	Remote Similarity	NPD4693	Phase 3
0.619	Remote Similarity	NPD4688	Approved
0.619	Remote Similarity	NPD4689	Approved
0.619	Remote Similarity	NPD5279	Phase 3
0.6186	Remote Similarity	NPD6371	Approved
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6174	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD6101	Approved
0.6168	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4632	Approved
0.616	Remote Similarity	NPD5988	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6148	Remote Similarity	NPD6317	Approved
0.6147	Remote Similarity	NPD5779	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