NPASS Compound

Structure

NPC173917 OpenBabel07101718242D 29 33 0 0 1 0 0 0 0 0999 V2000 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 -0.6994 1.9680 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 0.5878 -0.8090 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 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 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 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 23 1 0 0 0 0 2 23 1 0 0 0 0 5 28 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 18 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 6 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 6 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 24 3 1 6 0 0 0 25 4 1 6 0 0 0 26 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.31
Volume:	439.204
LogP:	6.0
LogD:	4.422
LogS:	-5.406
# Rotatable Bonds:	2
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	4.989
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615
MDCK Permeability:	1.4326978998724371e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.867

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	85.4054183959961%
Volume Distribution (VD):	1.968
Pgp-substrate:	9.616868019104004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	11.015
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.916
Carcinogencity:	0.586
Eye Corrosion:	0.346
Eye Irritation:	0.569
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC173917

Natural Product ID:	NPC173917
*Common Name:**	[(1R,5As,5Bs,7As,11Ar,11Bs,13As,13Br)-1-Methoxy-5B,8,8,13A-Tetramethyl-1,3,5,5A,6,7,7A,9,10,11,11B,12,13,13B-Tetradecahydrophenanthro[2,1-E][2]Benzofuran-11A-Yl]Methanol
IUPAC Name:	[(1R,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-methoxy-5b,8,8,13a-tetramethyl-1,3,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-11a-yl]methanol
Synonyms:
Standard InCHIKey:	QZOGSLSUTNSYEO-WAEZVMSBSA-N
Standard InCHI:	InChI=1S/C26H42O3/c1-23(2)11-6-12-26(16-27)18(23)9-13-24(3)19-8-7-17-15-29-22(28-5)21(17)25(19,4)14-10-20(24)26/h7,18-22,27H,6,8-16H2,1-5H3/t18-,19-,20-,21+,22+,24-,25-,26+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(CO)[C@H]1CC[C@@]1(C)[C@@H]3CC=C4CO[C@H]([C@@H]4[C@@]3(C)CC[C@H]21)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573401
PubChem CID:	25158952
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	1

Activity Type	# Activity
Cell Line	1
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	=	0.11	ug.mL-1	PMID[525693]
NPT4391	Individual Protein	Isocitrate lyase	Magnaporthe oryzae (strain 70-15 / FGSC 8958) (Rice blast fungus)(Pyricularia oryzae)	IC50	=	42.0	ug.mL-1	PMID[525693]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[525693]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[525693]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[525693]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[525693]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	6.25	ug.mL-1	PMID[525693]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[525693]

☑ 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 NPC173917 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	175
0.1-0.2	1462
0.2-0.3	5632
0.3-0.4	15388
0.4-0.5	8315
0.5-0.6	5997
0.6-0.7	4630
0.7-0.8	1036
0.8-0.85	44
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9125	High Similarity	NPC17550
0.9091	High Similarity	NPC100892
0.9091	High Similarity	NPC477970
0.8977	High Similarity	NPC189513
0.8876	High Similarity	NPC135224
0.8876	High Similarity	NPC477969
0.8824	High Similarity	NPC118266
0.8681	High Similarity	NPC76266
0.8523	High Similarity	NPC293044
0.8523	High Similarity	NPC470819
0.8511	High Similarity	NPC134077
0.8495	Intermediate Similarity	NPC219285
0.8495	Intermediate Similarity	NPC477968
0.8495	Intermediate Similarity	NPC228251
0.8495	Intermediate Similarity	NPC161527
0.8495	Intermediate Similarity	NPC20113
0.8495	Intermediate Similarity	NPC477972
0.8495	Intermediate Similarity	NPC477971
0.8488	Intermediate Similarity	NPC119001
0.8427	Intermediate Similarity	NPC470817
0.8404	Intermediate Similarity	NPC63249
0.8353	Intermediate Similarity	NPC122945
0.8353	Intermediate Similarity	NPC109938
0.8256	Intermediate Similarity	NPC324243
0.8222	Intermediate Similarity	NPC159876
0.8172	Intermediate Similarity	NPC8954
0.8172	Intermediate Similarity	NPC94905
0.8161	Intermediate Similarity	NPC46320
0.8161	Intermediate Similarity	NPC319238
0.8144	Intermediate Similarity	NPC222161
0.8118	Intermediate Similarity	NPC206062
0.8111	Intermediate Similarity	NPC473058
0.8085	Intermediate Similarity	NPC257726
0.8085	Intermediate Similarity	NPC98112
0.8085	Intermediate Similarity	NPC204054
0.8068	Intermediate Similarity	NPC42586
0.8068	Intermediate Similarity	NPC473251
0.8023	Intermediate Similarity	NPC7505
0.8023	Intermediate Similarity	NPC474683
0.8023	Intermediate Similarity	NPC474759
0.8023	Intermediate Similarity	NPC474731
0.8023	Intermediate Similarity	NPC82986
0.8023	Intermediate Similarity	NPC474752
0.8022	Intermediate Similarity	NPC469403
0.8021	Intermediate Similarity	NPC285231
0.8021	Intermediate Similarity	NPC21568
0.7959	Intermediate Similarity	NPC93352
0.7957	Intermediate Similarity	NPC104925
0.7957	Intermediate Similarity	NPC298973
0.7957	Intermediate Similarity	NPC324078
0.7957	Intermediate Similarity	NPC469697
0.7931	Intermediate Similarity	NPC304285
0.7917	Intermediate Similarity	NPC477721
0.7917	Intermediate Similarity	NPC477716
0.7917	Intermediate Similarity	NPC469942
0.7912	Intermediate Similarity	NPC477917
0.7895	Intermediate Similarity	NPC477719
0.7895	Intermediate Similarity	NPC477718
0.7872	Intermediate Similarity	NPC230347
0.7872	Intermediate Similarity	NPC275310
0.7872	Intermediate Similarity	NPC286612
0.7857	Intermediate Similarity	NPC471887
0.7857	Intermediate Similarity	NPC473123
0.7857	Intermediate Similarity	NPC471885
0.7857	Intermediate Similarity	NPC471888
0.7857	Intermediate Similarity	NPC473124
0.7857	Intermediate Similarity	NPC471450
0.7857	Intermediate Similarity	NPC471886
0.7849	Intermediate Similarity	NPC235126
0.7849	Intermediate Similarity	NPC91654
0.7849	Intermediate Similarity	NPC166346
0.7849	Intermediate Similarity	NPC242419
0.7849	Intermediate Similarity	NPC67398
0.7849	Intermediate Similarity	NPC246860
0.7849	Intermediate Similarity	NPC474792
0.7841	Intermediate Similarity	NPC472440
0.7835	Intermediate Similarity	NPC176406
0.7835	Intermediate Similarity	NPC470434
0.7835	Intermediate Similarity	NPC477717
0.7826	Intermediate Similarity	NPC92885
0.7826	Intermediate Similarity	NPC476226
0.7826	Intermediate Similarity	NPC77796
0.7826	Intermediate Similarity	NPC471432
0.7826	Intermediate Similarity	NPC471433
0.7812	Intermediate Similarity	NPC473154
0.78	Intermediate Similarity	NPC33053
0.7789	Intermediate Similarity	NPC207617
0.7789	Intermediate Similarity	NPC162346
0.7789	Intermediate Similarity	NPC73858
0.7778	Intermediate Similarity	NPC473127
0.7778	Intermediate Similarity	NPC110656
0.7778	Intermediate Similarity	NPC203354
0.7755	Intermediate Similarity	NPC238397
0.7755	Intermediate Similarity	NPC37207
0.7755	Intermediate Similarity	NPC471482
0.7755	Intermediate Similarity	NPC471363
0.7755	Intermediate Similarity	NPC300399
0.7755	Intermediate Similarity	NPC471889
0.7742	Intermediate Similarity	NPC477122
0.7742	Intermediate Similarity	NPC302584
0.7732	Intermediate Similarity	NPC146188
0.7732	Intermediate Similarity	NPC477720
0.7732	Intermediate Similarity	NPC282669
0.7727	Intermediate Similarity	NPC470049
0.7727	Intermediate Similarity	NPC155521
0.7723	Intermediate Similarity	NPC38376
0.7723	Intermediate Similarity	NPC80210
0.7717	Intermediate Similarity	NPC470734
0.7717	Intermediate Similarity	NPC473647
0.7711	Intermediate Similarity	NPC474743
0.7708	Intermediate Similarity	NPC243728
0.7708	Intermediate Similarity	NPC473890
0.7701	Intermediate Similarity	NPC473685
0.7692	Intermediate Similarity	NPC157441
0.7692	Intermediate Similarity	NPC474832
0.7677	Intermediate Similarity	NPC134270
0.7677	Intermediate Similarity	NPC127933
0.7677	Intermediate Similarity	NPC7644
0.7677	Intermediate Similarity	NPC7613
0.7677	Intermediate Similarity	NPC475889
0.7667	Intermediate Similarity	NPC157257
0.7667	Intermediate Similarity	NPC274448
0.7667	Intermediate Similarity	NPC477578
0.7667	Intermediate Similarity	NPC217394
0.7667	Intermediate Similarity	NPC472442
0.7667	Intermediate Similarity	NPC266511
0.766	Intermediate Similarity	NPC470656
0.766	Intermediate Similarity	NPC277721
0.766	Intermediate Similarity	NPC267266
0.7654	Intermediate Similarity	NPC476945
0.7647	Intermediate Similarity	NPC250089
0.7647	Intermediate Similarity	NPC195116
0.7647	Intermediate Similarity	NPC285253
0.7647	Intermediate Similarity	NPC157530
0.7647	Intermediate Similarity	NPC14630
0.7647	Intermediate Similarity	NPC472901
0.7647	Intermediate Similarity	NPC221110
0.7647	Intermediate Similarity	NPC180459
0.7634	Intermediate Similarity	NPC253186
0.7629	Intermediate Similarity	NPC158088
0.7624	Intermediate Similarity	NPC281939
0.7609	Intermediate Similarity	NPC471952
0.7609	Intermediate Similarity	NPC472810
0.7609	Intermediate Similarity	NPC472809
0.7609	Intermediate Similarity	NPC474629
0.76	Intermediate Similarity	NPC264867
0.76	Intermediate Similarity	NPC470321
0.76	Intermediate Similarity	NPC81567
0.76	Intermediate Similarity	NPC473207
0.76	Intermediate Similarity	NPC75608
0.76	Intermediate Similarity	NPC201880
0.7596	Intermediate Similarity	NPC194951
0.7596	Intermediate Similarity	NPC12046
0.7586	Intermediate Similarity	NPC28862
0.7586	Intermediate Similarity	NPC242767
0.7586	Intermediate Similarity	NPC109546
0.7586	Intermediate Similarity	NPC84694
0.7586	Intermediate Similarity	NPC143182
0.7586	Intermediate Similarity	NPC47982
0.7586	Intermediate Similarity	NPC81306
0.7579	Intermediate Similarity	NPC477927
0.7579	Intermediate Similarity	NPC72817
0.7579	Intermediate Similarity	NPC88507
0.7579	Intermediate Similarity	NPC305160
0.7579	Intermediate Similarity	NPC477722
0.7573	Intermediate Similarity	NPC170974
0.7573	Intermediate Similarity	NPC191439
0.7573	Intermediate Similarity	NPC103627
0.7558	Intermediate Similarity	NPC91594
0.7556	Intermediate Similarity	NPC470077
0.7553	Intermediate Similarity	NPC329842
0.7553	Intermediate Similarity	NPC120539
0.7553	Intermediate Similarity	NPC165904
0.7553	Intermediate Similarity	NPC234335
0.7553	Intermediate Similarity	NPC471453
0.7553	Intermediate Similarity	NPC65513
0.7553	Intermediate Similarity	NPC472811
0.7553	Intermediate Similarity	NPC179517
0.7551	Intermediate Similarity	NPC473790
0.7551	Intermediate Similarity	NPC64348
0.7531	Intermediate Similarity	NPC68703
0.7531	Intermediate Similarity	NPC197805
0.7531	Intermediate Similarity	NPC69649
0.7528	Intermediate Similarity	NPC5985
0.7526	Intermediate Similarity	NPC97867
0.7526	Intermediate Similarity	NPC240372
0.7526	Intermediate Similarity	NPC125551
0.7526	Intermediate Similarity	NPC177818
0.7526	Intermediate Similarity	NPC239547
0.7526	Intermediate Similarity	NPC155319
0.7526	Intermediate Similarity	NPC96597
0.7526	Intermediate Similarity	NPC26307
0.7526	Intermediate Similarity	NPC309503
0.7526	Intermediate Similarity	NPC91197
0.7526	Intermediate Similarity	NPC476893
0.7525	Intermediate Similarity	NPC172867
0.7525	Intermediate Similarity	NPC252296
0.7525	Intermediate Similarity	NPC472899
0.7525	Intermediate Similarity	NPC472898
0.7525	Intermediate Similarity	NPC472900

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 NPC173917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1583
0.2-0.3	4193
0.3-0.4	2306
0.4-0.5	505
0.5-0.6	258
0.6-0.7	136
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7326	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7525	Registered
0.7048	Intermediate Similarity	NPD6686	Approved
0.6989	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6412	Phase 2
0.6937	Remote Similarity	NPD7328	Approved
0.6937	Remote Similarity	NPD7327	Approved
0.6931	Remote Similarity	NPD7638	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.6875	Remote Similarity	NPD7516	Approved
0.6863	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD7640	Approved
0.6818	Remote Similarity	NPD4785	Approved
0.6818	Remote Similarity	NPD4784	Approved
0.6818	Remote Similarity	NPD6924	Approved
0.6818	Remote Similarity	NPD6926	Approved
0.6814	Remote Similarity	NPD8377	Approved
0.6814	Remote Similarity	NPD8294	Approved
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD6051	Approved
0.6782	Remote Similarity	NPD4243	Approved
0.6774	Remote Similarity	NPD3667	Approved
0.6771	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6399	Phase 3
0.6754	Remote Similarity	NPD8378	Approved
0.6754	Remote Similarity	NPD7503	Approved
0.6754	Remote Similarity	NPD8380	Approved
0.6754	Remote Similarity	NPD8296	Approved
0.6754	Remote Similarity	NPD8335	Approved
0.6754	Remote Similarity	NPD8379	Approved
0.6702	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6933	Approved
0.663	Remote Similarity	NPD6929	Approved
0.6602	Remote Similarity	NPD4225	Approved
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7509	Discontinued
0.6559	Remote Similarity	NPD6931	Approved
0.6559	Remote Similarity	NPD6930	Phase 2
0.6556	Remote Similarity	NPD8264	Approved
0.6552	Remote Similarity	NPD6923	Approved
0.6552	Remote Similarity	NPD6922	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7507	Approved
0.6522	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD7515	Phase 2
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6458	Remote Similarity	NPD3666	Approved
0.6458	Remote Similarity	NPD3133	Approved
0.6458	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD7524	Approved
0.6429	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD7750	Discontinued
0.6413	Remote Similarity	NPD6925	Approved
0.6413	Remote Similarity	NPD5776	Phase 2
0.6404	Remote Similarity	NPD7150	Approved
0.6404	Remote Similarity	NPD7151	Approved
0.6404	Remote Similarity	NPD7152	Approved
0.6383	Remote Similarity	NPD7332	Phase 2
0.6383	Remote Similarity	NPD6928	Phase 2
0.6383	Remote Similarity	NPD7514	Phase 3
0.6374	Remote Similarity	NPD4190	Phase 3
0.6374	Remote Similarity	NPD5275	Approved
0.6364	Remote Similarity	NPD7319	Approved
0.6346	Remote Similarity	NPD6083	Phase 2
0.6346	Remote Similarity	NPD6084	Phase 2
0.6344	Remote Similarity	NPD7145	Approved
0.6327	Remote Similarity	NPD7521	Approved
0.6327	Remote Similarity	NPD5330	Approved
0.6327	Remote Similarity	NPD7334	Approved
0.6327	Remote Similarity	NPD7146	Approved
0.6327	Remote Similarity	NPD6409	Approved
0.6327	Remote Similarity	NPD3618	Phase 1
0.6327	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6902	Approved
0.63	Remote Similarity	NPD5328	Approved
0.6277	Remote Similarity	NPD4195	Approved
0.6262	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD7115	Discovery
0.6237	Remote Similarity	NPD6932	Approved
0.6224	Remote Similarity	NPD6893	Approved
0.6224	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4748	Discontinued
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6903	Approved
0.62	Remote Similarity	NPD6672	Approved
0.6195	Remote Similarity	NPD6882	Approved
0.6176	Remote Similarity	NPD8035	Phase 2
0.6176	Remote Similarity	NPD8034	Phase 2
0.6176	Remote Similarity	NPD7637	Suspended
0.6176	Remote Similarity	NPD7087	Discontinued
0.6176	Remote Similarity	NPD6079	Approved
0.6173	Remote Similarity	NPD342	Phase 1
0.6168	Remote Similarity	NPD4159	Approved
0.6162	Remote Similarity	NPD4623	Approved
0.6162	Remote Similarity	NPD4519	Discontinued
0.6148	Remote Similarity	NPD7736	Approved
0.6146	Remote Similarity	NPD6898	Phase 1
0.6139	Remote Similarity	NPD4753	Phase 2
0.6139	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6370	Approved
0.6122	Remote Similarity	NPD3668	Phase 3
0.6121	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD368	Approved
0.6117	Remote Similarity	NPD4202	Approved
0.6105	Remote Similarity	NPD6683	Phase 2
0.6091	Remote Similarity	NPD5739	Approved
0.6091	Remote Similarity	NPD6675	Approved
0.6091	Remote Similarity	NPD6402	Approved
0.6091	Remote Similarity	NPD7128	Approved
0.6083	Remote Similarity	NPD6067	Discontinued
0.6083	Remote Similarity	NPD8328	Phase 3
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4221	Approved
0.6061	Remote Similarity	NPD1694	Approved
0.6061	Remote Similarity	NPD5329	Approved
0.605	Remote Similarity	NPD8516	Approved
0.605	Remote Similarity	NPD8515	Approved
0.605	Remote Similarity	NPD8513	Phase 3
0.605	Remote Similarity	NPD8517	Approved
0.6042	Remote Similarity	NPD4695	Discontinued
0.6022	Remote Similarity	NPD8039	Approved
0.602	Remote Similarity	NPD4788	Approved
0.6019	Remote Similarity	NPD5693	Phase 1
0.6019	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD1145	Discontinued
0.6	Remote Similarity	NPD6098	Approved
0.5982	Remote Similarity	NPD6899	Approved
0.5982	Remote Similarity	NPD6881	Approved
0.5982	Remote Similarity	NPD7320	Approved
0.5981	Remote Similarity	NPD5696	Approved
0.5977	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6054	Approved
0.5966	Remote Similarity	NPD6059	Approved
0.5965	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD8171	Discontinued
0.596	Remote Similarity	NPD4197	Approved
0.5952	Remote Similarity	NPD8449	Approved
0.5935	Remote Similarity	NPD8293	Discontinued
0.5929	Remote Similarity	NPD6373	Approved
0.5929	Remote Similarity	NPD6372	Approved
0.5929	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6053	Discontinued
0.5906	Remote Similarity	NPD8450	Suspended
0.59	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5697	Approved
0.5893	Remote Similarity	NPD5701	Approved
0.5888	Remote Similarity	NPD4755	Approved
0.5877	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD7290	Approved
0.5877	Remote Similarity	NPD7102	Approved
0.5868	Remote Similarity	NPD5126	Approved
0.5868	Remote Similarity	NPD5125	Phase 3
0.5849	Remote Similarity	NPD4629	Approved
0.5849	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5210	Approved
0.5842	Remote Similarity	NPD5205	Approved
0.5842	Remote Similarity	NPD4690	Approved
0.5842	Remote Similarity	NPD4693	Phase 3
0.5842	Remote Similarity	NPD4688	Approved
0.5842	Remote Similarity	NPD4689	Approved
0.5842	Remote Similarity	NPD4138	Approved
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD3617	Approved
0.5833	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD8130	Phase 1
0.5826	Remote Similarity	NPD6650	Approved
0.5826	Remote Similarity	NPD6617	Approved
0.5826	Remote Similarity	NPD6847	Approved
0.5826	Remote Similarity	NPD6649	Approved
0.5826	Remote Similarity	NPD6869	Approved
0.5825	Remote Similarity	NPD6080	Approved
0.5825	Remote Similarity	NPD6673	Approved
0.5825	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD6904	Approved
0.5825	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5211	Phase 2
0.581	Remote Similarity	NPD5779	Approved
0.581	Remote Similarity	NPD5778	Approved
0.5804	Remote Similarity	NPD6640	Phase 3
0.5794	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD5222	Approved
0.5794	Remote Similarity	NPD4697	Phase 3
0.5794	Remote Similarity	NPD5221	Approved
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5785	Remote Similarity	NPD6015	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