NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	1160.68
Volume:	1206.94
LogP:	6.969
LogD:	4.363
LogS:	-2.457
# Rotatable Bonds:	2
TPSA:	169.7
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	18
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.091
Synthetic Accessibility Score:	8.711
Fsp3:	0.583
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.8
MDCK Permeability:	1.4686627764604054e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.462
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	96.83690643310547%
Volume Distribution (VD):	1.6
Pgp-substrate:	4.537782669067383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.739
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.278
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.992
CYP3A4-substrate:	0.953

ADMET: Excretion

Clearance (CL):	4.323
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.978
Human Hepatotoxicity (H-HT):	0.999
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.459
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.944
Carcinogencity:	0.251
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC476493

Natural Product ID:	NPC476493
*Common Name:**	QNWBBGISMLEXSK-FHTKVFLTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QNWBBGISMLEXSK-FHTKVFLTSA-N
Standard InCHI:	InChI=1S/C72H88N8O6/c81-57-21-31-71-43-67-45-77-35-15-7-4-2-6-14-30-70(84,42-52(53(67)25-37-77)62-64-50(24-34-74-62)48-18-10-12-20-56(48)76-64)66(67)80(71)40-28-60(57)86-72-32-22-59(85-71)58(82)27-39-79(72)65-68(44-72)46-78-36-16-8-3-1-5-13-29-69(65,83)41-51(54(68)26-38-78)61-63-49(23-33-73-61)47-17-9-11-19-55(47)75-63/h1-2,5-6,9-12,17-20,23-24,33-34,41-42,53-54,57-60,65-66,75-76,81-84H,3-4,7-8,13-16,21-22,25-32,35-40,43-46H2/b5-1-,6-2-/t53-,54-,57+,58-,59+,60-,65+,66+,67-,68-,69-,70-,71+,72+/m0/s1
SMILES:	C1=CCC[C@@]2(C=C([C@@H]3CCN(CCCC1)C[C@]13C[C@]34CC[C@H]([C@H](CCN3[C@@H]21)O)O[C@]12CC[C@H]([C@H](CCN2[C@@H]2[C@@]3(C1)CN1CCCC/C=CCC[C@@]2(C=C([C@@H]3CC1)c1c2c(ccn1)c1ccccc1[nH]2)O)O4)O)c1c2c(ccn1)c1ccccc1[nH]2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3299035
PubChem CID:	90683388
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332848]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2004-Mar	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[16872140]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	collected from vertical slopes between 33 and 40 m from Knife Cape Manado, Indonesia	2002-May	PMID[16872140]
NPO33663	Acanthostrongylophora ingens	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[24902064]
NPO33663	Acanthostrongylophora ingens	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933894]
NPO33280	Acanthostrongylophora sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28452477]

☑ 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	5
MIC	6
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	1
Organism	6
Others	3
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	5400.0	nM	PMID[572922]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	12000.0	nM	PMID[572923]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	13000.0	nM	PMID[572923]
NPT1821	Individual Protein	Sortase	Staphylococcus aureus	IC50	>	150000.0	nM	PMID[572923]
NPT2	Others	Unspecified		IC50	=	130.0	nM	PMID[572922]
NPT2	Others	Unspecified		Inhibition	=	92.0	%	PMID[572922]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	0.1	ug.mL-1	PMID[572923]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.0016	ug.mL-1	PMID[572923]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	0.0016	ug.mL-1	PMID[572923]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	0.00078	ug.mL-1	PMID[572923]
NPT25245	ORGANISM	Proteus hauseri	Proteus hauseri	MIC	>	0.1	ug.mL-1	PMID[572923]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	0.1	ug.mL-1	PMID[572923]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	150000.0	nM	PMID[572923]
NPT2	Others	Unspecified		IC50	=	27000.0	nM	PMID[572923]

☑ 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 NPC476493 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	648
0.1-0.2	2440
0.2-0.3	16125
0.3-0.4	16543
0.4-0.5	3689
0.5-0.6	2217
0.6-0.7	971
0.7-0.8	58
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC471564
0.9095	High Similarity	NPC476492
0.8616	High Similarity	NPC471506
0.815	Intermediate Similarity	NPC472027
0.8142	Intermediate Similarity	NPC473757
0.8117	Intermediate Similarity	NPC473362
0.8117	Intermediate Similarity	NPC166492
0.8042	Intermediate Similarity	NPC81175
0.8034	Intermediate Similarity	NPC475258
0.8	Intermediate Similarity	NPC473310
0.7991	Intermediate Similarity	NPC475338
0.7991	Intermediate Similarity	NPC909
0.7948	Intermediate Similarity	NPC250835
0.7851	Intermediate Similarity	NPC475422
0.7838	Intermediate Similarity	NPC265576
0.7826	Intermediate Similarity	NPC475602
0.7763	Intermediate Similarity	NPC87755
0.7733	Intermediate Similarity	NPC471891
0.7675	Intermediate Similarity	NPC475288
0.7657	Intermediate Similarity	NPC6215
0.7607	Intermediate Similarity	NPC251936
0.7543	Intermediate Similarity	NPC126066
0.752	Intermediate Similarity	NPC41679
0.751	Intermediate Similarity	NPC476491
0.749	Intermediate Similarity	NPC477861
0.749	Intermediate Similarity	NPC476451
0.736	Intermediate Similarity	NPC473312
0.7353	Intermediate Similarity	NPC476041
0.7353	Intermediate Similarity	NPC304926
0.7308	Intermediate Similarity	NPC314957
0.7265	Intermediate Similarity	NPC33949
0.7249	Intermediate Similarity	NPC232130
0.7213	Intermediate Similarity	NPC313884
0.7213	Intermediate Similarity	NPC98371
0.7203	Intermediate Similarity	NPC107077
0.7203	Intermediate Similarity	NPC223791
0.7195	Intermediate Similarity	NPC314954
0.7195	Intermediate Similarity	NPC253580
0.7178	Intermediate Similarity	NPC477714
0.7175	Intermediate Similarity	NPC472108
0.7175	Intermediate Similarity	NPC139291
0.7154	Intermediate Similarity	NPC470126
0.7137	Intermediate Similarity	NPC477715
0.7108	Intermediate Similarity	NPC469554
0.7103	Intermediate Similarity	NPC478029
0.7101	Intermediate Similarity	NPC5145
0.7092	Intermediate Similarity	NPC478028
0.7061	Intermediate Similarity	NPC469501
0.7061	Intermediate Similarity	NPC469470
0.7059	Intermediate Similarity	NPC162860
0.7043	Intermediate Similarity	NPC107836
0.704	Intermediate Similarity	NPC133261
0.7035	Intermediate Similarity	NPC62510
0.7035	Intermediate Similarity	NPC15102
0.7034	Intermediate Similarity	NPC470500
0.7027	Intermediate Similarity	NPC280852
0.7024	Intermediate Similarity	NPC295228
0.7022	Intermediate Similarity	NPC472110
0.7022	Intermediate Similarity	NPC472109
0.7021	Intermediate Similarity	NPC155143
0.7021	Intermediate Similarity	NPC193761
0.7009	Intermediate Similarity	NPC187827
0.7009	Intermediate Similarity	NPC472105
0.6992	Remote Similarity	NPC162748
0.6987	Remote Similarity	NPC95783
0.6984	Remote Similarity	NPC325976
0.6979	Remote Similarity	NPC475506
0.6975	Remote Similarity	NPC54420
0.6972	Remote Similarity	NPC101543
0.6971	Remote Similarity	NPC75634
0.697	Remote Similarity	NPC472846
0.6967	Remote Similarity	NPC281049
0.6966	Remote Similarity	NPC100321
0.6955	Remote Similarity	NPC183407
0.6947	Remote Similarity	NPC48938
0.6941	Remote Similarity	NPC472207
0.694	Remote Similarity	NPC133366
0.6937	Remote Similarity	NPC472123
0.6932	Remote Similarity	NPC475859
0.6932	Remote Similarity	NPC475969
0.6923	Remote Similarity	NPC155444
0.6923	Remote Similarity	NPC473640
0.692	Remote Similarity	NPC56109
0.692	Remote Similarity	NPC191382
0.692	Remote Similarity	NPC59269
0.6916	Remote Similarity	NPC472294
0.6903	Remote Similarity	NPC314394
0.6898	Remote Similarity	NPC469594
0.6897	Remote Similarity	NPC474177
0.6892	Remote Similarity	NPC69843
0.6892	Remote Similarity	NPC470730
0.6892	Remote Similarity	NPC477175
0.6891	Remote Similarity	NPC475070
0.688	Remote Similarity	NPC110151
0.6878	Remote Similarity	NPC476874
0.6877	Remote Similarity	NPC70155
0.6875	Remote Similarity	NPC472122
0.6875	Remote Similarity	NPC24594
0.6872	Remote Similarity	NPC472444
0.6865	Remote Similarity	NPC477177
0.6861	Remote Similarity	NPC314603
0.6851	Remote Similarity	NPC171317
0.6846	Remote Similarity	NPC478158
0.6844	Remote Similarity	NPC326575
0.6844	Remote Similarity	NPC478157
0.6838	Remote Similarity	NPC165743
0.6838	Remote Similarity	NPC231342
0.6831	Remote Similarity	NPC151976
0.6825	Remote Similarity	NPC326363
0.682	Remote Similarity	NPC470505
0.6816	Remote Similarity	NPC204491
0.6813	Remote Similarity	NPC57690
0.6805	Remote Similarity	NPC127677
0.6803	Remote Similarity	NPC234078
0.6803	Remote Similarity	NPC229348
0.6803	Remote Similarity	NPC221100
0.6802	Remote Similarity	NPC193267
0.6802	Remote Similarity	NPC213530
0.68	Remote Similarity	NPC150048
0.68	Remote Similarity	NPC203754
0.68	Remote Similarity	NPC141428
0.6798	Remote Similarity	NPC19679
0.679	Remote Similarity	NPC320968
0.6772	Remote Similarity	NPC89987
0.677	Remote Similarity	NPC151939
0.6768	Remote Similarity	NPC14812
0.6763	Remote Similarity	NPC323927
0.6763	Remote Similarity	NPC46225
0.6756	Remote Similarity	NPC189812
0.6756	Remote Similarity	NPC329688
0.6753	Remote Similarity	NPC478009
0.6753	Remote Similarity	NPC478010
0.674	Remote Similarity	NPC472443
0.6735	Remote Similarity	NPC469592
0.6735	Remote Similarity	NPC471080
0.6734	Remote Similarity	NPC52254
0.6732	Remote Similarity	NPC474877
0.6726	Remote Similarity	NPC201700
0.6726	Remote Similarity	NPC317430
0.6725	Remote Similarity	NPC472104
0.6724	Remote Similarity	NPC65215
0.6724	Remote Similarity	NPC213629
0.6724	Remote Similarity	NPC46413
0.6724	Remote Similarity	NPC173028
0.6723	Remote Similarity	NPC249040
0.6716	Remote Similarity	NPC315467
0.6711	Remote Similarity	NPC300688
0.6708	Remote Similarity	NPC271862
0.6706	Remote Similarity	NPC472762
0.6696	Remote Similarity	NPC474897
0.6694	Remote Similarity	NPC87856
0.6693	Remote Similarity	NPC477176
0.6693	Remote Similarity	NPC64216
0.6693	Remote Similarity	NPC470729
0.6691	Remote Similarity	NPC471303
0.669	Remote Similarity	NPC472842
0.6682	Remote Similarity	NPC160105
0.6681	Remote Similarity	NPC204565
0.6681	Remote Similarity	NPC32200
0.6681	Remote Similarity	NPC317030
0.668	Remote Similarity	NPC63279
0.668	Remote Similarity	NPC203614
0.668	Remote Similarity	NPC132211
0.668	Remote Similarity	NPC310118
0.6679	Remote Similarity	NPC478006
0.6667	Remote Similarity	NPC141377
0.6667	Remote Similarity	NPC163421
0.6667	Remote Similarity	NPC270009
0.6667	Remote Similarity	NPC258062
0.6667	Remote Similarity	NPC229332
0.6667	Remote Similarity	NPC267965
0.6667	Remote Similarity	NPC188387
0.6655	Remote Similarity	NPC477633
0.6654	Remote Similarity	NPC263937
0.6654	Remote Similarity	NPC297642
0.6654	Remote Similarity	NPC94428
0.6653	Remote Similarity	NPC477114
0.6653	Remote Similarity	NPC205254
0.6653	Remote Similarity	NPC106771
0.6653	Remote Similarity	NPC303820
0.6653	Remote Similarity	NPC23420
0.6652	Remote Similarity	NPC63751
0.664	Remote Similarity	NPC267926
0.664	Remote Similarity	NPC24370
0.664	Remote Similarity	NPC319232
0.6639	Remote Similarity	NPC149708
0.6639	Remote Similarity	NPC476116
0.6639	Remote Similarity	NPC98715
0.6639	Remote Similarity	NPC52557
0.6638	Remote Similarity	NPC474707
0.6627	Remote Similarity	NPC174788
0.6627	Remote Similarity	NPC266192
0.6626	Remote Similarity	NPC477065
0.6626	Remote Similarity	NPC31385
0.6626	Remote Similarity	NPC225821
0.6626	Remote Similarity	NPC75726
0.6626	Remote Similarity	NPC110602
0.6625	Remote Similarity	NPC475935
0.6625	Remote Similarity	NPC94211
0.6625	Remote Similarity	NPC300183

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 NPC476493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	605
0.2-0.3	1184
0.3-0.4	2714
0.4-0.5	2639
0.5-0.6	1464
0.6-0.7	261
0.7-0.8	15
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
0.7306	Intermediate Similarity	NPD7824	Approved
0.7295	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6978	Phase 2
0.7224	Intermediate Similarity	NPD7730	Approved
0.7224	Intermediate Similarity	NPD7731	Approved
0.7218	Intermediate Similarity	NPD7950	Approved
0.7218	Intermediate Similarity	NPD7791	Approved
0.7218	Intermediate Similarity	NPD7951	Approved
0.7218	Intermediate Similarity	NPD7789	Approved
0.7218	Intermediate Similarity	NPD7952	Approved
0.7218	Intermediate Similarity	NPD7953	Approved
0.7218	Intermediate Similarity	NPD7790	Approved
0.7213	Intermediate Similarity	NPD7271	Approved
0.7213	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8322	Phase 2
0.7113	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8250	Phase 2
0.7078	Intermediate Similarity	NPD6455	Phase 3
0.7049	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7558	Phase 2
0.6933	Remote Similarity	NPD6595	Phase 3
0.692	Remote Similarity	NPD7781	Approved
0.692	Remote Similarity	NPD7780	Approved
0.6917	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8431	Approved
0.6862	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7957	Phase 1
0.6849	Remote Similarity	NPD4886	Phase 2
0.6844	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8408	Discontinued
0.6818	Remote Similarity	NPD8321	Discontinued
0.6797	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8289	Discontinued
0.6763	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3330	Phase 1
0.6749	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7665	Phase 2
0.6736	Remote Similarity	NPD7666	Phase 3
0.6722	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7921	Approved
0.6694	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8442	Discontinued
0.6681	Remote Similarity	NPD8020	Approved
0.6681	Remote Similarity	NPD5065	Approved
0.6681	Remote Similarity	NPD8021	Approved
0.668	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7948	Phase 1
0.6667	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6655	Remote Similarity	NPD7181	Phase 3
0.6653	Remote Similarity	NPD7470	Discontinued
0.6624	Remote Similarity	NPD8063	Discontinued
0.6622	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD6615	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5426	Phase 3
0.6612	Remote Similarity	NPD8272	Phase 2
0.6611	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4076	Approved
0.6594	Remote Similarity	NPD4079	Approved
0.6586	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7001	Phase 3
0.6583	Remote Similarity	NPD4601	Approved
0.6583	Remote Similarity	NPD4600	Approved
0.6579	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.656	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8093	Discontinued
0.6557	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.655	Remote Similarity	NPD3505	Approved
0.655	Remote Similarity	NPD3506	Approved
0.6537	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD3402	Phase 1
0.6519	Remote Similarity	NPD7772	Phase 3
0.6514	Remote Similarity	NPD8525	Approved
0.6513	Remote Similarity	NPD7944	Discontinued
0.6509	Remote Similarity	NPD5596	Phase 2
0.6504	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD8072	Approved
0.65	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8426	Approved
0.6489	Remote Similarity	NPD8425	Approved
0.6486	Remote Similarity	NPD8364	Approved
0.6486	Remote Similarity	NPD8363	Approved
0.648	Remote Similarity	NPD5612	Discontinued
0.6479	Remote Similarity	NPD7769	Phase 3
0.6478	Remote Similarity	NPD8122	Approved
0.6478	Remote Similarity	NPD8123	Approved
0.6475	Remote Similarity	NPD4034	Approved
0.6475	Remote Similarity	NPD4039	Approved
0.6475	Remote Similarity	NPD4122	Approved
0.6475	Remote Similarity	NPD4038	Approved
0.6475	Remote Similarity	NPD4036	Approved
0.6475	Remote Similarity	NPD4033	Approved
0.6475	Remote Similarity	NPD32	Approved
0.6475	Remote Similarity	NPD4035	Approved
0.6475	Remote Similarity	NPD31	Approved
0.6475	Remote Similarity	NPD4037	Approved
0.6473	Remote Similarity	NPD8395	Approved
0.6473	Remote Similarity	NPD8396	Approved
0.6468	Remote Similarity	NPD7194	Discontinued
0.6464	Remote Similarity	NPD8429	Approved
0.6464	Remote Similarity	NPD8428	Approved
0.6464	Remote Similarity	NPD8427	Approved
0.6461	Remote Similarity	NPD8073	Approved
0.646	Remote Similarity	NPD6456	Discontinued
0.6454	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD8325	Phase 3
0.6454	Remote Similarity	NPD8326	Phase 3
0.6454	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7674	Phase 3
0.6445	Remote Similarity	NPD7675	Phase 3
0.6445	Remote Similarity	NPD6352	Phase 2
0.6445	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8247	Approved
0.6444	Remote Similarity	NPD8246	Approved
0.644	Remote Similarity	NPD7188	Phase 3
0.6439	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6431	Remote Similarity	NPD7716	Approved
0.6431	Remote Similarity	NPD7717	Approved
0.6429	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3404	Approved
0.6426	Remote Similarity	NPD6992	Phase 2
0.6422	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.642	Remote Similarity	NPD8629	Discontinued
0.6416	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8115	Approved
0.6408	Remote Similarity	NPD8114	Approved
0.6407	Remote Similarity	NPD2144	Approved
0.6407	Remote Similarity	NPD8370	Discontinued
0.6406	Remote Similarity	NPD8466	Approved
0.6406	Remote Similarity	NPD8467	Approved
0.6406	Remote Similarity	NPD8465	Approved
0.6405	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6999	Discontinued
0.6404	Remote Similarity	NPD8358	Approved
0.64	Remote Similarity	NPD8094	Discontinued
0.6398	Remote Similarity	NPD3961	Discontinued
0.6398	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7867	Phase 1
0.6395	Remote Similarity	NPD3038	Discontinued
0.6393	Remote Similarity	NPD5486	Discontinued
0.6389	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD8257	Approved
0.6389	Remote Similarity	NPD8256	Approved
0.6385	Remote Similarity	NPD8119	Discontinued
0.6383	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7603	Discontinued
0.6379	Remote Similarity	NPD4500	Approved
0.6379	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8386	Phase 2
0.6379	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4501	Approved
0.6375	Remote Similarity	NPD4602	Approved
0.6371	Remote Similarity	NPD8374	Phase 3
0.6367	Remote Similarity	NPD8375	Approved
0.6361	Remote Similarity	NPD8421	Discontinued
0.636	Remote Similarity	NPD5862	Discovery
0.6357	Remote Similarity	NPD6164	Phase 2
0.6357	Remote Similarity	NPD6165	Phase 2
0.6354	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4440	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3394	Approved
0.6349	Remote Similarity	NPD3389	Approved
0.6349	Remote Similarity	NPD3393	Approved
0.6346	Remote Similarity	NPD8316	Phase 2
0.6346	Remote Similarity	NPD8317	Phase 2
0.6345	Remote Similarity	NPD6281	Approved
0.6341	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD8524	Approved
0.6336	Remote Similarity	NPD4181	Approved
0.6333	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7423	Phase 2
0.632	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD7711	Discontinued
0.6318	Remote Similarity	NPD3343	Phase 3
0.6318	Remote Similarity	NPD5913	Phase 3
0.6318	Remote Similarity	NPD8284	Discontinued
0.6316	Remote Similarity	NPD8459	Approved
0.6316	Remote Similarity	NPD8460	Approved
0.6316	Remote Similarity	NPD7770	Phase 3
0.6316	Remote Similarity	NPD5458	Discontinued
0.6314	Remote Similarity	NPD3082	Discontinued
0.6308	Remote Similarity	NPD8512	Phase 3
0.6307	Remote Similarity	NPD7619	Phase 3
0.6307	Remote Similarity	NPD7618	Phase 3
0.6306	Remote Similarity	NPD8468	Phase 2

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