NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	376.922
LogP:	1.027
LogD:	1.563
LogS:	-2.883
# Rotatable Bonds:	6
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	4.992
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.686
MDCK Permeability:	0.00014380957873072475
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.49
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623
Plasma Protein Binding (PPB):	62.68352508544922%
Volume Distribution (VD):	0.42
Pgp-substrate:	59.283477783203125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.395
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	6.533
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.777
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.576
Carcinogencity:	0.046
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.112

Download Data

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

Natural Product: NPC476804

Natural Product ID:	NPC476804
*Common Name:**	[(3R,3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 4-hydroxy-2-methylidenebutanoate
IUPAC Name:	[(3R,3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-3,6-dimethyl-2-oxo-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-4-yl] 4-hydroxy-2-methylidenebutanoate
Synonyms:
Standard InCHIKey:	DTSRWZQRWMWHDL-FEEDYBRVSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-12-5-4-6-15(11-22)10-17-18(14(3)20(24)26-17)16(9-12)25-19(23)13(2)7-8-21/h5,10,14,16-18,21-22H,2,4,6-9,11H2,1,3H3/b12-5+,15-10-/t14-,16+,17-,18-/m1/s1
SMILES:	C[C@@H]1[C@@H]2[C@H](C/C(=C/CC/C(=C/[C@H]2OC1=O)/CO)/C)OC(=O)C(=C)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	163087129
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	Aerial parts	Chra Mountain in Blida (North Algeria)	2006-APR	PMID[17979247]
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18280170]
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	14
Others	14

Activity Type	# Activity
Organism	28

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	0.3	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MBC	=	0.2	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	0.3	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MBC	=	0.3	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.4	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	0.4	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	0.3	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MBC	=	0.3	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.2	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	0.2	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	0.1	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MFC	=	0.2	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	0.2	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MFC	=	0.3	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MIC	=	0.1	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MFC	=	0.2	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MIC	=	0.2	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MFC	=	0.3	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MIC	=	0.1	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MFC	=	0.2	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	0.2	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MFC	=	0.3	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MIC	=	0.2	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MFC	=	0.3	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	0.2	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MFC	=	0.3	ug/ml	PMID[17979247]

☑ 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 NPC476804 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	171
0.1-0.2	1080
0.2-0.3	4774
0.3-0.4	12344
0.4-0.5	12040
0.5-0.6	6969
0.6-0.7	4022
0.7-0.8	1062
0.8-0.85	117
0.85-0.9	52
0.9-0.95	48
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC255307
0.962	High Similarity	NPC169575
0.962	High Similarity	NPC40746
0.962	High Similarity	NPC473390
0.962	High Similarity	NPC131669
0.9615	High Similarity	NPC24417
0.9615	High Similarity	NPC52861
0.9512	High Similarity	NPC476803
0.9512	High Similarity	NPC476805
0.9506	High Similarity	NPC475461
0.9506	High Similarity	NPC305475
0.95	High Similarity	NPC158756
0.95	High Similarity	NPC114979
0.95	High Similarity	NPC191476
0.95	High Similarity	NPC141193
0.95	High Similarity	NPC96259
0.9494	High Similarity	NPC229825
0.9383	High Similarity	NPC470755
0.9359	High Similarity	NPC98557
0.9359	High Similarity	NPC167881
0.9286	High Similarity	NPC469368
0.9268	High Similarity	NPC469910
0.9231	High Similarity	NPC471465
0.9231	High Similarity	NPC196653
0.9136	High Similarity	NPC59097
0.9103	High Similarity	NPC141789
0.9103	High Similarity	NPC171204
0.9103	High Similarity	NPC7563
0.9103	High Similarity	NPC320630
0.9103	High Similarity	NPC476028
0.9103	High Similarity	NPC116177
0.9059	High Similarity	NPC475855
0.9048	High Similarity	NPC475819
0.9036	High Similarity	NPC150755
0.8987	High Similarity	NPC108816
0.8987	High Similarity	NPC93763
0.8974	High Similarity	NPC68819
0.8916	High Similarity	NPC165162
0.8902	High Similarity	NPC116543
0.8875	High Similarity	NPC89128
0.8875	High Similarity	NPC270126
0.8851	High Similarity	NPC228451
0.8851	High Similarity	NPC125674
0.8851	High Similarity	NPC475838
0.8837	High Similarity	NPC144133
0.8837	High Similarity	NPC179394
0.8837	High Similarity	NPC474232
0.8824	High Similarity	NPC473715
0.878	High Similarity	NPC89555
0.8765	High Similarity	NPC281132
0.875	High Similarity	NPC474247
0.875	High Similarity	NPC267231
0.8736	High Similarity	NPC473321
0.8721	High Similarity	NPC474032
0.8636	High Similarity	NPC288240
0.8636	High Similarity	NPC295204
0.8636	High Similarity	NPC475302
0.8636	High Similarity	NPC162205
0.8636	High Similarity	NPC273579
0.8625	High Similarity	NPC97516
0.8625	High Similarity	NPC474760
0.8621	High Similarity	NPC473619
0.859	High Similarity	NPC295633
0.859	High Similarity	NPC58956
0.859	High Similarity	NPC269206
0.8556	High Similarity	NPC230800
0.8556	High Similarity	NPC279621
0.8539	High Similarity	NPC303942
0.8539	High Similarity	NPC57405
0.8506	High Similarity	NPC206001
0.8506	High Similarity	NPC218927
0.85	High Similarity	NPC235906
0.8481	Intermediate Similarity	NPC476355
0.8481	Intermediate Similarity	NPC140287
0.8471	Intermediate Similarity	NPC21469
0.8462	Intermediate Similarity	NPC163003
0.8462	Intermediate Similarity	NPC129665
0.8452	Intermediate Similarity	NPC250315
0.8452	Intermediate Similarity	NPC474703
0.8444	Intermediate Similarity	NPC477922
0.8444	Intermediate Similarity	NPC304886
0.8444	Intermediate Similarity	NPC471142
0.8434	Intermediate Similarity	NPC325031
0.8434	Intermediate Similarity	NPC141810
0.8434	Intermediate Similarity	NPC25684
0.8434	Intermediate Similarity	NPC470241
0.8434	Intermediate Similarity	NPC301477
0.8434	Intermediate Similarity	NPC281949
0.8427	Intermediate Similarity	NPC475912
0.8415	Intermediate Similarity	NPC470239
0.8415	Intermediate Similarity	NPC178277
0.8415	Intermediate Similarity	NPC470244
0.8409	Intermediate Similarity	NPC129419
0.8391	Intermediate Similarity	NPC477302
0.8391	Intermediate Similarity	NPC136879
0.8375	Intermediate Similarity	NPC155587
0.8372	Intermediate Similarity	NPC50637
0.8352	Intermediate Similarity	NPC473859
0.8352	Intermediate Similarity	NPC477921
0.8295	Intermediate Similarity	NPC268298
0.8295	Intermediate Similarity	NPC295312
0.828	Intermediate Similarity	NPC288876
0.8276	Intermediate Similarity	NPC160138
0.8272	Intermediate Similarity	NPC123360
0.8256	Intermediate Similarity	NPC261380
0.825	Intermediate Similarity	NPC476590
0.825	Intermediate Similarity	NPC114727
0.8242	Intermediate Similarity	NPC475659
0.8242	Intermediate Similarity	NPC36954
0.8242	Intermediate Similarity	NPC471141
0.8242	Intermediate Similarity	NPC270013
0.8242	Intermediate Similarity	NPC14961
0.8222	Intermediate Similarity	NPC469692
0.8222	Intermediate Similarity	NPC469645
0.8214	Intermediate Similarity	NPC471325
0.8202	Intermediate Similarity	NPC473448
0.8193	Intermediate Similarity	NPC19841
0.8193	Intermediate Similarity	NPC617
0.8182	Intermediate Similarity	NPC202672
0.8172	Intermediate Similarity	NPC141191
0.8171	Intermediate Similarity	NPC470240
0.8171	Intermediate Similarity	NPC476794
0.8171	Intermediate Similarity	NPC57744
0.8161	Intermediate Similarity	NPC469483
0.8161	Intermediate Similarity	NPC107787
0.8152	Intermediate Similarity	NPC306041
0.8152	Intermediate Similarity	NPC476315
0.8148	Intermediate Similarity	NPC329852
0.814	Intermediate Similarity	NPC295799
0.814	Intermediate Similarity	NPC82297
0.8132	Intermediate Similarity	NPC81386
0.8132	Intermediate Similarity	NPC470010
0.8132	Intermediate Similarity	NPC323008
0.8132	Intermediate Similarity	NPC474035
0.8132	Intermediate Similarity	NPC470013
0.8132	Intermediate Similarity	NPC477131
0.8132	Intermediate Similarity	NPC121825
0.8132	Intermediate Similarity	NPC262133
0.8132	Intermediate Similarity	NPC198853
0.8132	Intermediate Similarity	NPC474338
0.8118	Intermediate Similarity	NPC85772
0.8118	Intermediate Similarity	NPC474252
0.8111	Intermediate Similarity	NPC475925
0.8111	Intermediate Similarity	NPC261607
0.8111	Intermediate Similarity	NPC133698
0.8111	Intermediate Similarity	NPC111114
0.8111	Intermediate Similarity	NPC131209
0.8111	Intermediate Similarity	NPC300312
0.8111	Intermediate Similarity	NPC30515
0.8111	Intermediate Similarity	NPC184463
0.809	Intermediate Similarity	NPC166919
0.8072	Intermediate Similarity	NPC128276
0.8068	Intermediate Similarity	NPC237540
0.8068	Intermediate Similarity	NPC266957
0.8065	Intermediate Similarity	NPC161493
0.8065	Intermediate Similarity	NPC169205
0.8046	Intermediate Similarity	NPC78089
0.8043	Intermediate Similarity	NPC67584
0.8043	Intermediate Similarity	NPC52044
0.8043	Intermediate Similarity	NPC213698
0.8043	Intermediate Similarity	NPC170120
0.8025	Intermediate Similarity	NPC48641
0.8022	Intermediate Similarity	NPC179746
0.8022	Intermediate Similarity	NPC212486
0.8022	Intermediate Similarity	NPC81419
0.8022	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC474761
0.8	Intermediate Similarity	NPC150923
0.8	Intermediate Similarity	NPC472254
0.8	Intermediate Similarity	NPC51004
0.8	Intermediate Similarity	NPC476004
0.7979	Intermediate Similarity	NPC473326
0.7979	Intermediate Similarity	NPC471144
0.7979	Intermediate Similarity	NPC187268
0.7978	Intermediate Similarity	NPC207114
0.7978	Intermediate Similarity	NPC217983
0.7978	Intermediate Similarity	NPC287089
0.7976	Intermediate Similarity	NPC86971
0.7976	Intermediate Similarity	NPC475210
0.7957	Intermediate Similarity	NPC185553
0.7957	Intermediate Similarity	NPC213078
0.7957	Intermediate Similarity	NPC54731
0.7955	Intermediate Similarity	NPC261721
0.7952	Intermediate Similarity	NPC65603
0.7952	Intermediate Similarity	NPC187568
0.7952	Intermediate Similarity	NPC41780
0.7949	Intermediate Similarity	NPC194871
0.7935	Intermediate Similarity	NPC127019
0.7935	Intermediate Similarity	NPC167219
0.7931	Intermediate Similarity	NPC472958
0.7931	Intermediate Similarity	NPC472957
0.7931	Intermediate Similarity	NPC156485
0.7931	Intermediate Similarity	NPC243618
0.7931	Intermediate Similarity	NPC115786
0.7931	Intermediate Similarity	NPC165287
0.7931	Intermediate Similarity	NPC159635
0.7931	Intermediate Similarity	NPC70424
0.7927	Intermediate Similarity	NPC226669
0.7927	Intermediate Similarity	NPC193351
0.7927	Intermediate Similarity	NPC138408

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 NPC476804 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1627
0.2-0.3	3723
0.3-0.4	2474
0.4-0.5	718
0.5-0.6	341
0.6-0.7	80
0.7-0.8	28
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7154	Phase 3
0.7802	Intermediate Similarity	NPD5785	Approved
0.7674	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5363	Approved
0.7614	Intermediate Similarity	NPD5362	Discontinued
0.7609	Intermediate Similarity	NPD6698	Approved
0.7609	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD4269	Approved
0.7471	Intermediate Similarity	NPD4821	Approved
0.7471	Intermediate Similarity	NPD4820	Approved
0.7471	Intermediate Similarity	NPD4822	Approved
0.7471	Intermediate Similarity	NPD4819	Approved
0.7444	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4268	Approved
0.7442	Intermediate Similarity	NPD4271	Approved
0.7423	Intermediate Similarity	NPD4225	Approved
0.7363	Intermediate Similarity	NPD5786	Approved
0.7363	Intermediate Similarity	NPD4249	Approved
0.7312	Intermediate Similarity	NPD1695	Approved
0.7303	Intermediate Similarity	NPD6435	Approved
0.7283	Intermediate Similarity	NPD4250	Approved
0.7283	Intermediate Similarity	NPD4251	Approved
0.7273	Intermediate Similarity	NPD4252	Approved
0.7255	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6371	Approved
0.7191	Intermediate Similarity	NPD5369	Approved
0.7158	Intermediate Similarity	NPD7983	Approved
0.7111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5779	Approved
0.7083	Intermediate Similarity	NPD5778	Approved
0.7079	Intermediate Similarity	NPD5368	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7053	Intermediate Similarity	NPD7838	Discovery
0.7033	Intermediate Similarity	NPD5332	Approved
0.7033	Intermediate Similarity	NPD5331	Approved
0.7	Intermediate Similarity	NPD4790	Discontinued
0.69	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6686	Approved
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6739	Remote Similarity	NPD5209	Approved
0.6735	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD6411	Approved
0.6627	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6053	Discontinued
0.6602	Remote Similarity	NPD5344	Discontinued
0.6598	Remote Similarity	NPD5370	Suspended
0.6569	Remote Similarity	NPD7638	Approved
0.6556	Remote Similarity	NPD4756	Discovery
0.6517	Remote Similarity	NPD8039	Approved
0.6465	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD8516	Approved
0.6435	Remote Similarity	NPD8517	Approved
0.6435	Remote Similarity	NPD8515	Approved
0.6435	Remote Similarity	NPD8513	Phase 3
0.6346	Remote Similarity	NPD6648	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.6311	Remote Similarity	NPD7902	Approved
0.6296	Remote Similarity	NPD5697	Approved
0.6279	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5695	Phase 3
0.6265	Remote Similarity	NPD368	Approved
0.625	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6211	Remote Similarity	NPD3667	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.6176	Remote Similarity	NPD7748	Approved
0.6168	Remote Similarity	NPD6647	Phase 2
0.6167	Remote Similarity	NPD8074	Phase 3
0.6147	Remote Similarity	NPD5701	Approved
0.6146	Remote Similarity	NPD6110	Phase 1
0.6139	Remote Similarity	NPD7515	Phase 2
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD6422	Discontinued
0.6122	Remote Similarity	NPD7146	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6118	Remote Similarity	NPD3197	Phase 1
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4786	Approved
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD5211	Phase 2
0.6075	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6058	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6018	Remote Similarity	NPD8297	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.598	Remote Similarity	NPD5693	Phase 1
0.598	Remote Similarity	NPD5284	Approved
0.598	Remote Similarity	NPD5281	Approved
0.598	Remote Similarity	NPD8034	Phase 2
0.598	Remote Similarity	NPD8035	Phase 2
0.5979	Remote Similarity	NPD6695	Phase 3
0.5977	Remote Similarity	NPD7331	Phase 2
0.5963	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD5210	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.5941	Remote Similarity	NPD4753	Phase 2
0.5929	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD2204	Approved
0.5929	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6008	Approved
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5875	Remote Similarity	NPD3172	Approved
0.5872	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6274	Approved
0.5859	Remote Similarity	NPD1696	Phase 3
0.5856	Remote Similarity	NPD6412	Phase 2
0.5856	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4755	Approved
0.5841	Remote Similarity	NPD6421	Discontinued
0.5841	Remote Similarity	NPD6420	Discontinued
0.5841	Remote Similarity	NPD2067	Discontinued
0.5833	Remote Similarity	NPD3198	Approved
0.5825	Remote Similarity	NPD6079	Approved
0.5823	Remote Similarity	NPD6927	Phase 3
0.582	Remote Similarity	NPD7507	Approved
0.5814	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3194	Approved
0.5802	Remote Similarity	NPD3195	Phase 2
0.5802	Remote Similarity	NPD3196	Approved
0.5802	Remote Similarity	NPD4266	Approved
0.58	Remote Similarity	NPD4519	Discontinued
0.58	Remote Similarity	NPD4623	Approved
0.5795	Remote Similarity	NPD3704	Approved
0.5789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3732	Approved
0.5785	Remote Similarity	NPD7642	Approved
0.5785	Remote Similarity	NPD7830	Approved
0.5785	Remote Similarity	NPD7829	Approved
0.5784	Remote Similarity	NPD6051	Approved
0.5784	Remote Similarity	NPD5328	Approved
0.578	Remote Similarity	NPD5224	Approved
0.578	Remote Similarity	NPD5225	Approved
0.578	Remote Similarity	NPD5226	Approved
0.578	Remote Similarity	NPD4633	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5769	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7641	Discontinued
0.576	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD3668	Phase 3
0.5758	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD4697	Phase 3
0.5755	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD4228	Discovery
0.5755	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5221	Approved
0.5752	Remote Similarity	NPD6413	Approved
0.575	Remote Similarity	NPD6291	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data