NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	258.152
LogP:	2.121
LogD:	1.995
LogS:	-3.32
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	4.497
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:	-4.577
MDCK Permeability:	2.7855014195665717e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.425
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	55.92267608642578%
Volume Distribution (VD):	1.247
Pgp-substrate:	46.11310958862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.296
CYP2C9-substrate:	0.372
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	12.24
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.829
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.526
Carcinogencity:	0.915
Eye Corrosion:	0.884
Eye Irritation:	0.564
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: NPC21471

Natural Product ID:	NPC21471
*Common Name:**	Ambrosin
IUPAC Name:	(3aS,6S,6aR,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
Synonyms:	Ambrosin
Standard InCHIKey:	IFXGCKRDLITNAU-JHSUYXJUSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8-4-5-10-9(2)14(17)18-13(10)15(3)11(8)6-7-12(15)16/h6-8,10-11,13H,2,4-5H2,1,3H3/t8-,10-,11-,13+,15-/m0/s1
SMILES:	C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@@]2(C)[C@H]1C=CC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL115843
PubChem CID:	92119
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO16340	Heterostemma brownii	Species	Apocynaceae	Eukaryota	Stems	n.a.	n.a.	PMID[9358639]
NPO12932	Hymenoclea salsola	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12932	Hymenoclea salsola	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12932	Hymenoclea salsola	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO9557	Rumex bequaertii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16262	Bacillus mojavensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16152	Phlebia radiata	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14970	Vitex polygama	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11155	Ambrosia maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12242	Lactuca tatarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12932	Hymenoclea salsola	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16668	Lonas annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2736	Penstemon diffusus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29601	Abrus fruticulosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16340	Heterostemma brownii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13843	Peronema canescens	Species	Lamiaceae	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
EC50	2
ED50	2
GI50	11
Others	16

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1
Organism	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	1000.0	nM	PMID[456450]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	1800.0	nM	PMID[456450]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	=	2900.0	nM	PMID[456450]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	=	2200.0	nM	PMID[456450]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	=	4900.0	nM	PMID[456450]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	=	3400.0	nM	PMID[456450]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	4500.0	nM	PMID[456450]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3900.0	nM	PMID[456450]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.74	n.a.	PMID[456451]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.45	ug ml-1	PMID[456451]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.83	umol/L	PMID[456452]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	=	1000.0	nM	PMID[456454]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3900.0	nM	PMID[456454]
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	300000.0	nM	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	86.6	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	75.9	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	74.1	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	51.8	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	19.6	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	EC50	=	220000.0	nM	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	99.0	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	92.4	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	85.4	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	57.3	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	GI	=	22.9	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	26.7	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	28.3	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	36.7	%	PMID[456453]
NPT936	Organism	Avena fatua	Avena fatua	Activity	=	50.0	%	PMID[456453]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2200.0	nM	PMID[456454]

☑ 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 NPC21471 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	215
0.1-0.2	1408
0.2-0.3	6274
0.3-0.4	14586
0.4-0.5	10262
0.5-0.6	6468
0.6-0.7	2882
0.7-0.8	524
0.8-0.85	50
0.85-0.9	13
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33570
0.9506	High Similarity	NPC161957
0.95	High Similarity	NPC215294
0.9294	High Similarity	NPC70595
0.9294	High Similarity	NPC150978
0.9294	High Similarity	NPC123177
0.9294	High Similarity	NPC74103
0.9259	High Similarity	NPC39588
0.9176	High Similarity	NPC253144
0.9125	High Similarity	NPC69271
0.9125	High Similarity	NPC74673
0.908	High Similarity	NPC167219
0.907	High Similarity	NPC284185
0.8977	High Similarity	NPC48803
0.8977	High Similarity	NPC90121
0.8977	High Similarity	NPC275960
0.8977	High Similarity	NPC193645
0.8889	High Similarity	NPC302426
0.8889	High Similarity	NPC276356
0.8889	High Similarity	NPC6823
0.8778	High Similarity	NPC169205
0.8706	High Similarity	NPC70422
0.8706	High Similarity	NPC104961
0.8706	High Similarity	NPC70555
0.8681	High Similarity	NPC141191
0.8681	High Similarity	NPC54843
0.8667	High Similarity	NPC185553
0.8659	High Similarity	NPC223904
0.8554	High Similarity	NPC35089
0.8554	High Similarity	NPC10276
0.8537	High Similarity	NPC472965
0.8537	High Similarity	NPC264227
0.8537	High Similarity	NPC63649
0.8537	High Similarity	NPC182550
0.8519	High Similarity	NPC15975
0.8519	High Similarity	NPC65603
0.8519	High Similarity	NPC195785
0.85	High Similarity	NPC193351
0.85	High Similarity	NPC138408
0.85	High Similarity	NPC226669
0.8488	Intermediate Similarity	NPC107787
0.8471	Intermediate Similarity	NPC115786
0.8434	Intermediate Similarity	NPC293418
0.8434	Intermediate Similarity	NPC290508
0.8434	Intermediate Similarity	NPC73052
0.8427	Intermediate Similarity	NPC261607
0.8427	Intermediate Similarity	NPC300312
0.8427	Intermediate Similarity	NPC111114
0.8409	Intermediate Similarity	NPC52198
0.8409	Intermediate Similarity	NPC117405
0.8372	Intermediate Similarity	NPC78089
0.8295	Intermediate Similarity	NPC215831
0.8293	Intermediate Similarity	NPC476794
0.8293	Intermediate Similarity	NPC470240
0.8276	Intermediate Similarity	NPC238593
0.8272	Intermediate Similarity	NPC155587
0.825	Intermediate Similarity	NPC472956
0.8229	Intermediate Similarity	NPC203659
0.8211	Intermediate Similarity	NPC225353
0.8202	Intermediate Similarity	NPC73995
0.8193	Intermediate Similarity	NPC299235
0.8182	Intermediate Similarity	NPC201658
0.8182	Intermediate Similarity	NPC478144
0.8171	Intermediate Similarity	NPC266159
0.8171	Intermediate Similarity	NPC235906
0.8171	Intermediate Similarity	NPC472967
0.8161	Intermediate Similarity	NPC177932
0.8148	Intermediate Similarity	NPC143979
0.8148	Intermediate Similarity	NPC320537
0.814	Intermediate Similarity	NPC318468
0.814	Intermediate Similarity	NPC54468
0.8125	Intermediate Similarity	NPC110989
0.8118	Intermediate Similarity	NPC301477
0.8118	Intermediate Similarity	NPC281949
0.8118	Intermediate Similarity	NPC25684
0.8118	Intermediate Similarity	NPC255580
0.8118	Intermediate Similarity	NPC39411
0.8111	Intermediate Similarity	NPC62815
0.8095	Intermediate Similarity	NPC470244
0.8095	Intermediate Similarity	NPC470239
0.809	Intermediate Similarity	NPC91248
0.8072	Intermediate Similarity	NPC41780
0.8072	Intermediate Similarity	NPC187568
0.8072	Intermediate Similarity	NPC208223
0.8043	Intermediate Similarity	NPC289004
0.8023	Intermediate Similarity	NPC173609
0.8023	Intermediate Similarity	NPC178676
0.8	Intermediate Similarity	NPC168679
0.8	Intermediate Similarity	NPC268298
0.8	Intermediate Similarity	NPC4986
0.8	Intermediate Similarity	NPC12872
0.7979	Intermediate Similarity	NPC170143
0.7979	Intermediate Similarity	NPC108475
0.7979	Intermediate Similarity	NPC213947
0.7978	Intermediate Similarity	NPC72513
0.7978	Intermediate Similarity	NPC478145
0.7976	Intermediate Similarity	NPC128276
0.7976	Intermediate Similarity	NPC472960
0.7976	Intermediate Similarity	NPC253749
0.7957	Intermediate Similarity	NPC304886
0.7955	Intermediate Similarity	NPC125290
0.7955	Intermediate Similarity	NPC110405
0.7952	Intermediate Similarity	NPC123360
0.7935	Intermediate Similarity	NPC135776
0.7931	Intermediate Similarity	NPC22611
0.7931	Intermediate Similarity	NPC193198
0.7931	Intermediate Similarity	NPC475947
0.7927	Intermediate Similarity	NPC469641
0.7927	Intermediate Similarity	NPC469643
0.7927	Intermediate Similarity	NPC476355
0.7912	Intermediate Similarity	NPC129419
0.7912	Intermediate Similarity	NPC152467
0.7907	Intermediate Similarity	NPC471325
0.7907	Intermediate Similarity	NPC47635
0.7907	Intermediate Similarity	NPC42470
0.7907	Intermediate Similarity	NPC38642
0.7901	Intermediate Similarity	NPC163003
0.7889	Intermediate Similarity	NPC226863
0.7882	Intermediate Similarity	NPC469690
0.7882	Intermediate Similarity	NPC178277
0.7882	Intermediate Similarity	NPC617
0.7875	Intermediate Similarity	NPC296522
0.7875	Intermediate Similarity	NPC144511
0.7865	Intermediate Similarity	NPC38576
0.7865	Intermediate Similarity	NPC64153
0.7865	Intermediate Similarity	NPC279859
0.7857	Intermediate Similarity	NPC57744
0.7857	Intermediate Similarity	NPC122264
0.7849	Intermediate Similarity	NPC477131
0.7841	Intermediate Similarity	NPC156485
0.7841	Intermediate Similarity	NPC475100
0.7841	Intermediate Similarity	NPC165287
0.7826	Intermediate Similarity	NPC131209
0.7826	Intermediate Similarity	NPC133698
0.7826	Intermediate Similarity	NPC286341
0.7826	Intermediate Similarity	NPC191339
0.7805	Intermediate Similarity	NPC58956
0.7805	Intermediate Similarity	NPC269206
0.7805	Intermediate Similarity	NPC295633
0.7778	Intermediate Similarity	NPC237540
0.7778	Intermediate Similarity	NPC472955
0.7766	Intermediate Similarity	NPC474490
0.7753	Intermediate Similarity	NPC215364
0.7753	Intermediate Similarity	NPC96621
0.7753	Intermediate Similarity	NPC165162
0.7753	Intermediate Similarity	NPC235792
0.7742	Intermediate Similarity	NPC200237
0.7742	Intermediate Similarity	NPC473263
0.7742	Intermediate Similarity	NPC475657
0.7742	Intermediate Similarity	NPC473234
0.7742	Intermediate Similarity	NPC473273
0.7742	Intermediate Similarity	NPC60386
0.7742	Intermediate Similarity	NPC308656
0.7742	Intermediate Similarity	NPC153590
0.7738	Intermediate Similarity	NPC472959
0.7732	Intermediate Similarity	NPC171759
0.7732	Intermediate Similarity	NPC474742
0.7717	Intermediate Similarity	NPC469372
0.7717	Intermediate Similarity	NPC106510
0.7717	Intermediate Similarity	NPC145666
0.7717	Intermediate Similarity	NPC71533
0.7711	Intermediate Similarity	NPC140287
0.7701	Intermediate Similarity	NPC325031
0.7701	Intermediate Similarity	NPC141810
0.7701	Intermediate Similarity	NPC475665
0.7692	Intermediate Similarity	NPC469631
0.7692	Intermediate Similarity	NPC471047
0.7692	Intermediate Similarity	NPC469653
0.7692	Intermediate Similarity	NPC475906
0.7692	Intermediate Similarity	NPC469628
0.7683	Intermediate Similarity	NPC129665
0.7674	Intermediate Similarity	NPC469620
0.7674	Intermediate Similarity	NPC150646
0.7674	Intermediate Similarity	NPC270126
0.7667	Intermediate Similarity	NPC67493
0.7667	Intermediate Similarity	NPC284902
0.7667	Intermediate Similarity	NPC304558
0.7667	Intermediate Similarity	NPC261721
0.7667	Intermediate Similarity	NPC56593
0.766	Intermediate Similarity	NPC148463
0.766	Intermediate Similarity	NPC198853
0.766	Intermediate Similarity	NPC477130
0.766	Intermediate Similarity	NPC53685
0.766	Intermediate Similarity	NPC470697
0.766	Intermediate Similarity	NPC477129
0.766	Intermediate Similarity	NPC470010
0.766	Intermediate Similarity	NPC470013
0.766	Intermediate Similarity	NPC323008
0.766	Intermediate Similarity	NPC262133
0.766	Intermediate Similarity	NPC473331
0.7654	Intermediate Similarity	NPC5714
0.7654	Intermediate Similarity	NPC199557
0.7653	Intermediate Similarity	NPC474747
0.7647	Intermediate Similarity	NPC53581
0.7647	Intermediate Similarity	NPC474760
0.7647	Intermediate Similarity	NPC103987
0.764	Intermediate Similarity	NPC238197
0.7634	Intermediate Similarity	NPC472953
0.7619	Intermediate Similarity	NPC244166
0.7614	Intermediate Similarity	NPC246076

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 NPC21471 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1917
0.2-0.3	4014
0.3-0.4	2089
0.4-0.5	593
0.5-0.6	283
0.6-0.7	50
0.7-0.8	6
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD1698	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD1694	Approved
0.8	Intermediate Similarity	NPD1695	Approved
0.7816	Intermediate Similarity	NPD5209	Approved
0.7717	Intermediate Similarity	NPD5785	Approved
0.7416	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6371	Approved
0.7292	Intermediate Similarity	NPD5282	Discontinued
0.7174	Intermediate Similarity	NPD5363	Approved
0.7174	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD5369	Approved
0.6915	Remote Similarity	NPD6409	Approved
0.6915	Remote Similarity	NPD7334	Approved
0.6915	Remote Similarity	NPD5330	Approved
0.6915	Remote Similarity	NPD6684	Approved
0.6915	Remote Similarity	NPD7146	Approved
0.6915	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD4269	Approved
0.6848	Remote Similarity	NPD4270	Approved
0.6818	Remote Similarity	NPD8039	Approved
0.6804	Remote Similarity	NPD5207	Approved
0.6774	Remote Similarity	NPD5362	Discontinued
0.6771	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD4252	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6598	Remote Similarity	NPD6672	Approved
0.6598	Remote Similarity	NPD5737	Approved
0.6596	Remote Similarity	NPD7154	Phase 3
0.6593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD5693	Phase 1
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6399	Phase 3
0.6495	Remote Similarity	NPD3573	Approved
0.6449	Remote Similarity	NPD6008	Approved
0.6436	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7900	Approved
0.6436	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.63	Remote Similarity	NPD46	Approved
0.63	Remote Similarity	NPD6698	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7748	Approved
0.6263	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD7902	Approved
0.6238	Remote Similarity	NPD5694	Approved
0.6224	Remote Similarity	NPD3618	Phase 1
0.6214	Remote Similarity	NPD5695	Phase 3
0.62	Remote Similarity	NPD6080	Approved
0.62	Remote Similarity	NPD6673	Approved
0.62	Remote Similarity	NPD6904	Approved
0.619	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD7638	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD3133	Approved
0.6182	Remote Similarity	NPD6686	Approved
0.6146	Remote Similarity	NPD3667	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6139	Remote Similarity	NPD5692	Phase 3
0.6132	Remote Similarity	NPD7640	Approved
0.6132	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5368	Approved
0.6105	Remote Similarity	NPD4695	Discontinued
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD5332	Approved
0.6082	Remote Similarity	NPD5331	Approved
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD7637	Suspended
0.6078	Remote Similarity	NPD7983	Approved
0.6078	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD6079	Approved
0.6078	Remote Similarity	NPD6050	Approved
0.6078	Remote Similarity	NPD7515	Phase 2
0.6061	Remote Similarity	NPD6098	Approved
0.6061	Remote Similarity	NPD5279	Phase 3
0.6061	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4519	Discontinued
0.6061	Remote Similarity	NPD4249	Approved
0.6061	Remote Similarity	NPD4623	Approved
0.6042	Remote Similarity	NPD4790	Discontinued
0.604	Remote Similarity	NPD5370	Suspended
0.6036	Remote Similarity	NPD6881	Approved
0.6036	Remote Similarity	NPD6011	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.602	Remote Similarity	NPD3668	Phase 3
0.602	Remote Similarity	NPD4786	Approved
0.6018	Remote Similarity	NPD6650	Approved
0.6018	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD4251	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6053	Discontinued
0.5963	Remote Similarity	NPD6052	Approved
0.5955	Remote Similarity	NPD229	Approved
0.5938	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD4822	Approved
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5922	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD5690	Phase 2
0.5895	Remote Similarity	NPD4271	Approved
0.5895	Remote Similarity	NPD4268	Approved
0.5893	Remote Similarity	NPD7320	Approved
0.5888	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6051	Approved
0.5882	Remote Similarity	NPD5328	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5877	Remote Similarity	NPD6869	Approved
0.5876	Remote Similarity	NPD857	Phase 3
0.5862	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6402	Approved
0.5856	Remote Similarity	NPD5739	Approved
0.5856	Remote Similarity	NPD7128	Approved
0.5856	Remote Similarity	NPD6675	Approved
0.5849	Remote Similarity	NPD5222	Approved
0.5849	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7839	Suspended
0.5849	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5221	Approved
0.5841	Remote Similarity	NPD6372	Approved
0.5841	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD6882	Approved
0.5826	Remote Similarity	NPD8297	Approved
0.5824	Remote Similarity	NPD4691	Approved
0.582	Remote Similarity	NPD7492	Approved
0.5816	Remote Similarity	NPD4221	Approved
0.5816	Remote Similarity	NPD4223	Phase 3
0.5816	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4058	Approved
0.5804	Remote Similarity	NPD6614	Approved
0.5804	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5701	Approved
0.58	Remote Similarity	NPD1696	Phase 3
0.5794	Remote Similarity	NPD5173	Approved
0.5789	Remote Similarity	NPD4756	Discovery
0.5784	Remote Similarity	NPD4518	Approved
0.5772	Remote Similarity	NPD6616	Approved
0.5755	Remote Similarity	NPD5654	Approved
0.575	Remote Similarity	NPD6054	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5739	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.573	Remote Similarity	NPD7331	Phase 2
0.5728	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD4137	Phase 3
0.5714	Remote Similarity	NPD4202	Approved
0.5702	Remote Similarity	NPD6016	Approved
0.5702	Remote Similarity	NPD6015	Approved
0.5701	Remote Similarity	NPD7732	Phase 3
0.5701	Remote Similarity	NPD4697	Phase 3
0.57	Remote Similarity	NPD4197	Approved
0.5688	Remote Similarity	NPD6648	Approved
0.5688	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD5286	Approved
0.5688	Remote Similarity	NPD4696	Approved
0.568	Remote Similarity	NPD7736	Approved
0.5678	Remote Similarity	NPD6868	Approved
0.5676	Remote Similarity	NPD6647	Phase 2
0.5669	Remote Similarity	NPD7260	Phase 2
0.5656	Remote Similarity	NPD6370	Approved
0.5656	Remote Similarity	NPD5988	Approved
0.5652	Remote Similarity	NPD2067	Discontinued
0.5652	Remote Similarity	NPD4747	Approved
0.5652	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5959	Approved
0.5644	Remote Similarity	NPD5329	Approved
0.5641	Remote Similarity	NPD6858	Approved
0.5641	Remote Similarity	NPD4632	Approved
0.5641	Remote Similarity	NPD7094	Approved
0.5638	Remote Similarity	NPD4687	Approved
0.5636	Remote Similarity	NPD5223	Approved
0.5636	Remote Similarity	NPD5344	Discontinued

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