NPASS Compound

Structure

NPC69462 OpenBabel07101718202D 21 21 0 0 1 0 0 0 0 0999 V2000 -4.1225 -1.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 2.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4154 -1.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 -1.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1907 -0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -0.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 5 1 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 6 14 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 15 12 1 1 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 7 1 6 0 0 0 17 21 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.21
Volume:	323.92
LogP:	4.675
LogD:	4.017
LogS:	-4.942
# Rotatable Bonds:	10
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	4.095
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.476
MDCK Permeability:	2.4517103156540543e-05
Pgp-inhibitor:	0.913
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.066
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	93.04422760009766%
Volume Distribution (VD):	1.488
Pgp-substrate:	3.6143951416015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.369
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.447
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.492
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	10.048
Half-life (T1/2):	0.329

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.377
Drug-inuced Liver Injury (DILI):	0.806
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.728
Skin Sensitization:	0.291
Carcinogencity:	0.781
Eye Corrosion:	0.061
Eye Irritation:	0.177
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC69462

Natural Product ID:	NPC69462
*Common Name:**	Methyl (3R,6S,Z)-4,6-Diethyl-3,6-Epidioxydodeca-4-Enoate
IUPAC Name:	methyl 2-[(3R,6S)-4,6-diethyl-6-hexyl-3H-1,2-dioxin-3-yl]acetate
Synonyms:
Standard InCHIKey:	DVGHMGSERXEMNQ-WBVHZDCISA-N
Standard InCHI:	InChI=1S/C17H30O4/c1-5-8-9-10-11-17(7-3)13-14(6-2)15(20-21-17)12-16(18)19-4/h13,15H,5-12H2,1-4H3/t15-,17+/m1/s1
SMILES:	CCCCCC[C@]1(CC)OO[C@@H](C(=C1)CC)CC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451437
PubChem CID:	11174033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003416] Methyl esters

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26409	Plakortis simplex	Species	Plakinidae	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
IC50	12

Activity Type	# Activity
NON-MOLECULAR	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.3	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.7	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.9	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.2	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.4	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.1	ug.mL-1	PMID[482639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8.3	ug.mL-1	PMID[482640]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.7	ug.mL-1	PMID[482640]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.9	ug.mL-1	PMID[482640]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.2	ug.mL-1	PMID[482640]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.4	ug.mL-1	PMID[482640]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14.1	ug.mL-1	PMID[482640]

☑ 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 NPC69462 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	193
0.1-0.2	1337
0.2-0.3	6543
0.3-0.4	16980
0.4-0.5	9095
0.5-0.6	6490
0.6-0.7	1885
0.7-0.8	147
0.8-0.85	14
0.85-0.9	5
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC107130
0.9701	High Similarity	NPC238425
0.9701	High Similarity	NPC472018
0.9701	High Similarity	NPC474543
0.9559	High Similarity	NPC474551
0.9143	High Similarity	NPC199445
0.9118	High Similarity	NPC472017
0.9014	High Similarity	NPC474447
0.8714	High Similarity	NPC126061
0.8611	High Similarity	NPC60718
0.8592	High Similarity	NPC167145
0.8514	High Similarity	NPC121200
0.8472	Intermediate Similarity	NPC330016
0.8421	Intermediate Similarity	NPC79277
0.8421	Intermediate Similarity	NPC475481
0.8378	Intermediate Similarity	NPC281296
0.8378	Intermediate Similarity	NPC476264
0.8378	Intermediate Similarity	NPC476325
0.8356	Intermediate Similarity	NPC255060
0.8243	Intermediate Similarity	NPC239127
0.8	Intermediate Similarity	NPC469514
0.8	Intermediate Similarity	NPC266119
0.8	Intermediate Similarity	NPC284447
0.7975	Intermediate Similarity	NPC69469
0.7949	Intermediate Similarity	NPC476988
0.7922	Intermediate Similarity	NPC82488
0.7922	Intermediate Similarity	NPC308545
0.7821	Intermediate Similarity	NPC469920
0.7763	Intermediate Similarity	NPC476987
0.7763	Intermediate Similarity	NPC152754
0.7763	Intermediate Similarity	NPC59602
0.775	Intermediate Similarity	NPC475989
0.7722	Intermediate Similarity	NPC117960
0.7722	Intermediate Similarity	NPC172309
0.7722	Intermediate Similarity	NPC14044
0.7683	Intermediate Similarity	NPC476982
0.7683	Intermediate Similarity	NPC476104
0.7662	Intermediate Similarity	NPC474760
0.7625	Intermediate Similarity	NPC85772
0.7568	Intermediate Similarity	NPC475310
0.7564	Intermediate Similarity	NPC474341
0.7561	Intermediate Similarity	NPC471344
0.7532	Intermediate Similarity	NPC476985
0.7532	Intermediate Similarity	NPC474316
0.7532	Intermediate Similarity	NPC475744
0.7531	Intermediate Similarity	NPC475947
0.7531	Intermediate Similarity	NPC476983
0.75	Intermediate Similarity	NPC474758
0.75	Intermediate Similarity	NPC141810
0.747	Intermediate Similarity	NPC472009
0.7468	Intermediate Similarity	NPC254996
0.7468	Intermediate Similarity	NPC471740
0.7468	Intermediate Similarity	NPC268502
0.7468	Intermediate Similarity	NPC113363
0.7439	Intermediate Similarity	NPC295799
0.7436	Intermediate Similarity	NPC145898
0.7436	Intermediate Similarity	NPC107668
0.7436	Intermediate Similarity	NPC122847
0.7432	Intermediate Similarity	NPC477448
0.7432	Intermediate Similarity	NPC477449
0.7407	Intermediate Similarity	NPC475690
0.7407	Intermediate Similarity	NPC475936
0.7403	Intermediate Similarity	NPC475861
0.7381	Intermediate Similarity	NPC86005
0.7381	Intermediate Similarity	NPC472007
0.7368	Intermediate Similarity	NPC135703
0.7349	Intermediate Similarity	NPC261380
0.7349	Intermediate Similarity	NPC474369
0.7342	Intermediate Similarity	NPC128276
0.7342	Intermediate Similarity	NPC127526
0.7333	Intermediate Similarity	NPC472955
0.7333	Intermediate Similarity	NPC469660
0.7317	Intermediate Similarity	NPC16488
0.7317	Intermediate Similarity	NPC53867
0.7317	Intermediate Similarity	NPC318468
0.7317	Intermediate Similarity	NPC170286
0.7297	Intermediate Similarity	NPC276290
0.7294	Intermediate Similarity	NPC469631
0.7294	Intermediate Similarity	NPC475906
0.7294	Intermediate Similarity	NPC472008
0.7294	Intermediate Similarity	NPC469653
0.7294	Intermediate Similarity	NPC471047
0.7294	Intermediate Similarity	NPC469628
0.7284	Intermediate Similarity	NPC301477
0.7284	Intermediate Similarity	NPC286229
0.7284	Intermediate Similarity	NPC471325
0.7284	Intermediate Similarity	NPC281949
0.7284	Intermediate Similarity	NPC25684
0.7273	Intermediate Similarity	NPC476355
0.7273	Intermediate Similarity	NPC140287
0.7262	Intermediate Similarity	NPC262085
0.7262	Intermediate Similarity	NPC38576
0.7262	Intermediate Similarity	NPC469483
0.7262	Intermediate Similarity	NPC279859
0.725	Intermediate Similarity	NPC617
0.725	Intermediate Similarity	NPC473980
0.725	Intermediate Similarity	NPC178277
0.725	Intermediate Similarity	NPC473981
0.725	Intermediate Similarity	NPC471299
0.7237	Intermediate Similarity	NPC477084
0.7237	Intermediate Similarity	NPC129665
0.7237	Intermediate Similarity	NPC163003
0.7229	Intermediate Similarity	NPC243618
0.7229	Intermediate Similarity	NPC477576
0.7229	Intermediate Similarity	NPC477575
0.7229	Intermediate Similarity	NPC70424
0.7222	Intermediate Similarity	NPC34883
0.7215	Intermediate Similarity	NPC187568
0.7215	Intermediate Similarity	NPC171204
0.7215	Intermediate Similarity	NPC469867
0.7215	Intermediate Similarity	NPC476794
0.7215	Intermediate Similarity	NPC57744
0.7215	Intermediate Similarity	NPC41780
0.7215	Intermediate Similarity	NPC97516
0.7215	Intermediate Similarity	NPC470240
0.7215	Intermediate Similarity	NPC141789
0.7215	Intermediate Similarity	NPC476028
0.7209	Intermediate Similarity	NPC475971
0.7209	Intermediate Similarity	NPC471342
0.7209	Intermediate Similarity	NPC469866
0.72	Intermediate Similarity	NPC144511
0.72	Intermediate Similarity	NPC269841
0.72	Intermediate Similarity	NPC101622
0.72	Intermediate Similarity	NPC296522
0.72	Intermediate Similarity	NPC199557
0.7195	Intermediate Similarity	NPC475395
0.7195	Intermediate Similarity	NPC474252
0.7195	Intermediate Similarity	NPC476984
0.7179	Intermediate Similarity	NPC228978
0.7179	Intermediate Similarity	NPC469414
0.7179	Intermediate Similarity	NPC244166
0.7179	Intermediate Similarity	NPC324762
0.7179	Intermediate Similarity	NPC329852
0.7179	Intermediate Similarity	NPC329826
0.7176	Intermediate Similarity	NPC477959
0.7176	Intermediate Similarity	NPC471738
0.7162	Intermediate Similarity	NPC472266
0.716	Intermediate Similarity	NPC233377
0.716	Intermediate Similarity	NPC476265
0.716	Intermediate Similarity	NPC103634
0.716	Intermediate Similarity	NPC274522
0.7143	Intermediate Similarity	NPC472020
0.7143	Intermediate Similarity	NPC226602
0.7143	Intermediate Similarity	NPC125290
0.7143	Intermediate Similarity	NPC472019
0.7126	Intermediate Similarity	NPC51653
0.7125	Intermediate Similarity	NPC11796
0.7125	Intermediate Similarity	NPC471220
0.7125	Intermediate Similarity	NPC478122
0.7125	Intermediate Similarity	NPC475699
0.7125	Intermediate Similarity	NPC470905
0.7125	Intermediate Similarity	NPC218817
0.7125	Intermediate Similarity	NPC476986
0.7123	Intermediate Similarity	NPC326268
0.7123	Intermediate Similarity	NPC318420
0.7121	Intermediate Similarity	NPC216407
0.7108	Intermediate Similarity	NPC170377
0.7108	Intermediate Similarity	NPC475842
0.7108	Intermediate Similarity	NPC222358
0.7108	Intermediate Similarity	NPC474703
0.7105	Intermediate Similarity	NPC4299
0.7093	Intermediate Similarity	NPC475902
0.7089	Intermediate Similarity	NPC123360
0.7089	Intermediate Similarity	NPC235906
0.7089	Intermediate Similarity	NPC61863
0.7089	Intermediate Similarity	NPC279537
0.7089	Intermediate Similarity	NPC301525
0.7089	Intermediate Similarity	NPC110461
0.7089	Intermediate Similarity	NPC12740
0.7083	Intermediate Similarity	NPC54925
0.7083	Intermediate Similarity	NPC217940
0.7073	Intermediate Similarity	NPC47031
0.7073	Intermediate Similarity	NPC470241
0.7067	Intermediate Similarity	NPC218477
0.7059	Intermediate Similarity	NPC50637
0.7059	Intermediate Similarity	NPC316426
0.7059	Intermediate Similarity	NPC261721
0.7059	Intermediate Similarity	NPC116575
0.7059	Intermediate Similarity	NPC315395
0.7051	Intermediate Similarity	NPC160540
0.7051	Intermediate Similarity	NPC117746
0.7051	Intermediate Similarity	NPC294434
0.7051	Intermediate Similarity	NPC15499
0.7051	Intermediate Similarity	NPC259599
0.7045	Intermediate Similarity	NPC472705
0.7045	Intermediate Similarity	NPC166110
0.7042	Intermediate Similarity	NPC472021
0.7037	Intermediate Similarity	NPC246458
0.7037	Intermediate Similarity	NPC325869
0.7037	Intermediate Similarity	NPC28319
0.7037	Intermediate Similarity	NPC158565
0.7037	Intermediate Similarity	NPC150646
0.7037	Intermediate Similarity	NPC270126
0.7037	Intermediate Similarity	NPC201225
0.7037	Intermediate Similarity	NPC475210
0.7024	Intermediate Similarity	NPC158756
0.7024	Intermediate Similarity	NPC474359
0.7024	Intermediate Similarity	NPC120158
0.7024	Intermediate Similarity	NPC159635
0.7024	Intermediate Similarity	NPC72464

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 NPC69462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1961
0.2-0.3	4008
0.3-0.4	2083
0.4-0.5	669
0.5-0.6	203
0.6-0.7	52
0.7-0.8	5
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
0.7361	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8039	Approved
0.7108	Intermediate Similarity	NPD7154	Phase 3
0.7073	Intermediate Similarity	NPD5369	Approved
0.6988	Remote Similarity	NPD4270	Approved
0.6988	Remote Similarity	NPD4269	Approved
0.6966	Remote Similarity	NPD5779	Approved
0.6966	Remote Similarity	NPD5778	Approved
0.6951	Remote Similarity	NPD4821	Approved
0.6951	Remote Similarity	NPD4820	Approved
0.6951	Remote Similarity	NPD4822	Approved
0.6951	Remote Similarity	NPD4819	Approved
0.6905	Remote Similarity	NPD5362	Discontinued
0.686	Remote Similarity	NPD5786	Approved
0.6854	Remote Similarity	NPD7983	Approved
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6101	Approved
0.6786	Remote Similarity	NPD5209	Approved
0.6786	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4252	Approved
0.6744	Remote Similarity	NPD5363	Approved
0.6742	Remote Similarity	NPD46	Approved
0.6742	Remote Similarity	NPD6698	Approved
0.6739	Remote Similarity	NPD7839	Suspended
0.6707	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4268	Approved
0.6707	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6588	Remote Similarity	NPD6435	Approved
0.6579	Remote Similarity	NPD7331	Phase 2
0.6556	Remote Similarity	NPD5785	Approved
0.6552	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5368	Approved
0.6512	Remote Similarity	NPD5332	Approved
0.6512	Remote Similarity	NPD5331	Approved
0.6484	Remote Similarity	NPD7637	Suspended
0.6484	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4790	Discontinued
0.6471	Remote Similarity	NPD28	Approved
0.6471	Remote Similarity	NPD29	Approved
0.6444	Remote Similarity	NPD5370	Suspended
0.6386	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1694	Approved
0.6351	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3197	Phase 1
0.631	Remote Similarity	NPD3732	Approved
0.6292	Remote Similarity	NPD7146	Approved
0.6292	Remote Similarity	NPD6409	Approved
0.6292	Remote Similarity	NPD6422	Discontinued
0.6292	Remote Similarity	NPD7334	Approved
0.6292	Remote Similarity	NPD6684	Approved
0.6292	Remote Similarity	NPD5330	Approved
0.6292	Remote Similarity	NPD7521	Approved
0.6292	Remote Similarity	NPD4249	Approved
0.6286	Remote Similarity	NPD3172	Approved
0.6277	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6927	Phase 3
0.6222	Remote Similarity	NPD4250	Approved
0.6222	Remote Similarity	NPD4251	Approved
0.6212	Remote Similarity	NPD3174	Discontinued
0.6197	Remote Similarity	NPD3194	Approved
0.6197	Remote Similarity	NPD3196	Approved
0.6197	Remote Similarity	NPD3195	Phase 2
0.6197	Remote Similarity	NPD4266	Approved
0.617	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6139	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5695	Phase 3
0.6087	Remote Similarity	NPD6051	Approved
0.6076	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6399	Phase 3
0.6053	Remote Similarity	NPD368	Approved
0.604	Remote Similarity	NPD5048	Discontinued
0.6029	Remote Similarity	NPD5343	Approved
0.6026	Remote Similarity	NPD7341	Phase 2
0.6022	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7748	Approved
0.5979	Remote Similarity	NPD6083	Phase 2
0.5979	Remote Similarity	NPD6084	Phase 2
0.5962	Remote Similarity	NPD6371	Approved
0.5957	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD5693	Phase 1
0.5949	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD3173	Approved
0.5934	Remote Similarity	NPD6098	Approved
0.5926	Remote Similarity	NPD7115	Discovery
0.5918	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5696	Approved
0.5918	Remote Similarity	NPD7638	Approved
0.5914	Remote Similarity	NPD6673	Approved
0.5914	Remote Similarity	NPD6904	Approved
0.5914	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3668	Phase 3
0.587	Remote Similarity	NPD3573	Approved
0.5859	Remote Similarity	NPD7640	Approved
0.5859	Remote Similarity	NPD7639	Approved
0.5851	Remote Similarity	NPD5692	Phase 3
0.5849	Remote Similarity	NPD6053	Discontinued
0.5844	Remote Similarity	NPD4191	Approved
0.5844	Remote Similarity	NPD4194	Approved
0.5844	Remote Similarity	NPD4192	Approved
0.5844	Remote Similarity	NPD4193	Approved
0.5843	Remote Similarity	NPD3667	Approved
0.5816	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD5208	Approved
0.5795	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6050	Approved
0.5789	Remote Similarity	NPD5694	Approved
0.5773	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6686	Approved
0.5769	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3704	Approved
0.5745	Remote Similarity	NPD4753	Phase 2
0.5728	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD6675	Approved
0.5728	Remote Similarity	NPD5739	Approved
0.5728	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD8513	Phase 3
0.5714	Remote Similarity	NPD3666	Approved
0.57	Remote Similarity	NPD6648	Approved
0.5684	Remote Similarity	NPD3672	Approved
0.5684	Remote Similarity	NPD3673	Approved
0.5684	Remote Similarity	NPD5207	Approved
0.5676	Remote Similarity	NPD342	Phase 1
0.5673	Remote Similarity	NPD5697	Approved
0.5673	Remote Similarity	NPD5701	Approved
0.5667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5344	Discontinued
0.5625	Remote Similarity	NPD5284	Approved
0.5625	Remote Similarity	NPD5281	Approved
0.5619	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD6899	Approved
0.5619	Remote Similarity	NPD6881	Approved
0.5618	Remote Similarity	NPD4695	Discontinued
0.5604	Remote Similarity	NPD6110	Phase 1
0.5604	Remote Similarity	NPD6695	Phase 3

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