NPASS Compound

Structure

NPC473948 OpenBabel07101719402D 21 21 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -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 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 4 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 6 1 1 0 0 0 11 20 1 0 0 0 0 12 8 1 6 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 1 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 6 0 0 0 M END

Physi-Chem Properties

Molecular Weight:	300.16
Volume:	304.272
LogP:	1.625
LogD:	1.534
LogS:	-2.195
# Rotatable Bonds:	8
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.163
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.657
MDCK Permeability:	6.352604395942762e-05
Pgp-inhibitor:	0.7
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.335
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.268
Plasma Protein Binding (PPB):	29.273921966552734%
Volume Distribution (VD):	0.762
Pgp-substrate:	56.92628479003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.558
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	8.52
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.488
Rat Oral Acute Toxicity:	0.527
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.401
Carcinogencity:	0.189
Eye Corrosion:	0.023
Eye Irritation:	0.071
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC473948

Natural Product ID:	NPC473948
*Common Name:**	[(Z,3S)-1-[(2S,3S,4R)-3-Hydroxy-4-Methoxy-6-Oxooxan-2-Yl]Hept-1-En-3-Yl] Acetate
IUPAC Name:	[(Z,3S)-1-[(2S,3S,4R)-3-hydroxy-4-methoxy-6-oxooxan-2-yl]hept-1-en-3-yl] acetate
Synonyms:
Standard InCHIKey:	GKKOQWIEKASIGY-VMVKDKSBSA-N
Standard InCHI:	InChI=1S/C15H24O6/c1-4-5-6-11(20-10(2)16)7-8-12-15(18)13(19-3)9-14(17)21-12/h7-8,11-13,15,18H,4-6,9H2,1-3H3/b8-7-/t11-,12-,13+,15+/m0/s1
SMILES:	CCCC[C@H](OC(=O)C)/C=C[C@@H]1OC(=O)C[C@H]([C@@H]1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455891
PubChem CID:	10402531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496706]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO28865	Hyptis pectinata	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
ED50	11
MIC	5

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	4
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[525565]
NPT762	Cell Line	A-431	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[525565]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[525565]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[525565]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[525565]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[525565]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500.0	ug.mL-1	PMID[525565]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[525565]

☑ 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 NPC473948 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	153
0.1-0.2	1814
0.2-0.3	6391
0.3-0.4	15440
0.4-0.5	11741
0.5-0.6	5653
0.6-0.7	1366
0.7-0.8	130
0.8-0.85	4
0.85-0.9	0
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9041	High Similarity	NPC190400
0.9041	High Similarity	NPC49392
0.8701	High Similarity	NPC297440
0.8077	Intermediate Similarity	NPC127526
0.8026	Intermediate Similarity	NPC473489
0.7973	Intermediate Similarity	NPC475982
0.7945	Intermediate Similarity	NPC478100
0.7945	Intermediate Similarity	NPC25298
0.7922	Intermediate Similarity	NPC473582
0.7808	Intermediate Similarity	NPC478101
0.7792	Intermediate Similarity	NPC326504
0.775	Intermediate Similarity	NPC475210
0.7738	Intermediate Similarity	NPC478112
0.7733	Intermediate Similarity	NPC130618
0.7703	Intermediate Similarity	NPC478097
0.7671	Intermediate Similarity	NPC19769
0.7671	Intermediate Similarity	NPC478099
0.7671	Intermediate Similarity	NPC478098
0.7662	Intermediate Similarity	NPC470435
0.7632	Intermediate Similarity	NPC42526
0.7632	Intermediate Similarity	NPC202011
0.7625	Intermediate Similarity	NPC318481
0.7606	Intermediate Similarity	NPC81896
0.7606	Intermediate Similarity	NPC321919
0.7586	Intermediate Similarity	NPC274075
0.7568	Intermediate Similarity	NPC276299
0.7568	Intermediate Similarity	NPC201356
0.7532	Intermediate Similarity	NPC320119
0.7531	Intermediate Similarity	NPC99651
0.75	Intermediate Similarity	NPC474278
0.75	Intermediate Similarity	NPC474251
0.7473	Intermediate Similarity	NPC40812
0.747	Intermediate Similarity	NPC11383
0.747	Intermediate Similarity	NPC474959
0.747	Intermediate Similarity	NPC310450
0.747	Intermediate Similarity	NPC474252
0.747	Intermediate Similarity	NPC475046
0.7468	Intermediate Similarity	NPC161038
0.7467	Intermediate Similarity	NPC22101
0.7467	Intermediate Similarity	NPC330426
0.7467	Intermediate Similarity	NPC104537
0.7467	Intermediate Similarity	NPC148192
0.7467	Intermediate Similarity	NPC127091
0.7467	Intermediate Similarity	NPC271921
0.7432	Intermediate Similarity	NPC96414
0.7412	Intermediate Similarity	NPC182383
0.7407	Intermediate Similarity	NPC133377
0.7407	Intermediate Similarity	NPC182292
0.7391	Intermediate Similarity	NPC187761
0.7391	Intermediate Similarity	NPC83895
0.7386	Intermediate Similarity	NPC473311
0.7381	Intermediate Similarity	NPC286770
0.7381	Intermediate Similarity	NPC52923
0.7381	Intermediate Similarity	NPC284472
0.7381	Intermediate Similarity	NPC229799
0.7368	Intermediate Similarity	NPC48218
0.7368	Intermediate Similarity	NPC141481
0.7368	Intermediate Similarity	NPC473559
0.7368	Intermediate Similarity	NPC324981
0.7326	Intermediate Similarity	NPC278283
0.7326	Intermediate Similarity	NPC469910
0.7326	Intermediate Similarity	NPC112685
0.7326	Intermediate Similarity	NPC47937
0.7303	Intermediate Similarity	NPC9447
0.7297	Intermediate Similarity	NPC475221
0.7294	Intermediate Similarity	NPC243618
0.7294	Intermediate Similarity	NPC32676
0.7294	Intermediate Similarity	NPC70424
0.7284	Intermediate Similarity	NPC475711
0.7284	Intermediate Similarity	NPC275530
0.7284	Intermediate Similarity	NPC110813
0.7284	Intermediate Similarity	NPC474026
0.7273	Intermediate Similarity	NPC470436
0.726	Intermediate Similarity	NPC113293
0.725	Intermediate Similarity	NPC260396
0.7237	Intermediate Similarity	NPC475443
0.7237	Intermediate Similarity	NPC99619
0.7237	Intermediate Similarity	NPC26500
0.7237	Intermediate Similarity	NPC473829
0.7237	Intermediate Similarity	NPC49863
0.7222	Intermediate Similarity	NPC318306
0.7215	Intermediate Similarity	NPC325627
0.7215	Intermediate Similarity	NPC284006
0.7209	Intermediate Similarity	NPC470124
0.7209	Intermediate Similarity	NPC475034
0.7209	Intermediate Similarity	NPC21469
0.7204	Intermediate Similarity	NPC308567
0.7204	Intermediate Similarity	NPC261377
0.7204	Intermediate Similarity	NPC255592
0.72	Intermediate Similarity	NPC476655
0.72	Intermediate Similarity	NPC476654
0.72	Intermediate Similarity	NPC323477
0.72	Intermediate Similarity	NPC476657
0.7195	Intermediate Similarity	NPC473471
0.7195	Intermediate Similarity	NPC248775
0.7191	Intermediate Similarity	NPC474232
0.7191	Intermediate Similarity	NPC473619
0.7183	Intermediate Similarity	NPC323436
0.7179	Intermediate Similarity	NPC476660
0.7174	Intermediate Similarity	NPC477921
0.716	Intermediate Similarity	NPC301207
0.716	Intermediate Similarity	NPC127118
0.716	Intermediate Similarity	NPC209113
0.716	Intermediate Similarity	NPC470705
0.7159	Intermediate Similarity	NPC473715
0.7159	Intermediate Similarity	NPC476803
0.7159	Intermediate Similarity	NPC137368
0.7159	Intermediate Similarity	NPC470137
0.7143	Intermediate Similarity	NPC63873
0.7143	Intermediate Similarity	NPC71589
0.7143	Intermediate Similarity	NPC150502
0.7128	Intermediate Similarity	NPC324667
0.7126	Intermediate Similarity	NPC69082
0.7126	Intermediate Similarity	NPC279267
0.7125	Intermediate Similarity	NPC474280
0.7125	Intermediate Similarity	NPC92558
0.7111	Intermediate Similarity	NPC327760
0.7111	Intermediate Similarity	NPC473321
0.7108	Intermediate Similarity	NPC470149
0.7108	Intermediate Similarity	NPC473980
0.7108	Intermediate Similarity	NPC263574
0.7108	Intermediate Similarity	NPC473981
0.7108	Intermediate Similarity	NPC470148
0.7108	Intermediate Similarity	NPC469747
0.7108	Intermediate Similarity	NPC180725
0.7105	Intermediate Similarity	NPC476656
0.7105	Intermediate Similarity	NPC328653
0.7105	Intermediate Similarity	NPC476659
0.7093	Intermediate Similarity	NPC9868
0.7093	Intermediate Similarity	NPC158756
0.7089	Intermediate Similarity	NPC293114
0.7083	Intermediate Similarity	NPC309398
0.7079	Intermediate Similarity	NPC477011
0.7079	Intermediate Similarity	NPC14901
0.7079	Intermediate Similarity	NPC87306
0.7079	Intermediate Similarity	NPC280612
0.7079	Intermediate Similarity	NPC130359
0.7073	Intermediate Similarity	NPC125365
0.7073	Intermediate Similarity	NPC176329
0.7073	Intermediate Similarity	NPC49302
0.7073	Intermediate Similarity	NPC474818
0.7073	Intermediate Similarity	NPC51809
0.7067	Intermediate Similarity	NPC25747
0.7067	Intermediate Similarity	NPC148233
0.7065	Intermediate Similarity	NPC477922
0.7065	Intermediate Similarity	NPC471142
0.7059	Intermediate Similarity	NPC251026
0.7051	Intermediate Similarity	NPC473772
0.7045	Intermediate Similarity	NPC475037
0.7045	Intermediate Similarity	NPC86005
0.7045	Intermediate Similarity	NPC473248
0.7045	Intermediate Similarity	NPC178215
0.7037	Intermediate Similarity	NPC478195
0.7037	Intermediate Similarity	NPC60718
0.7037	Intermediate Similarity	NPC478191
0.7037	Intermediate Similarity	NPC478196
0.7037	Intermediate Similarity	NPC478192
0.7037	Intermediate Similarity	NPC478193
0.7037	Intermediate Similarity	NPC478194
0.7033	Intermediate Similarity	NPC295204
0.7033	Intermediate Similarity	NPC288240
0.7033	Intermediate Similarity	NPC273579
0.7033	Intermediate Similarity	NPC475912
0.7033	Intermediate Similarity	NPC162205
0.7027	Intermediate Similarity	NPC321838
0.7027	Intermediate Similarity	NPC26810
0.7024	Intermediate Similarity	NPC121374
0.7024	Intermediate Similarity	NPC233377
0.7024	Intermediate Similarity	NPC470147
0.7024	Intermediate Similarity	NPC47653
0.7024	Intermediate Similarity	NPC133226
0.7021	Intermediate Similarity	NPC471144
0.7013	Intermediate Similarity	NPC122627
0.7011	Intermediate Similarity	NPC103284
0.7011	Intermediate Similarity	NPC1083
0.7011	Intermediate Similarity	NPC231009
0.7011	Intermediate Similarity	NPC66346
0.7011	Intermediate Similarity	NPC473651
0.7011	Intermediate Similarity	NPC110710
0.7011	Intermediate Similarity	NPC470755
0.7011	Intermediate Similarity	NPC132496
0.7011	Intermediate Similarity	NPC107986
0.7011	Intermediate Similarity	NPC82795
0.7011	Intermediate Similarity	NPC223871
0.7011	Intermediate Similarity	NPC471156
0.7011	Intermediate Similarity	NPC283085
0.7011	Intermediate Similarity	NPC473669
0.7011	Intermediate Similarity	NPC473478
0.7011	Intermediate Similarity	NPC286338
0.7	Intermediate Similarity	NPC326024
0.7	Intermediate Similarity	NPC316228
0.7	Intermediate Similarity	NPC473455
0.7	Intermediate Similarity	NPC313670
0.6989	Remote Similarity	NPC473859
0.6988	Remote Similarity	NPC279214
0.6988	Remote Similarity	NPC11796
0.6988	Remote Similarity	NPC475699
0.6988	Remote Similarity	NPC218817
0.6988	Remote Similarity	NPC28049
0.6988	Remote Similarity	NPC221095

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 NPC473948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	2298
0.2-0.3	3891
0.3-0.4	1998
0.4-0.5	637
0.5-0.6	163
0.6-0.7	28
0.7-0.8	1
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
0.7237	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.6712	Remote Similarity	NPD8959	Approved
0.6702	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3197	Phase 1
0.6622	Remote Similarity	NPD6109	Phase 1
0.6622	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5779	Approved
0.6489	Remote Similarity	NPD5778	Approved
0.6458	Remote Similarity	NPD7839	Suspended
0.6437	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4252	Approved
0.6383	Remote Similarity	NPD6411	Approved
0.6375	Remote Similarity	NPD896	Approved
0.6375	Remote Similarity	NPD898	Approved
0.6375	Remote Similarity	NPD897	Approved
0.6327	Remote Similarity	NPD4225	Approved
0.6292	Remote Similarity	NPD6435	Approved
0.6292	Remote Similarity	NPD4269	Approved
0.6292	Remote Similarity	NPD4270	Approved
0.6286	Remote Similarity	NPD3173	Approved
0.6282	Remote Similarity	NPD8961	Approved
0.6277	Remote Similarity	NPD5785	Approved
0.6277	Remote Similarity	NPD7838	Discovery
0.6222	Remote Similarity	NPD7154	Phase 3
0.6216	Remote Similarity	NPD8515	Approved
0.6216	Remote Similarity	NPD8513	Phase 3
0.6216	Remote Similarity	NPD8516	Approved
0.6216	Remote Similarity	NPD8517	Approved
0.6207	Remote Similarity	NPD4268	Approved
0.6207	Remote Similarity	NPD4271	Approved
0.6184	Remote Similarity	NPD69	Approved
0.6184	Remote Similarity	NPD9119	Approved
0.618	Remote Similarity	NPD5369	Approved
0.6162	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5363	Approved
0.6087	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD8444	Approved
0.6067	Remote Similarity	NPD4819	Approved
0.6067	Remote Similarity	NPD5368	Approved
0.6067	Remote Similarity	NPD4822	Approved
0.6067	Remote Similarity	NPD4821	Approved
0.6067	Remote Similarity	NPD4820	Approved
0.6058	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD9118	Approved
0.6042	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6371	Approved
0.6027	Remote Similarity	NPD9007	Approved
0.6027	Remote Similarity	NPD9009	Approved
0.6027	Remote Similarity	NPD8960	Approved
0.6027	Remote Similarity	NPD9010	Approved
0.6027	Remote Similarity	NPD9008	Approved
0.6027	Remote Similarity	NPD72	Approved
0.6027	Remote Similarity	NPD66	Approved
0.6027	Remote Similarity	NPD9011	Approved
0.6027	Remote Similarity	NPD64	Approved
0.6027	Remote Similarity	NPD65	Approved
0.6022	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD819	Approved
0.5977	Remote Similarity	NPD818	Approved
0.5965	Remote Similarity	NPD7829	Approved
0.5965	Remote Similarity	NPD7642	Approved
0.5965	Remote Similarity	NPD7830	Approved
0.596	Remote Similarity	NPD4228	Discovery
0.5957	Remote Similarity	NPD4250	Approved
0.5957	Remote Similarity	NPD4251	Approved
0.5948	Remote Similarity	NPD8074	Phase 3
0.5948	Remote Similarity	NPD8448	Approved
0.5946	Remote Similarity	NPD3172	Approved
0.5915	Remote Similarity	NPD5343	Approved
0.5914	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.589	Remote Similarity	NPD6927	Phase 3
0.5876	Remote Similarity	NPD7637	Suspended
0.587	Remote Similarity	NPD6110	Phase 1
0.587	Remote Similarity	NPD5362	Discontinued
0.5867	Remote Similarity	NPD3194	Approved
0.5867	Remote Similarity	NPD3195	Phase 2
0.5867	Remote Similarity	NPD4266	Approved
0.5867	Remote Similarity	NPD3730	Approved
0.5867	Remote Similarity	NPD3196	Approved
0.5867	Remote Similarity	NPD3728	Approved
0.5857	Remote Similarity	NPD3174	Discontinued
0.5857	Remote Similarity	NPD4222	Approved
0.5856	Remote Similarity	NPD7115	Discovery
0.5849	Remote Similarity	NPD6686	Approved
0.5843	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2204	Approved
0.5798	Remote Similarity	NPD8392	Approved
0.5798	Remote Similarity	NPD8391	Approved
0.5798	Remote Similarity	NPD8390	Approved
0.5778	Remote Similarity	NPD7329	Approved
0.5776	Remote Similarity	NPD8340	Approved
0.5776	Remote Similarity	NPD8342	Approved
0.5776	Remote Similarity	NPD8341	Approved
0.5776	Remote Similarity	NPD8299	Approved
0.5761	Remote Similarity	NPD5209	Approved
0.573	Remote Similarity	NPD4756	Discovery
0.5728	Remote Similarity	NPD5344	Discontinued
0.5714	Remote Similarity	NPD73	Approved
0.5684	Remote Similarity	NPD6422	Discontinued
0.5682	Remote Similarity	NPD376	Approved
0.5682	Remote Similarity	NPD8039	Approved
0.5682	Remote Similarity	NPD11	Approved
0.5644	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD39	Approved
0.5632	Remote Similarity	NPD3181	Approved
0.5616	Remote Similarity	NPD8964	Approved
0.56	Remote Similarity	NPD5282	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