NPASS Compound

Structure

CID65080 OpenBabel06191715402D 21 24 0 0 0 0 0 0 0 0999 V2000 1.6531 2.8257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2786 2.3267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2419 0.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2421 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4316 1.4046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4319 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8098 2.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 2.8078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6209 0.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8100 1.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6211 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8111 1.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6211 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 0.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8107 -0.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8112 2.3398 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4628 -0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8106 -1.4369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4317 1.4036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 11 2 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 14 19 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	280.08
Volume:	278.339
LogP:	1.889
LogD:	1.693
LogS:	-4.084
# Rotatable Bonds:	1
TPSA:	52.71
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	2.821
Fsp3:	0.125
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:	-4.817
MDCK Permeability:	3.051050407520961e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.849
Plasma Protein Binding (PPB):	84.6344985961914%
Volume Distribution (VD):	0.807
Pgp-substrate:	4.711101055145264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.607
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.433
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.453
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	3.846
Half-life (T1/2):	0.497

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.298
AMES Toxicity:	0.955
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.042
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.335
Respiratory Toxicity:	0.439

Download Data

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

Natural Product: NPC65080

Natural Product ID:	NPC65080
*Common Name:**	HPAUUBGCMSMJQK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HPAUUBGCMSMJQK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12N2O3/c1-17-8-7-10-9-5-3-4-6-11(9)18-12(10)13(17)15(21-2)14(19)16(18)20/h3-8H,1-2H3
SMILES:	COc1c2n(C)ccc3c2n(c(=O)c1=O)c1c3cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1700463
PubChem CID:	5320558
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	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
Others	3
Potency	6

Activity Type	# Activity
Individual Protein	4
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[469824]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[469824]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[469824]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	76.6	%	PMID[469825]
NPT2	Others	Unspecified		Potency	n.a.	14581.0	nM	PMID[469824]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[469824]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[469824]
NPT5110	Organism	Meriones unguiculatus	Meriones unguiculatus	Activity	>	80.0	%	PMID[469826]
NPT5110	Organism	Meriones unguiculatus	Meriones unguiculatus	Activity	=	73.1	%	PMID[469826]

☑ 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 NPC65080 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	652
0.1-0.2	4781
0.2-0.3	12358
0.3-0.4	10493
0.4-0.5	10037
0.5-0.6	2426
0.6-0.7	1714
0.7-0.8	220
0.8-0.85	9
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9281	High Similarity	NPC281094
0.8387	Intermediate Similarity	NPC238499
0.8353	Intermediate Similarity	NPC12649
0.8217	Intermediate Similarity	NPC277157
0.8171	Intermediate Similarity	NPC311858
0.8081	Intermediate Similarity	NPC28848
0.8081	Intermediate Similarity	NPC14325
0.8043	Intermediate Similarity	NPC295898
0.8012	Intermediate Similarity	NPC478186
0.7976	Intermediate Similarity	NPC478182
0.7955	Intermediate Similarity	NPC470003
0.7904	Intermediate Similarity	NPC293487
0.7889	Intermediate Similarity	NPC129909
0.7886	Intermediate Similarity	NPC73994
0.7886	Intermediate Similarity	NPC24864
0.787	Intermediate Similarity	NPC478184
0.7826	Intermediate Similarity	NPC168911
0.7784	Intermediate Similarity	NPC81535
0.7778	Intermediate Similarity	NPC478183
0.773	Intermediate Similarity	NPC212213
0.773	Intermediate Similarity	NPC470440
0.7706	Intermediate Similarity	NPC478185
0.7688	Intermediate Similarity	NPC91895
0.7688	Intermediate Similarity	NPC32534
0.768	Intermediate Similarity	NPC61435
0.7654	Intermediate Similarity	NPC258480
0.7634	Intermediate Similarity	NPC239954
0.7609	Intermediate Similarity	NPC198673
0.7607	Intermediate Similarity	NPC20144
0.7602	Intermediate Similarity	NPC194881
0.7594	Intermediate Similarity	NPC192674
0.7571	Intermediate Similarity	NPC83774
0.7569	Intermediate Similarity	NPC66210
0.7557	Intermediate Similarity	NPC469529
0.7531	Intermediate Similarity	NPC104483
0.7529	Intermediate Similarity	NPC299594
0.75	Intermediate Similarity	NPC161861
0.7486	Intermediate Similarity	NPC471943
0.7486	Intermediate Similarity	NPC61011
0.7471	Intermediate Similarity	NPC114637
0.7418	Intermediate Similarity	NPC133003
0.7371	Intermediate Similarity	NPC56233
0.7371	Intermediate Similarity	NPC470509
0.7363	Intermediate Similarity	NPC46895
0.7356	Intermediate Similarity	NPC21174
0.7356	Intermediate Similarity	NPC271797
0.7356	Intermediate Similarity	NPC271734
0.7351	Intermediate Similarity	NPC472112
0.7351	Intermediate Similarity	NPC324091
0.7333	Intermediate Similarity	NPC11126
0.7322	Intermediate Similarity	NPC472107
0.7322	Intermediate Similarity	NPC79062
0.7293	Intermediate Similarity	NPC91179
0.7293	Intermediate Similarity	NPC15840
0.7284	Intermediate Similarity	NPC198988
0.7278	Intermediate Similarity	NPC234987
0.7278	Intermediate Similarity	NPC326575
0.7273	Intermediate Similarity	NPC472292
0.7273	Intermediate Similarity	NPC472113
0.7268	Intermediate Similarity	NPC21429
0.7268	Intermediate Similarity	NPC228835
0.725	Intermediate Similarity	NPC22079
0.7249	Intermediate Similarity	NPC79356
0.7249	Intermediate Similarity	NPC472116
0.7249	Intermediate Similarity	NPC472293
0.7249	Intermediate Similarity	NPC102592
0.7241	Intermediate Similarity	NPC255229
0.7241	Intermediate Similarity	NPC81229
0.7222	Intermediate Similarity	NPC151635
0.7213	Intermediate Similarity	NPC143533
0.7202	Intermediate Similarity	NPC469525
0.7195	Intermediate Similarity	NPC150259
0.7188	Intermediate Similarity	NPC121327
0.7186	Intermediate Similarity	NPC74562
0.7186	Intermediate Similarity	NPC316181
0.7186	Intermediate Similarity	NPC151781
0.7181	Intermediate Similarity	NPC47190
0.7174	Intermediate Similarity	NPC477003
0.7168	Intermediate Similarity	NPC51054
0.7158	Intermediate Similarity	NPC191415
0.7151	Intermediate Similarity	NPC200743
0.715	Intermediate Similarity	NPC471944
0.7135	Intermediate Similarity	NPC472297
0.7135	Intermediate Similarity	NPC472296
0.7135	Intermediate Similarity	NPC40070
0.7134	Intermediate Similarity	NPC325252
0.7128	Intermediate Similarity	NPC473763
0.7128	Intermediate Similarity	NPC117244
0.7127	Intermediate Similarity	NPC24594
0.7127	Intermediate Similarity	NPC472122
0.712	Intermediate Similarity	NPC472104
0.712	Intermediate Similarity	NPC470205
0.7113	Intermediate Similarity	NPC143977
0.7108	Intermediate Similarity	NPC88097
0.7107	Intermediate Similarity	NPC287208
0.7105	Intermediate Similarity	NPC57994
0.7105	Intermediate Similarity	NPC19692
0.7105	Intermediate Similarity	NPC289299
0.7105	Intermediate Similarity	NPC220151
0.7104	Intermediate Similarity	NPC16659
0.7104	Intermediate Similarity	NPC88110
0.7102	Intermediate Similarity	NPC242116
0.7097	Intermediate Similarity	NPC94752
0.7097	Intermediate Similarity	NPC478077
0.7097	Intermediate Similarity	NPC17273
0.7097	Intermediate Similarity	NPC141612
0.7097	Intermediate Similarity	NPC135601
0.7088	Intermediate Similarity	NPC284775
0.7088	Intermediate Similarity	NPC473380
0.7088	Intermediate Similarity	NPC240088
0.7081	Intermediate Similarity	NPC472119
0.7076	Intermediate Similarity	NPC37548
0.7072	Intermediate Similarity	NPC469938
0.7071	Intermediate Similarity	NPC477548
0.7071	Intermediate Similarity	NPC174758
0.7071	Intermediate Similarity	NPC174672
0.7065	Intermediate Similarity	NPC113626
0.7059	Intermediate Similarity	NPC472323
0.7059	Intermediate Similarity	NPC128115
0.7059	Intermediate Similarity	NPC17059
0.7049	Intermediate Similarity	NPC265710
0.7047	Intermediate Similarity	NPC74413
0.7041	Intermediate Similarity	NPC242556
0.7037	Intermediate Similarity	NPC476460
0.7031	Intermediate Similarity	NPC167710
0.7022	Intermediate Similarity	NPC115232
0.7021	Intermediate Similarity	NPC63199
0.7021	Intermediate Similarity	NPC196251
0.7021	Intermediate Similarity	NPC473666
0.7021	Intermediate Similarity	NPC111602
0.7021	Intermediate Similarity	NPC102338
0.702	Intermediate Similarity	NPC82548
0.7016	Intermediate Similarity	NPC294693
0.7014	Intermediate Similarity	NPC141053
0.7011	Intermediate Similarity	NPC187827
0.7011	Intermediate Similarity	NPC471458
0.7011	Intermediate Similarity	NPC470507
0.7011	Intermediate Similarity	NPC472105
0.701	Intermediate Similarity	NPC470497
0.7006	Intermediate Similarity	NPC471574
0.6995	Remote Similarity	NPC470499
0.6995	Remote Similarity	NPC157583
0.699	Remote Similarity	NPC317701
0.6989	Remote Similarity	NPC165495
0.6988	Remote Similarity	NPC314102
0.6988	Remote Similarity	NPC251722
0.6982	Remote Similarity	NPC190296
0.6977	Remote Similarity	NPC187951
0.6964	Remote Similarity	NPC2949
0.6964	Remote Similarity	NPC59084
0.6963	Remote Similarity	NPC269886
0.6963	Remote Similarity	NPC472295
0.6963	Remote Similarity	NPC247735
0.6963	Remote Similarity	NPC81802
0.6963	Remote Similarity	NPC472210
0.6961	Remote Similarity	NPC6982
0.6957	Remote Similarity	NPC248462
0.6957	Remote Similarity	NPC133261
0.6954	Remote Similarity	NPC200214
0.6952	Remote Similarity	NPC308931
0.6952	Remote Similarity	NPC99939
0.6947	Remote Similarity	NPC472097
0.6939	Remote Similarity	NPC260900
0.6935	Remote Similarity	NPC159125
0.6935	Remote Similarity	NPC472110
0.6935	Remote Similarity	NPC102755
0.6935	Remote Similarity	NPC472109
0.6931	Remote Similarity	NPC175474
0.6928	Remote Similarity	NPC218268
0.6923	Remote Similarity	NPC473868
0.6923	Remote Similarity	NPC63157
0.6923	Remote Similarity	NPC254240
0.6923	Remote Similarity	NPC312870
0.6923	Remote Similarity	NPC199851
0.6923	Remote Similarity	NPC294909
0.6923	Remote Similarity	NPC128265
0.6923	Remote Similarity	NPC252572
0.6919	Remote Similarity	NPC470111
0.6919	Remote Similarity	NPC469896
0.6919	Remote Similarity	NPC238457
0.6915	Remote Similarity	NPC118084
0.6914	Remote Similarity	NPC38736
0.6914	Remote Similarity	NPC476219
0.6911	Remote Similarity	NPC216550
0.6907	Remote Similarity	NPC473640
0.6906	Remote Similarity	NPC194411
0.6905	Remote Similarity	NPC110126
0.6905	Remote Similarity	NPC73767
0.6904	Remote Similarity	NPC200836
0.6904	Remote Similarity	NPC53144
0.6903	Remote Similarity	NPC148140
0.6902	Remote Similarity	NPC64436
0.6902	Remote Similarity	NPC68354
0.6901	Remote Similarity	NPC285731
0.6901	Remote Similarity	NPC314372
0.6898	Remote Similarity	NPC467063
0.6897	Remote Similarity	NPC472260
0.6893	Remote Similarity	NPC475990
0.6891	Remote Similarity	NPC245916
0.6888	Remote Similarity	NPC475506

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 NPC65080 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	693
0.2-0.3	848
0.3-0.4	1732
0.4-0.5	2770
0.5-0.6	1970
0.6-0.7	724
0.7-0.8	68
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
0.8171	Intermediate Similarity	NPD5444	Phase 1
0.8036	Intermediate Similarity	NPD2915	Discontinued
0.7889	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD6206	Phase 1
0.773	Intermediate Similarity	NPD6261	Phase 3
0.7714	Intermediate Similarity	NPD5104	Approved
0.7688	Intermediate Similarity	NPD6248	Phase 2
0.7688	Intermediate Similarity	NPD6249	Phase 2
0.768	Intermediate Similarity	NPD4334	Discontinued
0.7647	Intermediate Similarity	NPD5427	Suspended
0.7594	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5487	Phase 1
0.7487	Intermediate Similarity	NPD7573	Discontinued
0.7459	Intermediate Similarity	NPD4315	Phase 2
0.7438	Intermediate Similarity	NPD3385	Approved
0.7435	Intermediate Similarity	NPD3777	Phase 3
0.7427	Intermediate Similarity	NPD4326	Phase 2
0.7418	Intermediate Similarity	NPD5075	Discontinued
0.7405	Intermediate Similarity	NPD3654	Approved
0.7358	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3961	Discontinued
0.7296	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4047	Discontinued
0.7289	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4897	Phase 2
0.7234	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4640	Approved
0.7232	Intermediate Similarity	NPD4639	Approved
0.7232	Intermediate Similarity	NPD4638	Approved
0.7222	Intermediate Similarity	NPD4075	Phase 2
0.7158	Intermediate Similarity	NPD4848	Phase 1
0.7151	Intermediate Similarity	NPD4988	Discontinued
0.7126	Intermediate Similarity	NPD5020	Approved
0.7105	Intermediate Similarity	NPD4602	Approved
0.7105	Intermediate Similarity	NPD7944	Discontinued
0.7097	Intermediate Similarity	NPD5809	Phase 3
0.7071	Intermediate Similarity	NPD5834	Phase 3
0.7071	Intermediate Similarity	NPD5835	Phase 3
0.7059	Intermediate Similarity	NPD1683	Approved
0.7033	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5507	Approved
0.7024	Intermediate Similarity	NPD5506	Approved
0.7022	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4547	Phase 3
0.7005	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD45	Approved
0.6988	Remote Similarity	NPD6554	Approved
0.6984	Remote Similarity	NPD3321	Discontinued
0.6977	Remote Similarity	NPD3100	Discontinued
0.6964	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4463	Approved
0.6936	Remote Similarity	NPD4462	Approved
0.6923	Remote Similarity	NPD4501	Approved
0.6923	Remote Similarity	NPD4500	Approved
0.6919	Remote Similarity	NPD5897	Approved
0.6919	Remote Similarity	NPD5898	Approved
0.6919	Remote Similarity	NPD5899	Approved
0.6915	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5400	Approved
0.6907	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3505	Approved
0.6902	Remote Similarity	NPD3506	Approved
0.6898	Remote Similarity	NPD7483	Phase 2
0.6898	Remote Similarity	NPD7482	Phase 2
0.6897	Remote Similarity	NPD2882	Phase 1
0.6893	Remote Similarity	NPD1630	Approved
0.6888	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4079	Approved
0.6865	Remote Similarity	NPD4076	Approved
0.6851	Remote Similarity	NPD5021	Discontinued
0.6851	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6787	Phase 2
0.6845	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5254	Discontinued
0.6842	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7619	Phase 3
0.6839	Remote Similarity	NPD7618	Phase 3
0.6833	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD750	Phase 2
0.6829	Remote Similarity	NPD3475	Approved
0.6829	Remote Similarity	NPD3476	Approved
0.6828	Remote Similarity	NPD5473	Discontinued
0.6826	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7026	Phase 2
0.6825	Remote Similarity	NPD6217	Discontinued
0.6818	Remote Similarity	NPD6176	Phase 1
0.6816	Remote Similarity	NPD6771	Discontinued
0.6814	Remote Similarity	NPD5293	Phase 2
0.6811	Remote Similarity	NPD4398	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4957	Phase 2
0.6809	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7796	Approved
0.6808	Remote Similarity	NPD7797	Approved
0.6806	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4499	Approved
0.6805	Remote Similarity	NPD786	Approved
0.6805	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD4128	Approved
0.6791	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5538	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD1631	Approved
0.6778	Remote Similarity	NPD3583	Phase 2
0.6772	Remote Similarity	NPD5555	Phase 1
0.6772	Remote Similarity	NPD4336	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1952	Discontinued
0.6757	Remote Similarity	NPD5501	Discontinued
0.6755	Remote Similarity	NPD3318	Approved
0.6755	Remote Similarity	NPD3319	Phase 1
0.6755	Remote Similarity	NPD3320	Approved
0.6748	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2118	Approved
0.6748	Remote Similarity	NPD2119	Approved
0.6743	Remote Similarity	NPD3833	Phase 3
0.6743	Remote Similarity	NPD3835	Phase 3
0.6739	Remote Similarity	NPD4524	Discontinued
0.6726	Remote Similarity	NPD1256	Approved
0.6726	Remote Similarity	NPD1254	Approved
0.6726	Remote Similarity	NPD1253	Approved
0.6726	Remote Similarity	NPD1255	Approved
0.6725	Remote Similarity	NPD1722	Approved
0.672	Remote Similarity	NPD7564	Discontinued
0.6703	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4399	Phase 2
0.6701	Remote Similarity	NPD6239	Discontinued
0.6686	Remote Similarity	NPD2430	Phase 2
0.6686	Remote Similarity	NPD200	Phase 2
0.6686	Remote Similarity	NPD201	Phase 2
0.6686	Remote Similarity	NPD2006	Phase 2
0.6684	Remote Similarity	NPD3076	Approved
0.6684	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2336	Approved
0.6684	Remote Similarity	NPD1658	Discontinued
0.6684	Remote Similarity	NPD3078	Approved
0.6684	Remote Similarity	NPD3077	Approved
0.6684	Remote Similarity	NPD3079	Approved
0.6667	Remote Similarity	NPD6044	Discontinued
0.6667	Remote Similarity	NPD7001	Phase 3
0.6667	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4601	Approved
0.6667	Remote Similarity	NPD2837	Discontinued
0.6667	Remote Similarity	NPD7568	Phase 1
0.6667	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2511	Approved
0.6667	Remote Similarity	NPD4600	Approved
0.665	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4520	Approved
0.6649	Remote Similarity	NPD4922	Phase 2
0.6649	Remote Similarity	NPD6452	Discontinued
0.6649	Remote Similarity	NPD4940	Approved
0.6649	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2720	Phase 1
0.6648	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7716	Approved
0.6635	Remote Similarity	NPD7717	Approved
0.6633	Remote Similarity	NPD7817	Phase 1
0.6633	Remote Similarity	NPD7727	Phase 2
0.663	Remote Similarity	NPD1575	Approved
0.663	Remote Similarity	NPD5315	Discontinued
0.663	Remote Similarity	NPD1573	Approved
0.6629	Remote Similarity	NPD1661	Suspended
0.6629	Remote Similarity	NPD6285	Phase 2
0.6617	Remote Similarity	NPD8115	Approved
0.6617	Remote Similarity	NPD6987	Phase 1
0.6617	Remote Similarity	NPD8114	Approved
0.6616	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6999	Discontinued
0.6616	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4030	Approved
0.6607	Remote Similarity	NPD3942	Approved
0.6607	Remote Similarity	NPD3944	Approved
0.6607	Remote Similarity	NPD4029	Approved
0.6607	Remote Similarity	NPD4028	Approved
0.66	Remote Similarity	NPD2879	Approved
0.66	Remote Similarity	NPD2881	Approved
0.6598	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6448	Phase 1
0.6596	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD2580	Discontinued
0.6589	Remote Similarity	NPD7780	Approved
0.6589	Remote Similarity	NPD7781	Approved
0.6584	Remote Similarity	NPD6732	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