NPASS Compound

Structure

NPC475083 OpenBabel07101718242D 26 27 0 0 1 0 0 0 0 0999 V2000 -3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1780 0.1378 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 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 -1.8320 -0.7588 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 -4.2121 0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 11 1 0 0 0 0 9 13 2 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	391.297
LogP:	4.293
LogD:	1.694
LogS:	-3.612
# Rotatable Bonds:	5
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.342
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	2.1869362171855755e-05
Pgp-inhibitor:	0.925
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.323
30% Bioavailability (F30%):	0.539

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	94.36170959472656%
Volume Distribution (VD):	2.689
Pgp-substrate:	5.495607852935791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.505
CYP2C19-inhibitor:	0.411
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.197
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.568
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.919
CYP3A4-substrate:	0.658

ADMET: Excretion

Clearance (CL):	7.188
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.516
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.254
Carcinogencity:	0.441
Eye Corrosion:	0.011
Eye Irritation:	0.025
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC475083

Natural Product ID:	NPC475083
*Common Name:**	Petiolin A
IUPAC Name:	5-hydroxy-2,8,8-trimethyl-2-(4-methylpent-3-enyl)-6-(2-methylpropanoyl)chromen-7-one
Synonyms:
Standard InCHIKey:	WCWBRLFAEDFKAR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13(2)9-8-11-22(7)12-10-15-18(24)16(17(23)14(3)4)19(25)21(5,6)20(15)26-22/h9-10,12,14,24H,8,11H2,1-7H3
SMILES:	CC(C)C(=O)C1=C(C2=C(C(C1=O)(C)C)OC(C=C2)(C)CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496291
PubChem CID:	44576700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans

*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
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18430575]
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20598881]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.5	ug.mL-1	PMID[546616]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.8	ug.mL-1	PMID[546616]

☑ 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 NPC475083 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	189
0.1-0.2	1250
0.2-0.3	5349
0.3-0.4	11806
0.4-0.5	16248
0.5-0.6	6240
0.6-0.7	1499
0.7-0.8	102
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC103743
0.9506	High Similarity	NPC113370
0.9506	High Similarity	NPC476079
0.95	High Similarity	NPC307112
0.809	Intermediate Similarity	NPC213636
0.809	Intermediate Similarity	NPC280592
0.809	Intermediate Similarity	NPC253177
0.8	Intermediate Similarity	NPC471329
0.8	Intermediate Similarity	NPC296114
0.7882	Intermediate Similarity	NPC275766
0.7826	Intermediate Similarity	NPC477241
0.7778	Intermediate Similarity	NPC472676
0.7778	Intermediate Similarity	NPC472688
0.7766	Intermediate Similarity	NPC239895
0.775	Intermediate Similarity	NPC315597
0.775	Intermediate Similarity	NPC203819
0.7738	Intermediate Similarity	NPC248624
0.7738	Intermediate Similarity	NPC315765
0.7708	Intermediate Similarity	NPC469851
0.7701	Intermediate Similarity	NPC288281
0.7619	Intermediate Similarity	NPC316324
0.7609	Intermediate Similarity	NPC45579
0.7531	Intermediate Similarity	NPC315285
0.7527	Intermediate Similarity	NPC282644
0.7527	Intermediate Similarity	NPC29798
0.75	Intermediate Similarity	NPC313444
0.7474	Intermediate Similarity	NPC93271
0.7474	Intermediate Similarity	NPC135576
0.7473	Intermediate Similarity	NPC58532
0.7473	Intermediate Similarity	NPC472677
0.7473	Intermediate Similarity	NPC60765
0.7473	Intermediate Similarity	NPC143025
0.7419	Intermediate Similarity	NPC166110
0.7419	Intermediate Similarity	NPC32552
0.7407	Intermediate Similarity	NPC473277
0.74	Intermediate Similarity	NPC469852
0.7363	Intermediate Similarity	NPC125925
0.734	Intermediate Similarity	NPC248193
0.732	Intermediate Similarity	NPC35717
0.7317	Intermediate Similarity	NPC316029
0.7303	Intermediate Similarity	NPC16488
0.7283	Intermediate Similarity	NPC26078
0.7283	Intermediate Similarity	NPC473658
0.7253	Intermediate Similarity	NPC291712
0.7253	Intermediate Similarity	NPC315395
0.7253	Intermediate Similarity	NPC316426
0.7253	Intermediate Similarity	NPC234038
0.7234	Intermediate Similarity	NPC472705
0.7234	Intermediate Similarity	NPC32944
0.7234	Intermediate Similarity	NPC193396
0.7216	Intermediate Similarity	NPC208094
0.7216	Intermediate Similarity	NPC478233
0.7209	Intermediate Similarity	NPC315394
0.7204	Intermediate Similarity	NPC118011
0.7204	Intermediate Similarity	NPC95364
0.7204	Intermediate Similarity	NPC307092
0.7204	Intermediate Similarity	NPC142159
0.7204	Intermediate Similarity	NPC471054
0.7204	Intermediate Similarity	NPC51358
0.7204	Intermediate Similarity	NPC36668
0.7188	Intermediate Similarity	NPC295347
0.7188	Intermediate Similarity	NPC209355
0.7174	Intermediate Similarity	NPC23622
0.7172	Intermediate Similarity	NPC224172
0.7172	Intermediate Similarity	NPC244456
0.7172	Intermediate Similarity	NPC469657
0.7172	Intermediate Similarity	NPC206079
0.7159	Intermediate Similarity	NPC160582
0.7143	Intermediate Similarity	NPC64742
0.7143	Intermediate Similarity	NPC281172
0.7143	Intermediate Similarity	NPC470177
0.7128	Intermediate Similarity	NPC212369
0.7126	Intermediate Similarity	NPC264391
0.7125	Intermediate Similarity	NPC471565
0.7125	Intermediate Similarity	NPC471556
0.7125	Intermediate Similarity	NPC471566
0.7113	Intermediate Similarity	NPC9812
0.7111	Intermediate Similarity	NPC258985
0.7097	Intermediate Similarity	NPC472008
0.7097	Intermediate Similarity	NPC106051
0.7097	Intermediate Similarity	NPC72397
0.7097	Intermediate Similarity	NPC53454
0.7079	Intermediate Similarity	NPC44963
0.7079	Intermediate Similarity	NPC472684
0.7079	Intermediate Similarity	NPC189237
0.7071	Intermediate Similarity	NPC54705
0.7065	Intermediate Similarity	NPC477479
0.7065	Intermediate Similarity	NPC472009
0.7065	Intermediate Similarity	NPC477478
0.7065	Intermediate Similarity	NPC198314
0.7059	Intermediate Similarity	NPC32006
0.7059	Intermediate Similarity	NPC85529
0.7059	Intermediate Similarity	NPC122244
0.7045	Intermediate Similarity	NPC469617
0.7041	Intermediate Similarity	NPC53844
0.7037	Intermediate Similarity	NPC315115
0.7033	Intermediate Similarity	NPC196487
0.7033	Intermediate Similarity	NPC14575
0.703	Intermediate Similarity	NPC25666
0.703	Intermediate Similarity	NPC297281
0.703	Intermediate Similarity	NPC473144
0.703	Intermediate Similarity	NPC271059
0.7021	Intermediate Similarity	NPC210216
0.7021	Intermediate Similarity	NPC474918
0.7021	Intermediate Similarity	NPC212598
0.7021	Intermediate Similarity	NPC284561
0.7019	Intermediate Similarity	NPC137911
0.7019	Intermediate Similarity	NPC228477
0.7	Intermediate Similarity	NPC227925
0.7	Intermediate Similarity	NPC85772
0.699	Remote Similarity	NPC469853
0.699	Remote Similarity	NPC199107
0.699	Remote Similarity	NPC232969
0.6989	Remote Similarity	NPC472007
0.6989	Remote Similarity	NPC241054
0.6977	Remote Similarity	NPC315552
0.697	Remote Similarity	NPC316598
0.697	Remote Similarity	NPC306908
0.697	Remote Similarity	NPC244411
0.6966	Remote Similarity	NPC91332
0.6966	Remote Similarity	NPC162741
0.6957	Remote Similarity	NPC471223
0.6957	Remote Similarity	NPC15807
0.6957	Remote Similarity	NPC261380
0.6957	Remote Similarity	NPC67081
0.6957	Remote Similarity	NPC11804
0.6947	Remote Similarity	NPC145666
0.6947	Remote Similarity	NPC265856
0.6947	Remote Similarity	NPC469464
0.6941	Remote Similarity	NPC215745
0.6941	Remote Similarity	NPC12815
0.6941	Remote Similarity	NPC153660
0.6941	Remote Similarity	NPC238948
0.6939	Remote Similarity	NPC472734
0.6939	Remote Similarity	NPC472733
0.6932	Remote Similarity	NPC275494
0.6932	Remote Similarity	NPC478247
0.6932	Remote Similarity	NPC99182
0.6932	Remote Similarity	NPC478122
0.6932	Remote Similarity	NPC478246
0.6932	Remote Similarity	NPC471409
0.6931	Remote Similarity	NPC235369
0.6923	Remote Similarity	NPC220155
0.6923	Remote Similarity	NPC161045
0.6915	Remote Similarity	NPC478259
0.6915	Remote Similarity	NPC478261
0.6915	Remote Similarity	NPC478260
0.6915	Remote Similarity	NPC260343
0.6915	Remote Similarity	NPC472011
0.6907	Remote Similarity	NPC143210
0.6907	Remote Similarity	NPC53685
0.6907	Remote Similarity	NPC65829
0.6905	Remote Similarity	NPC59558
0.6893	Remote Similarity	NPC478052
0.6889	Remote Similarity	NPC470298
0.6889	Remote Similarity	NPC225515
0.6882	Remote Similarity	NPC186332
0.6882	Remote Similarity	NPC116575
0.6882	Remote Similarity	NPC203795
0.6882	Remote Similarity	NPC47220
0.6875	Remote Similarity	NPC478244
0.6875	Remote Similarity	NPC478243
0.6869	Remote Similarity	NPC472732
0.6869	Remote Similarity	NPC472731
0.6869	Remote Similarity	NPC202705
0.6869	Remote Similarity	NPC134083
0.6863	Remote Similarity	NPC473624
0.686	Remote Similarity	NPC147438
0.686	Remote Similarity	NPC215050
0.6842	Remote Similarity	NPC115179
0.6842	Remote Similarity	NPC106040
0.6842	Remote Similarity	NPC280833
0.6842	Remote Similarity	NPC295448
0.6837	Remote Similarity	NPC171395
0.6837	Remote Similarity	NPC214694
0.6837	Remote Similarity	NPC91408
0.6837	Remote Similarity	NPC12727
0.6832	Remote Similarity	NPC472637
0.6832	Remote Similarity	NPC62670
0.6832	Remote Similarity	NPC116139
0.6824	Remote Similarity	NPC84790
0.6824	Remote Similarity	NPC133098
0.6818	Remote Similarity	NPC471225
0.6818	Remote Similarity	NPC54996
0.6818	Remote Similarity	NPC473825
0.6809	Remote Similarity	NPC478145
0.6809	Remote Similarity	NPC181327
0.6804	Remote Similarity	NPC476049
0.6804	Remote Similarity	NPC242637
0.68	Remote Similarity	NPC472730
0.68	Remote Similarity	NPC476120
0.68	Remote Similarity	NPC153776
0.68	Remote Similarity	NPC472729
0.68	Remote Similarity	NPC177680
0.68	Remote Similarity	NPC166770
0.6796	Remote Similarity	NPC309190
0.6786	Remote Similarity	NPC151481
0.6782	Remote Similarity	NPC166018
0.6782	Remote Similarity	NPC169056
0.6782	Remote Similarity	NPC225665

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 NPC475083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1569
0.2-0.3	3868
0.3-0.4	2514
0.4-0.5	751
0.5-0.6	238
0.6-0.7	29
0.7-0.8	0
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
0.6818	Remote Similarity	NPD4756	Discovery
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.663	Remote Similarity	NPD5209	Approved
0.6627	Remote Similarity	NPD7331	Phase 2
0.6598	Remote Similarity	NPD5785	Approved
0.6593	Remote Similarity	NPD4695	Discontinued
0.6566	Remote Similarity	NPD5282	Discontinued
0.6531	Remote Similarity	NPD6411	Approved
0.6526	Remote Similarity	NPD4623	Approved
0.6526	Remote Similarity	NPD4519	Discontinued
0.6421	Remote Similarity	NPD1696	Phase 3
0.6413	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8039	Approved
0.6392	Remote Similarity	NPD4518	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6337	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6101	Approved
0.6316	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7341	Phase 2
0.6283	Remote Similarity	NPD7115	Discovery
0.6265	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7154	Phase 3
0.6211	Remote Similarity	NPD6110	Phase 1
0.62	Remote Similarity	NPD7983	Approved
0.62	Remote Similarity	NPD5281	Approved
0.62	Remote Similarity	NPD5284	Approved
0.6186	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4694	Approved
0.6186	Remote Similarity	NPD5280	Approved
0.6162	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4191	Approved
0.6145	Remote Similarity	NPD4194	Approved
0.6145	Remote Similarity	NPD4192	Approved
0.6145	Remote Similarity	NPD4193	Approved
0.6117	Remote Similarity	NPD7839	Suspended
0.6105	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4221	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD5363	Approved
0.6082	Remote Similarity	NPD1694	Approved
0.6047	Remote Similarity	NPD3704	Approved
0.6047	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD8264	Approved
0.604	Remote Similarity	NPD5694	Approved
0.604	Remote Similarity	NPD5693	Phase 1
0.602	Remote Similarity	NPD5690	Phase 2
0.602	Remote Similarity	NPD5786	Approved
0.602	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5909	Discontinued
0.5979	Remote Similarity	NPD4197	Approved
0.596	Remote Similarity	NPD3573	Approved
0.5957	Remote Similarity	NPD4195	Approved
0.5943	Remote Similarity	NPD7639	Approved
0.5943	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD5692	Phase 3
0.5941	Remote Similarity	NPD6698	Approved
0.5941	Remote Similarity	NPD46	Approved
0.5941	Remote Similarity	NPD4096	Approved
0.5941	Remote Similarity	NPD7838	Discovery
0.5941	Remote Similarity	NPD5207	Approved
0.5938	Remote Similarity	NPD4270	Approved
0.5938	Remote Similarity	NPD4269	Approved
0.5929	Remote Similarity	NPD6053	Discontinued
0.5918	Remote Similarity	NPD5329	Approved
0.5893	Remote Similarity	NPD6371	Approved
0.5882	Remote Similarity	NPD6050	Approved
0.5876	Remote Similarity	NPD6695	Phase 3
0.5865	Remote Similarity	NPD5695	Phase 3
0.5859	Remote Similarity	NPD4693	Phase 3
0.5859	Remote Similarity	NPD4689	Approved
0.5859	Remote Similarity	NPD4688	Approved
0.5859	Remote Similarity	NPD4138	Approved
0.5859	Remote Similarity	NPD5205	Approved
0.5859	Remote Similarity	NPD4690	Approved
0.5851	Remote Similarity	NPD3617	Approved
0.5851	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7638	Approved
0.5842	Remote Similarity	NPD4753	Phase 2
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD5369	Approved
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8513	Phase 3
0.5773	Remote Similarity	NPD3667	Approved
0.5769	Remote Similarity	NPD7748	Approved
0.5761	Remote Similarity	NPD4058	Approved
0.5761	Remote Similarity	NPD4687	Approved
0.5755	Remote Similarity	NPD6083	Phase 2
0.5755	Remote Similarity	NPD6084	Phase 2
0.5747	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4820	Approved
0.5729	Remote Similarity	NPD7514	Phase 3
0.5729	Remote Similarity	NPD4822	Approved
0.5729	Remote Similarity	NPD4819	Approved
0.5729	Remote Similarity	NPD4252	Approved
0.5729	Remote Similarity	NPD7332	Phase 2
0.5729	Remote Similarity	NPD4821	Approved
0.5729	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6079	Approved
0.5727	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD7500	Approved
0.5714	Remote Similarity	NPD5276	Approved
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD5362	Discontinued
0.5702	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5696	Approved
0.57	Remote Similarity	NPD4249	Approved
0.57	Remote Similarity	NPD3618	Phase 1
0.5686	Remote Similarity	NPD5328	Approved
0.5686	Remote Similarity	NPD6904	Approved
0.5686	Remote Similarity	NPD6673	Approved
0.5686	Remote Similarity	NPD6080	Approved
0.5673	Remote Similarity	NPD5133	Approved
0.5673	Remote Similarity	NPD6399	Phase 3
0.5667	Remote Similarity	NPD8516	Approved
0.5667	Remote Similarity	NPD8517	Approved
0.5667	Remote Similarity	NPD8515	Approved
0.5663	Remote Similarity	NPD8779	Phase 3
0.566	Remote Similarity	NPD5222	Approved
0.566	Remote Similarity	NPD5221	Approved
0.566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4786	Approved
0.5652	Remote Similarity	NPD4732	Discontinued
0.5648	Remote Similarity	NPD6648	Approved
0.5648	Remote Similarity	NPD5286	Approved
0.5648	Remote Similarity	NPD5285	Approved
0.5648	Remote Similarity	NPD4696	Approved
0.5647	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD4251	Approved
0.5644	Remote Similarity	NPD4250	Approved
0.5644	Remote Similarity	NPD7524	Approved
0.5644	Remote Similarity	NPD7750	Discontinued
0.5625	Remote Similarity	NPD5697	Approved
0.5619	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5173	Approved
0.5607	Remote Similarity	NPD7902	Approved
0.5607	Remote Similarity	NPD4755	Approved

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