NPASS Compound

Structure

CID31021 OpenBabel06191715362D 23 25 0 0 1 0 0 0 0 0999 V2000 0.7202 5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 3.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 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 3 10 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 22 1 0 0 0 0 9 2 1 6 0 0 0 9 16 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 18 1 0 0 0 0 13 19 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 6 0 0 0 14 17 1 0 0 0 0 15 18 1 1 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 4 1 1 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	322.347
LogP:	2.751
LogD:	0.72
LogS:	-2.721
# Rotatable Bonds:	3
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.96
Fsp3:	0.5
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:	-4.697
MDCK Permeability:	1.920995782711543e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.421
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.914
Plasma Protein Binding (PPB):	64.94684600830078%
Volume Distribution (VD):	1.975
Pgp-substrate:	43.491485595703125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.322
CYP1A2-substrate:	0.329
CYP2C19-inhibitor:	0.212
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.477
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	6.028
Half-life (T1/2):	0.577

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.704
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.868
Carcinogencity:	0.873
Eye Corrosion:	0.031
Eye Irritation:	0.037
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC31021

Natural Product ID:	NPC31021
*Common Name:**	Chermesinone B
IUPAC Name:	(6aR,9S,9aS)-3,6a-dimethyl-9-[(2S)-2-methylbutanoyl]-9,9a-dihydrofuro[2,3-h]isochromene-6,8-dione
Synonyms:	Chermesinone B
Standard InCHIKey:	MZMGICPQNSXAGE-SRSSHDMCSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-5-9(2)16(20)14-15-12-8-22-10(3)6-11(12)7-13(19)18(15,4)23-17(14)21/h6-9,14-15H,5H2,1-4H3/t9-,14-,15+,18-/m0/s1
SMILES:	CC[C@H](C)C(=O)[C@@H]1[C@H]2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801780
PubChem CID:	53355010
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	Eukaryota	isolated from the stem of the mangrove plant Kandelia candel	South China Sea in Guangdong Province, China	n.a.	PMID[21510637]
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510637]
NPO40080	Colletotrichum sp. BS4	Strain	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905687]
NPO1216	Aesculus indica	Species	Hippocastanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7400	Marsdenia cundurango	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8113	Streptomyces murayamaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11924	Sesuvium portulaca	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9828	Penicillium chermesinum	Species	Aspergillaceae	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	2
MIC	4

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	100000.0	nM	PMID[458411]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[458411]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	10.0	ug.mL-1	PMID[458412]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	10.0	ug.mL-1	PMID[458412]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	10.0	ug.mL-1	PMID[458412]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	10.0	ug.mL-1	PMID[458412]

☑ 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 NPC31021 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	220
0.1-0.2	1250
0.2-0.3	5446
0.3-0.4	12261
0.4-0.5	13891
0.5-0.6	6881
0.6-0.7	2527
0.7-0.8	195
0.8-0.85	15
0.85-0.9	2
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9263	High Similarity	NPC271059
0.9263	High Similarity	NPC25666
0.883	High Similarity	NPC318082
0.88	High Similarity	NPC23497
0.8602	High Similarity	NPC166110
0.8511	High Similarity	NPC248193
0.8462	Intermediate Similarity	NPC203795
0.8387	Intermediate Similarity	NPC142159
0.8387	Intermediate Similarity	NPC95364
0.8286	Intermediate Similarity	NPC326264
0.8211	Intermediate Similarity	NPC193396
0.8211	Intermediate Similarity	NPC32944
0.8056	Intermediate Similarity	NPC243298
0.7959	Intermediate Similarity	NPC471698
0.7921	Intermediate Similarity	NPC471699
0.7909	Intermediate Similarity	NPC245320
0.7838	Intermediate Similarity	NPC476815
0.7838	Intermediate Similarity	NPC31641
0.7838	Intermediate Similarity	NPC473145
0.7789	Intermediate Similarity	NPC38885
0.7789	Intermediate Similarity	NPC471739
0.7766	Intermediate Similarity	NPC281172
0.7766	Intermediate Similarity	NPC472686
0.7766	Intermediate Similarity	NPC290329
0.7745	Intermediate Similarity	NPC469851
0.77	Intermediate Similarity	NPC472674
0.77	Intermediate Similarity	NPC269492
0.77	Intermediate Similarity	NPC121036
0.7684	Intermediate Similarity	NPC38576
0.7684	Intermediate Similarity	NPC291712
0.7684	Intermediate Similarity	NPC279859
0.7596	Intermediate Similarity	NPC320294
0.7596	Intermediate Similarity	NPC297281
0.7596	Intermediate Similarity	NPC473144
0.7551	Intermediate Similarity	NPC469372
0.7551	Intermediate Similarity	NPC220454
0.7551	Intermediate Similarity	NPC212679
0.7551	Intermediate Similarity	NPC469595
0.7549	Intermediate Similarity	NPC472730
0.7549	Intermediate Similarity	NPC153776
0.7549	Intermediate Similarity	NPC177680
0.7549	Intermediate Similarity	NPC472729
0.7527	Intermediate Similarity	NPC474353
0.7526	Intermediate Similarity	NPC190718
0.7524	Intermediate Similarity	NPC272528
0.75	Intermediate Similarity	NPC143210
0.75	Intermediate Similarity	NPC56525
0.7476	Intermediate Similarity	NPC472727
0.7476	Intermediate Similarity	NPC472728
0.7476	Intermediate Similarity	NPC46761
0.7455	Intermediate Similarity	NPC321496
0.7455	Intermediate Similarity	NPC474271
0.7453	Intermediate Similarity	NPC469852
0.7453	Intermediate Similarity	NPC85529
0.7453	Intermediate Similarity	NPC32006
0.7449	Intermediate Similarity	NPC280833
0.7426	Intermediate Similarity	NPC12727
0.7426	Intermediate Similarity	NPC295347
0.7391	Intermediate Similarity	NPC478246
0.7391	Intermediate Similarity	NPC478247
0.7383	Intermediate Similarity	NPC469853
0.7374	Intermediate Similarity	NPC253177
0.7374	Intermediate Similarity	NPC223093
0.7374	Intermediate Similarity	NPC213636
0.7374	Intermediate Similarity	NPC280592
0.7353	Intermediate Similarity	NPC472733
0.7353	Intermediate Similarity	NPC472734
0.7353	Intermediate Similarity	NPC476275
0.734	Intermediate Similarity	NPC286229
0.7333	Intermediate Similarity	NPC163249
0.7327	Intermediate Similarity	NPC469819
0.7327	Intermediate Similarity	NPC114162
0.732	Intermediate Similarity	NPC229717
0.7312	Intermediate Similarity	NPC276647
0.7312	Intermediate Similarity	NPC28319
0.7312	Intermediate Similarity	NPC622
0.7312	Intermediate Similarity	NPC471740
0.73	Intermediate Similarity	NPC32552
0.73	Intermediate Similarity	NPC296114
0.73	Intermediate Similarity	NPC471329
0.729	Intermediate Similarity	NPC292588
0.7283	Intermediate Similarity	NPC283087
0.7282	Intermediate Similarity	NPC134083
0.7282	Intermediate Similarity	NPC472732
0.7282	Intermediate Similarity	NPC208094
0.7282	Intermediate Similarity	NPC27105
0.7282	Intermediate Similarity	NPC216904
0.7282	Intermediate Similarity	NPC471694
0.7282	Intermediate Similarity	NPC226986
0.7282	Intermediate Similarity	NPC472731
0.7281	Intermediate Similarity	NPC158963
0.7273	Intermediate Similarity	NPC34315
0.7273	Intermediate Similarity	NPC284561
0.7264	Intermediate Similarity	NPC179208
0.7263	Intermediate Similarity	NPC471326
0.7263	Intermediate Similarity	NPC221231
0.7255	Intermediate Similarity	NPC777
0.7255	Intermediate Similarity	NPC273197
0.7255	Intermediate Similarity	NPC234339
0.7248	Intermediate Similarity	NPC250018
0.7245	Intermediate Similarity	NPC181327
0.7238	Intermediate Similarity	NPC469657
0.7238	Intermediate Similarity	NPC244456
0.7228	Intermediate Similarity	NPC1108
0.7228	Intermediate Similarity	NPC476598
0.7228	Intermediate Similarity	NPC476597
0.7228	Intermediate Similarity	NPC477615
0.7216	Intermediate Similarity	NPC470177
0.7216	Intermediate Similarity	NPC133652
0.7216	Intermediate Similarity	NPC90287
0.7212	Intermediate Similarity	NPC471331
0.7212	Intermediate Similarity	NPC471330
0.7212	Intermediate Similarity	NPC472687
0.7212	Intermediate Similarity	NPC112753
0.7212	Intermediate Similarity	NPC54843
0.7212	Intermediate Similarity	NPC264378
0.7212	Intermediate Similarity	NPC275439
0.7212	Intermediate Similarity	NPC203388
0.7212	Intermediate Similarity	NPC99657
0.7207	Intermediate Similarity	NPC193948
0.7204	Intermediate Similarity	NPC35574
0.72	Intermediate Similarity	NPC471818
0.72	Intermediate Similarity	NPC152467
0.72	Intermediate Similarity	NPC469718
0.72	Intermediate Similarity	NPC329857
0.72	Intermediate Similarity	NPC224270
0.7196	Intermediate Similarity	NPC13385
0.7196	Intermediate Similarity	NPC213366
0.7193	Intermediate Similarity	NPC21326
0.7184	Intermediate Similarity	NPC472675
0.7184	Intermediate Similarity	NPC21681
0.7184	Intermediate Similarity	NPC301596
0.7184	Intermediate Similarity	NPC112654
0.7184	Intermediate Similarity	NPC299396
0.7184	Intermediate Similarity	NPC172998
0.7172	Intermediate Similarity	NPC471047
0.7172	Intermediate Similarity	NPC469653
0.7172	Intermediate Similarity	NPC469628
0.7172	Intermediate Similarity	NPC475906
0.7172	Intermediate Similarity	NPC472302
0.7172	Intermediate Similarity	NPC469631
0.7168	Intermediate Similarity	NPC270478
0.7158	Intermediate Similarity	NPC474085
0.7158	Intermediate Similarity	NPC475665
0.7157	Intermediate Similarity	NPC477129
0.7157	Intermediate Similarity	NPC473435
0.7157	Intermediate Similarity	NPC477130
0.7157	Intermediate Similarity	NPC476596
0.7157	Intermediate Similarity	NPC38830
0.7157	Intermediate Similarity	NPC473280
0.7157	Intermediate Similarity	NPC473431
0.7157	Intermediate Similarity	NPC470697
0.7157	Intermediate Similarity	NPC471078
0.7143	Intermediate Similarity	NPC215253
0.7143	Intermediate Similarity	NPC474802
0.7143	Intermediate Similarity	NPC185253
0.7143	Intermediate Similarity	NPC104861
0.7143	Intermediate Similarity	NPC477478
0.7143	Intermediate Similarity	NPC472929
0.7143	Intermediate Similarity	NPC477479
0.7143	Intermediate Similarity	NPC472972
0.7129	Intermediate Similarity	NPC20713
0.7117	Intermediate Similarity	NPC43775
0.7115	Intermediate Similarity	NPC239895
0.7115	Intermediate Similarity	NPC23680
0.7115	Intermediate Similarity	NPC478233
0.7113	Intermediate Similarity	NPC469569
0.7113	Intermediate Similarity	NPC139566
0.7103	Intermediate Similarity	NPC275583
0.71	Intermediate Similarity	NPC73995
0.71	Intermediate Similarity	NPC305039
0.71	Intermediate Similarity	NPC118011
0.71	Intermediate Similarity	NPC36668
0.7091	Intermediate Similarity	NPC220705
0.7083	Intermediate Similarity	NPC173609
0.7075	Intermediate Similarity	NPC323441
0.7075	Intermediate Similarity	NPC472685
0.7075	Intermediate Similarity	NPC473384
0.7075	Intermediate Similarity	NPC124211
0.7075	Intermediate Similarity	NPC472702
0.7071	Intermediate Similarity	NPC472007
0.7065	Intermediate Similarity	NPC324762
0.7064	Intermediate Similarity	NPC133422
0.7064	Intermediate Similarity	NPC199107
0.7064	Intermediate Similarity	NPC232969
0.7059	Intermediate Similarity	NPC165383
0.7059	Intermediate Similarity	NPC475302
0.7059	Intermediate Similarity	NPC263780
0.7059	Intermediate Similarity	NPC109414
0.7054	Intermediate Similarity	NPC66108
0.7048	Intermediate Similarity	NPC166770
0.7043	Intermediate Similarity	NPC17772
0.7043	Intermediate Similarity	NPC315974
0.7041	Intermediate Similarity	NPC110405
0.7041	Intermediate Similarity	NPC132228
0.7041	Intermediate Similarity	NPC8518
0.7041	Intermediate Similarity	NPC241512
0.7041	Intermediate Similarity	NPC263997
0.7041	Intermediate Similarity	NPC474680
0.7041	Intermediate Similarity	NPC6185

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 NPC31021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1663
0.2-0.3	3904
0.3-0.4	2304
0.4-0.5	751
0.5-0.6	234
0.6-0.7	99
0.7-0.8	8
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
0.7379	Intermediate Similarity	NPD5696	Approved
0.7374	Intermediate Similarity	NPD5692	Phase 3
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD5737	Approved
0.73	Intermediate Similarity	NPD5694	Approved
0.73	Intermediate Similarity	NPD6050	Approved
0.71	Intermediate Similarity	NPD6080	Approved
0.71	Intermediate Similarity	NPD6673	Approved
0.71	Intermediate Similarity	NPD6904	Approved
0.7087	Intermediate Similarity	NPD5695	Phase 3
0.703	Intermediate Similarity	NPD5207	Approved
0.699	Remote Similarity	NPD5282	Discontinued
0.6961	Remote Similarity	NPD5693	Phase 1
0.6952	Remote Similarity	NPD6084	Phase 2
0.6952	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD5654	Approved
0.6818	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6409	Approved
0.68	Remote Similarity	NPD6684	Approved
0.68	Remote Similarity	NPD7334	Approved
0.68	Remote Similarity	NPD7521	Approved
0.68	Remote Similarity	NPD7146	Approved
0.68	Remote Similarity	NPD5330	Approved
0.68	Remote Similarity	NPD6098	Approved
0.6792	Remote Similarity	NPD5959	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6765	Remote Similarity	NPD6101	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5697	Approved
0.6757	Remote Similarity	NPD5701	Approved
0.6737	Remote Similarity	NPD4756	Discovery
0.6733	Remote Similarity	NPD3573	Approved
0.6731	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD1694	Approved
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD6411	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6607	Remote Similarity	NPD6614	Approved
0.6604	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4629	Approved
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD5779	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4695	Discontinued
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD7748	Approved
0.6509	Remote Similarity	NPD6001	Approved
0.6505	Remote Similarity	NPD5208	Approved
0.6481	Remote Similarity	NPD7902	Approved
0.6471	Remote Similarity	NPD5280	Approved
0.6471	Remote Similarity	NPD5279	Phase 3
0.6471	Remote Similarity	NPD4694	Approved
0.6466	Remote Similarity	NPD6882	Approved
0.6466	Remote Similarity	NPD8297	Approved
0.6465	Remote Similarity	NPD5369	Approved
0.6449	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4753	Phase 2
0.6389	Remote Similarity	NPD4697	Phase 3
0.6387	Remote Similarity	NPD7115	Discovery
0.6374	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6319	Approved
0.633	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD7515	Phase 2
0.6311	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6274	Approved
0.629	Remote Similarity	NPD7492	Approved
0.6275	Remote Similarity	NPD4197	Approved
0.6275	Remote Similarity	NPD3668	Phase 3
0.6273	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD6317	Approved
0.624	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD5222	Approved
0.6239	Remote Similarity	NPD5221	Approved
0.6239	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7732	Phase 3
0.6238	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5209	Approved
0.6238	Remote Similarity	NPD3667	Approved
0.623	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD6059	Approved
0.6216	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.6214	Remote Similarity	NPD1696	Phase 3
0.6214	Remote Similarity	NPD5329	Approved
0.6214	Remote Similarity	NPD5363	Approved
0.6198	Remote Similarity	NPD6314	Approved
0.6198	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD6313	Approved
0.6196	Remote Similarity	NPD3704	Approved
0.6195	Remote Similarity	NPD6052	Approved
0.619	Remote Similarity	NPD7078	Approved
0.619	Remote Similarity	NPD8293	Discontinued
0.6182	Remote Similarity	NPD5173	Approved
0.6179	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6016	Approved
0.6179	Remote Similarity	NPD6015	Approved
0.6174	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6868	Approved
0.6162	Remote Similarity	NPD3617	Approved
0.6161	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD5690	Phase 2
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6142	Remote Similarity	NPD7736	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6132	Remote Similarity	NPD5328	Approved
0.6129	Remote Similarity	NPD6370	Approved
0.6129	Remote Similarity	NPD5988	Approved
0.6124	Remote Similarity	NPD7260	Phase 2
0.6117	Remote Similarity	NPD3666	Approved
0.6117	Remote Similarity	NPD4786	Approved
0.6117	Remote Similarity	NPD3665	Phase 1
0.6117	Remote Similarity	NPD3133	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5211	Phase 2
0.6106	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4633	Approved
0.6106	Remote Similarity	NPD5226	Approved
0.608	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD4270	Approved
0.6078	Remote Similarity	NPD4223	Phase 3
0.6078	Remote Similarity	NPD4221	Approved
0.6078	Remote Similarity	NPD4269	Approved
0.6075	Remote Similarity	NPD5785	Approved
0.6058	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4754	Approved
0.6053	Remote Similarity	NPD5175	Approved
0.6053	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD6908	Approved
0.6048	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD6909	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.604	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7331	Phase 2
0.602	Remote Similarity	NPD8039	Approved
0.6019	Remote Similarity	NPD6079	Approved
0.6019	Remote Similarity	NPD7154	Phase 3
0.6017	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD1695	Approved
0.5965	Remote Similarity	NPD5091	Approved
0.5963	Remote Similarity	NPD5133	Approved
0.5963	Remote Similarity	NPD4202	Approved
0.5954	Remote Similarity	NPD6845	Suspended
0.5952	Remote Similarity	NPD7604	Phase 2
0.5948	Remote Similarity	NPD4768	Approved
0.5948	Remote Similarity	NPD4767	Approved
0.5946	Remote Similarity	NPD7614	Phase 1
0.5922	Remote Similarity	NPD6435	Approved
0.592	Remote Similarity	NPD8516	Approved
0.592	Remote Similarity	NPD8515	Approved
0.592	Remote Similarity	NPD8517	Approved
0.5918	Remote Similarity	NPD4687	Approved
0.5918	Remote Similarity	NPD5733	Approved
0.5918	Remote Similarity	NPD4058	Approved
0.5914	Remote Similarity	NPD7341	Phase 2
0.5891	Remote Similarity	NPD6033	Approved
0.5888	Remote Similarity	NPD4518	Approved
0.5882	Remote Similarity	NPD2067	Discontinued
0.5882	Remote Similarity	NPD4252	Approved
0.5876	Remote Similarity	NPD5276	Approved
0.5872	Remote Similarity	NPD7983	Approved
0.587	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6110	Phase 1
0.5859	Remote Similarity	NPD6336	Discontinued
0.5849	Remote Similarity	NPD4690	Approved
0.5849	Remote Similarity	NPD4623	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