NPASS Compound

Structure

NPC95364 OpenBabel07101718202D 26 28 0 0 1 0 0 0 0 0999 V2000 4.0148 6.0769 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 3.3457 5.3338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3675 5.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6984 4.7985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 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 0.3601 3.3122 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 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 -0.3090 2.5691 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 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 -1.2872 2.7770 0.0000 O 0 0 0 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 -1.5878 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 4 1 0 0 0 0 2 13 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	371.599
LogP:	4.641
LogD:	2.666
LogS:	-5.157
# Rotatable Bonds:	7
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.394
Synthetic Accessibility Score:	3.954
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	2.607936221465934e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	88.97148132324219%
Volume Distribution (VD):	2.15
Pgp-substrate:	8.192872047424316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.74
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.45
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.307
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.292

ADMET: Excretion

Clearance (CL):	1.557
Half-life (T1/2):	0.618

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.971
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.954
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.547

Download Data

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

Natural Product: NPC95364

Natural Product ID:	NPC95364
*Common Name:**	(6Ar)-3,6A-Dimethyl-9-Octanoylfuro[2,3-H]Isochromene-6,8-Dione
IUPAC Name:	(6aR)-3,6a-dimethyl-9-octanoylfuro[2,3-h]isochromene-6,8-dione
Synonyms:
Standard InCHIKey:	YNVKQPJBOAUYIJ-NRFANRHFSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-4-5-6-7-8-9-16(22)18-19-15-12-25-13(2)10-14(15)11-17(23)21(19,3)26-20(18)24/h10-12H,4-9H2,1-3H3/t21-/m0/s1
SMILES:	CCCCCCCC(=O)C1=C2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215466
PubChem CID:	49864138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO33002	aspergillus deflectus cbs 109.55	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20655237]

☑ 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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[573494]
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	28000.0	nM	PMID[573494]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	>	28000.0	nM	PMID[573494]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	28000.0	nM	PMID[573494]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[573494]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[573494]

☑ 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 NPC95364 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	211
0.1-0.2	1337
0.2-0.3	5504
0.3-0.4	11961
0.4-0.5	15311
0.5-0.6	6235
0.6-0.7	1856
0.7-0.8	253
0.8-0.85	16
0.85-0.9	5
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC142159
0.9765	High Similarity	NPC193396
0.9765	High Similarity	NPC166110
0.9765	High Similarity	NPC32944
0.9651	High Similarity	NPC248193
0.9286	High Similarity	NPC281172
0.8953	High Similarity	NPC291712
0.8681	High Similarity	NPC143210
0.8587	High Similarity	NPC12727
0.8542	High Similarity	NPC271059
0.8542	High Similarity	NPC25666
0.8526	High Similarity	NPC469851
0.8462	Intermediate Similarity	NPC32552
0.8387	Intermediate Similarity	NPC31021
0.8387	Intermediate Similarity	NPC471698
0.8182	Intermediate Similarity	NPC469852
0.8152	Intermediate Similarity	NPC224270
0.8144	Intermediate Similarity	NPC471699
0.81	Intermediate Similarity	NPC469853
0.7981	Intermediate Similarity	NPC321496
0.7921	Intermediate Similarity	NPC232969
0.7921	Intermediate Similarity	NPC199107
0.7907	Intermediate Similarity	NPC471225
0.7849	Intermediate Similarity	NPC280833
0.7812	Intermediate Similarity	NPC295347
0.7789	Intermediate Similarity	NPC282644
0.7789	Intermediate Similarity	NPC29798
0.7742	Intermediate Similarity	NPC475902
0.7732	Intermediate Similarity	NPC318082
0.7653	Intermediate Similarity	NPC208094
0.7609	Intermediate Similarity	NPC307112
0.7553	Intermediate Similarity	NPC469653
0.7553	Intermediate Similarity	NPC473658
0.7553	Intermediate Similarity	NPC469628
0.7553	Intermediate Similarity	NPC472302
0.7553	Intermediate Similarity	NPC471047
0.7553	Intermediate Similarity	NPC475906
0.7553	Intermediate Similarity	NPC469631
0.7551	Intermediate Similarity	NPC301596
0.7551	Intermediate Similarity	NPC299396
0.7551	Intermediate Similarity	NPC172998
0.7549	Intermediate Similarity	NPC272528
0.7528	Intermediate Similarity	NPC150646
0.7527	Intermediate Similarity	NPC261721
0.7527	Intermediate Similarity	NPC38576
0.7527	Intermediate Similarity	NPC279859
0.7527	Intermediate Similarity	NPC472009
0.75	Intermediate Similarity	NPC327106
0.75	Intermediate Similarity	NPC180290
0.75	Intermediate Similarity	NPC316324
0.7474	Intermediate Similarity	NPC307092
0.7473	Intermediate Similarity	NPC471326
0.7473	Intermediate Similarity	NPC221231
0.7473	Intermediate Similarity	NPC475690
0.7471	Intermediate Similarity	NPC329826
0.7471	Intermediate Similarity	NPC469414
0.7449	Intermediate Similarity	NPC273197
0.7449	Intermediate Similarity	NPC234339
0.7447	Intermediate Similarity	NPC476079
0.7447	Intermediate Similarity	NPC113370
0.7447	Intermediate Similarity	NPC472007
0.7447	Intermediate Similarity	NPC103743
0.7431	Intermediate Similarity	NPC243298
0.7429	Intermediate Similarity	NPC23497
0.7423	Intermediate Similarity	NPC476597
0.7423	Intermediate Similarity	NPC476598
0.7423	Intermediate Similarity	NPC1108
0.7419	Intermediate Similarity	NPC189311
0.7416	Intermediate Similarity	NPC471220
0.74	Intermediate Similarity	NPC264378
0.74	Intermediate Similarity	NPC35717
0.7396	Intermediate Similarity	NPC253177
0.7396	Intermediate Similarity	NPC469372
0.7396	Intermediate Similarity	NPC212679
0.7396	Intermediate Similarity	NPC469595
0.7396	Intermediate Similarity	NPC220454
0.7396	Intermediate Similarity	NPC280592
0.7396	Intermediate Similarity	NPC213636
0.7391	Intermediate Similarity	NPC193198
0.7391	Intermediate Similarity	NPC288281
0.7381	Intermediate Similarity	NPC134385
0.7368	Intermediate Similarity	NPC472008
0.7368	Intermediate Similarity	NPC241507
0.7368	Intermediate Similarity	NPC26078
0.7347	Intermediate Similarity	NPC476596
0.7347	Intermediate Similarity	NPC38830
0.734	Intermediate Similarity	NPC203795
0.7333	Intermediate Similarity	NPC471299
0.7333	Intermediate Similarity	NPC471740
0.7327	Intermediate Similarity	NPC54705
0.732	Intermediate Similarity	NPC45579
0.732	Intermediate Similarity	NPC472705
0.732	Intermediate Similarity	NPC296114
0.732	Intermediate Similarity	NPC471329
0.7312	Intermediate Similarity	NPC474359
0.7312	Intermediate Similarity	NPC30486
0.73	Intermediate Similarity	NPC239895
0.7297	Intermediate Similarity	NPC245320
0.7294	Intermediate Similarity	NPC232812
0.7292	Intermediate Similarity	NPC51358
0.7292	Intermediate Similarity	NPC284561
0.7283	Intermediate Similarity	NPC268122
0.7282	Intermediate Similarity	NPC473144
0.7282	Intermediate Similarity	NPC297281
0.7273	Intermediate Similarity	NPC209355
0.7263	Intermediate Similarity	NPC125925
0.7263	Intermediate Similarity	NPC471739
0.7241	Intermediate Similarity	NPC287878
0.7234	Intermediate Similarity	NPC67081
0.7234	Intermediate Similarity	NPC130030
0.7234	Intermediate Similarity	NPC471223
0.7232	Intermediate Similarity	NPC473145
0.7232	Intermediate Similarity	NPC476815
0.7232	Intermediate Similarity	NPC31641
0.7222	Intermediate Similarity	NPC315765
0.7222	Intermediate Similarity	NPC128276
0.7209	Intermediate Similarity	NPC64234
0.7209	Intermediate Similarity	NPC37929
0.7204	Intermediate Similarity	NPC16488
0.7204	Intermediate Similarity	NPC475083
0.7204	Intermediate Similarity	NPC118423
0.7204	Intermediate Similarity	NPC222358
0.7191	Intermediate Similarity	NPC123360
0.7191	Intermediate Similarity	NPC27205
0.7184	Intermediate Similarity	NPC189609
0.7184	Intermediate Similarity	NPC197835
0.7184	Intermediate Similarity	NPC140591
0.7184	Intermediate Similarity	NPC291500
0.7184	Intermediate Similarity	NPC303653
0.7174	Intermediate Similarity	NPC471325
0.7174	Intermediate Similarity	NPC286229
0.7174	Intermediate Similarity	NPC282293
0.7174	Intermediate Similarity	NPC42470
0.7172	Intermediate Similarity	NPC469632
0.7172	Intermediate Similarity	NPC470697
0.7172	Intermediate Similarity	NPC477241
0.7159	Intermediate Similarity	NPC476355
0.7158	Intermediate Similarity	NPC168248
0.7158	Intermediate Similarity	NPC315395
0.7158	Intermediate Similarity	NPC316426
0.7158	Intermediate Similarity	NPC234038
0.7158	Intermediate Similarity	NPC220478
0.7157	Intermediate Similarity	NPC474012
0.7157	Intermediate Similarity	NPC469551
0.7157	Intermediate Similarity	NPC476299
0.7156	Intermediate Similarity	NPC326264
0.7143	Intermediate Similarity	NPC178277
0.7143	Intermediate Similarity	NPC473980
0.7143	Intermediate Similarity	NPC473981
0.7143	Intermediate Similarity	NPC20713
0.7129	Intermediate Similarity	NPC471694
0.7129	Intermediate Similarity	NPC134083
0.7129	Intermediate Similarity	NPC53844
0.7128	Intermediate Similarity	NPC470918
0.7128	Intermediate Similarity	NPC60951
0.7126	Intermediate Similarity	NPC133098
0.7113	Intermediate Similarity	NPC5509
0.7111	Intermediate Similarity	NPC187568
0.7111	Intermediate Similarity	NPC283087
0.7111	Intermediate Similarity	NPC57744
0.7111	Intermediate Similarity	NPC41780
0.7111	Intermediate Similarity	NPC473825
0.7111	Intermediate Similarity	NPC68156
0.7103	Intermediate Similarity	NPC137911
0.7103	Intermediate Similarity	NPC228477
0.7103	Intermediate Similarity	NPC38154
0.7097	Intermediate Similarity	NPC173609
0.7097	Intermediate Similarity	NPC85772
0.7093	Intermediate Similarity	NPC470693
0.7087	Intermediate Similarity	NPC244456
0.7087	Intermediate Similarity	NPC224172
0.7087	Intermediate Similarity	NPC168319
0.7087	Intermediate Similarity	NPC472643
0.7087	Intermediate Similarity	NPC194028
0.7087	Intermediate Similarity	NPC469657
0.7083	Intermediate Similarity	NPC181327
0.7083	Intermediate Similarity	NPC266957
0.7083	Intermediate Similarity	NPC478145
0.7083	Intermediate Similarity	NPC471738
0.7075	Intermediate Similarity	NPC266514
0.7071	Intermediate Similarity	NPC165383
0.7071	Intermediate Similarity	NPC271652
0.7064	Intermediate Similarity	NPC66108
0.7054	Intermediate Similarity	NPC315974
0.7053	Intermediate Similarity	NPC470177
0.7041	Intermediate Similarity	NPC8062
0.7041	Intermediate Similarity	NPC51486
0.7041	Intermediate Similarity	NPC475879
0.7041	Intermediate Similarity	NPC166554
0.7041	Intermediate Similarity	NPC471818
0.7041	Intermediate Similarity	NPC265856
0.7041	Intermediate Similarity	NPC316228
0.7041	Intermediate Similarity	NPC51653
0.7041	Intermediate Similarity	NPC131864
0.7037	Intermediate Similarity	NPC89408
0.7033	Intermediate Similarity	NPC299235
0.7033	Intermediate Similarity	NPC475699
0.703	Intermediate Similarity	NPC112654
0.7024	Intermediate Similarity	NPC133904
0.7021	Intermediate Similarity	NPC318468

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 NPC95364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1619
0.2-0.3	3768
0.3-0.4	2423
0.4-0.5	866
0.5-0.6	236
0.6-0.7	44
0.7-0.8	2
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
0.75	Intermediate Similarity	NPD4756	Discovery
0.697	Remote Similarity	NPD5693	Phase 1
0.6915	Remote Similarity	NPD5209	Approved
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8039	Approved
0.6869	Remote Similarity	NPD5692	Phase 3
0.6837	Remote Similarity	NPD5737	Approved
0.6837	Remote Similarity	NPD6672	Approved
0.68	Remote Similarity	NPD6050	Approved
0.68	Remote Similarity	NPD5694	Approved
0.6744	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1694	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD6673	Approved
0.66	Remote Similarity	NPD6904	Approved
0.66	Remote Similarity	NPD6080	Approved
0.6577	Remote Similarity	NPD2067	Discontinued
0.6552	Remote Similarity	NPD3704	Approved
0.6476	Remote Similarity	NPD6083	Phase 2
0.6476	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD5654	Approved
0.6437	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5696	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.6379	Remote Similarity	NPD7115	Discovery
0.6373	Remote Similarity	NPD5785	Approved
0.6346	Remote Similarity	NPD5282	Discontinued
0.6327	Remote Similarity	NPD7154	Phase 3
0.6321	Remote Similarity	NPD5959	Approved
0.6316	Remote Similarity	NPD6053	Discontinued
0.63	Remote Similarity	NPD7146	Approved
0.63	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD7334	Approved
0.63	Remote Similarity	NPD7521	Approved
0.63	Remote Similarity	NPD5330	Approved
0.63	Remote Similarity	NPD6684	Approved
0.63	Remote Similarity	NPD6098	Approved
0.6275	Remote Similarity	NPD6101	Approved
0.6275	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6214	Remote Similarity	NPD46	Approved
0.6214	Remote Similarity	NPD6698	Approved
0.6214	Remote Similarity	NPD5207	Approved
0.6207	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5363	Approved
0.62	Remote Similarity	NPD1696	Phase 3
0.6186	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6903	Approved
0.6176	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5697	Approved
0.6161	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD6411	Approved
0.6132	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD4225	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD6881	Approved
0.6106	Remote Similarity	NPD6899	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.6095	Remote Similarity	NPD6399	Phase 3
0.6078	Remote Similarity	NPD3573	Approved
0.6061	Remote Similarity	NPD4270	Approved
0.6061	Remote Similarity	NPD4269	Approved
0.6053	Remote Similarity	NPD6372	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD6373	Approved
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7900	Approved
0.6038	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD7748	Approved
0.6033	Remote Similarity	NPD8513	Phase 3
0.602	Remote Similarity	NPD4695	Discontinued
0.602	Remote Similarity	NPD4252	Approved
0.6019	Remote Similarity	NPD5208	Approved
0.6017	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD8779	Phase 3
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5786	Approved
0.598	Remote Similarity	NPD5280	Approved
0.598	Remote Similarity	NPD4694	Approved
0.598	Remote Similarity	NPD5279	Phase 3
0.5963	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7638	Approved
0.5962	Remote Similarity	NPD4753	Phase 2
0.5955	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6847	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD6649	Approved
0.5948	Remote Similarity	NPD6869	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6650	Approved
0.5948	Remote Similarity	NPD6617	Approved
0.5929	Remote Similarity	NPD6008	Approved
0.5926	Remote Similarity	NPD7839	Suspended
0.5909	Remote Similarity	NPD7639	Approved
0.5909	Remote Similarity	NPD7640	Approved
0.5902	Remote Similarity	NPD8516	Approved
0.5902	Remote Similarity	NPD8517	Approved
0.5902	Remote Similarity	NPD8515	Approved
0.59	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD8297	Approved
0.5877	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD6371	Approved
0.5849	Remote Similarity	NPD7637	Suspended
0.5849	Remote Similarity	NPD7515	Phase 2
0.5842	Remote Similarity	NPD5362	Discontinued
0.5842	Remote Similarity	NPD6110	Phase 1
0.5841	Remote Similarity	NPD5909	Discontinued
0.582	Remote Similarity	NPD6319	Approved
0.5812	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6051	Approved
0.581	Remote Similarity	NPD1695	Approved
0.5784	Remote Similarity	NPD3668	Phase 3
0.5784	Remote Similarity	NPD4197	Approved
0.5776	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7838	Discovery
0.575	Remote Similarity	NPD6274	Approved
0.5743	Remote Similarity	NPD3667	Approved
0.5741	Remote Similarity	NPD6001	Approved
0.5739	Remote Similarity	NPD6614	Approved
0.5736	Remote Similarity	NPD7260	Phase 2
0.5728	Remote Similarity	NPD5329	Approved
0.5727	Remote Similarity	NPD4755	Approved
0.5726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6317	Approved
0.5701	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6686	Approved
0.5688	Remote Similarity	NPD5210	Approved
0.5688	Remote Similarity	NPD4629	Approved
0.5673	Remote Similarity	NPD4519	Discontinued
0.5673	Remote Similarity	NPD4249	Approved
0.5673	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6422	Discontinued
0.5673	Remote Similarity	NPD4623	Approved
0.5673	Remote Similarity	NPD3618	Phase 1
0.5673	Remote Similarity	NPD5690	Phase 2
0.5669	Remote Similarity	NPD8074	Phase 3
0.5664	Remote Similarity	NPD5211	Phase 2
0.566	Remote Similarity	NPD5370	Suspended
0.5657	Remote Similarity	NPD3617	Approved
0.5657	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6314	Approved
0.5656	Remote Similarity	NPD6313	Approved
0.5656	Remote Similarity	NPD6335	Approved
0.5636	Remote Similarity	NPD5221	Approved
0.5636	Remote Similarity	NPD5222	Approved
0.5636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4697	Phase 3
0.5635	Remote Similarity	NPD7492	Approved
0.5631	Remote Similarity	NPD4786	Approved
0.5631	Remote Similarity	NPD3666	Approved
0.5631	Remote Similarity	NPD3133	Approved
0.5631	Remote Similarity	NPD3665	Phase 1
0.5625	Remote Similarity	NPD5286	Approved
0.5625	Remote Similarity	NPD4696	Approved
0.5625	Remote Similarity	NPD6648	Approved
0.5625	Remote Similarity	NPD5285	Approved
0.5625	Remote Similarity	NPD4700	Approved
0.562	Remote Similarity	NPD6868	Approved
0.5619	Remote Similarity	NPD4250	Approved
0.5619	Remote Similarity	NPD4251	Approved
0.561	Remote Similarity	NPD7101	Approved
0.561	Remote Similarity	NPD7100	Approved
0.56	Remote Similarity	NPD2838	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