NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.19
Volume:	303.937
LogP:	5.121
LogD:	3.945
LogS:	-3.59
# Rotatable Bonds:	6
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	3.161
Fsp3:	0.647
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:	-4.759
MDCK Permeability:	2.4502167434548028e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	96.7900161743164%
Volume Distribution (VD):	2.47
Pgp-substrate:	3.6967153549194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.744
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.513
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.841
CYP2D6-inhibitor:	0.727
CYP2D6-substrate:	0.628
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	8.761
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.949
Carcinogencity:	0.175
Eye Corrosion:	0.123
Eye Irritation:	0.962
Respiratory Toxicity:	0.889

Download Data

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

Natural Product: NPC282255

Natural Product ID:	NPC282255
*Common Name:**	Pseudoanguillosporin A
IUPAC Name:	(3R)-3-heptyl-5-methyl-3,4-dihydro-1H-isochromene-6,8-diol
Synonyms:
Standard InCHIKey:	CHHKGJIZUJUBDN-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C17H26O3/c1-3-4-5-6-7-8-13-9-14-12(2)16(18)10-17(19)15(14)11-20-13/h10,13,18-19H,3-9,11H2,1-2H3/t13-/m1/s1
SMILES:	CCCCCCC[C@@H]1Cc2c(C)c(cc(c2CO1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3580981
PubChem CID:	42605288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO32981	cadophora sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26035018]
NPO41397	Cosmospora sp. + Magnaporthe oryzae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[35054969]

☑ 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
MIC	9

Activity Type	# Activity
NON-MOLECULAR	1
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[506802]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[506802]

☑ 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 NPC282255 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	319
0.1-0.2	1540
0.2-0.3	4114
0.3-0.4	12315
0.4-0.5	6766
0.5-0.6	5210
0.6-0.7	8455
0.7-0.8	3495
0.8-0.85	448
0.85-0.9	29
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9823	High Similarity	NPC3239
0.9569	High Similarity	NPC57199
0.9328	High Similarity	NPC293801
0.9024	High Similarity	NPC474494
0.9024	High Similarity	NPC25729
0.8889	High Similarity	NPC24913
0.8889	High Similarity	NPC177712
0.8852	High Similarity	NPC105031
0.8819	High Similarity	NPC473107
0.8793	High Similarity	NPC107240
0.879	High Similarity	NPC311293
0.879	High Similarity	NPC148366
0.8783	High Similarity	NPC473521
0.875	High Similarity	NPC102639
0.8707	High Similarity	NPC263753
0.8699	High Similarity	NPC124030
0.8699	High Similarity	NPC476653
0.8678	High Similarity	NPC476633
0.8661	High Similarity	NPC476389
0.8629	High Similarity	NPC170485
0.8618	High Similarity	NPC134195
0.8618	High Similarity	NPC86502
0.8618	High Similarity	NPC246648
0.8618	High Similarity	NPC197351
0.8618	High Similarity	NPC106914
0.8609	High Similarity	NPC224870
0.8607	High Similarity	NPC74137
0.8594	High Similarity	NPC185777
0.8583	High Similarity	NPC160623
0.856	High Similarity	NPC473134
0.855	High Similarity	NPC32630
0.8548	High Similarity	NPC113495
0.8548	High Similarity	NPC285040
0.8548	High Similarity	NPC188022
0.8548	High Similarity	NPC17809
0.8548	High Similarity	NPC102540
0.8548	High Similarity	NPC103420
0.8534	High Similarity	NPC476632
0.8534	High Similarity	NPC165770
0.8534	High Similarity	NPC4493
0.8534	High Similarity	NPC225679
0.8516	High Similarity	NPC472798
0.8504	High Similarity	NPC470225
0.8504	High Similarity	NPC254000
0.8504	High Similarity	NPC27187
0.85	High Similarity	NPC131118
0.8492	Intermediate Similarity	NPC274717
0.8492	Intermediate Similarity	NPC38664
0.8492	Intermediate Similarity	NPC53986
0.8492	Intermediate Similarity	NPC215300
0.848	Intermediate Similarity	NPC82299
0.848	Intermediate Similarity	NPC276212
0.8468	Intermediate Similarity	NPC228503
0.8468	Intermediate Similarity	NPC138248
0.8462	Intermediate Similarity	NPC43525
0.8455	Intermediate Similarity	NPC36016
0.8455	Intermediate Similarity	NPC100099
0.8438	Intermediate Similarity	NPC164574
0.8438	Intermediate Similarity	NPC150011
0.8438	Intermediate Similarity	NPC268917
0.8438	Intermediate Similarity	NPC118114
0.8438	Intermediate Similarity	NPC237424
0.8438	Intermediate Similarity	NPC196765
0.8438	Intermediate Similarity	NPC206224
0.8438	Intermediate Similarity	NPC12875
0.8438	Intermediate Similarity	NPC129784
0.8438	Intermediate Similarity	NPC228369
0.8438	Intermediate Similarity	NPC236014
0.8438	Intermediate Similarity	NPC15543
0.8438	Intermediate Similarity	NPC476166
0.8438	Intermediate Similarity	NPC282508
0.8438	Intermediate Similarity	NPC271945
0.8438	Intermediate Similarity	NPC280653
0.8438	Intermediate Similarity	NPC17343
0.8438	Intermediate Similarity	NPC207892
0.8438	Intermediate Similarity	NPC181497
0.8438	Intermediate Similarity	NPC129106
0.8438	Intermediate Similarity	NPC300875
0.8438	Intermediate Similarity	NPC238168
0.8425	Intermediate Similarity	NPC472795
0.8425	Intermediate Similarity	NPC472796
0.8425	Intermediate Similarity	NPC16577
0.8425	Intermediate Similarity	NPC472797
0.8425	Intermediate Similarity	NPC93962
0.8421	Intermediate Similarity	NPC265075
0.8421	Intermediate Similarity	NPC472601
0.8421	Intermediate Similarity	NPC472600
0.8417	Intermediate Similarity	NPC474933
0.8417	Intermediate Similarity	NPC69261
0.8417	Intermediate Similarity	NPC33270
0.8413	Intermediate Similarity	NPC53781
0.8413	Intermediate Similarity	NPC473221
0.8413	Intermediate Similarity	NPC149796
0.84	Intermediate Similarity	NPC105718
0.84	Intermediate Similarity	NPC278955
0.8397	Intermediate Similarity	NPC234952
0.839	Intermediate Similarity	NPC319803
0.839	Intermediate Similarity	NPC117846
0.8387	Intermediate Similarity	NPC76465
0.8387	Intermediate Similarity	NPC38761
0.8372	Intermediate Similarity	NPC13005
0.8361	Intermediate Similarity	NPC135467
0.8361	Intermediate Similarity	NPC260832
0.8361	Intermediate Similarity	NPC223451
0.8358	Intermediate Similarity	NPC472605
0.8358	Intermediate Similarity	NPC472603
0.8358	Intermediate Similarity	NPC472604
0.8346	Intermediate Similarity	NPC38604
0.8346	Intermediate Similarity	NPC211179
0.8346	Intermediate Similarity	NPC38017
0.8333	Intermediate Similarity	NPC54507
0.8333	Intermediate Similarity	NPC26879
0.8333	Intermediate Similarity	NPC141090
0.8333	Intermediate Similarity	NPC229147
0.8333	Intermediate Similarity	NPC150624
0.8333	Intermediate Similarity	NPC283049
0.8333	Intermediate Similarity	NPC230479
0.8333	Intermediate Similarity	NPC85292
0.8333	Intermediate Similarity	NPC50315
0.8321	Intermediate Similarity	NPC473413
0.8308	Intermediate Similarity	NPC85435
0.8308	Intermediate Similarity	NPC474453
0.8295	Intermediate Similarity	NPC293203
0.8295	Intermediate Similarity	NPC103799
0.8295	Intermediate Similarity	NPC68205
0.8295	Intermediate Similarity	NPC211413
0.8295	Intermediate Similarity	NPC469907
0.8295	Intermediate Similarity	NPC164804
0.8295	Intermediate Similarity	NPC244888
0.8295	Intermediate Similarity	NPC118683
0.8291	Intermediate Similarity	NPC168657
0.8281	Intermediate Similarity	NPC471519
0.8281	Intermediate Similarity	NPC471518
0.8279	Intermediate Similarity	NPC184302
0.8276	Intermediate Similarity	NPC61885
0.8276	Intermediate Similarity	NPC63698
0.8268	Intermediate Similarity	NPC186889
0.8268	Intermediate Similarity	NPC471077
0.8264	Intermediate Similarity	NPC195466
0.8264	Intermediate Similarity	NPC50521
0.8264	Intermediate Similarity	NPC221549
0.8264	Intermediate Similarity	NPC244816
0.8258	Intermediate Similarity	NPC472800
0.8258	Intermediate Similarity	NPC470802
0.8254	Intermediate Similarity	NPC131397
0.8254	Intermediate Similarity	NPC470726
0.8254	Intermediate Similarity	NPC476254
0.825	Intermediate Similarity	NPC53906
0.825	Intermediate Similarity	NPC474486
0.825	Intermediate Similarity	NPC464
0.825	Intermediate Similarity	NPC808
0.825	Intermediate Similarity	NPC185541
0.8244	Intermediate Similarity	NPC97834
0.8244	Intermediate Similarity	NPC117048
0.8244	Intermediate Similarity	NPC115335
0.8244	Intermediate Similarity	NPC225696
0.8244	Intermediate Similarity	NPC198154
0.8244	Intermediate Similarity	NPC296915
0.8244	Intermediate Similarity	NPC223008
0.8244	Intermediate Similarity	NPC124085
0.824	Intermediate Similarity	NPC96940
0.8235	Intermediate Similarity	NPC123175
0.8235	Intermediate Similarity	NPC472610
0.8235	Intermediate Similarity	NPC473845
0.8235	Intermediate Similarity	NPC471731
0.8235	Intermediate Similarity	NPC159721
0.8235	Intermediate Similarity	NPC473108
0.8235	Intermediate Similarity	NPC176730
0.8235	Intermediate Similarity	NPC50250
0.8231	Intermediate Similarity	NPC321086
0.8226	Intermediate Similarity	NPC193364
0.8226	Intermediate Similarity	NPC54972
0.8226	Intermediate Similarity	NPC237667
0.8217	Intermediate Similarity	NPC126836
0.8217	Intermediate Similarity	NPC470727
0.8217	Intermediate Similarity	NPC99795
0.8211	Intermediate Similarity	NPC93398
0.8211	Intermediate Similarity	NPC258979
0.8211	Intermediate Similarity	NPC8283
0.8209	Intermediate Similarity	NPC88269
0.8205	Intermediate Similarity	NPC299568
0.8205	Intermediate Similarity	NPC186385
0.8205	Intermediate Similarity	NPC202647
0.8203	Intermediate Similarity	NPC47283
0.8203	Intermediate Similarity	NPC28765
0.8203	Intermediate Similarity	NPC39064
0.8197	Intermediate Similarity	NPC469609
0.8197	Intermediate Similarity	NPC471671
0.8197	Intermediate Similarity	NPC154030
0.8197	Intermediate Similarity	NPC190514
0.819	Intermediate Similarity	NPC61033
0.819	Intermediate Similarity	NPC305603
0.8189	Intermediate Similarity	NPC470724
0.8182	Intermediate Similarity	NPC137580
0.8182	Intermediate Similarity	NPC203113
0.8182	Intermediate Similarity	NPC241241
0.8182	Intermediate Similarity	NPC258780
0.8182	Intermediate Similarity	NPC123559
0.8182	Intermediate Similarity	NPC125579
0.8182	Intermediate Similarity	NPC37410

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 NPC282255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	962
0.2-0.3	1799
0.3-0.4	2854
0.4-0.5	1625
0.5-0.6	1023
0.6-0.7	518
0.7-0.8	68
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD4625	Phase 3
0.8359	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.824	Intermediate Similarity	NPD4749	Approved
0.8226	Intermediate Similarity	NPD1610	Phase 2
0.8217	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4750	Phase 3
0.8203	Intermediate Similarity	NPD4908	Phase 1
0.8189	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD940	Approved
0.807	Intermediate Similarity	NPD846	Approved
0.7903	Intermediate Similarity	NPD1548	Phase 1
0.7863	Intermediate Similarity	NPD3027	Phase 3
0.7846	Intermediate Similarity	NPD2861	Phase 2
0.782	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD6696	Suspended
0.771	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD1242	Phase 1
0.7652	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD4626	Approved
0.7626	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD5691	Approved
0.7556	Intermediate Similarity	NPD4060	Phase 1
0.7536	Intermediate Similarity	NPD6099	Approved
0.7536	Intermediate Similarity	NPD6100	Approved
0.752	Intermediate Similarity	NPD6671	Approved
0.7519	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1398	Phase 1
0.7482	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3091	Approved
0.7478	Intermediate Similarity	NPD1809	Phase 2
0.746	Intermediate Similarity	NPD7340	Approved
0.7436	Intermediate Similarity	NPD3020	Approved
0.7429	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7635	Approved
0.7385	Intermediate Similarity	NPD3092	Approved
0.7368	Intermediate Similarity	NPD6959	Discontinued
0.7361	Intermediate Similarity	NPD2533	Approved
0.7361	Intermediate Similarity	NPD2534	Approved
0.7361	Intermediate Similarity	NPD2532	Approved
0.7328	Intermediate Similarity	NPD844	Approved
0.7328	Intermediate Similarity	NPD2859	Approved
0.7328	Intermediate Similarity	NPD2860	Approved
0.7324	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4097	Suspended
0.7315	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7819	Suspended
0.7304	Intermediate Similarity	NPD845	Approved
0.7299	Intermediate Similarity	NPD2238	Phase 2
0.7295	Intermediate Similarity	NPD2342	Discontinued
0.7293	Intermediate Similarity	NPD3094	Phase 2
0.7279	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD288	Approved
0.7241	Intermediate Similarity	NPD2933	Approved
0.7241	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2934	Approved
0.7241	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD8651	Approved
0.7209	Intermediate Similarity	NPD7741	Discontinued
0.7203	Intermediate Similarity	NPD3892	Phase 2
0.72	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3018	Phase 2
0.7185	Intermediate Similarity	NPD5736	Approved
0.7177	Intermediate Similarity	NPD3021	Approved
0.7177	Intermediate Similarity	NPD3022	Approved
0.7174	Intermediate Similarity	NPD3620	Phase 2
0.7174	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7041	Phase 2
0.7172	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7212	Phase 2
0.7172	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7133	Intermediate Similarity	NPD6674	Discontinued
0.7133	Intermediate Similarity	NPD37	Approved
0.7124	Intermediate Similarity	NPD6234	Discontinued
0.7123	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7447	Phase 1
0.7122	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD3705	Approved
0.7121	Intermediate Similarity	NPD1091	Approved
0.7114	Intermediate Similarity	NPD4380	Phase 2
0.7113	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4967	Phase 2
0.7105	Intermediate Similarity	NPD4965	Approved
0.7105	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD6405	Approved
0.7101	Intermediate Similarity	NPD6407	Approved
0.7099	Intermediate Similarity	NPD3095	Discontinued
0.7099	Intermediate Similarity	NPD5126	Approved
0.7099	Intermediate Similarity	NPD5125	Phase 3
0.7097	Intermediate Similarity	NPD2684	Approved
0.7092	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3750	Approved
0.7071	Intermediate Similarity	NPD2157	Approved
0.7063	Intermediate Similarity	NPD228	Approved
0.7063	Intermediate Similarity	NPD1549	Phase 2
0.705	Intermediate Similarity	NPD1240	Approved
0.705	Intermediate Similarity	NPD4140	Approved
0.7023	Intermediate Similarity	NPD1651	Approved
0.702	Intermediate Similarity	NPD1934	Approved
0.7016	Intermediate Similarity	NPD290	Approved
0.7015	Intermediate Similarity	NPD2983	Phase 2
0.7015	Intermediate Similarity	NPD2982	Phase 2
0.7015	Intermediate Similarity	NPD1669	Approved
0.7	Intermediate Similarity	NPD230	Phase 1
0.6993	Remote Similarity	NPD5762	Approved
0.6993	Remote Similarity	NPD5763	Approved
0.6985	Remote Similarity	NPD6584	Phase 3
0.6985	Remote Similarity	NPD4624	Approved
0.6985	Remote Similarity	NPD3691	Phase 2
0.6985	Remote Similarity	NPD3690	Phase 2
0.6981	Remote Similarity	NPD5844	Phase 1
0.6978	Remote Similarity	NPD6663	Approved
0.6977	Remote Similarity	NPD7157	Approved
0.6972	Remote Similarity	NPD1753	Discontinued
0.6972	Remote Similarity	NPD1510	Phase 2
0.6972	Remote Similarity	NPD4108	Discontinued
0.697	Remote Similarity	NPD3019	Approved
0.697	Remote Similarity	NPD2932	Approved
0.697	Remote Similarity	NPD4059	Approved
0.6963	Remote Similarity	NPD1283	Approved
0.6954	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5283	Phase 1
0.695	Remote Similarity	NPD6353	Approved
0.695	Remote Similarity	NPD1607	Approved
0.6948	Remote Similarity	NPD7075	Discontinued
0.694	Remote Similarity	NPD2232	Approved
0.694	Remote Similarity	NPD2233	Approved
0.694	Remote Similarity	NPD2981	Phase 2
0.694	Remote Similarity	NPD2230	Approved
0.6939	Remote Similarity	NPD7390	Discontinued
0.6923	Remote Similarity	NPD2796	Approved
0.6923	Remote Similarity	NPD2935	Discontinued
0.6918	Remote Similarity	NPD7228	Approved
0.6912	Remote Similarity	NPD1131	Approved
0.6912	Remote Similarity	NPD1129	Approved
0.6912	Remote Similarity	NPD1133	Approved
0.6912	Remote Similarity	NPD1134	Approved
0.6912	Remote Similarity	NPD1135	Approved
0.6906	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4538	Approved
0.6901	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4536	Approved
0.6897	Remote Similarity	NPD2800	Approved
0.6897	Remote Similarity	NPD1652	Phase 2
0.6894	Remote Similarity	NPD4093	Discontinued
0.6883	Remote Similarity	NPD7768	Phase 2
0.6883	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7229	Phase 3
0.6879	Remote Similarity	NPD5710	Approved
0.6879	Remote Similarity	NPD6232	Discontinued
0.6879	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD7266	Discontinued
0.6875	Remote Similarity	NPD7843	Approved
0.6867	Remote Similarity	NPD1653	Approved
0.6863	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7466	Approved
0.6846	Remote Similarity	NPD709	Approved
0.6842	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1778	Approved
0.6842	Remote Similarity	NPD2286	Discontinued
0.6842	Remote Similarity	NPD7411	Suspended
0.6831	Remote Similarity	NPD2568	Approved
0.6831	Remote Similarity	NPD6651	Approved
0.6828	Remote Similarity	NPD2424	Discontinued
0.6821	Remote Similarity	NPD4005	Discontinued
0.6818	Remote Similarity	NPD9545	Approved
0.6812	Remote Similarity	NPD1712	Approved
0.6806	Remote Similarity	NPD4477	Approved
0.6806	Remote Similarity	NPD4476	Approved
0.6803	Remote Similarity	NPD2677	Approved
0.68	Remote Similarity	NPD968	Approved
0.6791	Remote Similarity	NPD3496	Discontinued
0.6788	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3764	Approved
0.6783	Remote Similarity	NPD2200	Suspended
0.6779	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1792	Phase 2
0.6767	Remote Similarity	NPD3445	Approved
0.6767	Remote Similarity	NPD3443	Approved
0.6767	Remote Similarity	NPD3444	Approved
0.6765	Remote Similarity	NPD6583	Phase 3
0.6765	Remote Similarity	NPD6582	Phase 2
0.6759	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6004	Phase 3
0.6759	Remote Similarity	NPD6005	Phase 3
0.6759	Remote Similarity	NPD6002	Phase 3
0.6757	Remote Similarity	NPD6667	Approved
0.6757	Remote Similarity	NPD6666	Approved
0.6754	Remote Similarity	NPD111	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