NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.15
Volume:	272.577
LogP:	4.586
LogD:	4.052
LogS:	-3.841
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.3
Fsp3:	0.375
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:	-4.684
MDCK Permeability:	2.4972794562927447e-05
Pgp-inhibitor:	0.398
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	97.91153717041016%
Volume Distribution (VD):	5.598
Pgp-substrate:	4.917080879211426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.305
CYP2C19-inhibitor:	0.877
CYP2C19-substrate:	0.644
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	17.408
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.901
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.929
Carcinogencity:	0.543
Eye Corrosion:	0.006
Eye Irritation:	0.513
Respiratory Toxicity:	0.73

Download Data

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

Natural Product: NPC474920

Natural Product ID:	NPC474920
*Common Name:**	Cordiachromene A
IUPAC Name:	2-methyl-2-(4-methylpent-3-enyl)chromen-6-ol
Synonyms:
Standard InCHIKey:	CEZCHPFUKBTQGN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H20O2/c1-12(2)5-4-9-16(3)10-8-13-11-14(17)6-7-15(13)18-16/h5-8,10-11,17H,4,9H2,1-3H3
SMILES:	CC(=CCCC1(C)C=Cc2cc(ccc2O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487808
PubChem CID:	124963
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-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
NPO33101	aplidium aff. densum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180826]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19368377]
NPO22854	Cordia globifera	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384317]
NPO40780	Amaroucium multiplicatum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2607356]
NPO40784	Aplidium antillense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[3404153]
NPO22854	Cordia globifera	Species	Cordiaceae	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	11
MIC	12
Others	3

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1
Organism	17
Others	1
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	36.0	ug.mL-1	PMID[521610]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.5	ug.mL-1	PMID[521610]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	=	30000.0	nM	PMID[521611]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[521613]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[521613]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[521613]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	256.0	ug.mL-1	PMID[521610]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[521610]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	64.0	ug.mL-1	PMID[521610]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	2.0	ug ml-1	PMID[521610]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MBC	=	1.0	ug ml-1	PMID[521610]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	2000000.0	nM	PMID[521611]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	510000.0	nM	PMID[521611]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	0.3	ug.mL-1	PMID[521612]
NPT2	Others	Unspecified		IC50	=	0.2	ug.mL-1	PMID[521612]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[521613]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	20.0	ug.mL-1	PMID[521613]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	11.2	ug.mL-1	PMID[521613]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[521613]

☑ 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 NPC474920 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	303
0.1-0.2	1959
0.2-0.3	6323
0.3-0.4	12990
0.4-0.5	3971
0.5-0.6	7166
0.6-0.7	7818
0.7-0.8	1995
0.8-0.85	118
0.85-0.9	36
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC473718
0.9369	High Similarity	NPC471449
0.9273	High Similarity	NPC154256
0.9273	High Similarity	NPC290470
0.9273	High Similarity	NPC69539
0.9196	High Similarity	NPC51341
0.9189	High Similarity	NPC187993
0.9189	High Similarity	NPC238176
0.9151	High Similarity	NPC233320
0.9123	High Similarity	NPC476165
0.9027	High Similarity	NPC32152
0.8947	High Similarity	NPC232295
0.8947	High Similarity	NPC474131
0.8938	High Similarity	NPC283616
0.8879	High Similarity	NPC302211
0.887	High Similarity	NPC45663
0.886	High Similarity	NPC85895
0.886	High Similarity	NPC137294
0.8839	High Similarity	NPC301321
0.8818	High Similarity	NPC275627
0.8793	High Similarity	NPC48623
0.8793	High Similarity	NPC168707
0.8783	High Similarity	NPC14177
0.8761	High Similarity	NPC163398
0.875	High Similarity	NPC475078
0.8739	High Similarity	NPC476006
0.8729	High Similarity	NPC61685
0.8729	High Similarity	NPC248557
0.8718	High Similarity	NPC204535
0.8718	High Similarity	NPC46586
0.8716	High Similarity	NPC241549
0.8707	High Similarity	NPC218753
0.8707	High Similarity	NPC473875
0.8667	High Similarity	NPC95034
0.8667	High Similarity	NPC142087
0.8644	High Similarity	NPC474130
0.8632	High Similarity	NPC212965
0.8609	High Similarity	NPC139047
0.8571	High Similarity	NPC190086
0.8571	High Similarity	NPC474237
0.8571	High Similarity	NPC147896
0.8571	High Similarity	NPC276962
0.8571	High Similarity	NPC98372
0.8571	High Similarity	NPC152097
0.8559	High Similarity	NPC120638
0.8559	High Similarity	NPC74137
0.8547	High Similarity	NPC475529
0.8519	High Similarity	NPC130817
0.8505	High Similarity	NPC80800
0.85	High Similarity	NPC476254
0.85	High Similarity	NPC131397
0.8491	Intermediate Similarity	NPC260775
0.8487	Intermediate Similarity	NPC261992
0.8443	Intermediate Similarity	NPC47288
0.8426	Intermediate Similarity	NPC108497
0.8421	Intermediate Similarity	NPC87563
0.8417	Intermediate Similarity	NPC270030
0.8411	Intermediate Similarity	NPC129373
0.8411	Intermediate Similarity	NPC130756
0.8411	Intermediate Similarity	NPC12931
0.8411	Intermediate Similarity	NPC248396
0.8411	Intermediate Similarity	NPC48730
0.8411	Intermediate Similarity	NPC70677
0.8403	Intermediate Similarity	NPC188997
0.839	Intermediate Similarity	NPC212559
0.839	Intermediate Similarity	NPC129176
0.8387	Intermediate Similarity	NPC82503
0.8378	Intermediate Similarity	NPC169450
0.8378	Intermediate Similarity	NPC75440
0.8365	Intermediate Similarity	NPC29373
0.8349	Intermediate Similarity	NPC12987
0.8349	Intermediate Similarity	NPC474603
0.8347	Intermediate Similarity	NPC133407
0.8347	Intermediate Similarity	NPC28476
0.8333	Intermediate Similarity	NPC248786
0.832	Intermediate Similarity	NPC317601
0.832	Intermediate Similarity	NPC329427
0.8319	Intermediate Similarity	NPC266932
0.8306	Intermediate Similarity	NPC475880
0.8293	Intermediate Similarity	NPC176590
0.8276	Intermediate Similarity	NPC33717
0.8276	Intermediate Similarity	NPC236070
0.8276	Intermediate Similarity	NPC242580
0.8276	Intermediate Similarity	NPC126759
0.8273	Intermediate Similarity	NPC470393
0.8261	Intermediate Similarity	NPC470837
0.8261	Intermediate Similarity	NPC161696
0.8257	Intermediate Similarity	NPC192596
0.824	Intermediate Similarity	NPC153019
0.8235	Intermediate Similarity	NPC96423
0.8226	Intermediate Similarity	NPC97326
0.8226	Intermediate Similarity	NPC59654
0.8226	Intermediate Similarity	NPC271832
0.8211	Intermediate Similarity	NPC46978
0.8205	Intermediate Similarity	NPC33270
0.8205	Intermediate Similarity	NPC69261
0.8205	Intermediate Similarity	NPC86947
0.8198	Intermediate Similarity	NPC155072
0.8198	Intermediate Similarity	NPC53740
0.8198	Intermediate Similarity	NPC113457
0.8198	Intermediate Similarity	NPC30416
0.8197	Intermediate Similarity	NPC252962
0.819	Intermediate Similarity	NPC808
0.8182	Intermediate Similarity	NPC108875
0.8182	Intermediate Similarity	NPC96940
0.8182	Intermediate Similarity	NPC38079
0.8174	Intermediate Similarity	NPC35344
0.8174	Intermediate Similarity	NPC141003
0.8167	Intermediate Similarity	NPC475839
0.8165	Intermediate Similarity	NPC51633
0.8165	Intermediate Similarity	NPC477685
0.816	Intermediate Similarity	NPC196621
0.8158	Intermediate Similarity	NPC255068
0.8158	Intermediate Similarity	NPC54373
0.8158	Intermediate Similarity	NPC195873
0.8145	Intermediate Similarity	NPC81261
0.8145	Intermediate Similarity	NPC201419
0.8136	Intermediate Similarity	NPC190514
0.8125	Intermediate Similarity	NPC194034
0.8125	Intermediate Similarity	NPC327382
0.8125	Intermediate Similarity	NPC320439
0.8125	Intermediate Similarity	NPC474352
0.812	Intermediate Similarity	NPC150624
0.8115	Intermediate Similarity	NPC74478
0.811	Intermediate Similarity	NPC211352
0.8108	Intermediate Similarity	NPC47284
0.8099	Intermediate Similarity	NPC474864
0.8099	Intermediate Similarity	NPC194626
0.8095	Intermediate Similarity	NPC474246
0.8095	Intermediate Similarity	NPC474143
0.8087	Intermediate Similarity	NPC228452
0.8087	Intermediate Similarity	NPC165646
0.8083	Intermediate Similarity	NPC277798
0.8083	Intermediate Similarity	NPC100108
0.808	Intermediate Similarity	NPC210655
0.807	Intermediate Similarity	NPC141068
0.8067	Intermediate Similarity	NPC184302
0.8065	Intermediate Similarity	NPC216836
0.8056	Intermediate Similarity	NPC470161
0.8053	Intermediate Similarity	NPC201959
0.8051	Intermediate Similarity	NPC263754
0.8051	Intermediate Similarity	NPC183154
0.8047	Intermediate Similarity	NPC71372
0.8036	Intermediate Similarity	NPC469913
0.8034	Intermediate Similarity	NPC53906
0.8034	Intermediate Similarity	NPC232165
0.8034	Intermediate Similarity	NPC283169
0.8031	Intermediate Similarity	NPC289624
0.8031	Intermediate Similarity	NPC118253
0.8031	Intermediate Similarity	NPC27578
0.8016	Intermediate Similarity	NPC214860
0.8016	Intermediate Similarity	NPC325003
0.8016	Intermediate Similarity	NPC220935
0.8016	Intermediate Similarity	NPC7569
0.8016	Intermediate Similarity	NPC474481
0.8016	Intermediate Similarity	NPC229231
0.8	Intermediate Similarity	NPC476171
0.8	Intermediate Similarity	NPC63179
0.8	Intermediate Similarity	NPC38604
0.8	Intermediate Similarity	NPC40377
0.8	Intermediate Similarity	NPC474874
0.8	Intermediate Similarity	NPC55300
0.8	Intermediate Similarity	NPC130976
0.8	Intermediate Similarity	NPC211179
0.8	Intermediate Similarity	NPC193193
0.8	Intermediate Similarity	NPC12221
0.8	Intermediate Similarity	NPC31314
0.7969	Intermediate Similarity	NPC37196
0.7969	Intermediate Similarity	NPC269528
0.7969	Intermediate Similarity	NPC94236
0.7967	Intermediate Similarity	NPC159132
0.7966	Intermediate Similarity	NPC203113
0.7953	Intermediate Similarity	NPC472590
0.7953	Intermediate Similarity	NPC142530
0.7951	Intermediate Similarity	NPC246967
0.7951	Intermediate Similarity	NPC77789
0.7951	Intermediate Similarity	NPC150026
0.7951	Intermediate Similarity	NPC476332
0.7951	Intermediate Similarity	NPC473464
0.7951	Intermediate Similarity	NPC135414
0.7951	Intermediate Similarity	NPC18128
0.7951	Intermediate Similarity	NPC49441
0.7949	Intermediate Similarity	NPC276737
0.7949	Intermediate Similarity	NPC22610
0.7949	Intermediate Similarity	NPC114144
0.7949	Intermediate Similarity	NPC180508
0.7949	Intermediate Similarity	NPC228287
0.7946	Intermediate Similarity	NPC8302
0.7939	Intermediate Similarity	NPC19869
0.7937	Intermediate Similarity	NPC96719
0.7937	Intermediate Similarity	NPC472795
0.7937	Intermediate Similarity	NPC266868
0.7937	Intermediate Similarity	NPC134360
0.7937	Intermediate Similarity	NPC472796
0.7937	Intermediate Similarity	NPC45824
0.7937	Intermediate Similarity	NPC472797
0.7937	Intermediate Similarity	NPC16577
0.7937	Intermediate Similarity	NPC222108
0.7934	Intermediate Similarity	NPC307253
0.7934	Intermediate Similarity	NPC102639

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 NPC474920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	297
0.1-0.2	1098
0.2-0.3	1571
0.3-0.4	2697
0.4-0.5	1695
0.5-0.6	1124
0.6-0.7	548
0.7-0.8	109
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9537	High Similarity	NPD6671	Approved
0.8704	High Similarity	NPD968	Approved
0.839	Intermediate Similarity	NPD3496	Discontinued
0.8333	Intermediate Similarity	NPD1398	Phase 1
0.8276	Intermediate Similarity	NPD7340	Approved
0.8264	Intermediate Similarity	NPD6696	Suspended
0.8211	Intermediate Similarity	NPD2861	Phase 2
0.8182	Intermediate Similarity	NPD4749	Approved
0.8125	Intermediate Similarity	NPD290	Approved
0.8073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD4625	Phase 3
0.7895	Intermediate Similarity	NPD2684	Approved
0.787	Intermediate Similarity	NPD844	Approved
0.7851	Intermediate Similarity	NPD1778	Approved
0.7845	Intermediate Similarity	NPD228	Approved
0.7833	Intermediate Similarity	NPD1548	Phase 1
0.781	Intermediate Similarity	NPD9295	Approved
0.7805	Intermediate Similarity	NPD2232	Approved
0.7805	Intermediate Similarity	NPD2235	Phase 2
0.7805	Intermediate Similarity	NPD2233	Approved
0.7805	Intermediate Similarity	NPD2230	Approved
0.7805	Intermediate Similarity	NPD2231	Phase 2
0.7788	Intermediate Similarity	NPD9697	Approved
0.7742	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD422	Phase 1
0.7724	Intermediate Similarity	NPD1611	Approved
0.7698	Intermediate Similarity	NPD6584	Phase 3
0.7636	Intermediate Similarity	NPD288	Approved
0.7627	Intermediate Similarity	NPD7843	Approved
0.7627	Intermediate Similarity	NPD821	Approved
0.7627	Intermediate Similarity	NPD7635	Approved
0.7623	Intermediate Similarity	NPD5585	Approved
0.7619	Intermediate Similarity	NPD2797	Approved
0.7615	Intermediate Similarity	NPD2934	Approved
0.7615	Intermediate Similarity	NPD4060	Phase 1
0.7615	Intermediate Similarity	NPD2933	Approved
0.7583	Intermediate Similarity	NPD7157	Approved
0.7583	Intermediate Similarity	NPD709	Approved
0.7581	Intermediate Similarity	NPD1091	Approved
0.7581	Intermediate Similarity	NPD1535	Discovery
0.7581	Intermediate Similarity	NPD1610	Phase 2
0.7578	Intermediate Similarity	NPD4908	Phase 1
0.7578	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4626	Approved
0.7545	Intermediate Similarity	NPD2859	Approved
0.7545	Intermediate Similarity	NPD2860	Approved
0.752	Intermediate Similarity	NPD1481	Phase 2
0.75	Intermediate Similarity	NPD3020	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD5535	Approved
0.7462	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6583	Phase 3
0.746	Intermediate Similarity	NPD6582	Phase 2
0.7459	Intermediate Similarity	NPD7644	Approved
0.7442	Intermediate Similarity	NPD596	Approved
0.7442	Intermediate Similarity	NPD600	Approved
0.7438	Intermediate Similarity	NPD2557	Approved
0.7419	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5283	Phase 1
0.7402	Intermediate Similarity	NPD3225	Approved
0.7398	Intermediate Similarity	NPD1182	Approved
0.7385	Intermediate Similarity	NPD7095	Approved
0.7381	Intermediate Similarity	NPD1608	Approved
0.7373	Intermediate Similarity	NPD4750	Phase 3
0.7364	Intermediate Similarity	NPD1712	Approved
0.7364	Intermediate Similarity	NPD845	Approved
0.7364	Intermediate Similarity	NPD2237	Approved
0.7348	Intermediate Similarity	NPD1613	Approved
0.7348	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6382	Discontinued
0.7339	Intermediate Similarity	NPD5691	Approved
0.7339	Intermediate Similarity	NPD3444	Approved
0.7339	Intermediate Similarity	NPD3445	Approved
0.7339	Intermediate Similarity	NPD3443	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7328	Intermediate Similarity	NPD3268	Approved
0.7323	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4359	Approved
0.7297	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3691	Phase 2
0.7287	Intermediate Similarity	NPD3690	Phase 2
0.7287	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2667	Approved
0.728	Intermediate Similarity	NPD2668	Approved
0.728	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD840	Approved
0.7273	Intermediate Similarity	NPD839	Approved
0.7265	Intermediate Similarity	NPD3134	Approved
0.7264	Intermediate Similarity	NPD111	Approved
0.7258	Intermediate Similarity	NPD2486	Discontinued
0.7252	Intermediate Similarity	NPD3027	Phase 3
0.7244	Intermediate Similarity	NPD9717	Approved
0.7227	Intermediate Similarity	NPD3021	Approved
0.7227	Intermediate Similarity	NPD5451	Approved
0.7227	Intermediate Similarity	NPD3022	Approved
0.7218	Intermediate Similarity	NPD2238	Phase 2
0.7217	Intermediate Similarity	NPD846	Approved
0.7217	Intermediate Similarity	NPD940	Approved
0.7209	Intermediate Similarity	NPD1203	Approved
0.7206	Intermediate Similarity	NPD6032	Approved
0.72	Intermediate Similarity	NPD3049	Approved
0.72	Intermediate Similarity	NPD1357	Approved
0.7188	Intermediate Similarity	NPD5327	Phase 3
0.7182	Intermediate Similarity	NPD9365	Approved
0.7164	Intermediate Similarity	NPD447	Suspended
0.7154	Intermediate Similarity	NPD4624	Approved
0.7154	Intermediate Similarity	NPD558	Phase 2
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD7477	Discontinued
0.7143	Intermediate Similarity	NPD2554	Approved
0.7143	Intermediate Similarity	NPD5846	Approved
0.7143	Intermediate Similarity	NPD6516	Phase 2
0.7143	Intermediate Similarity	NPD2556	Approved
0.7133	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4308	Phase 3
0.7132	Intermediate Similarity	NPD8651	Approved
0.7132	Intermediate Similarity	NPD7033	Discontinued
0.7131	Intermediate Similarity	NPD1241	Discontinued
0.7131	Intermediate Similarity	NPD592	Approved
0.7131	Intermediate Similarity	NPD594	Approved
0.713	Intermediate Similarity	NPD1242	Phase 1
0.7122	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1894	Discontinued
0.7113	Intermediate Similarity	NPD6090	Discontinued
0.7111	Intermediate Similarity	NPD2157	Approved
0.7111	Intermediate Similarity	NPD6653	Approved
0.7111	Intermediate Similarity	NPD6353	Approved
0.7109	Intermediate Similarity	NPD1840	Phase 2
0.7099	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3596	Phase 2
0.709	Intermediate Similarity	NPD4140	Approved
0.709	Intermediate Similarity	NPD1558	Phase 1
0.7087	Intermediate Similarity	NPD3294	Phase 2
0.708	Intermediate Similarity	NPD1809	Phase 2
0.7077	Intermediate Similarity	NPD4098	Discontinued
0.7071	Intermediate Similarity	NPD3692	Discontinued
0.7068	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD2313	Discontinued
0.7068	Intermediate Similarity	NPD411	Approved
0.7068	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD2342	Discontinued
0.7059	Intermediate Similarity	NPD1358	Approved
0.7054	Intermediate Similarity	NPD3685	Discontinued
0.705	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1138	Approved
0.7042	Intermediate Similarity	NPD2505	Approved
0.7042	Intermediate Similarity	NPD2504	Approved
0.704	Intermediate Similarity	NPD5536	Phase 2
0.7037	Intermediate Similarity	NPD5735	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD5763	Approved
0.7029	Intermediate Similarity	NPD5762	Approved
0.7023	Intermediate Similarity	NPD2798	Approved
0.7016	Intermediate Similarity	NPD6387	Discontinued
0.7014	Intermediate Similarity	NPD1653	Approved
0.7007	Intermediate Similarity	NPD5929	Approved
0.7007	Intermediate Similarity	NPD2801	Approved
0.7007	Intermediate Similarity	NPD2156	Approved
0.7007	Intermediate Similarity	NPD2155	Approved
0.7007	Intermediate Similarity	NPD2154	Approved
0.7	Intermediate Similarity	NPD2922	Phase 1
0.6991	Remote Similarity	NPD9296	Approved
0.6985	Remote Similarity	NPD4097	Suspended
0.6984	Remote Similarity	NPD6580	Approved
0.6984	Remote Similarity	NPD6581	Approved
0.6978	Remote Similarity	NPD2424	Discontinued
0.6977	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1444	Approved
0.6975	Remote Similarity	NPD1445	Approved
0.697	Remote Similarity	NPD3018	Phase 2
0.697	Remote Similarity	NPD4993	Discontinued
0.6967	Remote Similarity	NPD1139	Approved
0.6967	Remote Similarity	NPD1137	Approved
0.6953	Remote Similarity	NPD3847	Discontinued
0.695	Remote Similarity	NPD2677	Approved
0.6947	Remote Similarity	NPD3266	Approved
0.6947	Remote Similarity	NPD1794	Approved
0.6947	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3267	Approved
0.6947	Remote Similarity	NPD987	Approved
0.6942	Remote Similarity	NPD1792	Phase 2
0.694	Remote Similarity	NPD1048	Approved
0.694	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7985	Registered
0.6934	Remote Similarity	NPD7097	Phase 1
0.6929	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1651	Approved
0.6923	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9088	Approved
0.6923	Remote Similarity	NPD1669	Approved
0.6923	Remote Similarity	NPD291	Approved
0.6917	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2614	Approved
0.6912	Remote Similarity	NPD5124	Phase 1
0.6912	Remote Similarity	NPD5123	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