NPASS Compound

Structure

NPC472912 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 14 1 0 0 0 0 4 9 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 10 4 1 1 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	2.539
LogD:	2.775
LogS:	-3.811
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.01
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.824
MDCK Permeability:	9.864299499895424e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.807
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	97.96324920654297%
Volume Distribution (VD):	0.475
Pgp-substrate:	2.429558515548706%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.718
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.809
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	14.806
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.643
AMES Toxicity:	0.457
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.501
Skin Sensitization:	0.916
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.906
Respiratory Toxicity:	0.191

Download Data

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

Natural Product: NPC472912

Natural Product ID:	NPC472912
*Common Name:**	5,7-Dihydroxy-3-(3'-Hydroxy-4'-Methoxybenzyl)-4-Chromanone
IUPAC Name:	(3R)-5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	WIBOONWRYQFYQJ-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-22-14-3-2-9(5-12(14)19)4-10-8-23-15-7-11(18)6-13(20)16(15)17(10)21/h2-3,5-7,10,18-20H,4,8H2,1H3/t10-/m1/s1
SMILES:	COc1ccc(cc1O)C[C@@H]1COc2c(C1=O)c(O)cc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594087
PubChem CID:	638295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans [CHEMONTID:0002898] Homoisoflavanones

*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
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]

☑ 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
ED50	2
IC50	2
MIC	5

Activity Type	# Activity
Cell Line	4
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.33	uM	PMID[510187]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	ED50	=	2.78	uM	PMID[510187]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[510187]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	1000.0	nM	PMID[510187]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	138.0	ug.mL-1	PMID[510187]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	17.0	ug.mL-1	PMID[510187]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	138.0	ug.mL-1	PMID[510187]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	138.0	ug.mL-1	PMID[510187]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	138.0	ug.mL-1	PMID[510187]

☑ 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 NPC472912 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	391
0.1-0.2	1596
0.2-0.3	4224
0.3-0.4	10588
0.4-0.5	7379
0.5-0.6	3322
0.6-0.7	4757
0.7-0.8	5543
0.8-0.85	2678
0.85-0.9	1640
0.9-0.95	484
0.95-1	95

Similarity Score	Similarity Level	Natural Product ID
0.9863	High Similarity	NPC260979
0.9796	High Similarity	NPC18727
0.9796	High Similarity	NPC469550
0.9732	High Similarity	NPC472910
0.9732	High Similarity	NPC472913
0.9732	High Similarity	NPC472914
0.9732	High Similarity	NPC129684
0.9732	High Similarity	NPC222814
0.9732	High Similarity	NPC245758
0.9732	High Similarity	NPC96167
0.9732	High Similarity	NPC472911
0.9732	High Similarity	NPC299520
0.9728	High Similarity	NPC257648
0.9728	High Similarity	NPC477231
0.9728	High Similarity	NPC302950
0.9728	High Similarity	NPC219582
0.9728	High Similarity	NPC236637
0.9724	High Similarity	NPC3036
0.9664	High Similarity	NPC195796
0.9664	High Similarity	NPC291878
0.9664	High Similarity	NPC278778
0.9664	High Similarity	NPC35038
0.966	High Similarity	NPC31363
0.9658	High Similarity	NPC105512
0.96	High Similarity	NPC472598
0.96	High Similarity	NPC291508
0.96	High Similarity	NPC474055
0.96	High Similarity	NPC156057
0.96	High Similarity	NPC48208
0.96	High Similarity	NPC471515
0.96	High Similarity	NPC469584
0.96	High Similarity	NPC475267
0.96	High Similarity	NPC67876
0.96	High Similarity	NPC27337
0.96	High Similarity	NPC162869
0.96	High Similarity	NPC471479
0.96	High Similarity	NPC474208
0.96	High Similarity	NPC474836
0.9597	High Similarity	NPC477503
0.9597	High Similarity	NPC230149
0.9597	High Similarity	NPC168247
0.9597	High Similarity	NPC472909
0.9597	High Similarity	NPC255807
0.9597	High Similarity	NPC117992
0.9597	High Similarity	NPC470327
0.9597	High Similarity	NPC152951
0.9597	High Similarity	NPC45849
0.9597	High Similarity	NPC200761
0.9597	High Similarity	NPC57674
0.9597	High Similarity	NPC31018
0.9592	High Similarity	NPC338131
0.9592	High Similarity	NPC29231
0.9539	High Similarity	NPC266314
0.9533	High Similarity	NPC209614
0.9533	High Similarity	NPC326037
0.9533	High Similarity	NPC470328
0.9533	High Similarity	NPC472626
0.9533	High Similarity	NPC472916
0.9533	High Similarity	NPC13858
0.9533	High Similarity	NPC255106
0.9533	High Similarity	NPC235165
0.9533	High Similarity	NPC320825
0.9533	High Similarity	NPC471500
0.953	High Similarity	NPC273462
0.953	High Similarity	NPC49402
0.953	High Similarity	NPC227337
0.953	High Similarity	NPC192083
0.953	High Similarity	NPC70433
0.953	High Similarity	NPC213896
0.953	High Similarity	NPC33051
0.9524	High Similarity	NPC177298
0.9524	High Similarity	NPC223579
0.9524	High Similarity	NPC183950
0.9524	High Similarity	NPC48479
0.9524	High Similarity	NPC137062
0.9524	High Similarity	NPC52005
0.9524	High Similarity	NPC287101
0.9521	High Similarity	NPC95864
0.9477	High Similarity	NPC474162
0.9477	High Similarity	NPC474150
0.9474	High Similarity	NPC472624
0.9474	High Similarity	NPC474960
0.9474	High Similarity	NPC282009
0.9474	High Similarity	NPC36217
0.9474	High Similarity	NPC192686
0.9474	High Similarity	NPC119209
0.9474	High Similarity	NPC287328
0.9474	High Similarity	NPC118256
0.947	High Similarity	NPC210084
0.947	High Similarity	NPC52889
0.947	High Similarity	NPC78225
0.947	High Similarity	NPC52530
0.947	High Similarity	NPC181960
0.947	High Similarity	NPC472963
0.947	High Similarity	NPC108456
0.947	High Similarity	NPC99597
0.947	High Similarity	NPC223787
0.9467	High Similarity	NPC213622
0.9467	High Similarity	NPC37392
0.9467	High Similarity	NPC256925
0.9467	High Similarity	NPC226025
0.9467	High Similarity	NPC67396
0.9467	High Similarity	NPC2928
0.9467	High Similarity	NPC234255
0.9467	High Similarity	NPC321779
0.9463	High Similarity	NPC39732
0.9463	High Similarity	NPC199100
0.9463	High Similarity	NPC180234
0.9463	High Similarity	NPC60972
0.9463	High Similarity	NPC471982
0.9463	High Similarity	NPC120537
0.9463	High Similarity	NPC106976
0.9456	High Similarity	NPC321011
0.9456	High Similarity	NPC120464
0.9456	High Similarity	NPC196277
0.9456	High Similarity	NPC203747
0.9456	High Similarity	NPC188679
0.9456	High Similarity	NPC80710
0.9456	High Similarity	NPC43669
0.9456	High Similarity	NPC294852
0.9456	High Similarity	NPC272721
0.9456	High Similarity	NPC139364
0.9456	High Similarity	NPC195202
0.9456	High Similarity	NPC254702
0.9456	High Similarity	NPC194653
0.9412	High Similarity	NPC474038
0.9412	High Similarity	NPC472634
0.9412	High Similarity	NPC471499
0.9412	High Similarity	NPC472632
0.9412	High Similarity	NPC471210
0.9412	High Similarity	NPC26326
0.9412	High Similarity	NPC158188
0.9408	High Similarity	NPC184755
0.9408	High Similarity	NPC250214
0.9408	High Similarity	NPC74178
0.9408	High Similarity	NPC55738
0.9408	High Similarity	NPC204879
0.9408	High Similarity	NPC152904
0.9408	High Similarity	NPC95936
0.9408	High Similarity	NPC22192
0.9404	High Similarity	NPC474638
0.9404	High Similarity	NPC68093
0.9404	High Similarity	NPC24640
0.9404	High Similarity	NPC472455
0.9404	High Similarity	NPC472907
0.9404	High Similarity	NPC250922
0.9404	High Similarity	NPC191146
0.94	High Similarity	NPC292214
0.94	High Similarity	NPC167091
0.94	High Similarity	NPC298692
0.94	High Similarity	NPC255350
0.94	High Similarity	NPC472905
0.94	High Similarity	NPC271779
0.94	High Similarity	NPC472915
0.94	High Similarity	NPC160951
0.94	High Similarity	NPC231018
0.94	High Similarity	NPC274327
0.94	High Similarity	NPC270620
0.94	High Similarity	NPC183878
0.94	High Similarity	NPC88645
0.94	High Similarity	NPC47781
0.94	High Similarity	NPC176775
0.94	High Similarity	NPC69394
0.94	High Similarity	NPC74924
0.94	High Similarity	NPC145379
0.94	High Similarity	NPC78326
0.94	High Similarity	NPC236223
0.94	High Similarity	NPC179126
0.94	High Similarity	NPC141212
0.94	High Similarity	NPC206238
0.94	High Similarity	NPC22519
0.9396	High Similarity	NPC125062
0.9396	High Similarity	NPC252933
0.9396	High Similarity	NPC54394
0.9396	High Similarity	NPC256406
0.9396	High Similarity	NPC117579
0.9396	High Similarity	NPC200740
0.9392	High Similarity	NPC139293
0.9392	High Similarity	NPC69430
0.9392	High Similarity	NPC183959
0.9392	High Similarity	NPC333691
0.9392	High Similarity	NPC264550
0.9392	High Similarity	NPC1612
0.9392	High Similarity	NPC200060
0.9392	High Similarity	NPC40290
0.9392	High Similarity	NPC142876
0.9392	High Similarity	NPC264289
0.9392	High Similarity	NPC195763
0.9388	High Similarity	NPC62536
0.9388	High Similarity	NPC470511
0.9388	High Similarity	NPC33265
0.9388	High Similarity	NPC77378
0.9388	High Similarity	NPC12200
0.9388	High Similarity	NPC108406
0.9351	High Similarity	NPC472635
0.9351	High Similarity	NPC476247
0.9351	High Similarity	NPC474034
0.9351	High Similarity	NPC474033
0.9351	High Similarity	NPC201800
0.9351	High Similarity	NPC472964

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 NPC472912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	938
0.2-0.3	1703
0.3-0.4	2639
0.4-0.5	1740
0.5-0.6	1030
0.6-0.7	542
0.7-0.8	134
0.8-0.85	37
0.85-0.9	17
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9728	High Similarity	NPD1934	Approved
0.953	High Similarity	NPD2393	Clinical (unspecified phase)
0.94	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD3882	Suspended
0.9231	High Similarity	NPD6166	Phase 2
0.9231	High Similarity	NPD6167	Clinical (unspecified phase)
0.9231	High Similarity	NPD6168	Clinical (unspecified phase)
0.9184	High Similarity	NPD1511	Approved
0.906	High Similarity	NPD1512	Approved
0.9	High Similarity	NPD7074	Phase 3
0.8961	High Similarity	NPD3817	Phase 2
0.8938	High Similarity	NPD7054	Approved
0.8904	High Similarity	NPD1550	Clinical (unspecified phase)
0.8904	High Similarity	NPD1552	Clinical (unspecified phase)
0.8882	High Similarity	NPD7472	Approved
0.8875	High Similarity	NPD3818	Discontinued
0.8844	High Similarity	NPD1549	Phase 2
0.8782	High Similarity	NPD4868	Clinical (unspecified phase)
0.8742	High Similarity	NPD4378	Clinical (unspecified phase)
0.8734	High Similarity	NPD5494	Approved
0.8726	High Similarity	NPD7075	Discontinued
0.8712	High Similarity	NPD6797	Phase 2
0.8701	High Similarity	NPD4380	Phase 2
0.8659	High Similarity	NPD7251	Discontinued
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.8639	High Similarity	NPD1510	Phase 2
0.8608	High Similarity	NPD4381	Clinical (unspecified phase)
0.8606	High Similarity	NPD4338	Clinical (unspecified phase)
0.8606	High Similarity	NPD7808	Phase 3
0.8599	High Similarity	NPD8443	Clinical (unspecified phase)
0.8581	High Similarity	NPD2796	Approved
0.8553	High Similarity	NPD6799	Approved
0.8535	High Similarity	NPD7819	Suspended
0.8493	Intermediate Similarity	NPD1240	Approved
0.8466	Intermediate Similarity	NPD7473	Discontinued
0.8408	Intermediate Similarity	NPD7411	Suspended
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8378	Intermediate Similarity	NPD1607	Approved
0.8377	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD943	Approved
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8302	Intermediate Similarity	NPD1465	Phase 2
0.8263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.8224	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD3926	Phase 2
0.8107	Intermediate Similarity	NPD6559	Discontinued
0.8098	Intermediate Similarity	NPD919	Approved
0.8072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3027	Phase 3
0.8038	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5403	Approved
0.8025	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD6100	Approved
0.7974	Intermediate Similarity	NPD6099	Approved
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD5401	Approved
0.7904	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7852	Intermediate Similarity	NPD4908	Phase 1
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD447	Suspended
0.7829	Intermediate Similarity	NPD1933	Approved
0.7821	Intermediate Similarity	NPD2800	Approved
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.779	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD9494	Approved
0.7778	Intermediate Similarity	NPD6651	Approved
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1610	Phase 2
0.7692	Intermediate Similarity	NPD2344	Approved
0.7677	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3748	Approved
0.7677	Intermediate Similarity	NPD2799	Discontinued
0.7658	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1653	Approved
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1243	Approved
0.7593	Intermediate Similarity	NPD920	Approved
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD37	Approved
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7228	Approved
0.7558	Intermediate Similarity	NPD3751	Discontinued
0.7545	Intermediate Similarity	NPD4965	Approved
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7533	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD3787	Discontinued
0.7516	Intermediate Similarity	NPD3268	Approved
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7483	Intermediate Similarity	NPD2798	Approved
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD7033	Discontinued
0.745	Intermediate Similarity	NPD1608	Approved
0.7418	Intermediate Similarity	NPD4363	Phase 3
0.7418	Intermediate Similarity	NPD4360	Phase 2
0.7417	Intermediate Similarity	NPD2797	Approved
0.7407	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6798	Discontinued
0.7401	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.74	Intermediate Similarity	NPD4749	Approved
0.7384	Intermediate Similarity	NPD5242	Approved
0.7381	Intermediate Similarity	NPD5353	Approved
0.7372	Intermediate Similarity	NPD6355	Discontinued
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7337	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9717	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.7326	Intermediate Similarity	NPD5711	Approved
0.732	Intermediate Similarity	NPD2861	Phase 2
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7308	Intermediate Similarity	NPD4060	Phase 1
0.7305	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4361	Phase 2
0.7283	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5536	Phase 2
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7267	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5124	Phase 1
0.7248	Intermediate Similarity	NPD17	Approved
0.7241	Intermediate Similarity	NPD2403	Approved
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD9269	Phase 2
0.7202	Intermediate Similarity	NPD6385	Approved
0.7202	Intermediate Similarity	NPD6386	Approved
0.7195	Intermediate Similarity	NPD4357	Discontinued
0.719	Intermediate Similarity	NPD3267	Approved
0.719	Intermediate Similarity	NPD3266	Approved
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7179	Intermediate Similarity	NPD411	Approved
0.7173	Intermediate Similarity	NPD7584	Approved
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD4661	Approved
0.7152	Intermediate Similarity	NPD4662	Approved
0.7151	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7124	Intermediate Similarity	NPD3225	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD8166	Discontinued
0.7114	Intermediate Similarity	NPD9545	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