NPASS Compound

Structure

CID326037 OpenBabel06191716182D 23 25 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 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 3.4641 0.0000 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 -2.5981 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 0.0000 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 3.4641 -1.0000 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 -1.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 22 1 0 0 0 0 2 3 2 0 0 0 0 2 7 1 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 19 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	302.699
LogP:	1.238
LogD:	1.866
LogS:	-3.712
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.663
Synthetic Accessibility Score:	3.257
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.687
MDCK Permeability:	4.908798473479692e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	95.0733413696289%
Volume Distribution (VD):	0.659
Pgp-substrate:	6.264951229095459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.359
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.355
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.465
CYP2D6-substrate:	0.417
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	10.458
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.389
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.553
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.486
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC326037

Natural Product ID:	NPC326037
*Common Name:**	Dihydroisorhamnetin
IUPAC Name:	3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	Dihydroisorhamnetin
Standard InCHIKey:	JWYULKXTGMJKKM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,15-19,21H,1H3
SMILES:	COc1cc(ccc1O)C1Oc2cc(O)cc(c2C(=O)C1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822704
PubChem CID:	56658060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

*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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	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
EC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		EC50	>	100.0	ug	PMID[529643]

☑ 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 NPC326037 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	399
0.1-0.2	1613
0.2-0.3	4261
0.3-0.4	10126
0.4-0.5	7781
0.5-0.6	3502
0.6-0.7	4700
0.7-0.8	5401
0.8-0.85	2699
0.85-0.9	1571
0.9-0.95	545
0.95-1	99

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC320825
1.0	High Similarity	NPC13858
0.9933	High Similarity	NPC52530
0.9866	High Similarity	NPC250922
0.9801	High Similarity	NPC282009
0.9801	High Similarity	NPC287328
0.9801	High Similarity	NPC263449
0.98	High Similarity	NPC471515
0.98	High Similarity	NPC471479
0.9797	High Similarity	NPC302950
0.9797	High Similarity	NPC9743
0.9797	High Similarity	NPC219582
0.9797	High Similarity	NPC236637
0.9797	High Similarity	NPC260491
0.9797	High Similarity	NPC240476
0.9797	High Similarity	NPC246162
0.9797	High Similarity	NPC61506
0.9797	High Similarity	NPC36835
0.9737	High Similarity	NPC471499
0.9737	High Similarity	NPC308992
0.9735	High Similarity	NPC22192
0.9733	High Similarity	NPC471500
0.9732	High Similarity	NPC256346
0.9732	High Similarity	NPC27532
0.9732	High Similarity	NPC18727
0.9732	High Similarity	NPC246328
0.9732	High Similarity	NPC325028
0.9671	High Similarity	NPC470326
0.9671	High Similarity	NPC470183
0.9669	High Similarity	NPC67876
0.9669	High Similarity	NPC474055
0.9669	High Similarity	NPC472598
0.9664	High Similarity	NPC19721
0.961	High Similarity	NPC472625
0.9608	High Similarity	NPC173137
0.9605	High Similarity	NPC55738
0.9603	High Similarity	NPC195796
0.9603	High Similarity	NPC291878
0.9603	High Similarity	NPC255106
0.9603	High Similarity	NPC278778
0.9603	High Similarity	NPC474638
0.9603	High Similarity	NPC235165
0.9603	High Similarity	NPC35038
0.9603	High Similarity	NPC201837
0.96	High Similarity	NPC141212
0.9597	High Similarity	NPC200740
0.9597	High Similarity	NPC125062
0.9597	High Similarity	NPC252933
0.9597	High Similarity	NPC54394
0.9548	High Similarity	NPC36916
0.9548	High Similarity	NPC7154
0.9548	High Similarity	NPC7688
0.9548	High Similarity	NPC36
0.9548	High Similarity	NPC72787
0.9548	High Similarity	NPC125039
0.9548	High Similarity	NPC58223
0.9542	High Similarity	NPC471744
0.9539	High Similarity	NPC27337
0.9539	High Similarity	NPC291508
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC210084
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC99597
0.9536	High Similarity	NPC321779
0.9536	High Similarity	NPC477503
0.9536	High Similarity	NPC470327
0.9536	High Similarity	NPC45849
0.9536	High Similarity	NPC200761
0.9533	High Similarity	NPC260979
0.9533	High Similarity	NPC55205
0.9533	High Similarity	NPC279989
0.9533	High Similarity	NPC472912
0.9533	High Similarity	NPC82325
0.953	High Similarity	NPC338131
0.9527	High Similarity	NPC218569
0.9527	High Similarity	NPC294852
0.9527	High Similarity	NPC188679
0.9527	High Similarity	NPC321011
0.9487	High Similarity	NPC471213
0.9481	High Similarity	NPC26326
0.9481	High Similarity	NPC474038
0.9481	High Similarity	NPC158188
0.9481	High Similarity	NPC289771
0.9481	High Similarity	NPC472632
0.9481	High Similarity	NPC472634
0.9481	High Similarity	NPC112418
0.9477	High Similarity	NPC152904
0.9474	High Similarity	NPC472626
0.9474	High Similarity	NPC470328
0.9474	High Similarity	NPC209614
0.947	High Similarity	NPC192083
0.947	High Similarity	NPC213896
0.947	High Similarity	NPC78326
0.947	High Similarity	NPC469550
0.947	High Similarity	NPC236223
0.947	High Similarity	NPC270620
0.947	High Similarity	NPC179126
0.9467	High Similarity	NPC28274
0.9467	High Similarity	NPC50403
0.9467	High Similarity	NPC133953
0.9467	High Similarity	NPC31363
0.9463	High Similarity	NPC52005
0.9463	High Similarity	NPC183950
0.9463	High Similarity	NPC183959
0.9463	High Similarity	NPC87125
0.9463	High Similarity	NPC270465
0.9463	High Similarity	NPC137062
0.9463	High Similarity	NPC159103
0.9463	High Similarity	NPC1612
0.9463	High Similarity	NPC223579
0.9463	High Similarity	NPC287101
0.9459	High Similarity	NPC176869
0.9459	High Similarity	NPC21835
0.9459	High Similarity	NPC3779
0.9459	High Similarity	NPC122828
0.9459	High Similarity	NPC211466
0.9459	High Similarity	NPC476182
0.9459	High Similarity	NPC40086
0.9459	High Similarity	NPC44721
0.9423	High Similarity	NPC224280
0.9423	High Similarity	NPC475888
0.9423	High Similarity	NPC62261
0.9419	High Similarity	NPC472964
0.9419	High Similarity	NPC211107
0.9419	High Similarity	NPC474033
0.9419	High Similarity	NPC474034
0.9419	High Similarity	NPC471745
0.9419	High Similarity	NPC476247
0.9419	High Similarity	NPC472635
0.9416	High Similarity	NPC472631
0.9416	High Similarity	NPC36217
0.9416	High Similarity	NPC475784
0.9416	High Similarity	NPC192686
0.9416	High Similarity	NPC119209
0.9416	High Similarity	NPC472630
0.9416	High Similarity	NPC472902
0.9416	High Similarity	NPC472624
0.9416	High Similarity	NPC118256
0.9416	High Similarity	NPC174953
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC129684
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC299520
0.9412	High Similarity	NPC223787
0.9412	High Similarity	NPC472911
0.9412	High Similarity	NPC245758
0.9412	High Similarity	NPC470402
0.9408	High Similarity	NPC201451
0.9408	High Similarity	NPC67396
0.9408	High Similarity	NPC44079
0.9408	High Similarity	NPC226025
0.9408	High Similarity	NPC26227
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC2928
0.9404	High Similarity	NPC199100
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC180234
0.9404	High Similarity	NPC477231
0.9404	High Similarity	NPC120537
0.9404	High Similarity	NPC106976
0.9404	High Similarity	NPC123886
0.94	High Similarity	NPC286342
0.94	High Similarity	NPC29231
0.94	High Similarity	NPC166753
0.94	High Similarity	NPC188871
0.94	High Similarity	NPC149127
0.94	High Similarity	NPC50728
0.9396	High Similarity	NPC120464
0.9396	High Similarity	NPC3036
0.9396	High Similarity	NPC119059
0.9363	High Similarity	NPC477517
0.9359	High Similarity	NPC124038
0.9359	High Similarity	NPC474240
0.9355	High Similarity	NPC471210
0.9355	High Similarity	NPC66618
0.9355	High Similarity	NPC113163
0.9355	High Similarity	NPC165970
0.9355	High Similarity	NPC84324
0.9355	High Similarity	NPC288131
0.9355	High Similarity	NPC305987
0.9355	High Similarity	NPC142252
0.9351	High Similarity	NPC53545
0.9351	High Similarity	NPC172202
0.9351	High Similarity	NPC284127
0.9351	High Similarity	NPC476410
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9351	High Similarity	NPC473990
0.9351	High Similarity	NPC117418
0.9346	High Similarity	NPC303255
0.9346	High Similarity	NPC43243
0.9346	High Similarity	NPC472916
0.9346	High Similarity	NPC266960

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 NPC326037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	928
0.2-0.3	1804
0.3-0.4	2606
0.4-0.5	1784
0.5-0.6	971
0.6-0.7	502
0.7-0.8	136
0.8-0.85	35
0.85-0.9	14
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9797	High Similarity	NPD1934	Approved
0.9548	High Similarity	NPD6167	Clinical (unspecified phase)
0.9548	High Similarity	NPD6168	Clinical (unspecified phase)
0.9548	High Similarity	NPD6166	Phase 2
0.947	High Similarity	NPD2393	Clinical (unspecified phase)
0.9262	High Similarity	NPD1512	Approved
0.9221	High Similarity	NPD3882	Suspended
0.9216	High Similarity	NPD2801	Approved
0.9128	High Similarity	NPD1511	Approved
0.9068	High Similarity	NPD7074	Phase 3
0.9032	High Similarity	NPD3817	Phase 2
0.9012	High Similarity	NPD6797	Phase 2
0.9006	High Similarity	NPD7054	Approved
0.8957	High Similarity	NPD7251	Discontinued
0.8951	High Similarity	NPD7472	Approved
0.8944	High Similarity	NPD3818	Discontinued
0.8902	High Similarity	NPD4338	Clinical (unspecified phase)
0.8902	High Similarity	NPD7808	Phase 3
0.8851	High Similarity	NPD1550	Clinical (unspecified phase)
0.8851	High Similarity	NPD1552	Clinical (unspecified phase)
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD7075	Discontinued
0.8792	High Similarity	NPD1549	Phase 2
0.8774	High Similarity	NPD4380	Phase 2
0.8734	High Similarity	NPD4868	Clinical (unspecified phase)
0.8726	High Similarity	NPD7096	Clinical (unspecified phase)
0.8679	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD5494	Approved
0.8554	High Similarity	NPD7993	Clinical (unspecified phase)
0.8545	High Similarity	NPD7804	Clinical (unspecified phase)
0.8544	High Similarity	NPD6801	Discontinued
0.8506	High Similarity	NPD6799	Approved
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8446	Intermediate Similarity	NPD1613	Approved
0.8446	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5402	Approved
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8322	Intermediate Similarity	NPD1240	Approved
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8228	Intermediate Similarity	NPD5403	Approved
0.8217	Intermediate Similarity	NPD5401	Approved
0.8212	Intermediate Similarity	NPD1607	Approved
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD6959	Discontinued
0.8182	Intermediate Similarity	NPD1247	Approved
0.8176	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8171	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8121	Intermediate Similarity	NPD3027	Phase 3
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7871	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7848	Intermediate Similarity	NPD4628	Phase 3
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7811	Intermediate Similarity	NPD3787	Discontinued
0.7799	Intermediate Similarity	NPD6190	Approved
0.7792	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD2800	Approved
0.7784	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.773	Intermediate Similarity	NPD1653	Approved
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2935	Discontinued
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.7632	Intermediate Similarity	NPD9494	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD3748	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7467	Intermediate Similarity	NPD1610	Phase 2
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7453	Intermediate Similarity	NPD1243	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7033	Discontinued
0.7405	Intermediate Similarity	NPD6651	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7391	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4363	Phase 3
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7362	Intermediate Similarity	NPD2309	Approved
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7390	Discontinued
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7251	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.724	Intermediate Similarity	NPD7584	Approved
0.7239	Intermediate Similarity	NPD1652	Phase 2
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7232	Intermediate Similarity	NPD2163	Approved
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7216	Intermediate Similarity	NPD2403	Approved
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.719	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7178	Intermediate Similarity	NPD2424	Discontinued
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4662	Approved
0.7126	Intermediate Similarity	NPD4661	Approved
0.7125	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5124	Phase 1
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7074	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4361	Phase 2
0.7072	Intermediate Similarity	NPD7038	Approved
0.7072	Intermediate Similarity	NPD7240	Approved
0.7072	Intermediate Similarity	NPD7039	Approved
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7068	Intermediate Similarity	NPD2493	Approved
0.7068	Intermediate Similarity	NPD2494	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued

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