NPASS Compound

Structure

NPC250922 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 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 -2.5981 -0.5000 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 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 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 -3.4641 -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 0.8660 -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 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 3.4641 0.0000 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 -2.5981 2.5000 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 -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 -4.3301 1.5000 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 23 1 0 0 0 0 2 6 2 0 0 0 0 2 9 1 0 0 0 0 3 6 1 0 0 0 0 3 10 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 11 2 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 16 2 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 6 1 1 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.07
Volume:	311.489
LogP:	0.932
LogD:	1.493
LogS:	-3.603
# Rotatable Bonds:	2
TPSA:	136.68
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	3.54
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:	-6.081
MDCK Permeability:	4.770994110003812e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.095
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	93.41480255126953%
Volume Distribution (VD):	0.647
Pgp-substrate:	7.567239761352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.346
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.253
CYP2C9-substrate:	0.71
CYP2D6-inhibitor:	0.255
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.157

ADMET: Excretion

Clearance (CL):	9.594
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.415
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.891
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.77
Respiratory Toxicity:	0.107

Download Data

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

Natural Product: NPC250922

Natural Product ID:	NPC250922
*Common Name:**	(2R,3S)-4'-O-Methyl-2,3-Dihydromyricetin
IUPAC Name:	(2R,3S)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	NKPORGOKKIBGPG-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C16H14O8/c1-23-16-9(19)2-6(3-10(16)20)15-14(22)13(21)12-8(18)4-7(17)5-11(12)24-15/h2-5,14-15,17-20,22H,1H3/t14-,15-/m1/s1
SMILES:	COc1c(O)cc(cc1O)[C@H]1Oc2cc(O)cc(c2C(=O)[C@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484429
PubChem CID:	11244528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols [CHEMONTID:0001584] Catechins [CHEMONTID:0001594] Epigallocatechins

*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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	279.4	pg/ml	PMID[558386]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	470.4	pg/ml	PMID[558386]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[558386]

☑ 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 NPC250922 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	401
0.1-0.2	1655
0.2-0.3	4321
0.3-0.4	9965
0.4-0.5	7987
0.5-0.6	3614
0.6-0.7	4669
0.7-0.8	5344
0.8-0.85	2692
0.85-0.9	1590
0.9-0.95	391
0.95-1	68

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC326037
0.9866	High Similarity	NPC13858
0.9866	High Similarity	NPC320825
0.9801	High Similarity	NPC470326
0.98	High Similarity	NPC52530
0.9797	High Similarity	NPC19721
0.9737	High Similarity	NPC471499
0.9671	High Similarity	NPC282009
0.9671	High Similarity	NPC287328
0.9671	High Similarity	NPC263449
0.9669	High Similarity	NPC471515
0.9669	High Similarity	NPC471479
0.9664	High Similarity	NPC219582
0.9664	High Similarity	NPC36835
0.9664	High Similarity	NPC240476
0.9664	High Similarity	NPC246162
0.9664	High Similarity	NPC260491
0.9664	High Similarity	NPC302950
0.9664	High Similarity	NPC236637
0.9664	High Similarity	NPC9743
0.9664	High Similarity	NPC61506
0.9608	High Similarity	NPC308992
0.9605	High Similarity	NPC22192
0.9603	High Similarity	NPC471500
0.96	High Similarity	NPC27532
0.96	High Similarity	NPC18727
0.96	High Similarity	NPC256346
0.96	High Similarity	NPC325028
0.96	High Similarity	NPC246328
0.9597	High Similarity	NPC28274
0.9597	High Similarity	NPC50403
0.9597	High Similarity	NPC133953
0.9548	High Similarity	NPC72787
0.9548	High Similarity	NPC36916
0.9548	High Similarity	NPC7154
0.9548	High Similarity	NPC36
0.9548	High Similarity	NPC125039
0.9548	High Similarity	NPC7688
0.9548	High Similarity	NPC58223
0.9542	High Similarity	NPC472630
0.9542	High Similarity	NPC470183
0.9542	High Similarity	NPC472631
0.9542	High Similarity	NPC471744
0.9539	High Similarity	NPC474055
0.9539	High Similarity	NPC472598
0.9539	High Similarity	NPC67876
0.9536	High Similarity	NPC477503
0.9536	High Similarity	NPC470327
0.9536	High Similarity	NPC45849
0.9536	High Similarity	NPC200761
0.9533	High Similarity	NPC123886
0.953	High Similarity	NPC338131
0.9487	High Similarity	NPC471213
0.9484	High Similarity	NPC472625
0.9481	High Similarity	NPC472634
0.9481	High Similarity	NPC26326
0.9481	High Similarity	NPC158188
0.9481	High Similarity	NPC289771
0.9481	High Similarity	NPC173137
0.9481	High Similarity	NPC112418
0.9477	High Similarity	NPC55738
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC278778
0.9474	High Similarity	NPC472626
0.9474	High Similarity	NPC195796
0.9474	High Similarity	NPC474638
0.9474	High Similarity	NPC255106
0.9474	High Similarity	NPC470328
0.9474	High Similarity	NPC291878
0.9474	High Similarity	NPC35038
0.9474	High Similarity	NPC201837
0.9474	High Similarity	NPC209614
0.947	High Similarity	NPC141212
0.947	High Similarity	NPC58382
0.947	High Similarity	NPC162351
0.9467	High Similarity	NPC125062
0.9467	High Similarity	NPC252933
0.9467	High Similarity	NPC54394
0.9467	High Similarity	NPC200740
0.9459	High Similarity	NPC21835
0.9423	High Similarity	NPC470457
0.9423	High Similarity	NPC475888
0.9419	High Similarity	NPC211107
0.9419	High Similarity	NPC472635
0.9419	High Similarity	NPC471745
0.9416	High Similarity	NPC101731
0.9416	High Similarity	NPC174953
0.9412	High Similarity	NPC48208
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC474208
0.9412	High Similarity	NPC156057
0.9412	High Similarity	NPC223787
0.9412	High Similarity	NPC162869
0.9412	High Similarity	NPC474836
0.9412	High Similarity	NPC27337
0.9412	High Similarity	NPC475267
0.9412	High Similarity	NPC210084
0.9408	High Similarity	NPC321779
0.9404	High Similarity	NPC472912
0.9404	High Similarity	NPC106976
0.9404	High Similarity	NPC279989
0.9404	High Similarity	NPC260979
0.9404	High Similarity	NPC55205
0.9404	High Similarity	NPC82325
0.94	High Similarity	NPC219330
0.9396	High Similarity	NPC294852
0.9396	High Similarity	NPC120464
0.9396	High Similarity	NPC321011
0.9396	High Similarity	NPC218569
0.9396	High Similarity	NPC188679
0.9359	High Similarity	NPC474240
0.9359	High Similarity	NPC41301
0.9359	High Similarity	NPC470459
0.9355	High Similarity	NPC66618
0.9355	High Similarity	NPC113163
0.9355	High Similarity	NPC472632
0.9355	High Similarity	NPC471212
0.9355	High Similarity	NPC165970
0.9355	High Similarity	NPC84324
0.9355	High Similarity	NPC288131
0.9355	High Similarity	NPC142252
0.9355	High Similarity	NPC305987
0.9355	High Similarity	NPC471211
0.9355	High Similarity	NPC474038
0.9351	High Similarity	NPC53545
0.9351	High Similarity	NPC172202
0.9351	High Similarity	NPC284127
0.9351	High Similarity	NPC476410
0.9351	High Similarity	NPC473990
0.9351	High Similarity	NPC152904
0.9351	High Similarity	NPC117418
0.9346	High Similarity	NPC474520
0.9346	High Similarity	NPC200388
0.9346	High Similarity	NPC98661
0.9346	High Similarity	NPC247017
0.9346	High Similarity	NPC55619
0.9346	High Similarity	NPC100916
0.9342	High Similarity	NPC78326
0.9342	High Similarity	NPC74924
0.9342	High Similarity	NPC469550
0.9342	High Similarity	NPC298692
0.9342	High Similarity	NPC270620
0.9342	High Similarity	NPC236223
0.9342	High Similarity	NPC213896
0.9342	High Similarity	NPC192083
0.9342	High Similarity	NPC179126
0.9338	High Similarity	NPC31363
0.9338	High Similarity	NPC76376
0.9333	High Similarity	NPC48479
0.9333	High Similarity	NPC270465
0.9333	High Similarity	NPC159103
0.9333	High Similarity	NPC183950
0.9333	High Similarity	NPC177298
0.9333	High Similarity	NPC87125
0.9333	High Similarity	NPC183959
0.9333	High Similarity	NPC1612
0.9333	High Similarity	NPC52005
0.9333	High Similarity	NPC287101
0.9333	High Similarity	NPC137062
0.9333	High Similarity	NPC223579
0.9329	High Similarity	NPC44721
0.9329	High Similarity	NPC211466
0.9329	High Similarity	NPC40086
0.9329	High Similarity	NPC122828
0.9329	High Similarity	NPC176869
0.9329	High Similarity	NPC3779
0.9329	High Similarity	NPC476182
0.9308	High Similarity	NPC102277
0.9308	High Similarity	NPC279209
0.9304	High Similarity	NPC325555
0.9304	High Similarity	NPC295082
0.9304	High Similarity	NPC265530
0.9304	High Similarity	NPC470456
0.9304	High Similarity	NPC158761
0.9304	High Similarity	NPC226304
0.9299	High Similarity	NPC62261
0.9299	High Similarity	NPC224280
0.9295	High Similarity	NPC300537
0.9295	High Similarity	NPC476247
0.9295	High Similarity	NPC472964
0.9295	High Similarity	NPC474034
0.9295	High Similarity	NPC127782
0.9295	High Similarity	NPC474033
0.929	High Similarity	NPC472902
0.929	High Similarity	NPC118256
0.929	High Similarity	NPC36217
0.929	High Similarity	NPC119209
0.929	High Similarity	NPC472624
0.929	High Similarity	NPC475784
0.929	High Similarity	NPC192686
0.9286	High Similarity	NPC129684
0.9286	High Similarity	NPC96167
0.9286	High Similarity	NPC78302
0.9286	High Similarity	NPC472913
0.9286	High Similarity	NPC305663
0.9286	High Similarity	NPC176665
0.9286	High Similarity	NPC224137
0.9286	High Similarity	NPC235215
0.9286	High Similarity	NPC93376

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 NPC250922 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	1910
0.3-0.4	2589
0.4-0.5	1756
0.5-0.6	960
0.6-0.7	454
0.7-0.8	125
0.8-0.85	32
0.85-0.9	15
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9664	High Similarity	NPD1934	Approved
0.9548	High Similarity	NPD6166	Phase 2
0.9548	High Similarity	NPD6167	Clinical (unspecified phase)
0.9548	High Similarity	NPD6168	Clinical (unspecified phase)
0.9342	High Similarity	NPD2393	Clinical (unspecified phase)
0.9133	High Similarity	NPD1512	Approved
0.9097	High Similarity	NPD3882	Suspended
0.9091	High Similarity	NPD2801	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
0.9	High Similarity	NPD1511	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
0.8854	High Similarity	NPD4868	Clinical (unspecified phase)
0.8797	High Similarity	NPD7075	Discontinued
0.8774	High Similarity	NPD4380	Phase 2
0.8725	High Similarity	NPD1552	Clinical (unspecified phase)
0.8725	High Similarity	NPD1550	Clinical (unspecified phase)
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8679	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD7993	Clinical (unspecified phase)
0.8667	High Similarity	NPD1549	Phase 2
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8545	High Similarity	NPD7804	Clinical (unspecified phase)
0.8544	High Similarity	NPD6801	Discontinued
0.8457	Intermediate Similarity	NPD5494	Approved
0.8387	Intermediate Similarity	NPD6799	Approved
0.8375	Intermediate Similarity	NPD1465	Phase 2
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5402	Approved
0.8322	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1613	Approved
0.8293	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD2796	Approved
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8228	Intermediate Similarity	NPD5403	Approved
0.8217	Intermediate Similarity	NPD5401	Approved
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1240	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8108	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.8079	Intermediate Similarity	NPD943	Approved
0.8072	Intermediate Similarity	NPD1247	Approved
0.8061	Intermediate Similarity	NPD919	Approved
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7836	Intermediate Similarity	NPD3751	Discontinued
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6190	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.7738	Intermediate Similarity	NPD6234	Discontinued
0.7736	Intermediate Similarity	NPD3750	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.773	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
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
0.7651	Intermediate Similarity	NPD37	Approved
0.763	Intermediate Similarity	NPD7228	Approved
0.7619	Intermediate Similarity	NPD4965	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7619	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD4966	Approved
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2935	Discontinued
0.7595	Intermediate Similarity	NPD6099	Approved
0.7595	Intermediate Similarity	NPD6100	Approved
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7455	Intermediate Similarity	NPD920	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7438	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5953	Discontinued
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
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7351	Intermediate Similarity	NPD1610	Phase 2
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7273	Intermediate Similarity	NPD1203	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7256	Intermediate Similarity	NPD2309	Approved
0.7254	Intermediate Similarity	NPD8151	Discontinued
0.7251	Intermediate Similarity	NPD5353	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.724	Intermediate Similarity	NPD7584	Approved
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7266	Discontinued
0.7216	Intermediate Similarity	NPD2403	Approved
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD1548	Phase 1
0.719	Intermediate Similarity	NPD9269	Phase 2
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7167	Intermediate Similarity	NPD7240	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD2163	Approved
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7093	Intermediate Similarity	NPD8455	Phase 2
0.7078	Intermediate Similarity	NPD9717	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.707	Intermediate Similarity	NPD3018	Phase 2
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2354	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7044	Intermediate Similarity	NPD3268	Approved
0.7044	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD4661	Approved
0.7024	Intermediate Similarity	NPD4662	Approved
0.7019	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5124	Phase 1
0.7013	Intermediate Similarity	NPD422	Phase 1
0.7006	Intermediate Similarity	NPD2798	Approved
0.7005	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7801	Approved
0.7005	Intermediate Similarity	NPD7783	Phase 2
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6994	Remote Similarity	NPD4308	Phase 3
0.6984	Remote Similarity	NPD4361	Phase 2

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