NPASS Compound

Structure

CID101957 OpenBabel06191715442D 23 26 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 6.0622 -1.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 6.9282 -2.0000 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 3.4641 -3.0000 0.0000 O 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 12 2 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.08
Volume:	308.518
LogP:	4.306
LogD:	2.994
LogS:	-3.641
# Rotatable Bonds:	0
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.875
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.753
MDCK Permeability:	1.7678565200185403e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	97.82123565673828%
Volume Distribution (VD):	0.526
Pgp-substrate:	5.226353645324707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.599
CYP2C19-inhibitor:	0.606
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.82
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	1.901
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.625
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.428
Rat Oral Acute Toxicity:	0.375
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.886
Carcinogencity:	0.812
Eye Corrosion:	0.004
Eye Irritation:	0.802
Respiratory Toxicity:	0.615

Download Data

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

Natural Product: NPC101957

Natural Product ID:	NPC101957
*Common Name:**	5,8-Dihydroxy-2,2-Dimethylpyrano[3,2-B]Xanthen-6-One
IUPAC Name:	5,8-dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
Synonyms:
Standard InCHIKey:	AQJGDWRSGSISRW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O5/c1-18(2)6-5-10-13(23-18)8-14-15(16(10)20)17(21)11-7-9(19)3-4-12(11)22-14/h3-8,19-20H,1-2H3
SMILES:	CC1(C)C=Cc2c(cc3c(c2O)c(=O)c2cc(ccc2o3)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314602
PubChem CID:	6064803
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[24960143]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26101	Andropogon zizanioides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28994	Acacia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19038	Zanha golungensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25806	Streptomyces violaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26671	Hapalosiphon welwitschii	Species	Hapalosiphonaceae	Bacteria	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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[503207]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[503207]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	6100.0	nM	PMID[503207]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[503207]
NPT27	Others	Unspecified		IC50	=	6600.0	nM	PMID[503207]

☑ 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 NPC101957 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	437
0.1-0.2	1939
0.2-0.3	4531
0.3-0.4	11290
0.4-0.5	6583
0.5-0.6	3912
0.6-0.7	5438
0.7-0.8	4352
0.8-0.85	2060
0.85-0.9	1699
0.9-0.95	431
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120105
0.9722	High Similarity	NPC186397
0.9722	High Similarity	NPC37135
0.966	High Similarity	NPC95842
0.966	High Similarity	NPC280530
0.966	High Similarity	NPC178964
0.9655	High Similarity	NPC266499
0.9655	High Similarity	NPC223988
0.951	High Similarity	NPC159855
0.951	High Similarity	NPC169479
0.9463	High Similarity	NPC55662
0.9463	High Similarity	NPC166054
0.9456	High Similarity	NPC472633
0.9456	High Similarity	NPC227122
0.9444	High Similarity	NPC38219
0.9444	High Similarity	NPC219915
0.9408	High Similarity	NPC167678
0.9408	High Similarity	NPC29876
0.9388	High Similarity	NPC10027
0.9388	High Similarity	NPC65775
0.9379	High Similarity	NPC234629
0.9379	High Similarity	NPC311741
0.9375	High Similarity	NPC144499
0.9346	High Similarity	NPC329760
0.9346	High Similarity	NPC472448
0.9346	High Similarity	NPC83922
0.9342	High Similarity	NPC471976
0.9342	High Similarity	NPC204290
0.9338	High Similarity	NPC476981
0.9329	High Similarity	NPC142527
0.9324	High Similarity	NPC29777
0.9324	High Similarity	NPC37348
0.9324	High Similarity	NPC471115
0.932	High Similarity	NPC296869
0.932	High Similarity	NPC266572
0.931	High Similarity	NPC18585
0.931	High Similarity	NPC106985
0.931	High Similarity	NPC166138
0.9306	High Similarity	NPC64908
0.9306	High Similarity	NPC156590
0.9306	High Similarity	NPC205006
0.9306	High Similarity	NPC118840
0.9306	High Similarity	NPC147688
0.9281	High Similarity	NPC3629
0.9281	High Similarity	NPC259456
0.9272	High Similarity	NPC5322
0.9272	High Similarity	NPC6633
0.9272	High Similarity	NPC133970
0.9272	High Similarity	NPC276444
0.9267	High Similarity	NPC472462
0.9252	High Similarity	NPC166757
0.9252	High Similarity	NPC473077
0.9252	High Similarity	NPC104406
0.9252	High Similarity	NPC97716
0.9252	High Similarity	NPC296998
0.9252	High Similarity	NPC201731
0.9252	High Similarity	NPC79469
0.9252	High Similarity	NPC237635
0.9252	High Similarity	NPC24673
0.9252	High Similarity	NPC23728
0.9252	High Similarity	NPC110303
0.9252	High Similarity	NPC14001
0.9241	High Similarity	NPC226636
0.9241	High Similarity	NPC299080
0.9241	High Similarity	NPC59739
0.9241	High Similarity	NPC473042
0.9241	High Similarity	NPC11561
0.9241	High Similarity	NPC293852
0.9241	High Similarity	NPC214236
0.9241	High Similarity	NPC217083
0.9241	High Similarity	NPC78803
0.9241	High Similarity	NPC62840
0.9236	High Similarity	NPC305355
0.9236	High Similarity	NPC69769
0.9236	High Similarity	NPC235239
0.9236	High Similarity	NPC270883
0.9236	High Similarity	NPC475680
0.9236	High Similarity	NPC172986
0.9236	High Similarity	NPC145673
0.9236	High Similarity	NPC261227
0.9231	High Similarity	NPC18457
0.9231	High Similarity	NPC201395
0.9221	High Similarity	NPC229632
0.9216	High Similarity	NPC476980
0.9211	High Similarity	NPC196448
0.9211	High Similarity	NPC218871
0.9211	High Similarity	NPC476630
0.9211	High Similarity	NPC474681
0.9211	High Similarity	NPC218313
0.9205	High Similarity	NPC275575
0.9205	High Similarity	NPC200246
0.9205	High Similarity	NPC113906
0.92	High Similarity	NPC45934
0.9195	High Similarity	NPC471984
0.9189	High Similarity	NPC132592
0.9189	High Similarity	NPC39195
0.9189	High Similarity	NPC160821
0.9189	High Similarity	NPC244407
0.9189	High Similarity	NPC6511
0.9184	High Similarity	NPC312973
0.9184	High Similarity	NPC220418
0.9184	High Similarity	NPC88964
0.9184	High Similarity	NPC187282
0.9184	High Similarity	NPC111786
0.9184	High Similarity	NPC20488
0.9184	High Similarity	NPC301276
0.9184	High Similarity	NPC290133
0.9184	High Similarity	NPC124729
0.9184	High Similarity	NPC267375
0.9184	High Similarity	NPC54577
0.9184	High Similarity	NPC475052
0.9184	High Similarity	NPC83357
0.9184	High Similarity	NPC24136
0.9184	High Similarity	NPC196114
0.9184	High Similarity	NPC67805
0.9184	High Similarity	NPC176229
0.9184	High Similarity	NPC142405
0.9184	High Similarity	NPC477955
0.9184	High Similarity	NPC246948
0.9184	High Similarity	NPC195621
0.9184	High Similarity	NPC214774
0.9184	High Similarity	NPC470647
0.9178	High Similarity	NPC24821
0.9178	High Similarity	NPC9117
0.9178	High Similarity	NPC190637
0.9178	High Similarity	NPC293053
0.9178	High Similarity	NPC212932
0.9172	High Similarity	NPC103362
0.9172	High Similarity	NPC110969
0.9172	High Similarity	NPC3188
0.9167	High Similarity	NPC301217
0.9167	High Similarity	NPC303633
0.9167	High Similarity	NPC96565
0.9167	High Similarity	NPC220062
0.9167	High Similarity	NPC216978
0.9167	High Similarity	NPC18260
0.9167	High Similarity	NPC78913
0.9167	High Similarity	NPC55018
0.9161	High Similarity	NPC207690
0.9161	High Similarity	NPC306321
0.9161	High Similarity	NPC228661
0.9161	High Similarity	NPC303460
0.9161	High Similarity	NPC189473
0.9161	High Similarity	NPC23298
0.915	High Similarity	NPC185258
0.915	High Similarity	NPC172770
0.915	High Similarity	NPC204879
0.9145	High Similarity	NPC68093
0.9145	High Similarity	NPC138243
0.9145	High Similarity	NPC191146
0.9139	High Similarity	NPC469405
0.9139	High Similarity	NPC7989
0.9139	High Similarity	NPC472583
0.9139	High Similarity	NPC223701
0.9139	High Similarity	NPC170492
0.9133	High Similarity	NPC149614
0.9133	High Similarity	NPC117579
0.9133	High Similarity	NPC154345
0.9133	High Similarity	NPC305965
0.9128	High Similarity	NPC5173
0.9128	High Similarity	NPC317492
0.9128	High Similarity	NPC474052
0.9128	High Similarity	NPC269420
0.9122	High Similarity	NPC283234
0.9122	High Similarity	NPC308200
0.9122	High Similarity	NPC140120
0.9116	High Similarity	NPC303185
0.9116	High Similarity	NPC216538
0.9116	High Similarity	NPC326500
0.9116	High Similarity	NPC257236
0.9116	High Similarity	NPC273538
0.9116	High Similarity	NPC184649
0.9116	High Similarity	NPC209040
0.9116	High Similarity	NPC278175
0.911	High Similarity	NPC73028
0.911	High Similarity	NPC200694
0.9103	High Similarity	NPC239752
0.9103	High Similarity	NPC275780
0.9103	High Similarity	NPC150522
0.9103	High Similarity	NPC241100
0.9103	High Similarity	NPC472450
0.9103	High Similarity	NPC101366
0.9103	High Similarity	NPC159275
0.9097	High Similarity	NPC472402
0.9097	High Similarity	NPC261470
0.9091	High Similarity	NPC139036
0.9085	High Similarity	NPC65504
0.9085	High Similarity	NPC268360
0.9085	High Similarity	NPC473272
0.9085	High Similarity	NPC282390
0.9085	High Similarity	NPC262286
0.9085	High Similarity	NPC281137
0.9085	High Similarity	NPC79053
0.9085	High Similarity	NPC284820
0.9085	High Similarity	NPC36852
0.9085	High Similarity	NPC78225
0.9079	High Similarity	NPC476169
0.9079	High Similarity	NPC472280
0.9073	High Similarity	NPC166201
0.9073	High Similarity	NPC249570

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 NPC101957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	412
0.1-0.2	994
0.2-0.3	1610
0.3-0.4	2714
0.4-0.5	1855
0.5-0.6	1057
0.6-0.7	322
0.7-0.8	121
0.8-0.85	52
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9116	High Similarity	NPD7410	Clinical (unspecified phase)
0.9116	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD2801	Approved
0.8836	High Similarity	NPD1549	Phase 2
0.8816	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD1511	Approved
0.8767	High Similarity	NPD1552	Clinical (unspecified phase)
0.8767	High Similarity	NPD1550	Clinical (unspecified phase)
0.8759	High Similarity	NPD1510	Phase 2
0.8701	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD1512	Approved
0.8645	High Similarity	NPD7819	Suspended
0.8636	High Similarity	NPD7411	Suspended
0.8611	High Similarity	NPD1240	Approved
0.8608	High Similarity	NPD5494	Approved
0.859	High Similarity	NPD8443	Clinical (unspecified phase)
0.8571	High Similarity	NPD2796	Approved
0.8493	Intermediate Similarity	NPD1607	Approved
0.8481	Intermediate Similarity	NPD7075	Discontinued
0.8481	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD3749	Approved
0.8467	Intermediate Similarity	NPD3750	Approved
0.8446	Intermediate Similarity	NPD2935	Discontinued
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2800	Approved
0.8302	Intermediate Similarity	NPD3882	Suspended
0.8282	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5402	Approved
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8219	Intermediate Similarity	NPD2313	Discontinued
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3818	Discontinued
0.8158	Intermediate Similarity	NPD1243	Approved
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD3226	Approved
0.8146	Intermediate Similarity	NPD2346	Discontinued
0.8141	Intermediate Similarity	NPD920	Approved
0.8133	Intermediate Similarity	NPD7054	Approved
0.8133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3748	Approved
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD7472	Approved
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8065	Intermediate Similarity	NPD6799	Approved
0.8049	Intermediate Similarity	NPD6232	Discontinued
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6797	Phase 2
0.8026	Intermediate Similarity	NPD2344	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2534	Approved
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD7251	Discontinued
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7961	Intermediate Similarity	NPD6100	Approved
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7961	Intermediate Similarity	NPD6099	Approved
0.795	Intermediate Similarity	NPD1465	Phase 2
0.7941	Intermediate Similarity	NPD7808	Phase 3
0.7885	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6599	Discontinued
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7824	Intermediate Similarity	NPD5953	Discontinued
0.7821	Intermediate Similarity	NPD2309	Approved
0.7811	Intermediate Similarity	NPD7286	Phase 2
0.7799	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6651	Approved
0.7758	Intermediate Similarity	NPD919	Approved
0.7755	Intermediate Similarity	NPD1203	Approved
0.7733	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6844	Discontinued
0.7667	Intermediate Similarity	NPD4625	Phase 3
0.7662	Intermediate Similarity	NPD4308	Phase 3
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7603	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4908	Phase 1
0.7598	Intermediate Similarity	NPD4363	Phase 3
0.7598	Intermediate Similarity	NPD4360	Phase 2
0.7584	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD447	Suspended
0.7574	Intermediate Similarity	NPD3926	Phase 2
0.7551	Intermediate Similarity	NPD9717	Approved
0.7533	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1470	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.7486	Intermediate Similarity	NPD6779	Approved
0.7486	Intermediate Similarity	NPD6782	Approved
0.7486	Intermediate Similarity	NPD6778	Approved
0.7486	Intermediate Similarity	NPD6777	Approved
0.7486	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD6780	Approved
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7472	Intermediate Similarity	NPD4287	Approved
0.747	Intermediate Similarity	NPD4288	Approved
0.7468	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD5124	Phase 1
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3225	Approved
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7436	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7432	Intermediate Similarity	NPD1608	Approved
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD3787	Discontinued
0.7403	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1613	Approved
0.7403	Intermediate Similarity	NPD4307	Phase 2
0.74	Intermediate Similarity	NPD2797	Approved
0.7394	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD5404	Approved
0.7389	Intermediate Similarity	NPD5408	Approved
0.7389	Intermediate Similarity	NPD5405	Approved
0.7386	Intermediate Similarity	NPD411	Approved
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD3764	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7383	Intermediate Similarity	NPD4749	Approved
0.7378	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6832	Phase 2
0.7366	Intermediate Similarity	NPD7698	Approved
0.7366	Intermediate Similarity	NPD7696	Phase 3
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7366	Intermediate Similarity	NPD7697	Approved
0.7365	Intermediate Similarity	NPD1201	Approved
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1471	Phase 3
0.734	Intermediate Similarity	NPD7584	Approved
0.7333	Intermediate Similarity	NPD6585	Discontinued
0.7326	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD7871	Phase 2
0.7322	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7303	Intermediate Similarity	NPD2861	Phase 2
0.7285	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD3267	Approved
0.7268	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4361	Phase 2
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7262	Intermediate Similarity	NPD2296	Approved
0.7244	Intermediate Similarity	NPD1933	Approved
0.7241	Intermediate Similarity	NPD6671	Approved
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD17	Approved
0.7219	Intermediate Similarity	NPD6823	Phase 2
0.7213	Intermediate Similarity	NPD6535	Approved
0.7213	Intermediate Similarity	NPD6534	Approved
0.7211	Intermediate Similarity	NPD7701	Phase 2
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1481	Phase 2
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7186	Intermediate Similarity	NPD5890	Approved
0.7186	Intermediate Similarity	NPD5889	Approved
0.7171	Intermediate Similarity	NPD1164	Approved
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7161	Intermediate Similarity	NPD1296	Phase 2
0.7161	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD2654	Approved
0.7143	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7874	Approved
0.7133	Intermediate Similarity	NPD1535	Discovery
0.7108	Intermediate Similarity	NPD1653	Approved
0.7101	Intermediate Similarity	NPD5760	Phase 2
0.7101	Intermediate Similarity	NPD5761	Phase 2
0.7099	Intermediate Similarity	NPD7003	Approved
0.7098	Intermediate Similarity	NPD7801	Approved
0.7097	Intermediate Similarity	NPD7700	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