NPASS Compound

Structure

NPC86744 OpenBabel07101719402D 27 29 0 0 1 0 0 0 0 0999 V2000 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 6.0622 -1.5000 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 3.4641 0.0000 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 5.1962 -1.0000 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 2.5981 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 2 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 4.3301 -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 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 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 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 -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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 12 2 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 8 1 6 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 14 1 6 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.12
Volume:	363.377
LogP:	0.608
LogD:	-0.076
LogS:	-1.979
# Rotatable Bonds:	4
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	3.64
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.828
MDCK Permeability:	5.193217020860175e-06
Pgp-inhibitor:	0.051
Pgp-substrate:	0.636
Human Intestinal Absorption (HIA):	0.817
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	94.50470733642578%
Volume Distribution (VD):	0.674
Pgp-substrate:	5.968750476837158%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	1.565
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.671
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.16
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.197
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC86744

Natural Product ID:	NPC86744
*Common Name:**	Hyperinone
IUPAC Name:	[3,5-dihydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]-phenylmethanone
Synonyms:	Hyperinone
Standard InCHIKey:	IZLOXVHOHPOUQD-SFKBXODTSA-N
Standard InCHI:	InChI=1S/C19H20O8/c20-8-13-16(24)17(25)18(26)19(27-13)14-11(21)6-10(7-12(14)22)15(23)9-4-2-1-3-5-9/h1-7,13,16-22,24-26H,8H2/t13-,16-,17+,18-,19+/m1/s1
SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc(cc1O)C(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469430
PubChem CID:	21578953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.93	mM	PMID[489864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.24	mM	PMID[489864]

☑ 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 NPC86744 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	355
0.1-0.2	1306
0.2-0.3	3034
0.3-0.4	7787
0.4-0.5	11161
0.5-0.6	3970
0.6-0.7	6430
0.7-0.8	8247
0.8-0.85	396
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8904	High Similarity	NPC227485
0.8889	High Similarity	NPC81835
0.869	High Similarity	NPC469758
0.8639	High Similarity	NPC89442
0.8621	High Similarity	NPC469764
0.8611	High Similarity	NPC121573
0.8611	High Similarity	NPC190587
0.8611	High Similarity	NPC226738
0.8611	High Similarity	NPC22176
0.8581	High Similarity	NPC177308
0.8581	High Similarity	NPC124478
0.8533	High Similarity	NPC474622
0.8533	High Similarity	NPC474621
0.8467	Intermediate Similarity	NPC75069
0.8467	Intermediate Similarity	NPC474534
0.8467	Intermediate Similarity	NPC253904
0.8467	Intermediate Similarity	NPC474533
0.8467	Intermediate Similarity	NPC321363
0.8456	Intermediate Similarity	NPC140151
0.8446	Intermediate Similarity	NPC191634
0.8446	Intermediate Similarity	NPC218569
0.8435	Intermediate Similarity	NPC51513
0.8435	Intermediate Similarity	NPC470570
0.8435	Intermediate Similarity	NPC285122
0.8435	Intermediate Similarity	NPC202112
0.8429	Intermediate Similarity	NPC472591
0.8425	Intermediate Similarity	NPC300684
0.8425	Intermediate Similarity	NPC84568
0.8425	Intermediate Similarity	NPC48130
0.8425	Intermediate Similarity	NPC218866
0.8421	Intermediate Similarity	NPC208152
0.8421	Intermediate Similarity	NPC78492
0.84	Intermediate Similarity	NPC472422
0.84	Intermediate Similarity	NPC209846
0.84	Intermediate Similarity	NPC46564
0.84	Intermediate Similarity	NPC472420
0.84	Intermediate Similarity	NPC471676
0.84	Intermediate Similarity	NPC477897
0.84	Intermediate Similarity	NPC244577
0.84	Intermediate Similarity	NPC328740
0.84	Intermediate Similarity	NPC263384
0.84	Intermediate Similarity	NPC289774
0.84	Intermediate Similarity	NPC39819
0.84	Intermediate Similarity	NPC207346
0.8378	Intermediate Similarity	NPC71055
0.8378	Intermediate Similarity	NPC248257
0.8378	Intermediate Similarity	NPC21835
0.8378	Intermediate Similarity	NPC142528
0.8378	Intermediate Similarity	NPC120621
0.8377	Intermediate Similarity	NPC24164
0.8377	Intermediate Similarity	NPC471976
0.8367	Intermediate Similarity	NPC34482
0.8367	Intermediate Similarity	NPC170055
0.8366	Intermediate Similarity	NPC156818
0.8366	Intermediate Similarity	NPC38779
0.8366	Intermediate Similarity	NPC68324
0.8366	Intermediate Similarity	NPC114179
0.8366	Intermediate Similarity	NPC160512
0.8366	Intermediate Similarity	NPC289322
0.8355	Intermediate Similarity	NPC203757
0.8355	Intermediate Similarity	NPC175192
0.8355	Intermediate Similarity	NPC237560
0.8355	Intermediate Similarity	NPC326910
0.8345	Intermediate Similarity	NPC145673
0.8344	Intermediate Similarity	NPC161881
0.8344	Intermediate Similarity	NPC171651
0.8344	Intermediate Similarity	NPC478220
0.8344	Intermediate Similarity	NPC474656
0.8344	Intermediate Similarity	NPC244583
0.8344	Intermediate Similarity	NPC178173
0.8344	Intermediate Similarity	NPC243171
0.8344	Intermediate Similarity	NPC35567
0.8344	Intermediate Similarity	NPC56232
0.8344	Intermediate Similarity	NPC10807
0.8344	Intermediate Similarity	NPC150123
0.8333	Intermediate Similarity	NPC225854
0.8333	Intermediate Similarity	NPC18457
0.8333	Intermediate Similarity	NPC148366
0.8333	Intermediate Similarity	NPC105525
0.8333	Intermediate Similarity	NPC311293
0.8333	Intermediate Similarity	NPC12218
0.8333	Intermediate Similarity	NPC225036
0.8333	Intermediate Similarity	NPC127415
0.8333	Intermediate Similarity	NPC75763
0.8323	Intermediate Similarity	NPC3629
0.8322	Intermediate Similarity	NPC92117
0.8322	Intermediate Similarity	NPC42464
0.8312	Intermediate Similarity	NPC117418
0.8312	Intermediate Similarity	NPC53545
0.8312	Intermediate Similarity	NPC226287
0.8311	Intermediate Similarity	NPC268366
0.8311	Intermediate Similarity	NPC196114
0.8311	Intermediate Similarity	NPC316769
0.8311	Intermediate Similarity	NPC209278
0.8311	Intermediate Similarity	NPC1940
0.8311	Intermediate Similarity	NPC148011
0.8301	Intermediate Similarity	NPC300845
0.8301	Intermediate Similarity	NPC250436
0.8301	Intermediate Similarity	NPC88803
0.8301	Intermediate Similarity	NPC471787
0.8301	Intermediate Similarity	NPC104983
0.8301	Intermediate Similarity	NPC291948
0.8299	Intermediate Similarity	NPC207732
0.8299	Intermediate Similarity	NPC193703
0.8299	Intermediate Similarity	NPC59551
0.8299	Intermediate Similarity	NPC103910
0.8299	Intermediate Similarity	NPC21599
0.8299	Intermediate Similarity	NPC244691
0.8299	Intermediate Similarity	NPC48762
0.8289	Intermediate Similarity	NPC109594
0.8289	Intermediate Similarity	NPC125487
0.8289	Intermediate Similarity	NPC7989
0.8289	Intermediate Similarity	NPC303950
0.8289	Intermediate Similarity	NPC112701
0.8289	Intermediate Similarity	NPC18727
0.8289	Intermediate Similarity	NPC293286
0.8289	Intermediate Similarity	NPC256346
0.8289	Intermediate Similarity	NPC281703
0.8289	Intermediate Similarity	NPC246328
0.8289	Intermediate Similarity	NPC471981
0.8289	Intermediate Similarity	NPC268193
0.8289	Intermediate Similarity	NPC223701
0.8289	Intermediate Similarity	NPC472583
0.8289	Intermediate Similarity	NPC326592
0.8289	Intermediate Similarity	NPC135522
0.8289	Intermediate Similarity	NPC27532
0.8289	Intermediate Similarity	NPC469405
0.8289	Intermediate Similarity	NPC325028
0.828	Intermediate Similarity	NPC478022
0.828	Intermediate Similarity	NPC478020
0.828	Intermediate Similarity	NPC471788
0.828	Intermediate Similarity	NPC165720
0.8278	Intermediate Similarity	NPC471677
0.8278	Intermediate Similarity	NPC471229
0.8278	Intermediate Similarity	NPC70016
0.8278	Intermediate Similarity	NPC262038
0.8278	Intermediate Similarity	NPC278476
0.8278	Intermediate Similarity	NPC319910
0.8278	Intermediate Similarity	NPC254412
0.8278	Intermediate Similarity	NPC215921
0.8278	Intermediate Similarity	NPC262039
0.8276	Intermediate Similarity	NPC109232
0.8273	Intermediate Similarity	NPC109123
0.8269	Intermediate Similarity	NPC473961
0.8267	Intermediate Similarity	NPC200221
0.8267	Intermediate Similarity	NPC294502
0.8267	Intermediate Similarity	NPC1612
0.8267	Intermediate Similarity	NPC183959
0.8267	Intermediate Similarity	NPC306343
0.8258	Intermediate Similarity	NPC53889
0.8258	Intermediate Similarity	NPC472902
0.8258	Intermediate Similarity	NPC24627
0.8255	Intermediate Similarity	NPC40086
0.8255	Intermediate Similarity	NPC3779
0.8255	Intermediate Similarity	NPC44721
0.8255	Intermediate Similarity	NPC476182
0.8255	Intermediate Similarity	NPC140722
0.8255	Intermediate Similarity	NPC92054
0.8255	Intermediate Similarity	NPC14875
0.8255	Intermediate Similarity	NPC122828
0.8255	Intermediate Similarity	NPC176869
0.8255	Intermediate Similarity	NPC43123
0.8255	Intermediate Similarity	NPC222298
0.8255	Intermediate Similarity	NPC211466
0.8255	Intermediate Similarity	NPC46941
0.8255	Intermediate Similarity	NPC4958
0.8255	Intermediate Similarity	NPC51070
0.8252	Intermediate Similarity	NPC471345
0.8247	Intermediate Similarity	NPC474836
0.8247	Intermediate Similarity	NPC472598
0.8247	Intermediate Similarity	NPC48208
0.8247	Intermediate Similarity	NPC129684
0.8247	Intermediate Similarity	NPC99597
0.8247	Intermediate Similarity	NPC162869
0.8247	Intermediate Similarity	NPC52530
0.8247	Intermediate Similarity	NPC156457
0.8247	Intermediate Similarity	NPC210084
0.8247	Intermediate Similarity	NPC475267
0.8247	Intermediate Similarity	NPC197896
0.8247	Intermediate Similarity	NPC313163
0.8247	Intermediate Similarity	NPC156057
0.8247	Intermediate Similarity	NPC474208
0.8247	Intermediate Similarity	NPC299520
0.8247	Intermediate Similarity	NPC291508
0.8247	Intermediate Similarity	NPC161749
0.8247	Intermediate Similarity	NPC474010
0.8247	Intermediate Similarity	NPC474055
0.8247	Intermediate Similarity	NPC135222
0.8247	Intermediate Similarity	NPC258035
0.8247	Intermediate Similarity	NPC477833
0.8243	Intermediate Similarity	NPC306607
0.8243	Intermediate Similarity	NPC279417
0.8243	Intermediate Similarity	NPC62290
0.8243	Intermediate Similarity	NPC49130
0.8243	Intermediate Similarity	NPC208176
0.8243	Intermediate Similarity	NPC142731
0.8243	Intermediate Similarity	NPC4152
0.8243	Intermediate Similarity	NPC326506
0.8239	Intermediate Similarity	NPC222455
0.8235	Intermediate Similarity	NPC477958

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 NPC86744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	791
0.2-0.3	1497
0.3-0.4	2624
0.4-0.5	2139
0.5-0.6	1190
0.6-0.7	453
0.7-0.8	141
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8581	High Similarity	NPD4380	Phase 2
0.8301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1934	Approved
0.817	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6559	Discontinued
0.8082	Intermediate Similarity	NPD1549	Phase 2
0.8063	Intermediate Similarity	NPD3818	Discontinued
0.805	Intermediate Similarity	NPD6166	Phase 2
0.805	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7075	Discontinued
0.8013	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7972	Intermediate Similarity	NPD943	Approved
0.7935	Intermediate Similarity	NPD2801	Approved
0.7914	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD5401	Approved
0.7862	Intermediate Similarity	NPD1607	Approved
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7834	Intermediate Similarity	NPD3882	Suspended
0.7823	Intermediate Similarity	NPD1551	Phase 2
0.7821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1511	Approved
0.78	Intermediate Similarity	NPD6190	Approved
0.7793	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD7054	Approved
0.7791	Intermediate Similarity	NPD5844	Phase 1
0.7763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6801	Discontinued
0.7755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7744	Intermediate Similarity	NPD7472	Approved
0.7733	Intermediate Similarity	NPD3750	Approved
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.773	Intermediate Similarity	NPD1470	Approved
0.7724	Intermediate Similarity	NPD1240	Approved
0.7724	Intermediate Similarity	NPD1613	Approved
0.7724	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1512	Approved
0.7711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7819	Suspended
0.7703	Intermediate Similarity	NPD2796	Approved
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7697	Intermediate Similarity	NPD6797	Phase 2
0.7683	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7473	Discontinued
0.7665	Intermediate Similarity	NPD8312	Approved
0.7665	Intermediate Similarity	NPD8313	Approved
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7658	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7251	Discontinued
0.7633	Intermediate Similarity	NPD8150	Discontinued
0.7628	Intermediate Similarity	NPD6599	Discontinued
0.7616	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7808	Phase 3
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.7584	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6099	Approved
0.7584	Intermediate Similarity	NPD2935	Discontinued
0.7582	Intermediate Similarity	NPD6799	Approved
0.7582	Intermediate Similarity	NPD7390	Discontinued
0.758	Intermediate Similarity	NPD7411	Suspended
0.7578	Intermediate Similarity	NPD5494	Approved
0.7571	Intermediate Similarity	NPD1201	Approved
0.7558	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3027	Phase 3
0.7466	Intermediate Similarity	NPD3764	Approved
0.7452	Intermediate Similarity	NPD3226	Approved
0.7448	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD37	Approved
0.7419	Intermediate Similarity	NPD2532	Approved
0.7419	Intermediate Similarity	NPD2534	Approved
0.7419	Intermediate Similarity	NPD2533	Approved
0.7417	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD6234	Discontinued
0.74	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3748	Approved
0.74	Intermediate Similarity	NPD4308	Phase 3
0.7391	Intermediate Similarity	NPD4965	Approved
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7379	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6534	Approved
0.7371	Intermediate Similarity	NPD6535	Approved
0.7351	Intermediate Similarity	NPD5408	Approved
0.7351	Intermediate Similarity	NPD5404	Approved
0.7351	Intermediate Similarity	NPD5406	Approved
0.7351	Intermediate Similarity	NPD5405	Approved
0.7347	Intermediate Similarity	NPD2313	Discontinued
0.7325	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7289	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7279	Intermediate Similarity	NPD4625	Phase 3
0.7278	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7266	Intermediate Similarity	NPD9493	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7700	Phase 2
0.7247	Intermediate Similarity	NPD7699	Phase 2
0.7241	Intermediate Similarity	NPD1203	Approved
0.7239	Intermediate Similarity	NPD3749	Approved
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4749	Approved
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7211	Intermediate Similarity	NPD6832	Phase 2
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7205	Intermediate Similarity	NPD6844	Discontinued
0.7203	Intermediate Similarity	NPD1610	Phase 2
0.72	Intermediate Similarity	NPD447	Suspended
0.7192	Intermediate Similarity	NPD2798	Approved
0.7182	Intermediate Similarity	NPD6823	Phase 2
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7168	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7123	Intermediate Similarity	NPD2797	Approved
0.7114	Intermediate Similarity	NPD3268	Approved
0.7114	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7113	Intermediate Similarity	NPD9268	Approved
0.7104	Intermediate Similarity	NPD8320	Phase 1
0.7104	Intermediate Similarity	NPD8319	Approved
0.7103	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD8455	Phase 2
0.7051	Intermediate Similarity	NPD8166	Discontinued
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7047	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8151	Discontinued
0.7042	Intermediate Similarity	NPD1548	Phase 1
0.7037	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7685	Pre-registration
0.7034	Intermediate Similarity	NPD3972	Approved
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7027	Intermediate Similarity	NPD9494	Approved
0.7027	Intermediate Similarity	NPD2861	Phase 2
0.7024	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD2649	Approved
0.7019	Intermediate Similarity	NPD3455	Phase 2
0.7019	Intermediate Similarity	NPD2651	Approved
0.7015	Intermediate Similarity	NPD1237	Approved
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD411	Approved
0.6993	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7701	Phase 2
0.6987	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2800	Approved
0.6987	Remote Similarity	NPD1652	Phase 2
0.6981	Remote Similarity	NPD4662	Approved
0.6981	Remote Similarity	NPD4661	Approved
0.6977	Remote Similarity	NPD5953	Discontinued
0.6974	Remote Similarity	NPD6355	Discontinued
0.6974	Remote Similarity	NPD1933	Approved
0.6968	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2344	Approved
0.6966	Remote Similarity	NPD1091	Approved
0.6964	Remote Similarity	NPD5710	Approved
0.6964	Remote Similarity	NPD5711	Approved
0.6962	Remote Similarity	NPD3300	Phase 2
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6233	Phase 2
0.6948	Remote Similarity	NPD7033	Discontinued
0.6946	Remote Similarity	NPD6746	Phase 2
0.6943	Remote Similarity	NPD7003	Approved
0.6937	Remote Similarity	NPD6273	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