NPASS Compound

Structure

NPC476142 OpenBabel07101719522D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 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 -3.4641 3.0000 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 -4.3301 3.5000 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 -2.5981 0.5000 0.0000 C 0 0 1 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 -5.1962 3.0000 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 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 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 1.7321 -1.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 17 1 0 0 0 0 8 1 1 1 0 0 0 8 14 1 0 0 0 0 8 21 1 0 0 0 0 10 20 1 0 0 0 0 11 7 1 1 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 15 1 0 0 0 0 13 19 1 1 0 0 0 14 9 1 6 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 21 1 6 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.14
Volume:	313.245
LogP:	0.846
LogD:	0.998
LogS:	-2.083
# Rotatable Bonds:	3
TPSA:	97.61
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.946
Fsp3:	0.625
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:	-5.306
MDCK Permeability:	3.907216159859672e-05
Pgp-inhibitor:	0.292
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.238
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.518

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.204
Plasma Protein Binding (PPB):	37.47526168823242%
Volume Distribution (VD):	0.613
Pgp-substrate:	35.253665924072266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.382
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.629
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	5.798
Half-life (T1/2):	0.536

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.297
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.39
Carcinogencity:	0.473
Eye Corrosion:	0.005
Eye Irritation:	0.572
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC476142

Natural Product ID:	NPC476142
*Common Name:**	Oligandrumin E
IUPAC Name:	(2S,3S,4aS,6R,7S,8S,8aS)-6-(hydroxymethyl)-2-(4-methoxyphenyl)-3-methyl-3,4a,6,7,8,8a-hexahydro-2H-pyrano[2,3-b][1,4]dioxine-7,8-diol
Synonyms:	Oligandrumin E
Standard InCHIKey:	USUWYXHMWYBKFQ-VKUPVEMESA-N
Standard InCHI:	InChI=1S/C16H22O7/c1-8-14(9-3-5-10(20-2)6-4-9)23-15-13(19)12(18)11(7-17)22-16(15)21-8/h3-6,8,11-19H,7H2,1-2H3/t8-,11+,12+,13-,14+,15-,16-/m0/s1
SMILES:	CC1C(OC2C(C(C(OC2O1)CO)O)O)C3=CC=C(C=C3)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL540462
PubChem CID:	45270509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002011] Pyranodioxins

*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
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	pericarps	n.a.	n.a.	PMID[19159273]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19496609]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[21524101]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	root	n.a.	PMID[25966312]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	6.42	%	PMID[521667]

☑ 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 NPC476142 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	305
0.1-0.2	1330
0.2-0.3	3363
0.3-0.4	9139
0.4-0.5	9592
0.5-0.6	6666
0.6-0.7	9204
0.7-0.8	2695
0.8-0.85	308
0.85-0.9	85
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC469412
0.9487	High Similarity	NPC198734
0.9402	High Similarity	NPC60589
0.9402	High Similarity	NPC469708
0.9322	High Similarity	NPC269242
0.9174	High Similarity	NPC287429
0.912	High Similarity	NPC9912
0.9113	High Similarity	NPC26653
0.9113	High Similarity	NPC270849
0.906	High Similarity	NPC148055
0.906	High Similarity	NPC175771
0.9055	High Similarity	NPC35731
0.904	High Similarity	NPC472024
0.904	High Similarity	NPC80600
0.8968	High Similarity	NPC248307
0.8968	High Similarity	NPC65942
0.896	High Similarity	NPC295970
0.8952	High Similarity	NPC198798
0.8926	High Similarity	NPC226712
0.8926	High Similarity	NPC55608
0.8906	High Similarity	NPC187194
0.8889	High Similarity	NPC157338
0.8889	High Similarity	NPC313193
0.888	High Similarity	NPC302378
0.8846	High Similarity	NPC304152
0.8846	High Similarity	NPC87777
0.8846	High Similarity	NPC262328
0.8819	High Similarity	NPC475067
0.881	High Similarity	NPC97326
0.881	High Similarity	NPC307110
0.881	High Similarity	NPC166040
0.881	High Similarity	NPC248355
0.879	High Similarity	NPC470510
0.8769	High Similarity	NPC199459
0.8769	High Similarity	NPC177035
0.8769	High Similarity	NPC52277
0.876	High Similarity	NPC469702
0.876	High Similarity	NPC476411
0.876	High Similarity	NPC470881
0.876	High Similarity	NPC282409
0.874	High Similarity	NPC474491
0.8707	High Similarity	NPC30563
0.8702	High Similarity	NPC470413
0.8702	High Similarity	NPC138738
0.8692	High Similarity	NPC79957
0.8692	High Similarity	NPC238243
0.8692	High Similarity	NPC470236
0.8689	High Similarity	NPC201402
0.8689	High Similarity	NPC476445
0.8689	High Similarity	NPC469548
0.8689	High Similarity	NPC476448
0.8689	High Similarity	NPC160854
0.8689	High Similarity	NPC469704
0.8689	High Similarity	NPC469703
0.8682	High Similarity	NPC25821
0.8682	High Similarity	NPC215833
0.8682	High Similarity	NPC6836
0.8682	High Similarity	NPC69513
0.8682	High Similarity	NPC294166
0.8682	High Similarity	NPC115022
0.8672	High Similarity	NPC121376
0.8647	High Similarity	NPC108674
0.8629	High Similarity	NPC212176
0.8626	High Similarity	NPC165482
0.8626	High Similarity	NPC138350
0.8626	High Similarity	NPC197723
0.8626	High Similarity	NPC164857
0.8626	High Similarity	NPC3293
0.8626	High Similarity	NPC40664
0.8621	High Similarity	NPC276061
0.8621	High Similarity	NPC474148
0.8618	High Similarity	NPC469686
0.8615	High Similarity	NPC188555
0.8615	High Similarity	NPC471029
0.8615	High Similarity	NPC251981
0.8615	High Similarity	NPC130496
0.8615	High Similarity	NPC13745
0.8615	High Similarity	NPC107478
0.8615	High Similarity	NPC48863
0.8605	High Similarity	NPC26080
0.8605	High Similarity	NPC165686
0.8605	High Similarity	NPC252833
0.8605	High Similarity	NPC85799
0.8605	High Similarity	NPC162093
0.8605	High Similarity	NPC303422
0.8594	High Similarity	NPC262606
0.8583	High Similarity	NPC301651
0.8583	High Similarity	NPC473556
0.8582	High Similarity	NPC139976
0.8582	High Similarity	NPC128337
0.8582	High Similarity	NPC230718
0.8582	High Similarity	NPC49542
0.8582	High Similarity	NPC84207
0.8582	High Similarity	NPC5253
0.8571	High Similarity	NPC106944
0.8548	High Similarity	NPC471067
0.8538	High Similarity	NPC49074
0.8538	High Similarity	NPC132895
0.8527	High Similarity	NPC138777
0.8527	High Similarity	NPC46137
0.8527	High Similarity	NPC235294
0.8527	High Similarity	NPC246869
0.8527	High Similarity	NPC225384
0.8519	High Similarity	NPC278961
0.8519	High Similarity	NPC469367
0.8519	High Similarity	NPC116922
0.8519	High Similarity	NPC113680
0.8516	High Similarity	NPC218003
0.8507	High Similarity	NPC472711
0.8507	High Similarity	NPC210192
0.8507	High Similarity	NPC79908
0.8507	High Similarity	NPC76871
0.8504	High Similarity	NPC106677
0.8504	High Similarity	NPC288416
0.8496	Intermediate Similarity	NPC156376
0.8492	Intermediate Similarity	NPC12308
0.8485	Intermediate Similarity	NPC469383
0.8485	Intermediate Similarity	NPC166180
0.848	Intermediate Similarity	NPC178449
0.848	Intermediate Similarity	NPC232454
0.848	Intermediate Similarity	NPC470907
0.8473	Intermediate Similarity	NPC34456
0.8473	Intermediate Similarity	NPC87696
0.8462	Intermediate Similarity	NPC299144
0.8462	Intermediate Similarity	NPC254275
0.8462	Intermediate Similarity	NPC470270
0.8456	Intermediate Similarity	NPC471063
0.8456	Intermediate Similarity	NPC225445
0.8456	Intermediate Similarity	NPC177597
0.8448	Intermediate Similarity	NPC251306
0.8444	Intermediate Similarity	NPC178466
0.8444	Intermediate Similarity	NPC472353
0.8444	Intermediate Similarity	NPC469559
0.8444	Intermediate Similarity	NPC246947
0.8444	Intermediate Similarity	NPC60249
0.8444	Intermediate Similarity	NPC189115
0.8444	Intermediate Similarity	NPC48309
0.8444	Intermediate Similarity	NPC140502
0.8444	Intermediate Similarity	NPC63628
0.8443	Intermediate Similarity	NPC228907
0.8438	Intermediate Similarity	NPC245826
0.8438	Intermediate Similarity	NPC474178
0.8438	Intermediate Similarity	NPC146540
0.8438	Intermediate Similarity	NPC40377
0.8438	Intermediate Similarity	NPC252307
0.8435	Intermediate Similarity	NPC37714
0.8435	Intermediate Similarity	NPC152384
0.8425	Intermediate Similarity	NPC471157
0.8421	Intermediate Similarity	NPC134260
0.8421	Intermediate Similarity	NPC124149
0.8409	Intermediate Similarity	NPC55040
0.8409	Intermediate Similarity	NPC184938
0.8409	Intermediate Similarity	NPC101624
0.84	Intermediate Similarity	NPC52097
0.8397	Intermediate Similarity	NPC215037
0.8394	Intermediate Similarity	NPC100998
0.8394	Intermediate Similarity	NPC34927
0.8394	Intermediate Similarity	NPC34587
0.8394	Intermediate Similarity	NPC252292
0.8394	Intermediate Similarity	NPC476382
0.8382	Intermediate Similarity	NPC470950
0.8382	Intermediate Similarity	NPC473044
0.8382	Intermediate Similarity	NPC477898
0.8382	Intermediate Similarity	NPC46092
0.8382	Intermediate Similarity	NPC185307
0.8374	Intermediate Similarity	NPC135961
0.8372	Intermediate Similarity	NPC86030
0.8372	Intermediate Similarity	NPC5851
0.837	Intermediate Similarity	NPC80098
0.837	Intermediate Similarity	NPC273932
0.837	Intermediate Similarity	NPC89686
0.837	Intermediate Similarity	NPC471908
0.837	Intermediate Similarity	NPC469661
0.837	Intermediate Similarity	NPC257095
0.8358	Intermediate Similarity	NPC98777
0.8358	Intermediate Similarity	NPC212770
0.8346	Intermediate Similarity	NPC157554
0.8346	Intermediate Similarity	NPC242028
0.8346	Intermediate Similarity	NPC37468
0.8346	Intermediate Similarity	NPC126991
0.8346	Intermediate Similarity	NPC25695
0.8346	Intermediate Similarity	NPC203230
0.8346	Intermediate Similarity	NPC103409
0.8346	Intermediate Similarity	NPC172818
0.8346	Intermediate Similarity	NPC83218
0.8346	Intermediate Similarity	NPC294470
0.8346	Intermediate Similarity	NPC475628
0.8333	Intermediate Similarity	NPC276753
0.8333	Intermediate Similarity	NPC74320
0.8333	Intermediate Similarity	NPC205796
0.8333	Intermediate Similarity	NPC169398
0.8333	Intermediate Similarity	NPC107120
0.8333	Intermediate Similarity	NPC125755
0.8321	Intermediate Similarity	NPC471028
0.8321	Intermediate Similarity	NPC217635
0.8321	Intermediate Similarity	NPC79429
0.8321	Intermediate Similarity	NPC473045
0.8321	Intermediate Similarity	NPC168579
0.8321	Intermediate Similarity	NPC470235
0.8321	Intermediate Similarity	NPC138227

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 NPC476142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	785
0.2-0.3	1569
0.3-0.4	2815
0.4-0.5	1925
0.5-0.6	1126
0.6-0.7	600
0.7-0.8	66
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD1091	Approved
0.822	Intermediate Similarity	NPD2684	Approved
0.8099	Intermediate Similarity	NPD7843	Approved
0.8088	Intermediate Similarity	NPD7266	Discontinued
0.8058	Intermediate Similarity	NPD5058	Phase 3
0.8031	Intermediate Similarity	NPD3705	Approved
0.7983	Intermediate Similarity	NPD290	Approved
0.7955	Intermediate Similarity	NPD3027	Phase 3
0.7903	Intermediate Similarity	NPD7157	Approved
0.7868	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD4536	Approved
0.7868	Intermediate Similarity	NPD4538	Approved
0.7842	Intermediate Similarity	NPD6674	Discontinued
0.7795	Intermediate Similarity	NPD1357	Approved
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD8455	Phase 2
0.7734	Intermediate Similarity	NPD5126	Approved
0.7734	Intermediate Similarity	NPD5125	Phase 3
0.7714	Intermediate Similarity	NPD1652	Phase 2
0.771	Intermediate Similarity	NPD8651	Approved
0.7704	Intermediate Similarity	NPD6233	Phase 2
0.7681	Intermediate Similarity	NPD5588	Approved
0.7681	Intermediate Similarity	NPD5960	Phase 3
0.7655	Intermediate Similarity	NPD1653	Approved
0.7634	Intermediate Similarity	NPD3685	Discontinued
0.7612	Intermediate Similarity	NPD4908	Phase 1
0.7609	Intermediate Similarity	NPD7097	Phase 1
0.7597	Intermediate Similarity	NPD5846	Approved
0.7597	Intermediate Similarity	NPD6516	Phase 2
0.7589	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1548	Phase 1
0.7541	Intermediate Similarity	NPD1358	Approved
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7483	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1610	Phase 2
0.744	Intermediate Similarity	NPD228	Approved
0.7429	Intermediate Similarity	NPD4108	Discontinued
0.7426	Intermediate Similarity	NPD3180	Approved
0.7426	Intermediate Similarity	NPD3179	Approved
0.7407	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD821	Approved
0.7381	Intermediate Similarity	NPD5535	Approved
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4340	Discontinued
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7323	Intermediate Similarity	NPD5283	Phase 1
0.7319	Intermediate Similarity	NPD4062	Phase 3
0.7317	Intermediate Similarity	NPD3134	Approved
0.7317	Intermediate Similarity	NPD968	Approved
0.7292	Intermediate Similarity	NPD4628	Phase 3
0.7292	Intermediate Similarity	NPD4535	Phase 3
0.728	Intermediate Similarity	NPD5451	Approved
0.7278	Intermediate Similarity	NPD7054	Approved
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD291	Approved
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.726	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7472	Approved
0.7233	Intermediate Similarity	NPD7074	Phase 3
0.7219	Intermediate Similarity	NPD37	Approved
0.7218	Intermediate Similarity	NPD422	Phase 1
0.7215	Intermediate Similarity	NPD7228	Approved
0.7214	Intermediate Similarity	NPD6355	Discontinued
0.7214	Intermediate Similarity	NPD5735	Approved
0.7209	Intermediate Similarity	NPD6671	Approved
0.7192	Intermediate Similarity	NPD3122	Phase 3
0.719	Intermediate Similarity	NPD4966	Approved
0.719	Intermediate Similarity	NPD4965	Approved
0.719	Intermediate Similarity	NPD4967	Phase 2
0.7188	Intermediate Similarity	NPD6797	Phase 2
0.7183	Intermediate Similarity	NPD7033	Discontinued
0.7174	Intermediate Similarity	NPD7095	Approved
0.7165	Intermediate Similarity	NPD969	Suspended
0.7163	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD556	Approved
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7132	Intermediate Similarity	NPD1817	Approved
0.7132	Intermediate Similarity	NPD1820	Approved
0.7132	Intermediate Similarity	NPD1818	Approved
0.7132	Intermediate Similarity	NPD1819	Approved
0.7123	Intermediate Similarity	NPD2677	Approved
0.7122	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6582	Phase 2
0.7111	Intermediate Similarity	NPD2982	Phase 2
0.7111	Intermediate Similarity	NPD4749	Approved
0.7111	Intermediate Similarity	NPD6583	Phase 3
0.7111	Intermediate Similarity	NPD2983	Phase 2
0.7109	Intermediate Similarity	NPD1138	Approved
0.7103	Intermediate Similarity	NPD4237	Approved
0.7103	Intermediate Similarity	NPD4236	Phase 3
0.7099	Intermediate Similarity	NPD7808	Phase 3
0.7097	Intermediate Similarity	NPD6234	Discontinued
0.7094	Intermediate Similarity	NPD9365	Approved
0.7086	Intermediate Similarity	NPD4380	Phase 2
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD5763	Approved
0.7083	Intermediate Similarity	NPD1375	Discontinued
0.7075	Intermediate Similarity	NPD5756	Phase 2
0.7059	Intermediate Similarity	NPD2977	Approved
0.7059	Intermediate Similarity	NPD2978	Approved
0.7059	Intermediate Similarity	NPD2933	Approved
0.7059	Intermediate Similarity	NPD2934	Approved
0.705	Intermediate Similarity	NPD3166	Approved
0.705	Intermediate Similarity	NPD3164	Approved
0.705	Intermediate Similarity	NPD3167	Approved
0.705	Intermediate Similarity	NPD3165	Approved
0.7045	Intermediate Similarity	NPD1894	Discontinued
0.7037	Intermediate Similarity	NPD2231	Phase 2
0.7037	Intermediate Similarity	NPD7240	Approved
0.7037	Intermediate Similarity	NPD6559	Discontinued
0.7037	Intermediate Similarity	NPD2235	Phase 2
0.7037	Intermediate Similarity	NPD2981	Phase 2
0.7031	Intermediate Similarity	NPD1139	Approved
0.7031	Intermediate Similarity	NPD1137	Approved
0.7029	Intermediate Similarity	NPD3018	Phase 2
0.7021	Intermediate Similarity	NPD3620	Phase 2
0.7021	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2238	Phase 2
0.7021	Intermediate Similarity	NPD4140	Approved
0.7015	Intermediate Similarity	NPD3496	Discontinued
0.7007	Intermediate Similarity	NPD6362	Approved
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD2859	Approved
0.6985	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3536	Discontinued
0.6962	Remote Similarity	NPD3787	Discontinued
0.6957	Remote Similarity	NPD5647	Approved
0.6957	Remote Similarity	NPD3690	Phase 2
0.6957	Remote Similarity	NPD3691	Phase 2
0.6957	Remote Similarity	NPD6584	Phase 3
0.6957	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1423	Approved
0.6948	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2668	Approved
0.694	Remote Similarity	NPD1778	Approved
0.694	Remote Similarity	NPD2667	Approved
0.6934	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7685	Pre-registration
0.6929	Remote Similarity	NPD4625	Phase 3
0.6923	Remote Similarity	NPD1241	Discontinued
0.6923	Remote Similarity	NPD3054	Approved
0.6923	Remote Similarity	NPD3052	Approved
0.6917	Remote Similarity	NPD6581	Approved
0.6917	Remote Similarity	NPD6580	Approved
0.6913	Remote Similarity	NPD6799	Approved
0.6913	Remote Similarity	NPD7212	Phase 2
0.6913	Remote Similarity	NPD7213	Phase 3
0.6897	Remote Similarity	NPD2240	Approved
0.6897	Remote Similarity	NPD2239	Approved
0.6894	Remote Similarity	NPD3596	Phase 2
0.689	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1794	Approved
0.6884	Remote Similarity	NPD3094	Phase 2
0.6883	Remote Similarity	NPD1934	Approved
0.6871	Remote Similarity	NPD3060	Approved
0.6871	Remote Similarity	NPD5062	Approved
0.6871	Remote Similarity	NPD5061	Approved
0.6871	Remote Similarity	NPD7007	Discovery
0.6871	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5691	Approved
0.6861	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5327	Phase 3
0.6861	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD940	Approved
0.6855	Remote Similarity	NPD846	Approved
0.6849	Remote Similarity	NPD6002	Phase 3
0.6849	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6005	Phase 3
0.6849	Remote Similarity	NPD6004	Phase 3
0.6849	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5295	Discontinued
0.6842	Remote Similarity	NPD5536	Phase 2
0.6842	Remote Similarity	NPD3687	Approved
0.6842	Remote Similarity	NPD3686	Approved
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1535	Discovery
0.6835	Remote Similarity	NPD558	Phase 2
0.6831	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3020	Approved
0.6824	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6387	Discontinued
0.6818	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD709	Approved
0.6815	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4626	Approved
0.6815	Remote Similarity	NPD7075	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