NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	542.11
Volume:	500.742
LogP:	1.831
LogD:	0.681
LogS:	-4.211
# Rotatable Bonds:	6
TPSA:	216.58
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	4.121
Fsp3:	0.231
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.35
MDCK Permeability:	1.1503187124617398e-05
Pgp-inhibitor:	0.139
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.842
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	93.01264190673828%
Volume Distribution (VD):	0.656
Pgp-substrate:	15.060593605041504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.489
CYP1A2-substrate:	0.036
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.317
CYP2C9-substrate:	0.249
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.108
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	2.716
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.631
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.933
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.476
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC476623

Natural Product ID:	NPC476623
*Common Name:**	3'-O-benzoylmangiferin
IUPAC Name:	[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxyoxan-4-yl] benzoate
Synonyms:	3'-O-Benzoylmangiferin
Standard InCHIKey:	ANXOKJLEMDMTQX-FVFNWFHBSA-N
Standard InCHI:	InChI=1S/C26H22O13/c27-9-17-20(32)24(38-25(35)10-4-2-1-3-5-10)22(34)26(37-17)39-23-14(30)8-16-18(21(23)33)19(31)11-6-12(28)13(29)7-15(11)36-16/h1-8,17,20,22,24,26-30,32-34H,9H2/t17-,20-,22-,24+,26+/m1/s1
SMILES:	C1=CC=C(C=C1)C(=O)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)OC3=C(C4=C(C=C3O)OC5=CC(=C(C=C5C4=O)O)O)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45481966
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

*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
NPO33596	Arrabidaea patellifera	Species	Bignoniaceae	Eukaryota	leaves	Valle de Antn, los Llanitos, Panama	2003-APR	PMID[18950229]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		Ratio	=	0.35	n.a.	PMID[18950229]
NPT2	Others	Unspecified		EC50	=	1870	nM	PMID[18950229]

☑ 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 NPC476623 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	440
0.1-0.2	1939
0.2-0.3	4494
0.3-0.4	9723
0.4-0.5	8241
0.5-0.6	4239
0.6-0.7	5396
0.7-0.8	5121
0.8-0.85	1686
0.85-0.9	861
0.9-0.95	459
0.95-1	98

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476620
1.0	High Similarity	NPC476621
1.0	High Similarity	NPC476622
1.0	High Similarity	NPC476618
1.0	High Similarity	NPC476619
0.9879	High Similarity	NPC472387
0.9818	High Similarity	NPC472992
0.9818	High Similarity	NPC472991
0.9756	High Similarity	NPC47140
0.9756	High Similarity	NPC67134
0.9695	High Similarity	NPC471416
0.9695	High Similarity	NPC204937
0.9695	High Similarity	NPC34287
0.9695	High Similarity	NPC149011
0.9636	High Similarity	NPC472386
0.9634	High Similarity	NPC471457
0.9634	High Similarity	NPC170675
0.9634	High Similarity	NPC112755
0.9586	High Similarity	NPC36138
0.9581	High Similarity	NPC268533
0.9578	High Similarity	NPC172033
0.9578	High Similarity	NPC472993
0.9578	High Similarity	NPC51774
0.9578	High Similarity	NPC88560
0.9578	High Similarity	NPC236191
0.9578	High Similarity	NPC175230
0.9578	High Similarity	NPC239549
0.9576	High Similarity	NPC183357
0.9576	High Similarity	NPC22195
0.9576	High Similarity	NPC474434
0.9576	High Similarity	NPC44558
0.9576	High Similarity	NPC21190
0.9573	High Similarity	NPC45400
0.9529	High Similarity	NPC470416
0.9518	High Similarity	NPC301683
0.9518	High Similarity	NPC81332
0.9518	High Similarity	NPC205076
0.9518	High Similarity	NPC211594
0.9518	High Similarity	NPC267254
0.9518	High Similarity	NPC48773
0.9518	High Similarity	NPC3583
0.9518	High Similarity	NPC212038
0.9518	High Similarity	NPC307518
0.9518	High Similarity	NPC259152
0.9518	High Similarity	NPC262580
0.9518	High Similarity	NPC172807
0.9518	High Similarity	NPC254540
0.9518	High Similarity	NPC289396
0.9518	High Similarity	NPC271848
0.9515	High Similarity	NPC472381
0.9515	High Similarity	NPC183036
0.9515	High Similarity	NPC210042
0.9515	High Similarity	NPC472383
0.9515	High Similarity	NPC95855
0.9515	High Similarity	NPC229687
0.9464	High Similarity	NPC61904
0.9464	High Similarity	NPC472384
0.9464	High Similarity	NPC472382
0.9464	High Similarity	NPC144097
0.9464	High Similarity	NPC472380
0.9461	High Similarity	NPC204693
0.9458	High Similarity	NPC224462
0.9458	High Similarity	NPC51326
0.9458	High Similarity	NPC105511
0.9458	High Similarity	NPC231194
0.9455	High Similarity	NPC93099
0.9455	High Similarity	NPC45618
0.9455	High Similarity	NPC146792
0.9455	High Similarity	NPC116745
0.9455	High Similarity	NPC58716
0.9455	High Similarity	NPC14662
0.9451	High Similarity	NPC165720
0.9412	High Similarity	NPC469371
0.9408	High Similarity	NPC253521
0.9408	High Similarity	NPC37668
0.9408	High Similarity	NPC113836
0.9408	High Similarity	NPC217520
0.9408	High Similarity	NPC139571
0.9408	High Similarity	NPC35167
0.9405	High Similarity	NPC142996
0.9405	High Similarity	NPC43211
0.9405	High Similarity	NPC223426
0.9405	High Similarity	NPC210094
0.9405	High Similarity	NPC477848
0.9405	High Similarity	NPC115760
0.9405	High Similarity	NPC237435
0.9405	High Similarity	NPC34267
0.9405	High Similarity	NPC102028
0.9405	High Similarity	NPC214621
0.9405	High Similarity	NPC81042
0.9405	High Similarity	NPC135277
0.9405	High Similarity	NPC49344
0.9405	High Similarity	NPC101191
0.9401	High Similarity	NPC156977
0.9401	High Similarity	NPC475155
0.9398	High Similarity	NPC45638
0.9398	High Similarity	NPC105025
0.9398	High Similarity	NPC475942
0.9398	High Similarity	NPC58053
0.9398	High Similarity	NPC201292
0.9398	High Similarity	NPC226294
0.9398	High Similarity	NPC469931
0.9398	High Similarity	NPC186807
0.9398	High Similarity	NPC93337
0.9394	High Similarity	NPC5778
0.9394	High Similarity	NPC236934
0.939	High Similarity	NPC121290
0.939	High Similarity	NPC88043
0.939	High Similarity	NPC127415
0.939	High Similarity	NPC29830
0.936	High Similarity	NPC111490
0.936	High Similarity	NPC261623
0.9357	High Similarity	NPC470447
0.9357	High Similarity	NPC470445
0.9357	High Similarity	NPC470718
0.9357	High Similarity	NPC470449
0.9357	High Similarity	NPC470446
0.9353	High Similarity	NPC471030
0.9349	High Similarity	NPC233994
0.9349	High Similarity	NPC8573
0.9349	High Similarity	NPC169733
0.9349	High Similarity	NPC472385
0.9349	High Similarity	NPC198324
0.9349	High Similarity	NPC211532
0.9341	High Similarity	NPC245014
0.9341	High Similarity	NPC84265
0.9341	High Similarity	NPC282987
0.9341	High Similarity	NPC177731
0.9341	High Similarity	NPC293004
0.9341	High Similarity	NPC105095
0.9341	High Similarity	NPC44328
0.9341	High Similarity	NPC79056
0.9337	High Similarity	NPC243877
0.9337	High Similarity	NPC135345
0.9337	High Similarity	NPC229729
0.9329	High Similarity	NPC4013
0.9329	High Similarity	NPC90905
0.9329	High Similarity	NPC472876
0.931	High Similarity	NPC93065
0.931	High Similarity	NPC472720
0.931	High Similarity	NPC469652
0.931	High Similarity	NPC472724
0.931	High Similarity	NPC31208
0.931	High Similarity	NPC160543
0.931	High Similarity	NPC472721
0.9306	High Similarity	NPC179947
0.9302	High Similarity	NPC470720
0.9302	High Similarity	NPC21359
0.9302	High Similarity	NPC25946
0.9302	High Similarity	NPC470713
0.9302	High Similarity	NPC231254
0.9302	High Similarity	NPC460984
0.9302	High Similarity	NPC470717
0.9302	High Similarity	NPC470455
0.9302	High Similarity	NPC470451
0.9302	High Similarity	NPC49690
0.9294	High Similarity	NPC477895
0.9294	High Similarity	NPC258044
0.9294	High Similarity	NPC293626
0.9294	High Similarity	NPC217387
0.9294	High Similarity	NPC196127
0.9294	High Similarity	NPC267680
0.929	High Similarity	NPC264735
0.929	High Similarity	NPC253685
0.929	High Similarity	NPC472607
0.9286	High Similarity	NPC102851
0.9286	High Similarity	NPC476405
0.9286	High Similarity	NPC256760
0.9286	High Similarity	NPC117260
0.9286	High Similarity	NPC5786
0.9281	High Similarity	NPC43587
0.9281	High Similarity	NPC105283
0.9281	High Similarity	NPC195257
0.9281	High Similarity	NPC293629
0.9281	High Similarity	NPC86008
0.9281	High Similarity	NPC61791
0.9281	High Similarity	NPC209296
0.9277	High Similarity	NPC210073
0.9277	High Similarity	NPC115674
0.9277	High Similarity	NPC8856
0.9277	High Similarity	NPC99957
0.9277	High Similarity	NPC181616
0.9273	High Similarity	NPC191306
0.9273	High Similarity	NPC270335
0.9273	High Similarity	NPC168822
0.9253	High Similarity	NPC477081
0.9253	High Similarity	NPC240200
0.9253	High Similarity	NPC477083
0.9253	High Similarity	NPC158214
0.9253	High Similarity	NPC223534
0.9253	High Similarity	NPC473618
0.9253	High Similarity	NPC290289
0.9249	High Similarity	NPC470719
0.9249	High Similarity	NPC469650
0.9249	High Similarity	NPC473554
0.9249	High Similarity	NPC295625
0.9244	High Similarity	NPC35924
0.9244	High Similarity	NPC156785
0.9244	High Similarity	NPC97119
0.9244	High Similarity	NPC135831

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 NPC476623 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	958
0.2-0.3	2069
0.3-0.4	2675
0.4-0.5	1753
0.5-0.6	868
0.6-0.7	255
0.7-0.8	119
0.8-0.85	21
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9405	High Similarity	NPD4338	Clinical (unspecified phase)
0.9341	High Similarity	NPD7074	Phase 3
0.9281	High Similarity	NPD7054	Approved
0.9226	High Similarity	NPD7472	Approved
0.9222	High Similarity	NPD3818	Discontinued
0.9102	High Similarity	NPD6168	Clinical (unspecified phase)
0.9102	High Similarity	NPD6167	Clinical (unspecified phase)
0.9102	High Similarity	NPD6166	Phase 2
0.9059	High Similarity	NPD6797	Phase 2
0.9024	High Similarity	NPD4868	Clinical (unspecified phase)
0.9006	High Similarity	NPD7251	Discontinued
0.897	High Similarity	NPD4381	Clinical (unspecified phase)
0.8953	High Similarity	NPD7808	Phase 3
0.8837	High Similarity	NPD7993	Clinical (unspecified phase)
0.8727	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD2801	Approved
0.8613	High Similarity	NPD7804	Clinical (unspecified phase)
0.8563	High Similarity	NPD2393	Clinical (unspecified phase)
0.8506	High Similarity	NPD5844	Phase 1
0.8466	Intermediate Similarity	NPD6559	Discontinued
0.8421	Intermediate Similarity	NPD5494	Approved
0.8402	Intermediate Similarity	NPD5402	Approved
0.8402	Intermediate Similarity	NPD3817	Phase 2
0.8383	Intermediate Similarity	NPD4380	Phase 2
0.8373	Intermediate Similarity	NPD1653	Approved
0.8371	Intermediate Similarity	NPD8313	Approved
0.8371	Intermediate Similarity	NPD8312	Approved
0.8353	Intermediate Similarity	NPD3882	Suspended
0.8352	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD1465	Phase 2
0.8304	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD1511	Approved
0.8239	Intermediate Similarity	NPD7228	Approved
0.8225	Intermediate Similarity	NPD7411	Suspended
0.8218	Intermediate Similarity	NPD6232	Discontinued
0.8204	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7473	Discontinued
0.8144	Intermediate Similarity	NPD1512	Approved
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6801	Discontinued
0.8057	Intermediate Similarity	NPD7199	Phase 2
0.8057	Intermediate Similarity	NPD6959	Discontinued
0.8049	Intermediate Similarity	NPD1549	Phase 2
0.8034	Intermediate Similarity	NPD3751	Discontinued
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7819	Suspended
0.799	Intermediate Similarity	NPD8151	Discontinued
0.7988	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5403	Approved
0.7988	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD7685	Pre-registration
0.7943	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD8455	Phase 2
0.7917	Intermediate Similarity	NPD7435	Discontinued
0.7917	Intermediate Similarity	NPD6799	Approved
0.791	Intermediate Similarity	NPD3787	Discontinued
0.7908	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7783	Phase 2
0.7886	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD5401	Approved
0.787	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD37	Approved
0.7853	Intermediate Similarity	NPD6780	Approved
0.7853	Intermediate Similarity	NPD6782	Approved
0.7853	Intermediate Similarity	NPD6776	Approved
0.7853	Intermediate Similarity	NPD6777	Approved
0.7853	Intermediate Similarity	NPD6779	Approved
0.7853	Intermediate Similarity	NPD6778	Approved
0.7853	Intermediate Similarity	NPD6781	Approved
0.7829	Intermediate Similarity	NPD4966	Approved
0.7829	Intermediate Similarity	NPD4967	Phase 2
0.7829	Intermediate Similarity	NPD4965	Approved
0.7811	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6190	Approved
0.7771	Intermediate Similarity	NPD7266	Discontinued
0.7765	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7240	Approved
0.7758	Intermediate Similarity	NPD1510	Phase 2
0.7746	Intermediate Similarity	NPD6599	Discontinued
0.7732	Intermediate Similarity	NPD7696	Phase 3
0.7732	Intermediate Similarity	NPD7698	Approved
0.7732	Intermediate Similarity	NPD7697	Approved
0.7727	Intermediate Similarity	NPD7768	Phase 2
0.7711	Intermediate Similarity	NPD2796	Approved
0.7692	Intermediate Similarity	NPD7871	Phase 2
0.7692	Intermediate Similarity	NPD7870	Phase 2
0.7677	Intermediate Similarity	NPD7874	Approved
0.7677	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7701	Phase 2
0.7633	Intermediate Similarity	NPD3750	Approved
0.7633	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD943	Approved
0.7622	Intermediate Similarity	NPD1613	Approved
0.7622	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD2935	Discontinued
0.7592	Intermediate Similarity	NPD6534	Approved
0.7592	Intermediate Similarity	NPD6535	Approved
0.759	Intermediate Similarity	NPD6823	Phase 2
0.7576	Intermediate Similarity	NPD230	Phase 1
0.7576	Intermediate Similarity	NPD1933	Approved
0.7574	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3926	Phase 2
0.7565	Intermediate Similarity	NPD7700	Phase 2
0.7565	Intermediate Similarity	NPD7699	Phase 2
0.7556	Intermediate Similarity	NPD1247	Approved
0.7542	Intermediate Similarity	NPD919	Approved
0.7529	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.747	Intermediate Similarity	NPD447	Suspended
0.7463	Intermediate Similarity	NPD7801	Approved
0.7462	Intermediate Similarity	NPD7680	Approved
0.746	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7584	Approved
0.7436	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1607	Approved
0.7424	Intermediate Similarity	NPD8320	Phase 1
0.7424	Intermediate Similarity	NPD8319	Approved
0.7423	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD3226	Approved
0.7378	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6212	Phase 3
0.7358	Intermediate Similarity	NPD6213	Phase 3
0.7358	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2533	Approved
0.7356	Intermediate Similarity	NPD2534	Approved
0.7356	Intermediate Similarity	NPD2532	Approved
0.7337	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD3027	Phase 3
0.7326	Intermediate Similarity	NPD5953	Discontinued
0.7317	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD920	Approved
0.7257	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7549	Discontinued
0.7228	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7286	Phase 2
0.7186	Intermediate Similarity	NPD2313	Discontinued
0.7178	Intermediate Similarity	NPD7583	Approved
0.7156	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7135	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2799	Discontinued
0.7102	Intermediate Similarity	NPD7390	Discontinued
0.7097	Intermediate Similarity	NPD5242	Approved
0.7091	Intermediate Similarity	NPD1203	Approved
0.7088	Intermediate Similarity	NPD5353	Approved
0.7083	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7072	Intermediate Similarity	NPD6844	Discontinued
0.7069	Intermediate Similarity	NPD6674	Discontinued
0.7069	Intermediate Similarity	NPD1243	Approved
0.7069	Intermediate Similarity	NPD2800	Approved
0.7066	Intermediate Similarity	NPD6832	Phase 2
0.7066	Intermediate Similarity	NPD4908	Phase 1
0.7052	Intermediate Similarity	NPD2344	Approved
0.7044	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7033	Discontinued
0.7029	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4287	Approved
0.7016	Intermediate Similarity	NPD7039	Approved
0.7016	Intermediate Similarity	NPD7038	Approved
0.7012	Intermediate Similarity	NPD9269	Phase 2
0.7006	Intermediate Similarity	NPD9494	Approved
0.6995	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5006	Approved
0.698	Remote Similarity	NPD5005	Approved
0.6977	Remote Similarity	NPD7097	Phase 1
0.6977	Remote Similarity	NPD8059	Phase 3
0.6977	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7229	Phase 3
0.6952	Remote Similarity	NPD5710	Approved
0.6952	Remote Similarity	NPD5711	Approved
0.6951	Remote Similarity	NPD1091	Approved
0.6951	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6386	Approved
0.6923	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6385	Approved
0.6897	Remote Similarity	NPD5404	Approved
0.6897	Remote Similarity	NPD6099	Approved
0.6897	Remote Similarity	NPD6100	Approved
0.6897	Remote Similarity	NPD5405	Approved
0.6897	Remote Similarity	NPD5408	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