NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	288.12
Volume:	308.183
LogP:	5.153
LogD:	4.28
LogS:	-6.806
# Rotatable Bonds:	0
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.604
Synthetic Accessibility Score:	3.243
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.053
MDCK Permeability:	1.4512005691358354e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.155
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	98.90740966796875%
Volume Distribution (VD):	1.301
Pgp-substrate:	2.3079018592834473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.713
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.469
CYP2C9-substrate:	0.519
CYP2D6-inhibitor:	0.611
CYP2D6-substrate:	0.422
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	8.272
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.276
Human Hepatotoxicity (H-HT):	0.419
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.256
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.158
Carcinogencity:	0.935
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.846

Download Data

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

Natural Product: NPC478166

Natural Product ID:	NPC478166
*Common Name:**	Xestosaprol M
IUPAC Name:	(1S)-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2,4,6,8,10,13(20),15-heptaen-12-one
Synonyms:	Xestosaprol M
Standard InCHIKey:	OGCUHWUZNVTRNC-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C20H16O2/c1-20-8-4-7-14-11-22-19(17(14)20)18(21)15-9-12-5-2-3-6-13(12)10-16(15)20/h2-3,5-6,9-11H,4,7-8H2,1H3/t20-/m0/s1
SMILES:	C[C@@]12CCCC3=COC(=C31)C(=O)C4=CC5=CC=CC=C5C=C24
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46849027
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908959]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Caledonian	n.a.	PMID[1453184]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Thai	n.a.	PMID[14640515]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	thai	n.a.	PMID[15217287]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1710256]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	coral reef habitat at a depth of approximately 20 m from the sea bed surface, at Sangalaki, Indonesia (2 04 59 N, 118 23 41 E)	1996-MAR	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31260310]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Philippine	n.a.	PMID[7473578]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798966]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	104000	nM	PMID[20503979]

☑ 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 NPC478166 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	498
0.1-0.2	1829
0.2-0.3	3920
0.3-0.4	11036
0.4-0.5	8161
0.5-0.6	6557
0.6-0.7	8962
0.7-0.8	1671
0.8-0.85	44
0.85-0.9	15
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC245522
0.9504	High Similarity	NPC114513
0.911	High Similarity	NPC192069
0.8973	High Similarity	NPC281398
0.8933	High Similarity	NPC88958
0.8867	High Similarity	NPC282793
0.8836	High Similarity	NPC27798
0.8836	High Similarity	NPC93241
0.8808	High Similarity	NPC469966
0.8733	High Similarity	NPC144010
0.8707	High Similarity	NPC290038
0.8684	High Similarity	NPC179170
0.8675	High Similarity	NPC145830
0.8639	High Similarity	NPC117674
0.8553	High Similarity	NPC473945
0.8542	High Similarity	NPC307401
0.8531	High Similarity	NPC324117
0.8497	Intermediate Similarity	NPC10429
0.8483	Intermediate Similarity	NPC186647
0.8477	Intermediate Similarity	NPC95526
0.8452	Intermediate Similarity	NPC221992
0.8428	Intermediate Similarity	NPC472784
0.8425	Intermediate Similarity	NPC233707
0.8425	Intermediate Similarity	NPC202260
0.8421	Intermediate Similarity	NPC472298
0.8403	Intermediate Similarity	NPC209858
0.8378	Intermediate Similarity	NPC263337
0.8369	Intermediate Similarity	NPC59502
0.8356	Intermediate Similarity	NPC177262
0.8333	Intermediate Similarity	NPC470406
0.8323	Intermediate Similarity	NPC25351
0.8313	Intermediate Similarity	NPC41689
0.8299	Intermediate Similarity	NPC265181
0.8289	Intermediate Similarity	NPC478163
0.828	Intermediate Similarity	NPC299094
0.828	Intermediate Similarity	NPC10051
0.8278	Intermediate Similarity	NPC233763
0.8273	Intermediate Similarity	NPC178382
0.8269	Intermediate Similarity	NPC478159
0.8269	Intermediate Similarity	NPC478161
0.8258	Intermediate Similarity	NPC27615
0.8258	Intermediate Similarity	NPC44606
0.821	Intermediate Similarity	NPC44602
0.8176	Intermediate Similarity	NPC472782
0.8176	Intermediate Similarity	NPC472781
0.8169	Intermediate Similarity	NPC428300
0.8165	Intermediate Similarity	NPC472823
0.8165	Intermediate Similarity	NPC123153
0.8138	Intermediate Similarity	NPC293253
0.8125	Intermediate Similarity	NPC476035
0.8125	Intermediate Similarity	NPC14499
0.8125	Intermediate Similarity	NPC475039
0.8125	Intermediate Similarity	NPC472783
0.8125	Intermediate Similarity	NPC472780
0.8117	Intermediate Similarity	NPC472839
0.8113	Intermediate Similarity	NPC472299
0.8112	Intermediate Similarity	NPC50583
0.8105	Intermediate Similarity	NPC71821
0.8101	Intermediate Similarity	NPC7059
0.8095	Intermediate Similarity	NPC217914
0.8092	Intermediate Similarity	NPC472836
0.8069	Intermediate Similarity	NPC164295
0.8058	Intermediate Similarity	NPC97566
0.8026	Intermediate Similarity	NPC158871
0.8025	Intermediate Similarity	NPC24232
0.8014	Intermediate Similarity	NPC183103
0.8	Intermediate Similarity	NPC8389
0.7988	Intermediate Similarity	NPC88593
0.7987	Intermediate Similarity	NPC290601
0.7975	Intermediate Similarity	NPC41719
0.7975	Intermediate Similarity	NPC23559
0.7974	Intermediate Similarity	NPC308006
0.795	Intermediate Similarity	NPC79571
0.7949	Intermediate Similarity	NPC228842
0.7949	Intermediate Similarity	NPC212257
0.7945	Intermediate Similarity	NPC279596
0.7945	Intermediate Similarity	NPC473982
0.7945	Intermediate Similarity	NPC239134
0.7922	Intermediate Similarity	NPC262198
0.7919	Intermediate Similarity	NPC471670
0.7914	Intermediate Similarity	NPC308156
0.7914	Intermediate Similarity	NPC277618
0.7914	Intermediate Similarity	NPC137710
0.7908	Intermediate Similarity	NPC53016
0.7904	Intermediate Similarity	NPC167340
0.7898	Intermediate Similarity	NPC472406
0.7888	Intermediate Similarity	NPC250076
0.7885	Intermediate Similarity	NPC474107
0.7882	Intermediate Similarity	NPC472533
0.7881	Intermediate Similarity	NPC476191
0.7881	Intermediate Similarity	NPC148374
0.7879	Intermediate Similarity	NPC472660
0.7879	Intermediate Similarity	NPC302392
0.7866	Intermediate Similarity	NPC473766
0.7866	Intermediate Similarity	NPC473753
0.7862	Intermediate Similarity	NPC75310
0.7862	Intermediate Similarity	NPC290927
0.7862	Intermediate Similarity	NPC208389
0.7848	Intermediate Similarity	NPC121615
0.7848	Intermediate Similarity	NPC471613
0.7848	Intermediate Similarity	NPC294511
0.7847	Intermediate Similarity	NPC246392
0.7843	Intermediate Similarity	NPC27220
0.784	Intermediate Similarity	NPC471003
0.7832	Intermediate Similarity	NPC473885
0.7832	Intermediate Similarity	NPC471074
0.7826	Intermediate Similarity	NPC473368
0.7826	Intermediate Similarity	NPC474611
0.7823	Intermediate Similarity	NPC471817
0.7821	Intermediate Similarity	NPC478018
0.7821	Intermediate Similarity	NPC252208
0.7821	Intermediate Similarity	NPC198427
0.7818	Intermediate Similarity	NPC255787
0.7818	Intermediate Similarity	NPC291742
0.7815	Intermediate Similarity	NPC62735
0.7812	Intermediate Similarity	NPC3898
0.7812	Intermediate Similarity	NPC104736
0.7812	Intermediate Similarity	NPC41880
0.7808	Intermediate Similarity	NPC57552
0.7806	Intermediate Similarity	NPC478160
0.7805	Intermediate Similarity	NPC475779
0.7799	Intermediate Similarity	NPC130015
0.7799	Intermediate Similarity	NPC38361
0.7793	Intermediate Similarity	NPC476917
0.7793	Intermediate Similarity	NPC327527
0.7793	Intermediate Similarity	NPC329707
0.7793	Intermediate Similarity	NPC26532
0.7792	Intermediate Similarity	NPC238843
0.7792	Intermediate Similarity	NPC472840
0.7792	Intermediate Similarity	NPC478164
0.7792	Intermediate Similarity	NPC199044
0.7791	Intermediate Similarity	NPC109238
0.7785	Intermediate Similarity	NPC472787
0.7785	Intermediate Similarity	NPC13282
0.7785	Intermediate Similarity	NPC135303
0.7785	Intermediate Similarity	NPC148423
0.7778	Intermediate Similarity	NPC74612
0.7778	Intermediate Similarity	NPC287559
0.7778	Intermediate Similarity	NPC149780
0.7771	Intermediate Similarity	NPC472841
0.7771	Intermediate Similarity	NPC280025
0.7771	Intermediate Similarity	NPC306788
0.777	Intermediate Similarity	NPC212918
0.7764	Intermediate Similarity	NPC81405
0.7764	Intermediate Similarity	NPC288353
0.7764	Intermediate Similarity	NPC304692
0.7763	Intermediate Similarity	NPC470407
0.7763	Intermediate Similarity	NPC218204
0.7763	Intermediate Similarity	NPC61157
0.7763	Intermediate Similarity	NPC56197
0.7763	Intermediate Similarity	NPC473681
0.7762	Intermediate Similarity	NPC83115
0.7756	Intermediate Similarity	NPC224418
0.7756	Intermediate Similarity	NPC471346
0.7755	Intermediate Similarity	NPC61788
0.7744	Intermediate Similarity	NPC193998
0.7742	Intermediate Similarity	NPC56731
0.7742	Intermediate Similarity	NPC185456
0.774	Intermediate Similarity	NPC198904
0.7736	Intermediate Similarity	NPC306011
0.7736	Intermediate Similarity	NPC189773
0.7736	Intermediate Similarity	NPC475777
0.7736	Intermediate Similarity	NPC472838
0.7736	Intermediate Similarity	NPC115869
0.7736	Intermediate Similarity	NPC472407
0.7736	Intermediate Similarity	NPC246164
0.7733	Intermediate Similarity	NPC46896
0.7733	Intermediate Similarity	NPC214572
0.7733	Intermediate Similarity	NPC22644
0.773	Intermediate Similarity	NPC232958
0.773	Intermediate Similarity	NPC246214
0.773	Intermediate Similarity	NPC65784
0.773	Intermediate Similarity	NPC18986
0.7727	Intermediate Similarity	NPC69755
0.7727	Intermediate Similarity	NPC243577
0.7727	Intermediate Similarity	NPC201297
0.7724	Intermediate Similarity	NPC177925
0.7724	Intermediate Similarity	NPC474737
0.7722	Intermediate Similarity	NPC226578
0.7719	Intermediate Similarity	NPC104682
0.7716	Intermediate Similarity	NPC140952
0.7716	Intermediate Similarity	NPC67197
0.7714	Intermediate Similarity	NPC243704
0.7711	Intermediate Similarity	NPC296558
0.7711	Intermediate Similarity	NPC298071
0.7708	Intermediate Similarity	NPC179354
0.7708	Intermediate Similarity	NPC303010
0.7707	Intermediate Similarity	NPC150215
0.7702	Intermediate Similarity	NPC233776
0.7701	Intermediate Similarity	NPC472358
0.7698	Intermediate Similarity	NPC79202
0.7698	Intermediate Similarity	NPC59035
0.7697	Intermediate Similarity	NPC132054
0.7692	Intermediate Similarity	NPC471292
0.7692	Intermediate Similarity	NPC62799
0.7692	Intermediate Similarity	NPC16922
0.7688	Intermediate Similarity	NPC471863
0.7688	Intermediate Similarity	NPC60211
0.7687	Intermediate Similarity	NPC476925
0.7682	Intermediate Similarity	NPC163029

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 NPC478166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	1016
0.2-0.3	1266
0.3-0.4	2786
0.4-0.5	2146
0.5-0.6	1097
0.6-0.7	348
0.7-0.8	50
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8299	Intermediate Similarity	NPD1471	Phase 3
0.7933	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7003	Approved
0.7756	Intermediate Similarity	NPD6273	Approved
0.7692	Intermediate Similarity	NPD3972	Approved
0.7606	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD3226	Approved
0.7365	Intermediate Similarity	NPD1247	Approved
0.7351	Intermediate Similarity	NPD8032	Phase 2
0.7349	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1876	Approved
0.7333	Intermediate Similarity	NPD7008	Discontinued
0.7283	Intermediate Similarity	NPD6764	Approved
0.7283	Intermediate Similarity	NPD6765	Approved
0.7278	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7262	Intermediate Similarity	NPD6959	Discontinued
0.726	Intermediate Similarity	NPD1281	Approved
0.726	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD919	Approved
0.7239	Intermediate Similarity	NPD6599	Discontinued
0.7233	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4628	Phase 3
0.7195	Intermediate Similarity	NPD7411	Suspended
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7179	Intermediate Similarity	NPD2796	Approved
0.7169	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD6280	Approved
0.7152	Intermediate Similarity	NPD6279	Approved
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6784	Approved
0.7119	Intermediate Similarity	NPD6785	Approved
0.7115	Intermediate Similarity	NPD2799	Discontinued
0.7115	Intermediate Similarity	NPD3748	Approved
0.7114	Intermediate Similarity	NPD1283	Approved
0.7113	Intermediate Similarity	NPD1241	Discontinued
0.711	Intermediate Similarity	NPD5844	Phase 1
0.7108	Intermediate Similarity	NPD5760	Phase 2
0.7108	Intermediate Similarity	NPD5761	Phase 2
0.7108	Intermediate Similarity	NPD7819	Suspended
0.7086	Intermediate Similarity	NPD6559	Discontinued
0.7083	Intermediate Similarity	NPD3749	Approved
0.7067	Intermediate Similarity	NPD3267	Approved
0.7067	Intermediate Similarity	NPD3266	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD2313	Discontinued
0.7055	Intermediate Similarity	NPD3869	Phase 3
0.7055	Intermediate Similarity	NPD3873	Phase 3
0.7055	Intermediate Similarity	NPD5691	Approved
0.7047	Intermediate Similarity	NPD5327	Phase 3
0.7044	Intermediate Similarity	NPD1243	Approved
0.7037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7768	Phase 2
0.7024	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2798	Approved
0.7019	Intermediate Similarity	NPD7236	Approved
0.7018	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5494	Approved
0.6981	Remote Similarity	NPD2897	Discontinued
0.6977	Remote Similarity	NPD3926	Phase 2
0.6968	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD2531	Phase 2
0.6962	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD3887	Approved
0.6948	Remote Similarity	NPD3268	Approved
0.6948	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD6355	Discontinued
0.6909	Remote Similarity	NPD7239	Suspended
0.6894	Remote Similarity	NPD3750	Approved
0.6886	Remote Similarity	NPD5889	Approved
0.6886	Remote Similarity	NPD5890	Approved
0.6883	Remote Similarity	NPD7095	Approved
0.6882	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD6799	Approved
0.6859	Remote Similarity	NPD4140	Approved
0.6859	Remote Similarity	NPD4060	Phase 1
0.6855	Remote Similarity	NPD5408	Approved
0.6855	Remote Similarity	NPD4476	Approved
0.6855	Remote Similarity	NPD5405	Approved
0.6855	Remote Similarity	NPD4477	Approved
0.6855	Remote Similarity	NPD5406	Approved
0.6855	Remote Similarity	NPD5404	Approved
0.6853	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6801	Discontinued
0.6842	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3764	Approved
0.6839	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5951	Approved
0.6824	Remote Similarity	NPD3882	Suspended
0.6824	Remote Similarity	NPD5585	Approved
0.6813	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2353	Approved
0.6802	Remote Similarity	NPD710	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1611	Approved
0.6795	Remote Similarity	NPD6233	Phase 2
0.6792	Remote Similarity	NPD4308	Phase 3
0.6788	Remote Similarity	NPD5049	Phase 3
0.6783	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4626	Approved
0.6779	Remote Similarity	NPD17	Approved
0.6779	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2296	Approved
0.6763	Remote Similarity	NPD8127	Discontinued
0.6755	Remote Similarity	NPD4107	Approved
0.6752	Remote Similarity	NPD3140	Approved
0.6752	Remote Similarity	NPD3142	Approved
0.675	Remote Similarity	NPD6099	Approved
0.675	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD2935	Discontinued
0.6747	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7427	Discontinued
0.6746	Remote Similarity	NPD7577	Discontinued
0.6739	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2797	Approved
0.6731	Remote Similarity	NPD7294	Phase 1
0.6727	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2533	Approved
0.6727	Remote Similarity	NPD2534	Approved
0.6727	Remote Similarity	NPD2532	Approved
0.6726	Remote Similarity	NPD6585	Discontinued
0.6724	Remote Similarity	NPD6232	Discontinued
0.6722	Remote Similarity	NPD8313	Approved
0.6722	Remote Similarity	NPD8312	Approved
0.6721	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6709	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7473	Discontinued
0.6688	Remote Similarity	NPD7713	Phase 3
0.6687	Remote Similarity	NPD8166	Discontinued
0.6684	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD2163	Approved
0.6667	Remote Similarity	NPD1607	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD7693	Approved
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6166	Phase 2
0.6647	Remote Similarity	NPD5403	Approved
0.6646	Remote Similarity	NPD1551	Phase 2
0.6646	Remote Similarity	NPD2354	Approved
0.6645	Remote Similarity	NPD1608	Approved
0.6632	Remote Similarity	NPD4482	Phase 3
0.663	Remote Similarity	NPD2968	Approved
0.663	Remote Similarity	NPD2971	Approved
0.6629	Remote Similarity	NPD7229	Phase 3
0.6627	Remote Similarity	NPD4380	Phase 2
0.6627	Remote Similarity	NPD5401	Approved
0.6626	Remote Similarity	NPD2800	Approved
0.6623	Remote Similarity	NPD3026	Approved
0.6623	Remote Similarity	NPD3023	Approved
0.6605	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5735	Approved
0.6601	Remote Similarity	NPD4359	Approved
0.6597	Remote Similarity	NPD2972	Approved
0.6597	Remote Similarity	NPD3533	Approved
0.6591	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.659	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1510	Phase 2
0.6582	Remote Similarity	NPD7961	Discontinued
0.6579	Remote Similarity	NPD6287	Discontinued
0.6579	Remote Similarity	NPD1201	Approved
0.6575	Remote Similarity	NPD5535	Approved
0.6575	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5402	Approved
0.6568	Remote Similarity	NPD2651	Approved
0.6568	Remote Similarity	NPD2649	Approved
0.6566	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7037	Approved
0.6562	Remote Similarity	NPD6353	Approved
0.6561	Remote Similarity	NPD4625	Phase 3
0.6556	Remote Similarity	NPD2932	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