NPASS Compound

Structure

NPC131801 OpenBabel07101719512D 29 30 0 0 1 0 0 0 0 0999 V2000 -6.9936 0.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8259 0.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5666 -1.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 -1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3937 -1.8363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8207 -0.0729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2891 -0.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0117 -0.6607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5847 -2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7343 -0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8440 -1.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9485 -2.1984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5433 1.1081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4943 1.4172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 -1.3849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4943 -0.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0982 -0.2540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9305 -0.7971 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6711 -2.0173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5433 0.1081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8621 -2.6051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9666 -3.5996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0821 0.6081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 1 0 0 0 0 7 18 1 0 0 0 0 8 18 2 0 0 0 0 9 20 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 23 2 0 0 0 0 16 21 2 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 28 1 0 0 0 0 19 2 1 1 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 23 29 1 0 0 0 0 24 26 2 0 0 0 0 25 27 2 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.23
Volume:	437.912
LogP:	5.374
LogD:	4.718
LogS:	-4.959
# Rotatable Bonds:	11
TPSA:	63.58
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	3.538
Fsp3:	0.4
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:	-4.853
MDCK Permeability:	2.3422933736583218e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.24
20% Bioavailability (F20%):	0.331
30% Bioavailability (F30%):	0.092

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	93.59944915771484%
Volume Distribution (VD):	2.199
Pgp-substrate:	1.2674150466918945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.445
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.809
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.932
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.82
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	6.549
Half-life (T1/2):	0.767

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.716
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.93
Carcinogencity:	0.748
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC131801

Natural Product ID:	NPC131801
*Common Name:**	Psammocinin A1
IUPAC Name:	(5Z)-5-[(2R,6E,10E)-13-(furan-3-yl)-2,6,10-trimethyl-5-oxotrideca-6,10-dienylidene]-3-methylfuran-2-one
Synonyms:	Psammocinin A1
Standard InCHIKey:	BEQGJLVJAVYVFJ-OJOBNHNESA-N
Standard InCHI:	InChI=1S/C25H32O4/c1-18(8-6-10-22-13-14-28-17-22)7-5-9-20(3)24(26)12-11-19(2)15-23-16-21(4)25(27)29-23/h8-9,13-17,19H,5-7,10-12H2,1-4H3/b18-8+,20-9+,23-15-/t19-/m1/s1
SMILES:	C/C(=CCCc1ccoc1)/CC/C=C(C)/C(=O)CC[C@@H](C)/C=C1/C=C(C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456525
PubChem CID:	11234873
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270579]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	Korean	n.a.	PMID[23489626]
NPO33102	psammocinia sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621941]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[565958]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[565958]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	7.5	ug ml-1	PMID[565958]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	28.1	ug ml-1	PMID[565958]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	20.5	ug ml-1	PMID[565958]

☑ 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 NPC131801 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	248
0.1-0.2	1526
0.2-0.3	4963
0.3-0.4	10957
0.4-0.5	9839
0.5-0.6	11137
0.6-0.7	3545
0.7-0.8	397
0.8-0.85	51
0.85-0.9	16
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC473969
0.9391	High Similarity	NPC289911
0.9391	High Similarity	NPC283284
0.931	High Similarity	NPC475818
0.9304	High Similarity	NPC474136
0.9273	High Similarity	NPC105249
0.9174	High Similarity	NPC473356
0.9174	High Similarity	NPC471521
0.9153	High Similarity	NPC71274
0.9153	High Similarity	NPC75557
0.9145	High Similarity	NPC476351
0.9138	High Similarity	NPC1848
0.9076	High Similarity	NPC329922
0.9076	High Similarity	NPC474260
0.9076	High Similarity	NPC329694
0.9076	High Similarity	NPC81912
0.9052	High Similarity	NPC474817
0.8966	High Similarity	NPC4898
0.8957	High Similarity	NPC144745
0.8957	High Similarity	NPC208906
0.8926	High Similarity	NPC474438
0.8926	High Similarity	NPC474279
0.885	High Similarity	NPC1811
0.885	High Similarity	NPC26157
0.8843	High Similarity	NPC476016
0.8783	High Similarity	NPC28054
0.8718	High Similarity	NPC21831
0.8718	High Similarity	NPC187547
0.8689	High Similarity	NPC474830
0.8678	High Similarity	NPC474829
0.8632	High Similarity	NPC217180
0.8632	High Similarity	NPC312525
0.8595	High Similarity	NPC65735
0.8595	High Similarity	NPC188377
0.8537	High Similarity	NPC137570
0.8504	High Similarity	NPC288209
0.8475	Intermediate Similarity	NPC227660
0.8462	Intermediate Similarity	NPC205523
0.845	Intermediate Similarity	NPC170604
0.845	Intermediate Similarity	NPC215109
0.8443	Intermediate Similarity	NPC243269
0.843	Intermediate Similarity	NPC263870
0.8421	Intermediate Similarity	NPC177331
0.8403	Intermediate Similarity	NPC243704
0.839	Intermediate Similarity	NPC45536
0.8387	Intermediate Similarity	NPC471501
0.8387	Intermediate Similarity	NPC471554
0.8387	Intermediate Similarity	NPC473355
0.8387	Intermediate Similarity	NPC471573
0.8374	Intermediate Similarity	NPC471559
0.8374	Intermediate Similarity	NPC179354
0.8361	Intermediate Similarity	NPC16922
0.8346	Intermediate Similarity	NPC471817
0.8295	Intermediate Similarity	NPC14650
0.8293	Intermediate Similarity	NPC118853
0.8281	Intermediate Similarity	NPC470740
0.8279	Intermediate Similarity	NPC317217
0.8268	Intermediate Similarity	NPC17681
0.8268	Intermediate Similarity	NPC136340
0.8235	Intermediate Similarity	NPC476031
0.8235	Intermediate Similarity	NPC476014
0.822	Intermediate Similarity	NPC292036
0.8203	Intermediate Similarity	NPC45358
0.8203	Intermediate Similarity	NPC97740
0.816	Intermediate Similarity	NPC216810
0.816	Intermediate Similarity	NPC74612
0.816	Intermediate Similarity	NPC138139
0.816	Intermediate Similarity	NPC46536
0.8151	Intermediate Similarity	NPC150895
0.8145	Intermediate Similarity	NPC477038
0.8145	Intermediate Similarity	NPC477965
0.814	Intermediate Similarity	NPC474407
0.814	Intermediate Similarity	NPC474425
0.814	Intermediate Similarity	NPC474426
0.813	Intermediate Similarity	NPC477967
0.813	Intermediate Similarity	NPC471549
0.813	Intermediate Similarity	NPC473379
0.8125	Intermediate Similarity	NPC475092
0.8125	Intermediate Similarity	NPC89133
0.8125	Intermediate Similarity	NPC298190
0.8095	Intermediate Similarity	NPC95567
0.8095	Intermediate Similarity	NPC83178
0.8095	Intermediate Similarity	NPC319140
0.8092	Intermediate Similarity	NPC146872
0.8087	Intermediate Similarity	NPC140688
0.8051	Intermediate Similarity	NPC22678
0.8047	Intermediate Similarity	NPC21460
0.8033	Intermediate Similarity	NPC67345
0.8033	Intermediate Similarity	NPC244862
0.8031	Intermediate Similarity	NPC112706
0.8031	Intermediate Similarity	NPC207294
0.8015	Intermediate Similarity	NPC159786
0.8015	Intermediate Similarity	NPC92941
0.7985	Intermediate Similarity	NPC56197
0.797	Intermediate Similarity	NPC236532
0.7969	Intermediate Similarity	NPC208389
0.7955	Intermediate Similarity	NPC303217
0.7951	Intermediate Similarity	NPC291619
0.7951	Intermediate Similarity	NPC254958
0.7951	Intermediate Similarity	NPC293424
0.7937	Intermediate Similarity	NPC471074
0.7937	Intermediate Similarity	NPC473885
0.7923	Intermediate Similarity	NPC473982
0.7903	Intermediate Similarity	NPC79557
0.7895	Intermediate Similarity	NPC307401
0.7895	Intermediate Similarity	NPC470742
0.7895	Intermediate Similarity	NPC42400
0.7891	Intermediate Similarity	NPC476917
0.7891	Intermediate Similarity	NPC477123
0.7891	Intermediate Similarity	NPC477039
0.7891	Intermediate Similarity	NPC477040
0.7891	Intermediate Similarity	NPC327527
0.7891	Intermediate Similarity	NPC477966
0.7883	Intermediate Similarity	NPC307346
0.7883	Intermediate Similarity	NPC267004
0.7883	Intermediate Similarity	NPC261733
0.7883	Intermediate Similarity	NPC218712
0.7876	Intermediate Similarity	NPC156768
0.7845	Intermediate Similarity	NPC42471
0.784	Intermediate Similarity	NPC36255
0.7836	Intermediate Similarity	NPC220094
0.7836	Intermediate Similarity	NPC476943
0.7826	Intermediate Similarity	NPC34056
0.7812	Intermediate Similarity	NPC141059
0.781	Intermediate Similarity	NPC80635
0.7805	Intermediate Similarity	NPC87466
0.7795	Intermediate Similarity	NPC230979
0.7786	Intermediate Similarity	NPC15083
0.7786	Intermediate Similarity	NPC470976
0.7786	Intermediate Similarity	NPC196979
0.7786	Intermediate Similarity	NPC470977
0.7778	Intermediate Similarity	NPC107571
0.7778	Intermediate Similarity	NPC90953
0.7778	Intermediate Similarity	NPC202260
0.7778	Intermediate Similarity	NPC474615
0.7769	Intermediate Similarity	NPC476925
0.7761	Intermediate Similarity	NPC310830
0.7761	Intermediate Similarity	NPC473268
0.776	Intermediate Similarity	NPC97566
0.7754	Intermediate Similarity	NPC238843
0.7754	Intermediate Similarity	NPC199044
0.7742	Intermediate Similarity	NPC137710
0.7734	Intermediate Similarity	NPC23086
0.7734	Intermediate Similarity	NPC83301
0.7727	Intermediate Similarity	NPC293253
0.7727	Intermediate Similarity	NPC471006
0.7717	Intermediate Similarity	NPC83115
0.771	Intermediate Similarity	NPC183348
0.771	Intermediate Similarity	NPC282230
0.7698	Intermediate Similarity	NPC270807
0.7698	Intermediate Similarity	NPC195920
0.7698	Intermediate Similarity	NPC174915
0.7698	Intermediate Similarity	NPC56731
0.7692	Intermediate Similarity	NPC198904
0.7692	Intermediate Similarity	NPC59502
0.7681	Intermediate Similarity	NPC267632
0.7681	Intermediate Similarity	NPC223415
0.7681	Intermediate Similarity	NPC22248
0.7669	Intermediate Similarity	NPC106247
0.7661	Intermediate Similarity	NPC206007
0.7643	Intermediate Similarity	NPC471292
0.7642	Intermediate Similarity	NPC76844
0.7642	Intermediate Similarity	NPC474987
0.7642	Intermediate Similarity	NPC59035
0.7642	Intermediate Similarity	NPC79202
0.7634	Intermediate Similarity	NPC66246
0.7634	Intermediate Similarity	NPC170546
0.763	Intermediate Similarity	NPC186626
0.763	Intermediate Similarity	NPC286130
0.7626	Intermediate Similarity	NPC142113
0.7623	Intermediate Similarity	NPC252004
0.7615	Intermediate Similarity	NPC26532
0.7609	Intermediate Similarity	NPC121158
0.7606	Intermediate Similarity	NPC329180
0.7597	Intermediate Similarity	NPC52035
0.7591	Intermediate Similarity	NPC282973
0.7591	Intermediate Similarity	NPC148374
0.7589	Intermediate Similarity	NPC216755
0.7589	Intermediate Similarity	NPC71821
0.7589	Intermediate Similarity	NPC471174
0.7578	Intermediate Similarity	NPC130275
0.7576	Intermediate Similarity	NPC61788
0.7576	Intermediate Similarity	NPC477645
0.7561	Intermediate Similarity	NPC11821
0.7557	Intermediate Similarity	NPC120836
0.7557	Intermediate Similarity	NPC223063
0.7554	Intermediate Similarity	NPC254198
0.7554	Intermediate Similarity	NPC470741
0.7554	Intermediate Similarity	NPC110305
0.7538	Intermediate Similarity	NPC290955
0.7538	Intermediate Similarity	NPC246392
0.7536	Intermediate Similarity	NPC20500
0.7535	Intermediate Similarity	NPC93666
0.7522	Intermediate Similarity	NPC146316
0.7521	Intermediate Similarity	NPC277525
0.7519	Intermediate Similarity	NPC471545
0.7519	Intermediate Similarity	NPC471544
0.7519	Intermediate Similarity	NPC473344
0.7518	Intermediate Similarity	NPC475864
0.7518	Intermediate Similarity	NPC276676

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 NPC131801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1054
0.2-0.3	2018
0.3-0.4	2960
0.4-0.5	1857
0.5-0.6	830
0.6-0.7	192
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7518	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD6832	Phase 2
0.7395	Intermediate Similarity	NPD3134	Approved
0.7258	Intermediate Similarity	NPD1241	Discontinued
0.719	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7099	Intermediate Similarity	NPD9717	Approved
0.7068	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2799	Discontinued
0.694	Remote Similarity	NPD3266	Approved
0.694	Remote Similarity	NPD3267	Approved
0.6939	Remote Similarity	NPD920	Approved
0.6923	Remote Similarity	NPD5585	Approved
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1876	Approved
0.6842	Remote Similarity	NPD3972	Approved
0.6835	Remote Similarity	NPD4307	Phase 2
0.6828	Remote Similarity	NPD3887	Approved
0.6815	Remote Similarity	NPD1203	Approved
0.6815	Remote Similarity	NPD2797	Approved
0.6812	Remote Similarity	NPD2313	Discontinued
0.6812	Remote Similarity	NPD3268	Approved
0.6803	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1933	Approved
0.6786	Remote Similarity	NPD6355	Discontinued
0.6776	Remote Similarity	NPD5761	Phase 2
0.6776	Remote Similarity	NPD5760	Phase 2
0.6772	Remote Similarity	NPD5535	Approved
0.6769	Remote Similarity	NPD9092	Discovery
0.6765	Remote Similarity	NPD2798	Approved
0.6765	Remote Similarity	NPD5647	Approved
0.6759	Remote Similarity	NPD4628	Phase 3
0.6748	Remote Similarity	NPD9697	Approved
0.6742	Remote Similarity	NPD17	Approved
0.672	Remote Similarity	NPD2182	Approved
0.6718	Remote Similarity	NPD9545	Approved
0.6714	Remote Similarity	NPD3142	Approved
0.6714	Remote Similarity	NPD3140	Approved
0.6713	Remote Similarity	NPD1551	Phase 2
0.6692	Remote Similarity	NPD3496	Discontinued
0.6691	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD1243	Approved
0.6667	Remote Similarity	NPD4359	Approved
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD2353	Approved
0.6644	Remote Similarity	NPD6273	Approved
0.6643	Remote Similarity	NPD4308	Phase 3
0.6643	Remote Similarity	NPD8032	Phase 2
0.6643	Remote Similarity	NPD3748	Approved
0.6623	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6799	Approved
0.6617	Remote Similarity	NPD1778	Approved
0.6612	Remote Similarity	NPD1238	Approved
0.6603	Remote Similarity	NPD919	Approved
0.6597	Remote Similarity	NPD2796	Approved
0.6593	Remote Similarity	NPD1608	Approved
0.6591	Remote Similarity	NPD1894	Discontinued
0.6571	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6798	Discontinued
0.6571	Remote Similarity	NPD411	Approved
0.6565	Remote Similarity	NPD9493	Approved
0.6554	Remote Similarity	NPD7440	Discontinued
0.6552	Remote Similarity	NPD6005	Phase 3
0.6552	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6004	Phase 3
0.6552	Remote Similarity	NPD6002	Phase 3
0.6552	Remote Similarity	NPD2346	Discontinued
0.6552	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4622	Approved
0.6549	Remote Similarity	NPD4618	Approved
0.6549	Remote Similarity	NPD447	Suspended
0.6541	Remote Similarity	NPD5691	Approved
0.6538	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2067	Discontinued
0.6515	Remote Similarity	NPD5536	Phase 2
0.6512	Remote Similarity	NPD7843	Approved
0.6503	Remote Similarity	NPD6653	Approved
0.6497	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.649	Remote Similarity	NPD3869	Phase 3
0.649	Remote Similarity	NPD3873	Phase 3
0.6486	Remote Similarity	NPD2354	Approved
0.6486	Remote Similarity	NPD2309	Approved
0.6483	Remote Similarity	NPD2935	Discontinued
0.6479	Remote Similarity	NPD2979	Phase 3
0.6478	Remote Similarity	NPD6808	Phase 2
0.6475	Remote Similarity	NPD9494	Approved
0.6471	Remote Similarity	NPD6599	Discontinued
0.6463	Remote Similarity	NPD6765	Approved
0.6463	Remote Similarity	NPD6764	Approved
0.6458	Remote Similarity	NPD5689	Approved
0.6458	Remote Similarity	NPD5688	Approved
0.6457	Remote Similarity	NPD2684	Approved
0.6452	Remote Similarity	NPD7819	Suspended
0.6452	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3847	Discontinued
0.6429	Remote Similarity	NPD7411	Suspended
0.6424	Remote Similarity	NPD2186	Approved
0.642	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3750	Approved
0.6414	Remote Similarity	NPD7033	Discontinued
0.6408	Remote Similarity	NPD4062	Phase 3
0.6408	Remote Similarity	NPD6233	Phase 2
0.6405	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7458	Discontinued
0.64	Remote Similarity	NPD164	Approved
0.64	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD1281	Approved
0.6387	Remote Similarity	NPD6280	Approved
0.6387	Remote Similarity	NPD6279	Approved
0.6382	Remote Similarity	NPD5403	Approved
0.6382	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3225	Approved
0.637	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD8434	Phase 2
0.6364	Remote Similarity	NPD7157	Approved
0.6358	Remote Similarity	NPD5401	Approved
0.635	Remote Similarity	NPD1481	Phase 2
0.6345	Remote Similarity	NPD7097	Phase 1
0.6338	Remote Similarity	NPD3764	Approved
0.6329	Remote Similarity	NPD7075	Discontinued
0.6323	Remote Similarity	NPD5890	Approved
0.6323	Remote Similarity	NPD5889	Approved
0.6316	Remote Similarity	NPD5049	Phase 3
0.6312	Remote Similarity	NPD2614	Approved
0.631	Remote Similarity	NPD6784	Approved
0.631	Remote Similarity	NPD6785	Approved
0.6309	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD7003	Approved
0.6309	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD4110	Phase 3
0.6294	Remote Similarity	NPD4870	Approved
0.6286	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1549	Phase 2
0.6282	Remote Similarity	NPD6801	Discontinued
0.6277	Remote Similarity	NPD1535	Discovery
0.6277	Remote Similarity	NPD6287	Discontinued
0.6268	Remote Similarity	NPD7095	Approved
0.6268	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD7768	Phase 2
0.6265	Remote Similarity	NPD6559	Discontinued
0.6259	Remote Similarity	NPD2531	Phase 2
0.6259	Remote Similarity	NPD4477	Approved
0.6259	Remote Similarity	NPD1283	Approved
0.6259	Remote Similarity	NPD4476	Approved
0.6259	Remote Similarity	NPD2438	Suspended
0.625	Remote Similarity	NPD4626	Approved
0.625	Remote Similarity	NPD4662	Approved
0.625	Remote Similarity	NPD4661	Approved
0.6241	Remote Similarity	NPD454	Approved
0.6234	Remote Similarity	NPD957	Approved
0.6226	Remote Similarity	NPD3749	Approved
0.6225	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1296	Phase 2
0.6216	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1247	Approved
0.6194	Remote Similarity	NPD3226	Approved
0.619	Remote Similarity	NPD9261	Approved
0.619	Remote Similarity	NPD6647	Phase 2
0.6187	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7577	Discontinued
0.6176	Remote Similarity	NPD1651	Approved
0.6174	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2897	Discontinued
0.6174	Remote Similarity	NPD5958	Discontinued
0.6173	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6585	Discontinued
0.6149	Remote Similarity	NPD5494	Approved
0.6149	Remote Similarity	NPD2239	Approved
0.6149	Remote Similarity	NPD2240	Approved
0.6144	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD4140	Approved
0.6138	Remote Similarity	NPD1240	Approved
0.6138	Remote Similarity	NPD4060	Phase 1
0.6127	Remote Similarity	NPD2237	Approved
0.6125	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD290	Approved
0.6115	Remote Similarity	NPD6385	Approved
0.6115	Remote Similarity	NPD6873	Phase 2
0.6115	Remote Similarity	NPD958	Approved
0.6115	Remote Similarity	NPD6386	Approved
0.6111	Remote Similarity	NPD5262	Discontinued
0.6107	Remote Similarity	NPD5762	Approved
0.6107	Remote Similarity	NPD5763	Approved
0.6101	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD3817	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data