NPASS Compound

Structure

NPC471650 OpenBabel07101719522D 33 36 0 0 0 0 0 0 0 0999 V2000 14.3899 2.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4009 3.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6375 0.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8021 2.0544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6266 0.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2198 1.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0388 -0.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4565 -1.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7928 -1.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9838 -0.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8076 2.1589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0442 -0.2681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4619 -0.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9619 -0.1066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 4 2 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 20 2 0 0 0 0 7 21 1 0 0 0 0 8 9 2 0 0 0 0 8 22 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 28 1 0 0 0 0 11 13 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 29 1 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 16 24 2 0 0 0 0 17 22 1 0 0 0 0 17 28 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 19 33 1 0 0 0 0 23 27 1 0 0 0 0 24 31 1 0 0 0 0 25 26 2 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 29 1 0 0 0 0 27 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.24
Volume:	474.749
LogP:	4.674
LogD:	4.255
LogS:	-4.662
# Rotatable Bonds:	9
TPSA:	55.15
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	2.994
Fsp3:	0.37
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:	-4.882
MDCK Permeability:	2.1030091374996118e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	97.8781967163086%
Volume Distribution (VD):	2.247
Pgp-substrate:	1.3938959836959839%

ADMET: Metabolism

CYP1A2-inhibitor:	0.614
CYP1A2-substrate:	0.365
CYP2C19-inhibitor:	0.878
CYP2C19-substrate:	0.647
CYP2C9-inhibitor:	0.395
CYP2C9-substrate:	0.455
CYP2D6-inhibitor:	0.983
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.575

ADMET: Excretion

Clearance (CL):	11.026
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.948
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.783
Maximum Recommended Daily Dose:	0.856
Skin Sensitization:	0.151
Carcinogencity:	0.592
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC471650

Natural Product ID:	NPC471650
*Common Name:**	[4-(1,3-Benzodioxol-5-Ylmethyl)Piperazin-1-Yl]-[5-[(1E,5Z)-2,6-Dimethylocta-1,5,7-Trienyl]Furan-3-Yl]Methanone
IUPAC Name:	[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-[5-[(1E,5Z)-2,6-dimethylocta-1,5,7-trienyl]furan-3-yl]methanone
Synonyms:
Standard InCHIKey:	XKWPNWVIZUVFJG-OZRABKAVSA-N
Standard InCHI:	InChI=1S/C27H32N2O4/c1-4-20(2)6-5-7-21(3)14-24-16-23(18-31-24)27(30)29-12-10-28(11-13-29)17-22-8-9-25-26(15-22)33-19-32-25/h4,6,8-9,14-16,18H,1,5,7,10-13,17,19H2,2-3H3/b20-6-,21-14+
SMILES:	C=C/C(=CCC/C(=C/c1occ(c1)C(=O)N1CCN(CC1)Cc1ccc2c(c1)OCO2)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3087066
PubChem CID:	72543913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO32605	sinularia kavarattiensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24144848]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	15900.0	nM	PMID[486018]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	50800.0	nM	PMID[486018]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	44200.0	nM	PMID[486018]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	45500.0	nM	PMID[486018]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	17900.0	nM	PMID[486018]

☑ 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 NPC471650 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	312
0.1-0.2	1838
0.2-0.3	8483
0.3-0.4	9674
0.4-0.5	7090
0.5-0.6	13033
0.6-0.7	2147
0.7-0.8	115
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8623	High Similarity	NPC471649
0.8229	Intermediate Similarity	NPC471651
0.8144	Intermediate Similarity	NPC471646
0.8144	Intermediate Similarity	NPC471647
0.7946	Intermediate Similarity	NPC116007
0.7946	Intermediate Similarity	NPC83511
0.7895	Intermediate Similarity	NPC477258
0.788	Intermediate Similarity	NPC27887
0.7874	Intermediate Similarity	NPC470708
0.7861	Intermediate Similarity	NPC477259
0.7861	Intermediate Similarity	NPC169387
0.7833	Intermediate Similarity	NPC471648
0.7717	Intermediate Similarity	NPC308267
0.7701	Intermediate Similarity	NPC102760
0.7692	Intermediate Similarity	NPC86469
0.7624	Intermediate Similarity	NPC231198
0.7619	Intermediate Similarity	NPC470707
0.7619	Intermediate Similarity	NPC220923
0.7609	Intermediate Similarity	NPC303581
0.7609	Intermediate Similarity	NPC67978
0.7605	Intermediate Similarity	NPC251454
0.7605	Intermediate Similarity	NPC255817
0.7605	Intermediate Similarity	NPC73883
0.7605	Intermediate Similarity	NPC136330
0.7605	Intermediate Similarity	NPC196609
0.7605	Intermediate Similarity	NPC205178
0.7605	Intermediate Similarity	NPC277042
0.7605	Intermediate Similarity	NPC230698
0.7577	Intermediate Similarity	NPC24228
0.756	Intermediate Similarity	NPC99078
0.7545	Intermediate Similarity	NPC167096
0.7543	Intermediate Similarity	NPC470088
0.7515	Intermediate Similarity	NPC252107
0.7514	Intermediate Similarity	NPC469978
0.75	Intermediate Similarity	NPC180647
0.7487	Intermediate Similarity	NPC222524
0.7461	Intermediate Similarity	NPC226708
0.7458	Intermediate Similarity	NPC119669
0.7449	Intermediate Similarity	NPC124302
0.7449	Intermediate Similarity	NPC70290
0.7449	Intermediate Similarity	NPC215098
0.7449	Intermediate Similarity	NPC46744
0.7449	Intermediate Similarity	NPC73020
0.7449	Intermediate Similarity	NPC14622
0.744	Intermediate Similarity	NPC103947
0.744	Intermediate Similarity	NPC328419
0.744	Intermediate Similarity	NPC193673
0.744	Intermediate Similarity	NPC45783
0.744	Intermediate Similarity	NPC94280
0.744	Intermediate Similarity	NPC159150
0.7412	Intermediate Similarity	NPC225745
0.74	Intermediate Similarity	NPC268077
0.7396	Intermediate Similarity	NPC96406
0.7387	Intermediate Similarity	NPC119818
0.7387	Intermediate Similarity	NPC328700
0.7387	Intermediate Similarity	NPC202771
0.7387	Intermediate Similarity	NPC2173
0.7374	Intermediate Similarity	NPC226652
0.7374	Intermediate Similarity	NPC120671
0.7374	Intermediate Similarity	NPC72788
0.7374	Intermediate Similarity	NPC314100
0.7354	Intermediate Similarity	NPC121400
0.7353	Intermediate Similarity	NPC145446
0.7353	Intermediate Similarity	NPC469808
0.7353	Intermediate Similarity	NPC137172
0.735	Intermediate Similarity	NPC41216
0.735	Intermediate Similarity	NPC207971
0.7321	Intermediate Similarity	NPC318862
0.7321	Intermediate Similarity	NPC217574
0.731	Intermediate Similarity	NPC28641
0.731	Intermediate Similarity	NPC95366
0.731	Intermediate Similarity	NPC194359
0.731	Intermediate Similarity	NPC248505
0.7303	Intermediate Similarity	NPC223125
0.7236	Intermediate Similarity	NPC207239
0.7228	Intermediate Similarity	NPC153631
0.7222	Intermediate Similarity	NPC223124
0.7213	Intermediate Similarity	NPC106786
0.7191	Intermediate Similarity	NPC475959
0.7189	Intermediate Similarity	NPC59567
0.7186	Intermediate Similarity	NPC112937
0.7186	Intermediate Similarity	NPC71124
0.7181	Intermediate Similarity	NPC474708
0.7179	Intermediate Similarity	NPC166979
0.7179	Intermediate Similarity	NPC208890
0.7179	Intermediate Similarity	NPC45389
0.7174	Intermediate Similarity	NPC135006
0.7172	Intermediate Similarity	NPC125924
0.7166	Intermediate Similarity	NPC284842
0.7151	Intermediate Similarity	NPC306669
0.7151	Intermediate Similarity	NPC7018
0.7151	Intermediate Similarity	NPC416184
0.7143	Intermediate Similarity	NPC169742
0.7143	Intermediate Similarity	NPC78733
0.7128	Intermediate Similarity	NPC475845
0.7127	Intermediate Similarity	NPC148898
0.7127	Intermediate Similarity	NPC471073
0.7127	Intermediate Similarity	NPC233029
0.7127	Intermediate Similarity	NPC270811
0.7127	Intermediate Similarity	NPC210148
0.7121	Intermediate Similarity	NPC469816
0.7121	Intermediate Similarity	NPC469815
0.712	Intermediate Similarity	NPC5167
0.7107	Intermediate Similarity	NPC475597
0.7107	Intermediate Similarity	NPC473716
0.7107	Intermediate Similarity	NPC63152
0.7104	Intermediate Similarity	NPC234392
0.7104	Intermediate Similarity	NPC31311
0.7097	Intermediate Similarity	NPC471652
0.7076	Intermediate Similarity	NPC266425
0.7074	Intermediate Similarity	NPC57812
0.7074	Intermediate Similarity	NPC474324
0.7071	Intermediate Similarity	NPC254957
0.7065	Intermediate Similarity	NPC5374
0.7049	Intermediate Similarity	NPC41178
0.7049	Intermediate Similarity	NPC138487
0.7049	Intermediate Similarity	NPC216459
0.7049	Intermediate Similarity	NPC93593
0.7037	Intermediate Similarity	NPC241055
0.7027	Intermediate Similarity	NPC477080
0.7026	Intermediate Similarity	NPC475981
0.7026	Intermediate Similarity	NPC474746
0.7016	Intermediate Similarity	NPC4669
0.7011	Intermediate Similarity	NPC146288
0.7005	Intermediate Similarity	NPC141440
0.699	Remote Similarity	NPC18306
0.6982	Remote Similarity	NPC172403
0.6966	Remote Similarity	NPC244338
0.6959	Remote Similarity	NPC474745
0.6954	Remote Similarity	NPC230098
0.6943	Remote Similarity	NPC85613
0.6943	Remote Similarity	NPC474470
0.6915	Remote Similarity	NPC33256
0.6907	Remote Similarity	NPC474325
0.6898	Remote Similarity	NPC26353
0.6898	Remote Similarity	NPC97072
0.6898	Remote Similarity	NPC215829
0.6897	Remote Similarity	NPC123859
0.6891	Remote Similarity	NPC304675
0.6889	Remote Similarity	NPC327052
0.6887	Remote Similarity	NPC38964
0.6885	Remote Similarity	NPC476579
0.6878	Remote Similarity	NPC35345
0.6878	Remote Similarity	NPC168409
0.6875	Remote Similarity	NPC231572
0.6863	Remote Similarity	NPC475654
0.6859	Remote Similarity	NPC158148
0.6859	Remote Similarity	NPC266176
0.6859	Remote Similarity	NPC290759
0.6859	Remote Similarity	NPC82533
0.6856	Remote Similarity	NPC237044
0.6856	Remote Similarity	NPC475964
0.6839	Remote Similarity	NPC329992
0.6834	Remote Similarity	NPC237579
0.6832	Remote Similarity	NPC470646
0.6828	Remote Similarity	NPC476443
0.6828	Remote Similarity	NPC133817
0.6828	Remote Similarity	NPC57512
0.6823	Remote Similarity	NPC75958
0.6822	Remote Similarity	NPC82056
0.6813	Remote Similarity	NPC37144
0.6813	Remote Similarity	NPC59907
0.6809	Remote Similarity	NPC76458
0.6809	Remote Similarity	NPC82733
0.6806	Remote Similarity	NPC100566
0.6804	Remote Similarity	NPC5674
0.6802	Remote Similarity	NPC73492
0.6802	Remote Similarity	NPC299990
0.6802	Remote Similarity	NPC160193
0.6798	Remote Similarity	NPC474915
0.6798	Remote Similarity	NPC188163
0.6798	Remote Similarity	NPC328750
0.6798	Remote Similarity	NPC213206
0.6789	Remote Similarity	NPC238530
0.6789	Remote Similarity	NPC232514
0.6789	Remote Similarity	NPC276944
0.6789	Remote Similarity	NPC247972
0.6788	Remote Similarity	NPC225597
0.6788	Remote Similarity	NPC65403
0.6788	Remote Similarity	NPC477640
0.6788	Remote Similarity	NPC470739
0.6786	Remote Similarity	NPC290304
0.6786	Remote Similarity	NPC99723
0.6786	Remote Similarity	NPC236327
0.6779	Remote Similarity	NPC80472
0.6774	Remote Similarity	NPC76079
0.6774	Remote Similarity	NPC308555
0.6773	Remote Similarity	NPC470847
0.6771	Remote Similarity	NPC475686
0.6771	Remote Similarity	NPC58766
0.6769	Remote Similarity	NPC35680
0.6768	Remote Similarity	NPC276120
0.6761	Remote Similarity	NPC55470
0.6757	Remote Similarity	NPC476580
0.6755	Remote Similarity	NPC111485
0.6755	Remote Similarity	NPC261484
0.6754	Remote Similarity	NPC206941
0.6754	Remote Similarity	NPC474858
0.6753	Remote Similarity	NPC41853
0.6749	Remote Similarity	NPC149962

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 NPC471650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	674
0.2-0.3	1223
0.3-0.4	2156
0.4-0.5	2789
0.5-0.6	1718
0.6-0.7	361
0.7-0.8	30
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
0.799	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7281	Phase 3
0.7742	Intermediate Similarity	NPD7280	Phase 3
0.7732	Intermediate Similarity	NPD5457	Discontinued
0.7605	Intermediate Similarity	NPD2492	Phase 1
0.7592	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD3885	Approved
0.7449	Intermediate Similarity	NPD4420	Approved
0.7421	Intermediate Similarity	NPD6618	Phase 2
0.7387	Intermediate Similarity	NPD5005	Approved
0.7387	Intermediate Similarity	NPD5006	Approved
0.736	Intermediate Similarity	NPD824	Approved
0.7287	Intermediate Similarity	NPD5313	Approved
0.7287	Intermediate Similarity	NPD5312	Approved
0.7268	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD5262	Discontinued
0.7222	Intermediate Similarity	NPD5564	Approved
0.7216	Intermediate Similarity	NPD7291	Discontinued
0.7158	Intermediate Similarity	NPD5978	Approved
0.7158	Intermediate Similarity	NPD5977	Approved
0.7135	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6386	Approved
0.7088	Intermediate Similarity	NPD6385	Approved
0.7079	Intermediate Similarity	NPD5297	Approved
0.7062	Intermediate Similarity	NPD6853	Approved
0.7062	Intermediate Similarity	NPD6851	Approved
0.7052	Intermediate Similarity	NPD743	Approved
0.703	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4166	Phase 2
0.6995	Remote Similarity	NPD7110	Phase 1
0.6995	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1670	Discontinued
0.6959	Remote Similarity	NPD5718	Phase 2
0.6957	Remote Similarity	NPD7317	Phase 3
0.6943	Remote Similarity	NPD6297	Approved
0.6941	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5071	Phase 2
0.6927	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7559	Phase 2
0.6915	Remote Similarity	NPD5677	Discontinued
0.6907	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD1309	Phase 2
0.6898	Remote Similarity	NPD1307	Phase 2
0.6887	Remote Similarity	NPD7047	Phase 3
0.6882	Remote Similarity	NPD7318	Phase 3
0.6879	Remote Similarity	NPD3142	Approved
0.6879	Remote Similarity	NPD3140	Approved
0.6875	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3639	Approved
0.6868	Remote Similarity	NPD3641	Approved
0.6868	Remote Similarity	NPD3640	Phase 3
0.6865	Remote Similarity	NPD6844	Discontinued
0.6864	Remote Similarity	NPD3442	Approved
0.6864	Remote Similarity	NPD3441	Approved
0.6861	Remote Similarity	NPD4846	Phase 2
0.6836	Remote Similarity	NPD3656	Approved
0.6831	Remote Similarity	NPD4210	Discontinued
0.6814	Remote Similarity	NPD7811	Phase 3
0.6814	Remote Similarity	NPD7810	Phase 3
0.6811	Remote Similarity	NPD6873	Phase 2
0.6798	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6107	Approved
0.6788	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6030	Approved
0.6776	Remote Similarity	NPD6031	Approved
0.6757	Remote Similarity	NPD6875	Approved
0.6757	Remote Similarity	NPD6876	Approved
0.6733	Remote Similarity	NPD4466	Phase 1
0.6732	Remote Similarity	NPD1880	Phase 3
0.6729	Remote Similarity	NPD5025	Approved
0.6719	Remote Similarity	NPD5242	Approved
0.6717	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7626	Approved
0.6715	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7627	Approved
0.6711	Remote Similarity	NPD7048	Phase 3
0.6702	Remote Similarity	NPD5353	Approved
0.6701	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4107	Approved
0.6697	Remote Similarity	NPD6997	Phase 2
0.6685	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6280	Approved
0.6684	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6279	Approved
0.6684	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD1424	Approved
0.6667	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4584	Approved
0.6667	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4773	Phase 2
0.6631	Remote Similarity	NPD4772	Phase 2
0.6629	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7584	Approved
0.6587	Remote Similarity	NPD6321	Discontinued
0.6587	Remote Similarity	NPD4482	Phase 3
0.6585	Remote Similarity	NPD5582	Discontinued
0.658	Remote Similarity	NPD6071	Discontinued
0.658	Remote Similarity	NPD6808	Phase 2
0.6579	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6625	Approved
0.6576	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD3146	Approved
0.6573	Remote Similarity	NPD5914	Approved
0.6564	Remote Similarity	NPD3446	Phase 1
0.6562	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5773	Approved
0.6561	Remote Similarity	NPD5772	Approved
0.6561	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2325	Approved
0.6545	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6493	Phase 3
0.6535	Remote Similarity	NPD7693	Approved
0.6535	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD2245	Discovery
0.6531	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5967	Approved
0.6524	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD2653	Approved
0.6516	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7225	Discontinued
0.6502	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD8156	Discontinued
0.6493	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD6788	Approved
0.6488	Remote Similarity	NPD6181	Discontinued
0.6485	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4162	Approved
0.6482	Remote Similarity	NPD7039	Approved
0.6482	Remote Similarity	NPD7038	Approved
0.648	Remote Similarity	NPD6895	Approved
0.648	Remote Similarity	NPD6896	Approved
0.6476	Remote Similarity	NPD3057	Approved
0.6465	Remote Similarity	NPD683	Approved
0.6461	Remote Similarity	NPD1933	Approved
0.6458	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7831	Phase 2
0.6458	Remote Similarity	NPD7833	Phase 2
0.6458	Remote Similarity	NPD5604	Discontinued
0.6457	Remote Similarity	NPD7224	Discontinued
0.6457	Remote Similarity	NPD7223	Discontinued
0.6447	Remote Similarity	NPD8251	Approved
0.6447	Remote Similarity	NPD8099	Discontinued
0.6447	Remote Similarity	NPD8252	Approved
0.6441	Remote Similarity	NPD554	Clinical (unspecified phase)
0.644	Remote Similarity	NPD2563	Approved
0.644	Remote Similarity	NPD2560	Approved
0.6429	Remote Similarity	NPD5536	Phase 2
0.6429	Remote Similarity	NPD2898	Approved
0.6429	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6862	Phase 2
0.6425	Remote Similarity	NPD7907	Approved
0.6422	Remote Similarity	NPD8149	Discontinued
0.6421	Remote Similarity	NPD5720	Discontinued
0.6421	Remote Similarity	NPD7298	Approved
0.6421	Remote Similarity	NPD7577	Discontinued
0.6421	Remote Similarity	NPD7248	Discontinued
0.6419	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5183	Approved
0.641	Remote Similarity	NPD5186	Approved
0.6409	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2592	Discontinued
0.6402	Remote Similarity	NPD4859	Phase 1
0.6398	Remote Similarity	NPD3448	Approved
0.6398	Remote Similarity	NPD2491	Approved
0.6398	Remote Similarity	NPD2972	Approved
0.6398	Remote Similarity	NPD3533	Approved
0.6398	Remote Similarity	NPD4123	Phase 3
0.6396	Remote Similarity	NPD3366	Approved
0.6394	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2904	Discontinued
0.6385	Remote Similarity	NPD8161	Suspended
0.6368	Remote Similarity	NPD5889	Approved
0.6368	Remote Similarity	NPD5890	Approved
0.6364	Remote Similarity	NPD2163	Approved
0.6349	Remote Similarity	NPD4017	Approved
0.6345	Remote Similarity	NPD4481	Phase 3
0.6341	Remote Similarity	NPD5896	Clinical (unspecified phase)

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