NPASS Compound

Structure

CID44161 OpenBabel06191715372D 28 29 0 0 0 0 0 0 0 0999 V2000 -6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 15 24 2 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 23 1 0 0 0 0 21 25 1 0 0 0 0 21 26 2 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 2 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.25
Volume:	431.329
LogP:	6.635
LogD:	4.817
LogS:	-4.387
# Rotatable Bonds:	8
TPSA:	47.17
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	3.232
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:	-4.83
MDCK Permeability:	2.713190406211652e-05
Pgp-inhibitor:	0.357
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.416

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	99.19071960449219%
Volume Distribution (VD):	1.256
Pgp-substrate:	0.7773863673210144%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.25
CYP2C19-substrate:	0.453
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.452
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	5.55
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.807
Skin Sensitization:	0.925
Carcinogencity:	0.05
Eye Corrosion:	0.004
Eye Irritation:	0.893
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC44161

Natural Product ID:	NPC44161
*Common Name:**	Aurachin B
IUPAC Name:	2-methyl-1-oxido-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]quinolin-1-ium-3-ol
Synonyms:
Standard InCHIKey:	ZNSLRZHNFFXDSE-YEFHWUCQSA-N
Standard InCHI:	InChI=1S/C25H33NO2/c1-18(2)10-8-11-19(3)12-9-13-20(4)16-17-23-22-14-6-7-15-24(22)26(28)21(5)25(23)27/h6-7,10,12,14-16,27H,8-9,11,13,17H2,1-5H3/b19-12+,20-16+
SMILES:	CC(=CCC/C(=C/CC/C(=C/Cc1c2ccccc2n(=O)c(C)c1O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574536
PubChem CID:	6439168
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18701458]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18989924]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21979787]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22741921]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22907798]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24367422]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3106289]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	4

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	3.2	ug.mL-1	PMID[464831]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.036	ug.mL-1	PMID[464831]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.078	ug.mL-1	PMID[464831]
NPT2	Others	Unspecified		IC50	=	14.0	ug.mL-1	PMID[464831]

☑ 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 NPC44161 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	415
0.1-0.2	2944
0.2-0.3	13532
0.3-0.4	10194
0.4-0.5	10486
0.5-0.6	3260
0.6-0.7	1600
0.7-0.8	252
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8269	Intermediate Similarity	NPC60553
0.8217	Intermediate Similarity	NPC470394
0.8217	Intermediate Similarity	NPC470403
0.8217	Intermediate Similarity	NPC470404
0.8155	Intermediate Similarity	NPC473764
0.8155	Intermediate Similarity	NPC314940
0.814	Intermediate Similarity	NPC478032
0.8113	Intermediate Similarity	NPC470395
0.8012	Intermediate Similarity	NPC257142
0.8	Intermediate Similarity	NPC252590
0.7977	Intermediate Similarity	NPC472168
0.7927	Intermediate Similarity	NPC26872
0.7919	Intermediate Similarity	NPC283152
0.7917	Intermediate Similarity	NPC118511
0.791	Intermediate Similarity	NPC314573
0.7866	Intermediate Similarity	NPC284348
0.7853	Intermediate Similarity	NPC42591
0.7784	Intermediate Similarity	NPC26850
0.7759	Intermediate Similarity	NPC288943
0.7758	Intermediate Similarity	NPC153769
0.7751	Intermediate Similarity	NPC177404
0.7688	Intermediate Similarity	NPC280853
0.765	Intermediate Similarity	NPC230403
0.7644	Intermediate Similarity	NPC474409
0.764	Intermediate Similarity	NPC285016
0.764	Intermediate Similarity	NPC245657
0.7625	Intermediate Similarity	NPC471596
0.7622	Intermediate Similarity	NPC161292
0.7619	Intermediate Similarity	NPC477889
0.76	Intermediate Similarity	NPC95898
0.76	Intermediate Similarity	NPC303225
0.7592	Intermediate Similarity	NPC477111
0.7586	Intermediate Similarity	NPC158129
0.7582	Intermediate Similarity	NPC144381
0.7571	Intermediate Similarity	NPC88363
0.7544	Intermediate Similarity	NPC47298
0.7544	Intermediate Similarity	NPC315214
0.754	Intermediate Similarity	NPC476167
0.7527	Intermediate Similarity	NPC230805
0.7516	Intermediate Similarity	NPC471594
0.7515	Intermediate Similarity	NPC141353
0.75	Intermediate Similarity	NPC62069
0.75	Intermediate Similarity	NPC159319
0.75	Intermediate Similarity	NPC190007
0.75	Intermediate Similarity	NPC312872
0.75	Intermediate Similarity	NPC471598
0.75	Intermediate Similarity	NPC32028
0.7487	Intermediate Similarity	NPC192315
0.7486	Intermediate Similarity	NPC3715
0.7486	Intermediate Similarity	NPC469497
0.7486	Intermediate Similarity	NPC106833
0.7473	Intermediate Similarity	NPC66083
0.7472	Intermediate Similarity	NPC72980
0.7471	Intermediate Similarity	NPC116573
0.7459	Intermediate Similarity	NPC94943
0.7458	Intermediate Similarity	NPC203754
0.7458	Intermediate Similarity	NPC150048
0.7433	Intermediate Similarity	NPC267928
0.7432	Intermediate Similarity	NPC128751
0.7432	Intermediate Similarity	NPC246700
0.7429	Intermediate Similarity	NPC126481
0.7418	Intermediate Similarity	NPC194040
0.7403	Intermediate Similarity	NPC320394
0.7396	Intermediate Similarity	NPC477113
0.7386	Intermediate Similarity	NPC476688
0.7386	Intermediate Similarity	NPC105758
0.7386	Intermediate Similarity	NPC476686
0.7384	Intermediate Similarity	NPC322644
0.7371	Intermediate Similarity	NPC278874
0.7363	Intermediate Similarity	NPC314002
0.736	Intermediate Similarity	NPC134586
0.7356	Intermediate Similarity	NPC471178
0.7353	Intermediate Similarity	NPC63562
0.7348	Intermediate Similarity	NPC212535
0.7345	Intermediate Similarity	NPC259545
0.7345	Intermediate Similarity	NPC471294
0.7341	Intermediate Similarity	NPC79911
0.7341	Intermediate Similarity	NPC124542
0.7341	Intermediate Similarity	NPC471177
0.7341	Intermediate Similarity	NPC224632
0.7341	Intermediate Similarity	NPC59779
0.734	Intermediate Similarity	NPC474188
0.7337	Intermediate Similarity	NPC32771
0.7325	Intermediate Similarity	NPC278451
0.7322	Intermediate Similarity	NPC171171
0.7321	Intermediate Similarity	NPC288445
0.7318	Intermediate Similarity	NPC211997
0.7316	Intermediate Similarity	NPC249040
0.7312	Intermediate Similarity	NPC99666
0.7308	Intermediate Similarity	NPC204717
0.7299	Intermediate Similarity	NPC473057
0.7293	Intermediate Similarity	NPC144114
0.7293	Intermediate Similarity	NPC314394
0.7293	Intermediate Similarity	NPC477891
0.7283	Intermediate Similarity	NPC120798
0.7267	Intermediate Similarity	NPC132680
0.7267	Intermediate Similarity	NPC269919
0.7263	Intermediate Similarity	NPC128823
0.7254	Intermediate Similarity	NPC47059
0.7254	Intermediate Similarity	NPC264166
0.7254	Intermediate Similarity	NPC274291
0.7254	Intermediate Similarity	NPC329708
0.7254	Intermediate Similarity	NPC118832
0.7254	Intermediate Similarity	NPC165349
0.7253	Intermediate Similarity	NPC220765
0.7249	Intermediate Similarity	NPC153042
0.7247	Intermediate Similarity	NPC208060
0.7241	Intermediate Similarity	NPC48192
0.724	Intermediate Similarity	NPC470678
0.724	Intermediate Similarity	NPC66815
0.7238	Intermediate Similarity	NPC168486
0.7238	Intermediate Similarity	NPC222592
0.7237	Intermediate Similarity	NPC81561
0.7219	Intermediate Similarity	NPC324149
0.7216	Intermediate Similarity	NPC304183
0.7202	Intermediate Similarity	NPC475774
0.7202	Intermediate Similarity	NPC223427
0.7202	Intermediate Similarity	NPC220523
0.7202	Intermediate Similarity	NPC476098
0.7194	Intermediate Similarity	NPC469589
0.7189	Intermediate Similarity	NPC46580
0.7186	Intermediate Similarity	NPC242556
0.7184	Intermediate Similarity	NPC63338
0.7184	Intermediate Similarity	NPC25899
0.7184	Intermediate Similarity	NPC324203
0.7184	Intermediate Similarity	NPC322976
0.7182	Intermediate Similarity	NPC42979
0.7182	Intermediate Similarity	NPC232340
0.7181	Intermediate Similarity	NPC79293
0.7181	Intermediate Similarity	NPC279401
0.7173	Intermediate Similarity	NPC280714
0.7173	Intermediate Similarity	NPC18487
0.7171	Intermediate Similarity	NPC148140
0.7167	Intermediate Similarity	NPC224764
0.7167	Intermediate Similarity	NPC194724
0.7165	Intermediate Similarity	NPC470500
0.7158	Intermediate Similarity	NPC243834
0.7158	Intermediate Similarity	NPC70956
0.7157	Intermediate Similarity	NPC5145
0.7151	Intermediate Similarity	NPC471458
0.7151	Intermediate Similarity	NPC242928
0.7151	Intermediate Similarity	NPC34508
0.715	Intermediate Similarity	NPC477110
0.7143	Intermediate Similarity	NPC276517
0.7135	Intermediate Similarity	NPC477888
0.7135	Intermediate Similarity	NPC204385
0.7128	Intermediate Similarity	NPC474145
0.7128	Intermediate Similarity	NPC475841
0.7127	Intermediate Similarity	NPC184964
0.7126	Intermediate Similarity	NPC84508
0.7118	Intermediate Similarity	NPC37548
0.7104	Intermediate Similarity	NPC474798
0.7104	Intermediate Similarity	NPC206201
0.7102	Intermediate Similarity	NPC263439
0.7102	Intermediate Similarity	NPC211187
0.7092	Intermediate Similarity	NPC53344
0.7092	Intermediate Similarity	NPC283117
0.7086	Intermediate Similarity	NPC131718
0.7077	Intermediate Similarity	NPC475070
0.7072	Intermediate Similarity	NPC84347
0.7071	Intermediate Similarity	NPC85273
0.7068	Intermediate Similarity	NPC77555
0.7065	Intermediate Similarity	NPC133306
0.7059	Intermediate Similarity	NPC110741
0.7059	Intermediate Similarity	NPC183805
0.7047	Intermediate Similarity	NPC19872
0.7039	Intermediate Similarity	NPC164664
0.7037	Intermediate Similarity	NPC114335
0.7037	Intermediate Similarity	NPC141915
0.7037	Intermediate Similarity	NPC280964
0.7035	Intermediate Similarity	NPC294375
0.7033	Intermediate Similarity	NPC293472
0.7031	Intermediate Similarity	NPC306376
0.703	Intermediate Similarity	NPC293151
0.7022	Intermediate Similarity	NPC108469
0.702	Intermediate Similarity	NPC476116
0.702	Intermediate Similarity	NPC209769
0.7018	Intermediate Similarity	NPC187951
0.7018	Intermediate Similarity	NPC124005
0.7011	Intermediate Similarity	NPC266551
0.7011	Intermediate Similarity	NPC285469
0.7006	Intermediate Similarity	NPC97367
0.7006	Intermediate Similarity	NPC102423
0.7006	Intermediate Similarity	NPC476118
0.7005	Intermediate Similarity	NPC132631
0.7005	Intermediate Similarity	NPC103687
0.7	Intermediate Similarity	NPC329541
0.7	Intermediate Similarity	NPC129042
0.6995	Remote Similarity	NPC270009
0.6995	Remote Similarity	NPC472443
0.6994	Remote Similarity	NPC36168
0.6989	Remote Similarity	NPC476319
0.6989	Remote Similarity	NPC473320
0.6987	Remote Similarity	NPC215519
0.698	Remote Similarity	NPC470799
0.698	Remote Similarity	NPC8022
0.6979	Remote Similarity	NPC232130
0.6979	Remote Similarity	NPC90229
0.6979	Remote Similarity	NPC156704
0.6974	Remote Similarity	NPC211813

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 NPC44161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	664
0.2-0.3	844
0.3-0.4	1144
0.4-0.5	3040
0.5-0.6	2424
0.6-0.7	674
0.7-0.8	95
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD6159	Phase 2
0.8045	Intermediate Similarity	NPD9695	Approved
0.8012	Intermediate Similarity	NPD9690	Approved
0.7975	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6158	Phase 2
0.7923	Intermediate Similarity	NPD2177	Approved
0.7923	Intermediate Similarity	NPD2176	Approved
0.7923	Intermediate Similarity	NPD2175	Phase 3
0.7898	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD112	Approved
0.7798	Intermediate Similarity	NPD9705	Discontinued
0.7765	Intermediate Similarity	NPD2383	Phase 1
0.7764	Intermediate Similarity	NPD3525	Discontinued
0.7758	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2882	Phase 1
0.7753	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4203	Approved
0.7684	Intermediate Similarity	NPD4204	Approved
0.767	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5255	Approved
0.7624	Intermediate Similarity	NPD408	Approved
0.7544	Intermediate Similarity	NPD1685	Approved
0.7544	Intermediate Similarity	NPD1684	Approved
0.7527	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6590	Discontinued
0.75	Intermediate Similarity	NPD863	Approved
0.75	Intermediate Similarity	NPD862	Approved
0.75	Intermediate Similarity	NPD861	Approved
0.7474	Intermediate Similarity	NPD5936	Approved
0.7474	Intermediate Similarity	NPD5939	Approved
0.7459	Intermediate Similarity	NPD6227	Discontinued
0.7458	Intermediate Similarity	NPD2382	Approved
0.7458	Intermediate Similarity	NPD2381	Approved
0.7458	Intermediate Similarity	NPD2380	Approved
0.7448	Intermediate Similarity	NPD6290	Phase 2
0.7427	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9689	Approved
0.7401	Intermediate Similarity	NPD6492	Phase 2
0.7394	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4502	Phase 2
0.738	Intermediate Similarity	NPD5512	Phase 3
0.7358	Intermediate Similarity	NPD7222	Phase 2
0.7297	Intermediate Similarity	NPD1213	Phase 3
0.7287	Intermediate Similarity	NPD6550	Discontinued
0.7273	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9382	Approved
0.7267	Intermediate Similarity	NPD9383	Approved
0.7257	Intermediate Similarity	NPD925	Approved
0.7257	Intermediate Similarity	NPD926	Approved
0.7254	Intermediate Similarity	NPD32	Approved
0.7254	Intermediate Similarity	NPD31	Approved
0.7254	Intermediate Similarity	NPD4035	Approved
0.7254	Intermediate Similarity	NPD4034	Approved
0.7254	Intermediate Similarity	NPD4122	Approved
0.7254	Intermediate Similarity	NPD4036	Approved
0.7254	Intermediate Similarity	NPD4037	Approved
0.7254	Intermediate Similarity	NPD4038	Approved
0.7254	Intermediate Similarity	NPD4039	Approved
0.7254	Intermediate Similarity	NPD4033	Approved
0.725	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7948	Phase 1
0.7234	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD424	Approved
0.7216	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD425	Approved
0.7211	Intermediate Similarity	NPD2727	Phase 2
0.7204	Intermediate Similarity	NPD5316	Approved
0.7191	Intermediate Similarity	NPD2123	Phase 3
0.7184	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3920	Phase 2
0.7182	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7453	Approved
0.7179	Intermediate Similarity	NPD7452	Approved
0.7175	Intermediate Similarity	NPD2781	Approved
0.7173	Intermediate Similarity	NPD9688	Approved
0.7173	Intermediate Similarity	NPD9687	Approved
0.717	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1592	Phase 3
0.7168	Intermediate Similarity	NPD2581	Approved
0.7168	Intermediate Similarity	NPD2582	Approved
0.7159	Intermediate Similarity	NPD2780	Approved
0.7159	Intermediate Similarity	NPD2782	Approved
0.7158	Intermediate Similarity	NPD6988	Phase 1
0.7136	Intermediate Similarity	NPD2615	Phase 3
0.7136	Intermediate Similarity	NPD2616	Phase 3
0.7111	Intermediate Similarity	NPD5065	Approved
0.7105	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3477	Phase 2
0.7093	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5429	Discontinued
0.7081	Intermediate Similarity	NPD2762	Phase 2
0.7076	Intermediate Similarity	NPD4463	Approved
0.7076	Intermediate Similarity	NPD4462	Approved
0.7072	Intermediate Similarity	NPD5100	Phase 3
0.7068	Intermediate Similarity	NPD1229	Phase 2
0.7065	Intermediate Similarity	NPD5596	Phase 2
0.7059	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4702	Approved
0.7059	Intermediate Similarity	NPD4703	Approved
0.7053	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6452	Discontinued
0.7043	Intermediate Similarity	NPD5256	Discontinued
0.7039	Intermediate Similarity	NPD1325	Approved
0.7039	Intermediate Similarity	NPD1326	Approved
0.7037	Intermediate Similarity	NPD6569	Phase 2
0.7026	Intermediate Similarity	NPD6991	Approved
0.7011	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5138	Approved
0.7006	Intermediate Similarity	NPD5140	Approved
0.7005	Intermediate Similarity	NPD7603	Discontinued
0.6984	Remote Similarity	NPD2334	Discontinued
0.6976	Remote Similarity	NPD7726	Phase 1
0.6974	Remote Similarity	NPD3931	Approved
0.6974	Remote Similarity	NPD6975	Discontinued
0.6974	Remote Similarity	NPD3928	Approved
0.697	Remote Similarity	NPD2916	Discontinued
0.6963	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5530	Phase 1
0.6923	Remote Similarity	NPD4511	Phase 1
0.6919	Remote Similarity	NPD7867	Phase 1
0.6915	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1038	Approved
0.6907	Remote Similarity	NPD8396	Approved
0.6907	Remote Similarity	NPD8395	Approved
0.6902	Remote Similarity	NPD3417	Phase 1
0.6891	Remote Similarity	NPD5003	Discontinued
0.6884	Remote Similarity	NPD7671	Approved
0.6884	Remote Similarity	NPD7672	Approved
0.6882	Remote Similarity	NPD3813	Approved
0.6875	Remote Similarity	NPD4418	Discontinued
0.6872	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD484	Approved
0.6869	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3003	Approved
0.6868	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD43	Approved
0.6868	Remote Similarity	NPD6182	Approved
0.6868	Remote Similarity	NPD3224	Phase 2
0.6866	Remote Similarity	NPD6220	Phase 3
0.6866	Remote Similarity	NPD5416	Discontinued
0.6866	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5164	Discontinued
0.686	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4945	Discontinued
0.6851	Remote Similarity	NPD7474	Suspended
0.6851	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4897	Phase 2
0.6842	Remote Similarity	NPD2564	Approved
0.6842	Remote Similarity	NPD2565	Phase 2
0.6836	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3330	Phase 1
0.6823	Remote Similarity	NPD802	Phase 2
0.6821	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7112	Discontinued
0.6814	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4889	Approved
0.6796	Remote Similarity	NPD5862	Discovery
0.6784	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4326	Phase 2
0.6779	Remote Similarity	NPD1856	Discontinued
0.6776	Remote Similarity	NPD7418	Discontinued
0.6771	Remote Similarity	NPD3922	Approved
0.6771	Remote Similarity	NPD3924	Approved
0.6771	Remote Similarity	NPD3923	Approved
0.6771	Remote Similarity	NPD3921	Approved
0.6765	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5020	Approved
0.6763	Remote Similarity	NPD1661	Suspended
0.6761	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6642	Approved
0.6757	Remote Similarity	NPD6641	Approved
0.6754	Remote Similarity	NPD3321	Discontinued
0.6754	Remote Similarity	NPD2410	Phase 2
0.675	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7395	Discontinued
0.6748	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3385	Approved
0.6736	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6361	Phase 2
0.6735	Remote Similarity	NPD3814	Phase 1
0.6735	Remote Similarity	NPD1768	Approved
0.6734	Remote Similarity	NPD4795	Phase 2
0.6732	Remote Similarity	NPD5612	Discontinued
0.6732	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3717	Discontinued
0.6721	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5913	Phase 3
0.6719	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6769	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