NPASS Compound

Structure

CID156077 OpenBabel06191715522D 32 36 0 0 1 0 0 0 0 0999 V2000 -1.2142 -0.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1230 1.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8599 1.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2263 -1.8665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3684 -2.3817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5034 -2.8850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2731 -5.3063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8100 -1.2461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3178 -5.5094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4017 -2.0605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2469 0.1350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5034 0.1349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4829 -3.9377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8527 -2.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3684 -1.3751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3752 -4.3350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8526 -1.5572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3751 0.6382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3751 -2.3816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2469 -0.8717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2210 -3.8466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0382 -0.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3685 0.6382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3751 -1.3750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5034 -0.8718 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0668 -4.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1434 0.0356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1706 -4.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8100 -2.8749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2210 -2.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1186 -1.3750 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 15 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 19 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 17 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 28 1 0 0 0 0 14 17 2 0 0 0 0 14 29 1 0 0 0 0 15 25 1 1 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 11 1 6 0 0 0 18 23 1 0 0 0 0 19 24 1 1 0 0 0 19 30 1 0 0 0 0 20 24 1 6 0 0 0 20 31 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 27 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 1 0 0 0 25 12 1 1 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.2
Volume:	443.887
LogP:	4.937
LogD:	4.036
LogS:	-4.352
# Rotatable Bonds:	6
TPSA:	88.11
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.615
Synthetic Accessibility Score:	5.806
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.963
MDCK Permeability:	3.229506910429336e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.62455749511719%
Volume Distribution (VD):	2.033
Pgp-substrate:	9.280471801757812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.582
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.385
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.349
CYP2D6-substrate:	0.366
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	13.28
Half-life (T1/2):	0.347

ADMET: Toxicity

hERG Blockers:	0.2
Human Hepatotoxicity (H-HT):	0.506
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.988
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.05
Carcinogencity:	0.835
Eye Corrosion:	0.004
Eye Irritation:	0.191
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC156077

Natural Product ID:	NPC156077
*Common Name:**	LLWXHZLLARPDFR-PGJQBQEHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LLWXHZLLARPDFR-PGJQBQEHSA-N
Standard InCHI:	InChI=1S/C25H30O7/c1-15-5-6-19(30-21(26)16-7-9-28-13-16)24(4)20(31-22(27)17-8-10-29-14-17)11-18-12-25(15,24)32-23(18,2)3/h7-10,13-15,18-20H,5-6,11-12H2,1-4H3/t15-,18-,19+,20+,24+,25+/m1/s1
SMILES:	C[C@@H]1CC[C@@H]([C@@]2(C)[C@H](C[C@@H]3C[C@]12OC3(C)C)OC(=O)c1ccoc1)OC(=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1164985
PubChem CID:	46850689
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[19743809]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499922]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24892518]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25924111]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8117	Aureolaria virginica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2871	Canistrocarpus cervicornis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	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
MIC	7

Activity Type	# Activity
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.5	ug	PMID[448270]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	10.0	ug	PMID[448270]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	0.5	ug	PMID[448270]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	10.0	ug	PMID[448270]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.01	ug	PMID[448270]
NPT1	Others	Radical scavenging activity		MIC	=	10.0	ug	PMID[448270]

☑ 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 NPC156077 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	332
0.1-0.2	1622
0.2-0.3	3899
0.3-0.4	7106
0.4-0.5	12920
0.5-0.6	11794
0.6-0.7	4415
0.7-0.8	538
0.8-0.85	50
0.85-0.9	2
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9429	High Similarity	NPC243165
0.9296	High Similarity	NPC6815
0.9296	High Similarity	NPC294803
0.9231	High Similarity	NPC147340
0.9231	High Similarity	NPC271460
0.9097	High Similarity	NPC240214
0.8446	Intermediate Similarity	NPC195325
0.8435	Intermediate Similarity	NPC221809
0.8403	Intermediate Similarity	NPC20500
0.8288	Intermediate Similarity	NPC470741
0.8288	Intermediate Similarity	NPC223415
0.8269	Intermediate Similarity	NPC276735
0.8219	Intermediate Similarity	NPC475519
0.8217	Intermediate Similarity	NPC86800
0.8212	Intermediate Similarity	NPC18135
0.8194	Intermediate Similarity	NPC191828
0.8146	Intermediate Similarity	NPC476936
0.8146	Intermediate Similarity	NPC476122
0.8138	Intermediate Similarity	NPC474722
0.8125	Intermediate Similarity	NPC470742
0.8108	Intermediate Similarity	NPC251865
0.8069	Intermediate Similarity	NPC236532
0.8065	Intermediate Similarity	NPC299038
0.8056	Intermediate Similarity	NPC146872
0.8039	Intermediate Similarity	NPC75906
0.8039	Intermediate Similarity	NPC476201
0.8026	Intermediate Similarity	NPC196864
0.8026	Intermediate Similarity	NPC477404
0.8026	Intermediate Similarity	NPC156189
0.8013	Intermediate Similarity	NPC475967
0.8012	Intermediate Similarity	NPC294512
0.8	Intermediate Similarity	NPC62799
0.7987	Intermediate Similarity	NPC57998
0.7987	Intermediate Similarity	NPC472141
0.7987	Intermediate Similarity	NPC282445
0.7986	Intermediate Similarity	NPC92941
0.7975	Intermediate Similarity	NPC419
0.7961	Intermediate Similarity	NPC470790
0.7961	Intermediate Similarity	NPC472654
0.7961	Intermediate Similarity	NPC470791
0.7949	Intermediate Similarity	NPC261597
0.7947	Intermediate Similarity	NPC470941
0.7935	Intermediate Similarity	NPC44675
0.7935	Intermediate Similarity	NPC476262
0.7935	Intermediate Similarity	NPC214541
0.7922	Intermediate Similarity	NPC268905
0.7922	Intermediate Similarity	NPC469503
0.7922	Intermediate Similarity	NPC322546
0.7922	Intermediate Similarity	NPC308205
0.7919	Intermediate Similarity	NPC267632
0.7908	Intermediate Similarity	NPC159927
0.7908	Intermediate Similarity	NPC469335
0.7898	Intermediate Similarity	NPC475226
0.7895	Intermediate Similarity	NPC19747
0.7885	Intermediate Similarity	NPC104736
0.7881	Intermediate Similarity	NPC346
0.7867	Intermediate Similarity	NPC84479
0.7866	Intermediate Similarity	NPC56953
0.7866	Intermediate Similarity	NPC176413
0.7862	Intermediate Similarity	NPC469846
0.7852	Intermediate Similarity	NPC121158
0.7852	Intermediate Similarity	NPC473152
0.7843	Intermediate Similarity	NPC211625
0.7834	Intermediate Similarity	NPC1408
0.7834	Intermediate Similarity	NPC304692
0.7834	Intermediate Similarity	NPC167142
0.7834	Intermediate Similarity	NPC36655
0.7834	Intermediate Similarity	NPC187149
0.7834	Intermediate Similarity	NPC469847
0.7834	Intermediate Similarity	NPC246841
0.7834	Intermediate Similarity	NPC472772
0.7834	Intermediate Similarity	NPC249021
0.7834	Intermediate Similarity	NPC81405
0.7829	Intermediate Similarity	NPC10088
0.7829	Intermediate Similarity	NPC250228
0.7829	Intermediate Similarity	NPC255414
0.7823	Intermediate Similarity	NPC476943
0.7821	Intermediate Similarity	NPC469850
0.7806	Intermediate Similarity	NPC29695
0.7806	Intermediate Similarity	NPC182427
0.7806	Intermediate Similarity	NPC476939
0.7806	Intermediate Similarity	NPC476940
0.78	Intermediate Similarity	NPC205071
0.7785	Intermediate Similarity	NPC140952
0.7771	Intermediate Similarity	NPC209364
0.7771	Intermediate Similarity	NPC107646
0.7771	Intermediate Similarity	NPC126723
0.7771	Intermediate Similarity	NPC204663
0.777	Intermediate Similarity	NPC90953
0.7763	Intermediate Similarity	NPC276676
0.7756	Intermediate Similarity	NPC34421
0.7756	Intermediate Similarity	NPC98206
0.7756	Intermediate Similarity	NPC30222
0.7756	Intermediate Similarity	NPC237259
0.7756	Intermediate Similarity	NPC178932
0.7755	Intermediate Similarity	NPC310830
0.775	Intermediate Similarity	NPC471168
0.775	Intermediate Similarity	NPC165218
0.775	Intermediate Similarity	NPC224394
0.775	Intermediate Similarity	NPC472139
0.775	Intermediate Similarity	NPC663
0.7748	Intermediate Similarity	NPC476944
0.7736	Intermediate Similarity	NPC305016
0.7733	Intermediate Similarity	NPC52412
0.7727	Intermediate Similarity	NPC69647
0.7727	Intermediate Similarity	NPC471001
0.7727	Intermediate Similarity	NPC125182
0.7722	Intermediate Similarity	NPC286722
0.7722	Intermediate Similarity	NPC472777
0.7722	Intermediate Similarity	NPC472776
0.7722	Intermediate Similarity	NPC472778
0.7722	Intermediate Similarity	NPC195131
0.7722	Intermediate Similarity	NPC470118
0.7722	Intermediate Similarity	NPC214495
0.7722	Intermediate Similarity	NPC470119
0.7708	Intermediate Similarity	NPC298190
0.7707	Intermediate Similarity	NPC469336
0.7707	Intermediate Similarity	NPC35000
0.7702	Intermediate Similarity	NPC56358
0.7702	Intermediate Similarity	NPC472664
0.7688	Intermediate Similarity	NPC472771
0.7688	Intermediate Similarity	NPC472668
0.7688	Intermediate Similarity	NPC197596
0.7688	Intermediate Similarity	NPC82851
0.7688	Intermediate Similarity	NPC470939
0.7688	Intermediate Similarity	NPC200782
0.7682	Intermediate Similarity	NPC476946
0.7682	Intermediate Similarity	NPC243577
0.7677	Intermediate Similarity	NPC5180
0.7673	Intermediate Similarity	NPC474611
0.7673	Intermediate Similarity	NPC474932
0.7673	Intermediate Similarity	NPC473473
0.7673	Intermediate Similarity	NPC475295
0.7669	Intermediate Similarity	NPC271235
0.7662	Intermediate Similarity	NPC476942
0.7662	Intermediate Similarity	NPC476941
0.7658	Intermediate Similarity	NPC263265
0.7658	Intermediate Similarity	NPC60973
0.7658	Intermediate Similarity	NPC41880
0.7647	Intermediate Similarity	NPC262198
0.7643	Intermediate Similarity	NPC114880
0.764	Intermediate Similarity	NPC134254
0.764	Intermediate Similarity	NPC285567
0.764	Intermediate Similarity	NPC283209
0.764	Intermediate Similarity	NPC472773
0.764	Intermediate Similarity	NPC39986
0.764	Intermediate Similarity	NPC476197
0.764	Intermediate Similarity	NPC472669
0.764	Intermediate Similarity	NPC302369
0.7636	Intermediate Similarity	NPC469848
0.7635	Intermediate Similarity	NPC186626
0.7635	Intermediate Similarity	NPC42400
0.7632	Intermediate Similarity	NPC142113
0.7628	Intermediate Similarity	NPC291150
0.7628	Intermediate Similarity	NPC116717
0.7625	Intermediate Similarity	NPC475381
0.7625	Intermediate Similarity	NPC472653
0.7625	Intermediate Similarity	NPC335761
0.7622	Intermediate Similarity	NPC88593
0.761	Intermediate Similarity	NPC475066
0.761	Intermediate Similarity	NPC472283
0.7607	Intermediate Similarity	NPC472651
0.7607	Intermediate Similarity	NPC476861
0.7607	Intermediate Similarity	NPC476850
0.7607	Intermediate Similarity	NPC270312
0.7603	Intermediate Similarity	NPC470740
0.76	Intermediate Similarity	NPC67003
0.7597	Intermediate Similarity	NPC476937
0.7597	Intermediate Similarity	NPC476938
0.7595	Intermediate Similarity	NPC264943
0.7593	Intermediate Similarity	NPC61967
0.7593	Intermediate Similarity	NPC123088
0.7593	Intermediate Similarity	NPC159520
0.7593	Intermediate Similarity	NPC470182
0.7584	Intermediate Similarity	NPC220094
0.7582	Intermediate Similarity	NPC41182
0.7582	Intermediate Similarity	NPC5676
0.758	Intermediate Similarity	NPC472672
0.758	Intermediate Similarity	NPC471002
0.7578	Intermediate Similarity	NPC471166
0.7578	Intermediate Similarity	NPC472767
0.7578	Intermediate Similarity	NPC18347
0.7578	Intermediate Similarity	NPC470792
0.7578	Intermediate Similarity	NPC149896
0.7578	Intermediate Similarity	NPC6326
0.7578	Intermediate Similarity	NPC188649
0.7578	Intermediate Similarity	NPC471167
0.7578	Intermediate Similarity	NPC5079
0.7578	Intermediate Similarity	NPC329938
0.7576	Intermediate Similarity	NPC475237
0.7576	Intermediate Similarity	NPC475641
0.7568	Intermediate Similarity	NPC46896
0.7564	Intermediate Similarity	NPC212257
0.7562	Intermediate Similarity	NPC237155
0.7562	Intermediate Similarity	NPC307383
0.7562	Intermediate Similarity	NPC472671
0.7561	Intermediate Similarity	NPC296558
0.7561	Intermediate Similarity	NPC472652
0.7561	Intermediate Similarity	NPC327922
0.7552	Intermediate Similarity	NPC95567

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 NPC156077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	1199
0.2-0.3	2754
0.3-0.4	2709
0.4-0.5	1595
0.5-0.6	531
0.6-0.7	84
0.7-0.8	2
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
0.7595	Intermediate Similarity	NPD5760	Phase 2
0.7595	Intermediate Similarity	NPD5761	Phase 2
0.7195	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8434	Phase 2
0.7	Intermediate Similarity	NPD920	Approved
0.6875	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1471	Phase 3
0.6752	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.675	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6599	Discontinued
0.6648	Remote Similarity	NPD6559	Discontinued
0.6647	Remote Similarity	NPD5494	Approved
0.6647	Remote Similarity	NPD7819	Suspended
0.6609	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD919	Approved
0.6582	Remote Similarity	NPD1551	Phase 2
0.6582	Remote Similarity	NPD2796	Approved
0.6562	Remote Similarity	NPD1243	Approved
0.6554	Remote Similarity	NPD6764	Approved
0.6554	Remote Similarity	NPD6765	Approved
0.6536	Remote Similarity	NPD6832	Phase 2
0.6529	Remote Similarity	NPD3749	Approved
0.6522	Remote Similarity	NPD4628	Phase 3
0.6519	Remote Similarity	NPD2799	Discontinued
0.6506	Remote Similarity	NPD3226	Approved
0.6463	Remote Similarity	NPD2532	Approved
0.6463	Remote Similarity	NPD2534	Approved
0.6463	Remote Similarity	NPD2533	Approved
0.645	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2346	Discontinued
0.6437	Remote Similarity	NPD3926	Phase 2
0.6433	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6273	Approved
0.6416	Remote Similarity	NPD1247	Approved
0.6415	Remote Similarity	NPD3748	Approved
0.6409	Remote Similarity	NPD6785	Approved
0.6409	Remote Similarity	NPD6784	Approved
0.6402	Remote Similarity	NPD6799	Approved
0.6379	Remote Similarity	NPD6808	Phase 2
0.6375	Remote Similarity	NPD2935	Discontinued
0.6374	Remote Similarity	NPD7768	Phase 2
0.6337	Remote Similarity	NPD7075	Discontinued
0.6335	Remote Similarity	NPD2344	Approved
0.6331	Remote Similarity	NPD7411	Suspended
0.6319	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5402	Approved
0.6294	Remote Similarity	NPD6801	Discontinued
0.6286	Remote Similarity	NPD6232	Discontinued
0.6279	Remote Similarity	NPD4967	Phase 2
0.6279	Remote Similarity	NPD4966	Approved
0.6279	Remote Similarity	NPD4965	Approved
0.6271	Remote Similarity	NPD7473	Discontinued
0.6265	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2800	Approved
0.6257	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2313	Discontinued
0.6228	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD3817	Phase 2
0.622	Remote Similarity	NPD3750	Approved
0.6213	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6234	Discontinued
0.6201	Remote Similarity	NPD5844	Phase 1
0.62	Remote Similarity	NPD8404	Phase 2
0.62	Remote Similarity	NPD5585	Approved
0.6196	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1549	Phase 2
0.619	Remote Similarity	NPD5403	Approved
0.6185	Remote Similarity	NPD3882	Suspended
0.6182	Remote Similarity	NPD2309	Approved
0.6168	Remote Similarity	NPD5401	Approved
0.6164	Remote Similarity	NPD4307	Phase 2
0.6159	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.615	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3818	Discontinued
0.6136	Remote Similarity	NPD6959	Discontinued
0.6135	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.612	Remote Similarity	NPD8312	Approved
0.612	Remote Similarity	NPD8313	Approved
0.6111	Remote Similarity	NPD7033	Discontinued
0.6105	Remote Similarity	NPD37	Approved
0.6105	Remote Similarity	NPD6280	Approved
0.6105	Remote Similarity	NPD6279	Approved
0.6105	Remote Similarity	NPD1934	Approved
0.6092	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.609	Remote Similarity	NPD1019	Discontinued
0.6082	Remote Similarity	NPD4380	Phase 2
0.6078	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD1876	Approved
0.6062	Remote Similarity	NPD2979	Phase 3
0.6062	Remote Similarity	NPD4140	Approved
0.6057	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD17	Approved
0.6045	Remote Similarity	NPD8127	Discontinued
0.6044	Remote Similarity	NPD5953	Discontinued
0.6039	Remote Similarity	NPD3972	Approved
0.6038	Remote Similarity	NPD3764	Approved
0.6038	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD6004	Phase 3
0.6037	Remote Similarity	NPD6002	Phase 3
0.6037	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6037	Remote Similarity	NPD6005	Phase 3
0.6037	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD1203	Approved
0.6025	Remote Similarity	NPD1933	Approved
0.6024	Remote Similarity	NPD7003	Approved
0.6012	Remote Similarity	NPD4308	Phase 3
0.6012	Remote Similarity	NPD1510	Phase 2
0.6011	Remote Similarity	NPD7229	Phase 3
0.6011	Remote Similarity	NPD5710	Approved
0.6011	Remote Similarity	NPD5711	Approved
0.6	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8032	Phase 2
0.6	Remote Similarity	NPD4359	Approved
0.5988	Remote Similarity	NPD1607	Approved
0.5987	Remote Similarity	NPD5691	Approved
0.5987	Remote Similarity	NPD2798	Approved
0.5977	Remote Similarity	NPD2801	Approved
0.5976	Remote Similarity	NPD2438	Suspended
0.5967	Remote Similarity	NPD7228	Approved
0.5963	Remote Similarity	NPD1240	Approved
0.5951	Remote Similarity	NPD7097	Phase 1
0.5939	Remote Similarity	NPD5762	Approved
0.5939	Remote Similarity	NPD5763	Approved
0.5938	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD9717	Approved
0.5935	Remote Similarity	NPD1608	Approved
0.5934	Remote Similarity	NPD7286	Phase 2
0.5926	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5124	Phase 1
0.5926	Remote Similarity	NPD447	Suspended
0.5926	Remote Similarity	NPD6355	Discontinued
0.5924	Remote Similarity	NPD3267	Approved
0.5924	Remote Similarity	NPD3266	Approved
0.5924	Remote Similarity	NPD2797	Approved
0.5901	Remote Similarity	NPD4870	Approved
0.5897	Remote Similarity	NPD5327	Phase 3
0.5879	Remote Similarity	NPD6100	Approved
0.5879	Remote Similarity	NPD6099	Approved
0.5876	Remote Similarity	NPD8285	Discontinued
0.5875	Remote Similarity	NPD7095	Approved
0.5871	Remote Similarity	NPD1611	Approved
0.5871	Remote Similarity	NPD1281	Approved
0.5866	Remote Similarity	NPD7199	Phase 2
0.5864	Remote Similarity	NPD4060	Phase 1
0.5862	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6166	Phase 2
0.5847	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD1778	Approved
0.5839	Remote Similarity	NPD411	Approved
0.5839	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD3268	Approved
0.5839	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5838	Remote Similarity	NPD7435	Discontinued
0.5838	Remote Similarity	NPD7458	Discontinued
0.5838	Remote Similarity	NPD7240	Approved
0.5833	Remote Similarity	NPD7047	Phase 3
0.5833	Remote Similarity	NPD4110	Phase 3
0.5833	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4420	Approved
0.5824	Remote Similarity	NPD1511	Approved
0.5815	Remote Similarity	NPD7074	Phase 3
0.5813	Remote Similarity	NPD4908	Phase 1
0.5808	Remote Similarity	NPD2424	Discontinued
0.5806	Remote Similarity	NPD3496	Discontinued
0.5806	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5801	Remote Similarity	NPD5242	Approved
0.5801	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.5799	Remote Similarity	NPD3887	Approved
0.5792	Remote Similarity	NPD3751	Discontinued
0.5789	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4287	Approved
0.5787	Remote Similarity	NPD5005	Approved
0.5787	Remote Similarity	NPD5006	Approved
0.5786	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD6032	Approved
0.5783	Remote Similarity	NPD2531	Phase 2
0.5776	Remote Similarity	NPD4625	Phase 3
0.5771	Remote Similarity	NPD5890	Approved
0.5771	Remote Similarity	NPD5889	Approved
0.5769	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD2403	Approved
0.5767	Remote Similarity	NPD8150	Discontinued
0.5765	Remote Similarity	NPD7236	Approved
0.5765	Remote Similarity	NPD6779	Approved
0.5765	Remote Similarity	NPD6778	Approved
0.5765	Remote Similarity	NPD6777	Approved
0.5765	Remote Similarity	NPD6776	Approved
0.5765	Remote Similarity	NPD6782	Approved
0.5765	Remote Similarity	NPD6781	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