NPASS Compound

Structure

NPC75944 OpenBabel07101719242D 29 35 0 0 1 0 0 0 0 0999 V2000 4.3301 -3.5000 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 -2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.4757 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 -1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -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 3.4641 -2.0000 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 10 27 1 0 0 0 0 11 14 1 0 0 0 0 11 28 1 0 0 0 0 12 16 1 0 0 0 0 12 25 1 6 0 0 0 13 22 2 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 15 26 1 6 0 0 0 16 19 1 1 0 0 0 16 23 1 0 0 0 0 17 19 1 6 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 6 0 0 0 19 20 1 1 0 0 0 19 29 1 0 0 0 0 20 13 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.1
Volume:	366.38
LogP:	2.4
LogD:	2.32
LogS:	-4.442
# Rotatable Bonds:	1
TPSA:	110.28
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	5.468
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.34
MDCK Permeability:	4.466135578695685e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.728
Plasma Protein Binding (PPB):	90.24159240722656%
Volume Distribution (VD):	0.571
Pgp-substrate:	2.378164529800415%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.667
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	11.187
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.994
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.964
Rat Oral Acute Toxicity:	0.737
Maximum Recommended Daily Dose:	0.116
Skin Sensitization:	0.914
Carcinogencity:	0.811
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC75944

Natural Product ID:	NPC75944
*Common Name:**	WGCFPWGLKTUIGC-BTDHYDEWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WGCFPWGLKTUIGC-BTDHYDEWSA-N
Standard InCHI:	InChI=1S/C21H18O8/c1-25-12-8-13(22)20-19(29-20,16(12)23)17(24)15-18(26-15)21(20)27-10-6-2-4-9-5-3-7-11(28-21)14(9)10/h2-7,12,15-18,23-24H,8H2,1H3/t12-,15-,16+,17+,18-,19+,20+/m1/s1
SMILES:	CO[C@@H]1CC(=O)[C@]23[C@]([C@H]1O)([C@H]([C@@H]1[C@H](C42Oc2cccc5cccc(c25)O4)O1)O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342628
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33512	berkleasmium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25237727]

☑ 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	6
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8700.0	nM	PMID[512850]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[512850]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	=	37.5	ug.mL-1	PMID[512850]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	37.5	ug.mL-1	PMID[512850]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	37.5	ug.mL-1	PMID[512850]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	50.0	ug.mL-1	PMID[512850]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	50.0	ug.mL-1	PMID[512850]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	37.5	ug.mL-1	PMID[512850]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[512850]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6400.0	nM	PMID[512850]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[512850]

☑ 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 NPC75944 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	431
0.1-0.2	1708
0.2-0.3	3658
0.3-0.4	9030
0.4-0.5	9303
0.5-0.6	5843
0.6-0.7	8027
0.7-0.8	4646
0.8-0.85	35
0.85-0.9	9
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC120677
0.9935	High Similarity	NPC74371
0.9806	High Similarity	NPC472153
0.9437	High Similarity	NPC175082
0.9437	High Similarity	NPC472150
0.9427	High Similarity	NPC472156
0.897	High Similarity	NPC137460
0.8909	High Similarity	NPC103633
0.8855	High Similarity	NPC472152
0.8839	High Similarity	NPC173630
0.8788	High Similarity	NPC297404
0.8788	High Similarity	NPC11608
0.8774	High Similarity	NPC472155
0.8662	High Similarity	NPC288531
0.8606	High Similarity	NPC316457
0.8606	High Similarity	NPC73148
0.8599	High Similarity	NPC472154
0.8485	Intermediate Similarity	NPC183402
0.8418	Intermediate Similarity	NPC151704
0.8382	Intermediate Similarity	NPC272656
0.8373	Intermediate Similarity	NPC193749
0.8365	Intermediate Similarity	NPC271076
0.8365	Intermediate Similarity	NPC23807
0.8363	Intermediate Similarity	NPC265214
0.8354	Intermediate Similarity	NPC197461
0.8324	Intermediate Similarity	NPC470667
0.8324	Intermediate Similarity	NPC186800
0.8313	Intermediate Similarity	NPC97662
0.8304	Intermediate Similarity	NPC217378
0.8304	Intermediate Similarity	NPC67424
0.8286	Intermediate Similarity	NPC114257
0.8286	Intermediate Similarity	NPC299149
0.8286	Intermediate Similarity	NPC277710
0.8286	Intermediate Similarity	NPC153578
0.8276	Intermediate Similarity	NPC65563
0.8276	Intermediate Similarity	NPC470949
0.8268	Intermediate Similarity	NPC314672
0.8266	Intermediate Similarity	NPC470438
0.8266	Intermediate Similarity	NPC45522
0.8266	Intermediate Similarity	NPC169977
0.8266	Intermediate Similarity	NPC42773
0.8266	Intermediate Similarity	NPC85368
0.8266	Intermediate Similarity	NPC24043
0.8266	Intermediate Similarity	NPC470335
0.8266	Intermediate Similarity	NPC101026
0.8266	Intermediate Similarity	NPC470336
0.8266	Intermediate Similarity	NPC21666
0.8256	Intermediate Similarity	NPC95866
0.8246	Intermediate Similarity	NPC84362
0.8246	Intermediate Similarity	NPC173637
0.8246	Intermediate Similarity	NPC127546
0.8246	Intermediate Similarity	NPC52550
0.8246	Intermediate Similarity	NPC223424
0.8246	Intermediate Similarity	NPC317489
0.8239	Intermediate Similarity	NPC208069
0.8239	Intermediate Similarity	NPC315221
0.8235	Intermediate Similarity	NPC472049
0.8229	Intermediate Similarity	NPC470334
0.8229	Intermediate Similarity	NPC35167
0.8225	Intermediate Similarity	NPC326278
0.8225	Intermediate Similarity	NPC478229
0.8218	Intermediate Similarity	NPC264735
0.8208	Intermediate Similarity	NPC471725
0.8208	Intermediate Similarity	NPC176740
0.8208	Intermediate Similarity	NPC203259
0.8208	Intermediate Similarity	NPC134532
0.8208	Intermediate Similarity	NPC190003
0.8208	Intermediate Similarity	NPC117260
0.8208	Intermediate Similarity	NPC471748
0.8208	Intermediate Similarity	NPC245452
0.8208	Intermediate Similarity	NPC33054
0.8208	Intermediate Similarity	NPC476405
0.8208	Intermediate Similarity	NPC155877
0.8208	Intermediate Similarity	NPC175107
0.8198	Intermediate Similarity	NPC219904
0.8198	Intermediate Similarity	NPC120099
0.8198	Intermediate Similarity	NPC225434
0.8198	Intermediate Similarity	NPC203050
0.8198	Intermediate Similarity	NPC52382
0.8198	Intermediate Similarity	NPC270578
0.8198	Intermediate Similarity	NPC222455
0.8198	Intermediate Similarity	NPC223747
0.8192	Intermediate Similarity	NPC36138
0.8192	Intermediate Similarity	NPC313452
0.8187	Intermediate Similarity	NPC73855
0.8187	Intermediate Similarity	NPC328940
0.8187	Intermediate Similarity	NPC179950
0.8187	Intermediate Similarity	NPC253662
0.8187	Intermediate Similarity	NPC308404
0.8187	Intermediate Similarity	NPC113093
0.8187	Intermediate Similarity	NPC276222
0.8187	Intermediate Similarity	NPC274618
0.8187	Intermediate Similarity	NPC135599
0.8187	Intermediate Similarity	NPC145038
0.8187	Intermediate Similarity	NPC56077
0.8187	Intermediate Similarity	NPC88789
0.8187	Intermediate Similarity	NPC113968
0.8187	Intermediate Similarity	NPC118284
0.8187	Intermediate Similarity	NPC277174
0.8187	Intermediate Similarity	NPC281131
0.8182	Intermediate Similarity	NPC241423
0.8182	Intermediate Similarity	NPC110941
0.8182	Intermediate Similarity	NPC473571
0.8182	Intermediate Similarity	NPC473682
0.8182	Intermediate Similarity	NPC244903
0.8182	Intermediate Similarity	NPC470443
0.8182	Intermediate Similarity	NPC126784
0.8182	Intermediate Similarity	NPC470444
0.8171	Intermediate Similarity	NPC61904
0.8171	Intermediate Similarity	NPC475246
0.8171	Intermediate Similarity	NPC144097
0.8171	Intermediate Similarity	NPC169733
0.8171	Intermediate Similarity	NPC8573
0.8171	Intermediate Similarity	NPC472384
0.8171	Intermediate Similarity	NPC472382
0.8171	Intermediate Similarity	NPC472385
0.8171	Intermediate Similarity	NPC198324
0.8171	Intermediate Similarity	NPC472380
0.8166	Intermediate Similarity	NPC163242
0.8166	Intermediate Similarity	NPC116458
0.8166	Intermediate Similarity	NPC265885
0.8166	Intermediate Similarity	NPC182045
0.8166	Intermediate Similarity	NPC476215
0.8166	Intermediate Similarity	NPC276377
0.8166	Intermediate Similarity	NPC173582
0.8166	Intermediate Similarity	NPC473438
0.8166	Intermediate Similarity	NPC215710
0.8166	Intermediate Similarity	NPC470125
0.8166	Intermediate Similarity	NPC249281
0.8166	Intermediate Similarity	NPC181465
0.8166	Intermediate Similarity	NPC246943
0.8166	Intermediate Similarity	NPC253788
0.8166	Intermediate Similarity	NPC139320
0.8165	Intermediate Similarity	NPC193920
0.8161	Intermediate Similarity	NPC4390
0.8155	Intermediate Similarity	NPC111929
0.8155	Intermediate Similarity	NPC472459
0.8155	Intermediate Similarity	NPC41121
0.8155	Intermediate Similarity	NPC320283
0.815	Intermediate Similarity	NPC244776
0.815	Intermediate Similarity	NPC155763
0.815	Intermediate Similarity	NPC67326
0.815	Intermediate Similarity	NPC206123
0.815	Intermediate Similarity	NPC29958
0.815	Intermediate Similarity	NPC235260
0.815	Intermediate Similarity	NPC116864
0.815	Intermediate Similarity	NPC282987
0.815	Intermediate Similarity	NPC293004
0.815	Intermediate Similarity	NPC156869
0.815	Intermediate Similarity	NPC84265
0.815	Intermediate Similarity	NPC20505
0.815	Intermediate Similarity	NPC255157
0.815	Intermediate Similarity	NPC259896
0.815	Intermediate Similarity	NPC254855
0.815	Intermediate Similarity	NPC287884
0.815	Intermediate Similarity	NPC136042
0.815	Intermediate Similarity	NPC67105
0.815	Intermediate Similarity	NPC245014
0.815	Intermediate Similarity	NPC8704
0.8146	Intermediate Similarity	NPC231254
0.8146	Intermediate Similarity	NPC470416
0.814	Intermediate Similarity	NPC226304
0.814	Intermediate Similarity	NPC265530
0.814	Intermediate Similarity	NPC135345
0.814	Intermediate Similarity	NPC295082
0.814	Intermediate Similarity	NPC325555
0.814	Intermediate Similarity	NPC160156
0.814	Intermediate Similarity	NPC92565
0.8136	Intermediate Similarity	NPC6709
0.8136	Intermediate Similarity	NPC473071
0.8136	Intermediate Similarity	NPC473073
0.8129	Intermediate Similarity	NPC277205
0.8129	Intermediate Similarity	NPC19388
0.8129	Intermediate Similarity	NPC475497
0.8129	Intermediate Similarity	NPC55786
0.8129	Intermediate Similarity	NPC475366
0.8129	Intermediate Similarity	NPC284277
0.8129	Intermediate Similarity	NPC240431
0.8125	Intermediate Similarity	NPC168584
0.8125	Intermediate Similarity	NPC139571
0.8125	Intermediate Similarity	NPC217520
0.8125	Intermediate Similarity	NPC293626
0.8125	Intermediate Similarity	NPC113836
0.8125	Intermediate Similarity	NPC37668
0.8125	Intermediate Similarity	NPC196127
0.8125	Intermediate Similarity	NPC258044
0.8125	Intermediate Similarity	NPC217387
0.8125	Intermediate Similarity	NPC477895
0.8125	Intermediate Similarity	NPC253521
0.8125	Intermediate Similarity	NPC267680
0.8118	Intermediate Similarity	NPC240306
0.8118	Intermediate Similarity	NPC150164
0.8118	Intermediate Similarity	NPC216752
0.8118	Intermediate Similarity	NPC27942
0.8114	Intermediate Similarity	NPC3718
0.8114	Intermediate Similarity	NPC220173
0.8114	Intermediate Similarity	NPC223426
0.8114	Intermediate Similarity	NPC210094
0.8114	Intermediate Similarity	NPC34267
0.8114	Intermediate Similarity	NPC19108

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 NPC75944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	922
0.2-0.3	1973
0.3-0.4	2742
0.4-0.5	1845
0.5-0.6	910
0.6-0.7	302
0.7-0.8	89
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9871	High Similarity	NPD3787	Discontinued
0.9379	High Similarity	NPD3751	Discontinued
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.8156	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7808	Phase 3
0.8114	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7054	Approved
0.7965	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7074	Phase 3
0.7943	Intermediate Similarity	NPD7472	Approved
0.7882	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5402	Approved
0.787	Intermediate Similarity	NPD3817	Phase 2
0.7849	Intermediate Similarity	NPD7199	Phase 2
0.7754	Intermediate Similarity	NPD6776	Approved
0.7754	Intermediate Similarity	NPD6779	Approved
0.7754	Intermediate Similarity	NPD6777	Approved
0.7754	Intermediate Similarity	NPD6781	Approved
0.7754	Intermediate Similarity	NPD6780	Approved
0.7754	Intermediate Similarity	NPD6778	Approved
0.7754	Intermediate Similarity	NPD6782	Approved
0.7746	Intermediate Similarity	NPD6959	Discontinued
0.7727	Intermediate Similarity	NPD3818	Discontinued
0.7725	Intermediate Similarity	NPD7435	Discontinued
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8455	Phase 2
0.7697	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD5844	Phase 1
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7647	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD1934	Approved
0.7627	Intermediate Similarity	NPD7228	Approved
0.7616	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD4965	Approved
0.7616	Intermediate Similarity	NPD3882	Suspended
0.7616	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7819	Suspended
0.7602	Intermediate Similarity	NPD2801	Approved
0.7602	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6799	Approved
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8313	Approved
0.7569	Intermediate Similarity	NPD8312	Approved
0.756	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD5401	Approved
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.7539	Intermediate Similarity	NPD7696	Phase 3
0.7539	Intermediate Similarity	NPD7698	Approved
0.7539	Intermediate Similarity	NPD7697	Approved
0.7529	Intermediate Similarity	NPD4380	Phase 2
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD7874	Approved
0.7487	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6534	Approved
0.7487	Intermediate Similarity	NPD6535	Approved
0.7486	Intermediate Similarity	NPD5494	Approved
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.747	Intermediate Similarity	NPD6190	Approved
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6559	Discontinued
0.7459	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6233	Phase 2
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.7401	Intermediate Similarity	NPD6232	Discontinued
0.7396	Intermediate Similarity	NPD1512	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6798	Discontinued
0.7374	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.736	Intermediate Similarity	NPD7801	Approved
0.7356	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7337	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6823	Phase 2
0.7299	Intermediate Similarity	NPD1465	Phase 2
0.7283	Intermediate Similarity	NPD7411	Suspended
0.7278	Intermediate Similarity	NPD1511	Approved
0.7273	Intermediate Similarity	NPD6100	Approved
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD6099	Approved
0.7259	Intermediate Similarity	NPD8151	Discontinued
0.7258	Intermediate Similarity	NPD8434	Phase 2
0.7256	Intermediate Similarity	NPD7097	Phase 1
0.7239	Intermediate Similarity	NPD6355	Discontinued
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7229	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7207	Intermediate Similarity	NPD7229	Phase 3
0.7186	Intermediate Similarity	NPD1549	Phase 2
0.7178	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1613	Approved
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.7169	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7135	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1653	Approved
0.7107	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7095	Approved
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7072	Intermediate Similarity	NPD3926	Phase 2
0.7069	Intermediate Similarity	NPD3226	Approved
0.7056	Intermediate Similarity	NPD1247	Approved
0.7052	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4908	Phase 1
0.7025	Intermediate Similarity	NPD1091	Approved
0.7024	Intermediate Similarity	NPD5763	Approved
0.7024	Intermediate Similarity	NPD5762	Approved
0.7022	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD4628	Phase 3
0.7	Intermediate Similarity	NPD3750	Approved
0.6994	Remote Similarity	NPD4625	Phase 3
0.6982	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6213	Phase 3
0.6979	Remote Similarity	NPD6212	Phase 3
0.6977	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8285	Discontinued
0.6971	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2973	Approved
0.6959	Remote Similarity	NPD2974	Approved
0.6959	Remote Similarity	NPD2975	Approved
0.6951	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD919	Approved
0.6941	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4580	Approved
0.6933	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2346	Discontinued
0.6909	Remote Similarity	NPD4062	Phase 3
0.6905	Remote Similarity	NPD1510	Phase 2
0.6905	Remote Similarity	NPD3748	Approved
0.6904	Remote Similarity	NPD2494	Approved
0.6904	Remote Similarity	NPD2493	Approved
0.6901	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3027	Phase 3
0.6888	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4583	Approved
0.6884	Remote Similarity	NPD4582	Approved
0.6882	Remote Similarity	NPD2897	Discontinued
0.6879	Remote Similarity	NPD7390	Discontinued
0.6875	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD2533	Approved
0.6834	Remote Similarity	NPD4004	Approved
0.6834	Remote Similarity	NPD7680	Approved
0.6834	Remote Similarity	NPD4002	Approved
0.6826	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD7266	Discontinued
0.6818	Remote Similarity	NPD3450	Approved
0.6818	Remote Similarity	NPD3452	Approved
0.6802	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2424	Discontinued
0.6768	Remote Similarity	NPD2861	Phase 2
0.6766	Remote Similarity	NPD1240	Approved
0.676	Remote Similarity	NPD6844	Discontinued
0.6747	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3268	Approved
0.6744	Remote Similarity	NPD1652	Phase 2
0.6733	Remote Similarity	NPD7584	Approved
0.6724	Remote Similarity	NPD5058	Phase 3
0.6714	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8059	Phase 3
0.6708	Remote Similarity	NPD1610	Phase 2
0.6707	Remote Similarity	NPD5647	Approved
0.6705	Remote Similarity	NPD6273	Approved
0.6687	Remote Similarity	NPD17	Approved
0.6686	Remote Similarity	NPD1607	Approved
0.6686	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2438	Suspended
0.6667	Remote Similarity	NPD2677	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD7930	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