NPASS Compound

Structure

NPC120251 OpenBabel07101719252D 30 33 0 0 0 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9016 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4839 -2.2205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 -1.0409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9839 0.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3084 -3.8385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8907 -3.1341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1595 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9785 0.7862 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 -0.1045 -0.9945 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 -1.4894 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5772 -0.2319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3029 -3.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5662 -0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 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 -1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 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 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7096 -4.8566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5608 0.0817 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 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 23 2 0 0 0 0 22 25 1 0 0 0 0 22 29 2 0 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	401.13
Volume:	412.745
LogP:	4.016
LogD:	2.992
LogS:	-3.962
# Rotatable Bonds:	5
TPSA:	102.92
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	2.5
Fsp3:	0.042
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:	-4.735
MDCK Permeability:	8.48605213832343e-06
Pgp-inhibitor:	0.38
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.036

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	98.82910919189453%
Volume Distribution (VD):	0.47
Pgp-substrate:	1.258664608001709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.65
CYP2D6-substrate:	0.607
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.421

ADMET: Excretion

Clearance (CL):	12.132
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.393
Carcinogencity:	0.314
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC120251

Natural Product ID:	NPC120251
*Common Name:**	Neolamellarin B
IUPAC Name:	3,4-bis(4-hydroxyphenyl)-1-[2-(4-hydroxyphenyl)acetyl]-2H-pyrrol-5-one
Synonyms:	neolamellarin B
Standard InCHIKey:	DNEWORVDDXZWKZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H19NO5/c26-18-7-1-15(2-8-18)13-22(29)25-14-21(16-3-9-19(27)10-4-16)23(24(25)30)17-5-11-20(28)12-6-17/h1-12,26-28H,13-14H2
SMILES:	c1cc(ccc1CC(=O)N1CC(=C(c2ccc(cc2)O)C1=O)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400695
PubChem CID:	24179371
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33428	dendrilla nigra	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17958397]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	<	20.0	%	PMID[465298]
NPT2	Others	Unspecified		Inhibition	=	23.0	%	PMID[465298]
NPT2	Others	Unspecified		Activity	=	42.0	%	PMID[465298]

☑ 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 NPC120251 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	219
0.1-0.2	1627
0.2-0.3	6368
0.3-0.4	11062
0.4-0.5	7333
0.5-0.6	13716
0.6-0.7	2248
0.7-0.8	117
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9683	High Similarity	NPC473360
0.8583	High Similarity	NPC268348
0.8421	Intermediate Similarity	NPC257390
0.812	Intermediate Similarity	NPC218323
0.8	Intermediate Similarity	NPC150712
0.797	Intermediate Similarity	NPC171372
0.7899	Intermediate Similarity	NPC266425
0.7877	Intermediate Similarity	NPC233702
0.7742	Intermediate Similarity	NPC70843
0.7724	Intermediate Similarity	NPC16188
0.7721	Intermediate Similarity	NPC305717
0.7643	Intermediate Similarity	NPC132308
0.7638	Intermediate Similarity	NPC21162
0.761	Intermediate Similarity	NPC256935
0.7606	Intermediate Similarity	NPC242159
0.7606	Intermediate Similarity	NPC313694
0.76	Intermediate Similarity	NPC95178
0.76	Intermediate Similarity	NPC29989
0.76	Intermediate Similarity	NPC69332
0.7571	Intermediate Similarity	NPC244866
0.7559	Intermediate Similarity	NPC88141
0.7552	Intermediate Similarity	NPC238412
0.7535	Intermediate Similarity	NPC109580
0.7534	Intermediate Similarity	NPC473804
0.75	Intermediate Similarity	NPC116842
0.7483	Intermediate Similarity	NPC119569
0.748	Intermediate Similarity	NPC24101
0.748	Intermediate Similarity	NPC155847
0.748	Intermediate Similarity	NPC96224
0.748	Intermediate Similarity	NPC289381
0.7469	Intermediate Similarity	NPC73555
0.7467	Intermediate Similarity	NPC202198
0.746	Intermediate Similarity	NPC188677
0.7448	Intermediate Similarity	NPC251439
0.7447	Intermediate Similarity	NPC328070
0.744	Intermediate Similarity	NPC8931
0.744	Intermediate Similarity	NPC261573
0.744	Intermediate Similarity	NPC120693
0.7424	Intermediate Similarity	NPC128249
0.7413	Intermediate Similarity	NPC196708
0.7394	Intermediate Similarity	NPC474473
0.7394	Intermediate Similarity	NPC169766
0.7379	Intermediate Similarity	NPC476989
0.736	Intermediate Similarity	NPC68269
0.7357	Intermediate Similarity	NPC325651
0.7348	Intermediate Similarity	NPC160179
0.7344	Intermediate Similarity	NPC17525
0.7315	Intermediate Similarity	NPC9373
0.7313	Intermediate Similarity	NPC311091
0.7313	Intermediate Similarity	NPC471033
0.731	Intermediate Similarity	NPC471201
0.7286	Intermediate Similarity	NPC17374
0.7278	Intermediate Similarity	NPC141957
0.7278	Intermediate Similarity	NPC328649
0.7273	Intermediate Similarity	NPC285350
0.7261	Intermediate Similarity	NPC223207
0.7259	Intermediate Similarity	NPC319950
0.7258	Intermediate Similarity	NPC130193
0.7254	Intermediate Similarity	NPC45191
0.7246	Intermediate Similarity	NPC307020
0.7241	Intermediate Similarity	NPC473055
0.7241	Intermediate Similarity	NPC473052
0.7239	Intermediate Similarity	NPC311737
0.7239	Intermediate Similarity	NPC38458
0.7226	Intermediate Similarity	NPC142577
0.7218	Intermediate Similarity	NPC23402
0.7218	Intermediate Similarity	NPC322197
0.7215	Intermediate Similarity	NPC304074
0.7215	Intermediate Similarity	NPC471771
0.7215	Intermediate Similarity	NPC290755
0.7209	Intermediate Similarity	NPC153690
0.7197	Intermediate Similarity	NPC133470
0.7197	Intermediate Similarity	NPC289776
0.7197	Intermediate Similarity	NPC191863
0.7192	Intermediate Similarity	NPC322526
0.7188	Intermediate Similarity	NPC231705
0.7177	Intermediate Similarity	NPC201967
0.7176	Intermediate Similarity	NPC177576
0.7176	Intermediate Similarity	NPC268388
0.7171	Intermediate Similarity	NPC144691
0.7164	Intermediate Similarity	NPC188867
0.7164	Intermediate Similarity	NPC82963
0.7164	Intermediate Similarity	NPC106551
0.7164	Intermediate Similarity	NPC299252
0.7164	Intermediate Similarity	NPC277394
0.7164	Intermediate Similarity	NPC61062
0.7164	Intermediate Similarity	NPC281686
0.7153	Intermediate Similarity	NPC56634
0.7152	Intermediate Similarity	NPC2672
0.7143	Intermediate Similarity	NPC231572
0.7134	Intermediate Similarity	NPC241794
0.7133	Intermediate Similarity	NPC125852
0.7132	Intermediate Similarity	NPC141523
0.7132	Intermediate Similarity	NPC142297
0.7122	Intermediate Similarity	NPC285394
0.7121	Intermediate Similarity	NPC17693
0.712	Intermediate Similarity	NPC280869
0.7113	Intermediate Similarity	NPC478147
0.7105	Intermediate Similarity	NPC473491
0.7103	Intermediate Similarity	NPC470441
0.7101	Intermediate Similarity	NPC27581
0.7099	Intermediate Similarity	NPC222905
0.7099	Intermediate Similarity	NPC252544
0.7099	Intermediate Similarity	NPC321252
0.7092	Intermediate Similarity	NPC476353
0.7091	Intermediate Similarity	NPC271792
0.7087	Intermediate Similarity	NPC135784
0.7087	Intermediate Similarity	NPC178902
0.707	Intermediate Similarity	NPC469243
0.7067	Intermediate Similarity	NPC297322
0.7063	Intermediate Similarity	NPC52472
0.7059	Intermediate Similarity	NPC122009
0.7059	Intermediate Similarity	NPC249435
0.7055	Intermediate Similarity	NPC136797
0.7055	Intermediate Similarity	NPC6913
0.7054	Intermediate Similarity	NPC6984
0.7054	Intermediate Similarity	NPC45033
0.7042	Intermediate Similarity	NPC165726
0.7042	Intermediate Similarity	NPC213969
0.7042	Intermediate Similarity	NPC296712
0.704	Intermediate Similarity	NPC260000
0.7037	Intermediate Similarity	NPC89831
0.7037	Intermediate Similarity	NPC19290
0.7029	Intermediate Similarity	NPC294361
0.7029	Intermediate Similarity	NPC236520
0.7023	Intermediate Similarity	NPC258056
0.7023	Intermediate Similarity	NPC79543
0.7023	Intermediate Similarity	NPC95172
0.7014	Intermediate Similarity	NPC326966
0.7007	Intermediate Similarity	NPC239697
0.7007	Intermediate Similarity	NPC316906
0.7007	Intermediate Similarity	NPC268572
0.7007	Intermediate Similarity	NPC307682
0.7	Intermediate Similarity	NPC226699
0.7	Intermediate Similarity	NPC14141
0.6993	Remote Similarity	NPC124802
0.6993	Remote Similarity	NPC283079
0.6992	Remote Similarity	NPC286222
0.6985	Remote Similarity	NPC283468
0.6984	Remote Similarity	NPC125732
0.6984	Remote Similarity	NPC245561
0.6981	Remote Similarity	NPC199737
0.698	Remote Similarity	NPC33011
0.6978	Remote Similarity	NPC196976
0.6978	Remote Similarity	NPC474862
0.6977	Remote Similarity	NPC13495
0.697	Remote Similarity	NPC474149
0.6962	Remote Similarity	NPC103250
0.6962	Remote Similarity	NPC475544
0.6959	Remote Similarity	NPC225745
0.6954	Remote Similarity	NPC81026
0.6951	Remote Similarity	NPC159767
0.6951	Remote Similarity	NPC155506
0.695	Remote Similarity	NPC164014
0.695	Remote Similarity	NPC288945
0.6944	Remote Similarity	NPC126859
0.6944	Remote Similarity	NPC259665
0.6944	Remote Similarity	NPC89769
0.6937	Remote Similarity	NPC63931
0.6935	Remote Similarity	NPC151715
0.6929	Remote Similarity	NPC91478
0.6923	Remote Similarity	NPC8305
0.6923	Remote Similarity	NPC66177
0.6923	Remote Similarity	NPC268763
0.6923	Remote Similarity	NPC476268
0.6909	Remote Similarity	NPC196243
0.6906	Remote Similarity	NPC473051
0.6906	Remote Similarity	NPC473050
0.6903	Remote Similarity	NPC262166
0.6903	Remote Similarity	NPC56685
0.6903	Remote Similarity	NPC261934
0.6903	Remote Similarity	NPC5194
0.6901	Remote Similarity	NPC318965
0.6899	Remote Similarity	NPC319320
0.6899	Remote Similarity	NPC287757
0.6892	Remote Similarity	NPC106606
0.689	Remote Similarity	NPC137627
0.6887	Remote Similarity	NPC266741
0.6884	Remote Similarity	NPC158222
0.6883	Remote Similarity	NPC324081
0.688	Remote Similarity	NPC26244
0.6875	Remote Similarity	NPC472585
0.6871	Remote Similarity	NPC474855
0.6871	Remote Similarity	NPC151706
0.6871	Remote Similarity	NPC118099
0.6871	Remote Similarity	NPC475318
0.6871	Remote Similarity	NPC475598
0.6871	Remote Similarity	NPC260045
0.6871	Remote Similarity	NPC476102
0.6871	Remote Similarity	NPC9687
0.6871	Remote Similarity	NPC49577
0.6871	Remote Similarity	NPC90194
0.6871	Remote Similarity	NPC293377
0.6871	Remote Similarity	NPC474787
0.6871	Remote Similarity	NPC273907
0.6871	Remote Similarity	NPC79465
0.6871	Remote Similarity	NPC76785
0.6871	Remote Similarity	NPC474811
0.6866	Remote Similarity	NPC51698
0.6859	Remote Similarity	NPC39431

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 NPC120251 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	656
0.2-0.3	923
0.3-0.4	1682
0.4-0.5	2829
0.5-0.6	2295
0.6-0.7	586
0.7-0.8	31
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
0.7793	Intermediate Similarity	NPD6884	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4093	Discontinued
0.75	Intermediate Similarity	NPD7450	Phase 2
0.7462	Intermediate Similarity	NPD2228	Approved
0.7462	Intermediate Similarity	NPD2229	Approved
0.7462	Intermediate Similarity	NPD2234	Approved
0.7372	Intermediate Similarity	NPD1755	Approved
0.7357	Intermediate Similarity	NPD4207	Discontinued
0.7355	Intermediate Similarity	NPD5967	Approved
0.7333	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6817	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3229	Phase 2
0.7246	Intermediate Similarity	NPD4659	Approved
0.7241	Intermediate Similarity	NPD743	Approved
0.7237	Intermediate Similarity	NPD1670	Discontinued
0.7219	Intermediate Similarity	NPD5556	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5304	Approved
0.7185	Intermediate Similarity	NPD5303	Approved
0.7183	Intermediate Similarity	NPD4497	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5823	Approved
0.7164	Intermediate Similarity	NPD9568	Approved
0.7143	Intermediate Similarity	NPD4103	Phase 2
0.7143	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7131	Phase 3
0.7122	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5157	Phase 1
0.7122	Intermediate Similarity	NPD5159	Phase 2
0.7114	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7086	Phase 2
0.7073	Intermediate Similarity	NPD6020	Phase 2
0.7059	Intermediate Similarity	NPD1759	Phase 1
0.7055	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2562	Approved
0.705	Intermediate Similarity	NPD2561	Approved
0.7042	Intermediate Similarity	NPD4208	Discontinued
0.7037	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD824	Approved
0.703	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1792	Phase 2
0.7013	Intermediate Similarity	NPD7427	Discontinued
0.7007	Intermediate Similarity	NPD7230	Approved
0.7007	Intermediate Similarity	NPD7231	Approved
0.7006	Intermediate Similarity	NPD7577	Discontinued
0.6993	Remote Similarity	NPD3594	Approved
0.6993	Remote Similarity	NPD3595	Approved
0.6985	Remote Similarity	NPD1758	Phase 1
0.6972	Remote Similarity	NPD7451	Discontinued
0.6972	Remote Similarity	NPD4980	Approved
0.6963	Remote Similarity	NPD255	Approved
0.6963	Remote Similarity	NPD256	Approved
0.695	Remote Similarity	NPD5310	Approved
0.695	Remote Similarity	NPD5311	Approved
0.6944	Remote Similarity	NPD5156	Approved
0.6944	Remote Similarity	NPD5155	Approved
0.6943	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2933	Approved
0.6935	Remote Similarity	NPD2934	Approved
0.6934	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3636	Approved
0.6923	Remote Similarity	NPD1445	Approved
0.6923	Remote Similarity	NPD3635	Approved
0.6923	Remote Similarity	NPD3637	Approved
0.6923	Remote Similarity	NPD1444	Approved
0.6918	Remote Similarity	NPD3142	Approved
0.6918	Remote Similarity	NPD3140	Approved
0.6909	Remote Similarity	NPD7177	Discontinued
0.6903	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3055	Approved
0.6901	Remote Similarity	NPD3053	Approved
0.6899	Remote Similarity	NPD7011	Discontinued
0.6897	Remote Similarity	NPD3764	Approved
0.6894	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5445	Approved
0.688	Remote Similarity	NPD2859	Approved
0.688	Remote Similarity	NPD2860	Approved
0.6879	Remote Similarity	NPD6583	Phase 3
0.6879	Remote Similarity	NPD6582	Phase 2
0.6875	Remote Similarity	NPD2606	Approved
0.6875	Remote Similarity	NPD2605	Approved
0.6861	Remote Similarity	NPD856	Approved
0.6861	Remote Similarity	NPD16	Approved
0.6857	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7714	Approved
0.6849	Remote Similarity	NPD7715	Approved
0.6842	Remote Similarity	NPD5481	Discontinued
0.6839	Remote Similarity	NPD7303	Discontinued
0.6835	Remote Similarity	NPD3019	Approved
0.6835	Remote Similarity	NPD1751	Approved
0.6835	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2668	Approved
0.6835	Remote Similarity	NPD2667	Approved
0.6835	Remote Similarity	NPD7110	Phase 1
0.6829	Remote Similarity	NPD5137	Approved
0.6826	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4656	Approved
0.6822	Remote Similarity	NPD4658	Approved
0.6807	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6346	Approved
0.6792	Remote Similarity	NPD8019	Approved
0.6781	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD9608	Approved
0.6769	Remote Similarity	NPD9610	Approved
0.6765	Remote Similarity	NPD1793	Approved
0.6765	Remote Similarity	NPD1791	Approved
0.6759	Remote Similarity	NPD2614	Approved
0.6753	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3366	Approved
0.6742	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6584	Phase 3
0.6735	Remote Similarity	NPD6405	Approved
0.6735	Remote Similarity	NPD6407	Approved
0.6732	Remote Similarity	NPD3400	Discontinued
0.6728	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3020	Approved
0.6714	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2932	Approved
0.6713	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6792	Phase 3
0.6712	Remote Similarity	NPD3136	Phase 2
0.6711	Remote Similarity	NPD2492	Phase 1
0.6711	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.671	Remote Similarity	NPD8165	Discontinued
0.6692	Remote Similarity	NPD3682	Approved
0.6692	Remote Similarity	NPD4229	Approved
0.6692	Remote Similarity	NPD4231	Approved
0.6692	Remote Similarity	NPD3680	Approved
0.6691	Remote Similarity	NPD3598	Phase 3
0.669	Remote Similarity	NPD9569	Approved
0.6689	Remote Similarity	NPD3062	Approved
0.6689	Remote Similarity	NPD4452	Approved
0.6689	Remote Similarity	NPD3061	Approved
0.6689	Remote Similarity	NPD4453	Approved
0.6689	Remote Similarity	NPD4477	Approved
0.6689	Remote Similarity	NPD4445	Approved
0.6689	Remote Similarity	NPD4476	Approved
0.6689	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD6876	Approved
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD2592	Discontinued
0.6667	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6747	Phase 1
0.6667	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3421	Phase 3
0.6667	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6875	Approved
0.6647	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2791	Discontinued
0.6644	Remote Similarity	NPD5201	Approved
0.6644	Remote Similarity	NPD4617	Approved
0.6644	Remote Similarity	NPD4620	Approved
0.6644	Remote Similarity	NPD5203	Approved
0.6643	Remote Similarity	NPD4102	Approved
0.6643	Remote Similarity	NPD6994	Approved
0.6643	Remote Similarity	NPD4105	Approved
0.6643	Remote Similarity	NPD6993	Approved
0.6642	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD520	Approved
0.662	Remote Similarity	NPD1201	Approved
0.6619	Remote Similarity	NPD318	Approved
0.6619	Remote Similarity	NPD317	Approved
0.6617	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4817	Approved
0.6615	Remote Similarity	NPD4818	Approved
0.6609	Remote Similarity	NPD7693	Approved
0.6608	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6457	Approved
0.6605	Remote Similarity	NPD5978	Approved
0.6605	Remote Similarity	NPD5977	Approved
0.6604	Remote Similarity	NPD3455	Phase 2
0.6601	Remote Similarity	NPD7037	Approved
0.66	Remote Similarity	NPD2568	Approved
0.66	Remote Similarity	NPD5314	Approved
0.66	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5163	Phase 2
0.6597	Remote Similarity	NPD2079	Discontinued
0.6593	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6894	Phase 1
0.6584	Remote Similarity	NPD6844	Discontinued
0.6582	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1537	Approved
0.6579	Remote Similarity	NPD1538	Phase 1
0.6579	Remote Similarity	NPD1519	Approved
0.6577	Remote Similarity	NPD6310	Approved
0.6577	Remote Similarity	NPD6311	Approved
0.6577	Remote Similarity	NPD6309	Approved
0.6575	Remote Similarity	NPD4212	Discontinued
0.6575	Remote Similarity	NPD5204	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