NPASS Compound

Structure

NPC288531 OpenBabel07101719242D 27 33 0 0 1 0 0 0 0 0999 V2000 3.3594 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 -1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3594 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3532 -1.2137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5195 1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0062 -1.2137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8398 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5195 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6797 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 1.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6797 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.9698 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6797 1.9395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8398 0.4849 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8398 2.4244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3594 2.9093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 0.4849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5195 2.4244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6797 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4547 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 -0.0000 2.9093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 9 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 8 2 0 0 0 0 7 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 25 1 0 0 0 0 11 14 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 6 0 0 0 12 21 1 0 0 0 0 13 19 1 6 0 0 0 13 22 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 6 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 6 0 0 0 18 27 1 0 0 0 0 19 20 1 6 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.09
Volume:	340.294
LogP:	1.784
LogD:	1.543
LogS:	-4.195
# Rotatable Bonds:	0
TPSA:	104.21
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.482
Fsp3:	0.4
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:	-5.632
MDCK Permeability:	3.643995296442881e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.24
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.875
Plasma Protein Binding (PPB):	94.66410827636719%
Volume Distribution (VD):	0.582
Pgp-substrate:	3.216157913208008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	10.019
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.993
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.839
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.511
Skin Sensitization:	0.174
Carcinogencity:	0.856
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC288531

Natural Product ID:	NPC288531
*Common Name:**	XYDXCACUXWHZSX-VLWVFBAFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XYDXCACUXWHZSX-VLWVFBAFSA-N
Standard InCHI:	InChI=1S/C20H16O7/c21-12-7-8-13(22)19-18(12,27-19)16(23)15-17(24-15)20(19)25-10-5-1-3-9-4-2-6-11(26-20)14(9)10/h1-8,12-13,15-17,21-23H/t12-,13+,15+,16-,17+,18-,19-/m0/s1
SMILES:	c1cc2cccc3c2c(c1)OC1([C@H]2[C@@H]([C@@H]([C@@]45[C@H](C=C[C@H]([C@@]14O5)O)O)O)O2)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342642
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	>	10000.0	nM	PMID[505106]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[505106]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[505106]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[505106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[505106]

☑ 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 NPC288531 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	518
0.1-0.2	1812
0.2-0.3	4569
0.3-0.4	10616
0.4-0.5	8013
0.5-0.6	5468
0.6-0.7	9235
0.7-0.8	2385
0.8-0.85	63
0.85-0.9	8
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC472154
0.9784	High Similarity	NPC173630
0.9571	High Similarity	NPC472155
0.9433	High Similarity	NPC151704
0.9424	High Similarity	NPC193920
0.9366	High Similarity	NPC271076
0.9231	High Similarity	NPC23807
0.9078	High Similarity	NPC472151
0.8726	High Similarity	NPC175082
0.8723	High Similarity	NPC138940
0.8718	High Similarity	NPC74371
0.8718	High Similarity	NPC120677
0.8714	High Similarity	NPC284232
0.8701	High Similarity	NPC472156
0.8662	High Similarity	NPC75944
0.8608	High Similarity	NPC472150
0.859	High Similarity	NPC472153
0.8553	High Similarity	NPC21902
0.8497	Intermediate Similarity	NPC20050
0.8497	Intermediate Similarity	NPC306267
0.8462	Intermediate Similarity	NPC193749
0.8431	Intermediate Similarity	NPC233467
0.8414	Intermediate Similarity	NPC92932
0.8411	Intermediate Similarity	NPC175976
0.84	Intermediate Similarity	NPC99515
0.84	Intermediate Similarity	NPC190714
0.8389	Intermediate Similarity	NPC138227
0.8389	Intermediate Similarity	NPC469313
0.8389	Intermediate Similarity	NPC168579
0.8389	Intermediate Similarity	NPC76176
0.8378	Intermediate Similarity	NPC472353
0.8377	Intermediate Similarity	NPC78809
0.8356	Intermediate Similarity	NPC134260
0.8345	Intermediate Similarity	NPC164787
0.8344	Intermediate Similarity	NPC15538
0.8344	Intermediate Similarity	NPC473480
0.8344	Intermediate Similarity	NPC183402
0.8322	Intermediate Similarity	NPC121376
0.8322	Intermediate Similarity	NPC81638
0.8322	Intermediate Similarity	NPC472451
0.8322	Intermediate Similarity	NPC252169
0.8322	Intermediate Similarity	NPC37793
0.8322	Intermediate Similarity	NPC473044
0.8312	Intermediate Similarity	NPC322899
0.8312	Intermediate Similarity	NPC44192
0.8312	Intermediate Similarity	NPC469944
0.8312	Intermediate Similarity	NPC46283
0.8312	Intermediate Similarity	NPC474442
0.8312	Intermediate Similarity	NPC134911
0.8312	Intermediate Similarity	NPC272552
0.8312	Intermediate Similarity	NPC226108
0.8311	Intermediate Similarity	NPC178054
0.8311	Intermediate Similarity	NPC210192
0.831	Intermediate Similarity	NPC218003
0.8291	Intermediate Similarity	NPC100936
0.8291	Intermediate Similarity	NPC1253
0.8289	Intermediate Similarity	NPC280945
0.8288	Intermediate Similarity	NPC302701
0.8288	Intermediate Similarity	NPC269091
0.8288	Intermediate Similarity	NPC234952
0.8278	Intermediate Similarity	NPC162193
0.8278	Intermediate Similarity	NPC155564
0.8278	Intermediate Similarity	NPC102280
0.8278	Intermediate Similarity	NPC125755
0.8278	Intermediate Similarity	NPC248053
0.8276	Intermediate Similarity	NPC188555
0.8276	Intermediate Similarity	NPC130496
0.8267	Intermediate Similarity	NPC473045
0.8267	Intermediate Similarity	NPC25292
0.8264	Intermediate Similarity	NPC303422
0.8264	Intermediate Similarity	NPC85799
0.8264	Intermediate Similarity	NPC26080
0.8264	Intermediate Similarity	NPC165686
0.8255	Intermediate Similarity	NPC475084
0.8255	Intermediate Similarity	NPC60249
0.8243	Intermediate Similarity	NPC109240
0.8235	Intermediate Similarity	NPC44452
0.8231	Intermediate Similarity	NPC87777
0.8231	Intermediate Similarity	NPC262328
0.8224	Intermediate Similarity	NPC474397
0.8224	Intermediate Similarity	NPC227902
0.8219	Intermediate Similarity	NPC61946
0.8219	Intermediate Similarity	NPC79957
0.8219	Intermediate Similarity	NPC238243
0.8219	Intermediate Similarity	NPC151224
0.8212	Intermediate Similarity	NPC161700
0.8212	Intermediate Similarity	NPC475096
0.8212	Intermediate Similarity	NPC277867
0.8207	Intermediate Similarity	NPC115022
0.8207	Intermediate Similarity	NPC263064
0.8207	Intermediate Similarity	NPC215037
0.8207	Intermediate Similarity	NPC294166
0.82	Intermediate Similarity	NPC197461
0.8194	Intermediate Similarity	NPC325860
0.8194	Intermediate Similarity	NPC475067
0.8194	Intermediate Similarity	NPC59692
0.8188	Intermediate Similarity	NPC76871
0.8188	Intermediate Similarity	NPC108674
0.8188	Intermediate Similarity	NPC471389
0.8188	Intermediate Similarity	NPC469661
0.8182	Intermediate Similarity	NPC260781
0.8182	Intermediate Similarity	NPC214326
0.8182	Intermediate Similarity	NPC218041
0.8182	Intermediate Similarity	NPC185955
0.8182	Intermediate Similarity	NPC225815
0.8182	Intermediate Similarity	NPC9933
0.8182	Intermediate Similarity	NPC238140
0.8182	Intermediate Similarity	NPC469707
0.8182	Intermediate Similarity	NPC182368
0.8182	Intermediate Similarity	NPC97326
0.8182	Intermediate Similarity	NPC145979
0.8182	Intermediate Similarity	NPC469706
0.8182	Intermediate Similarity	NPC158784
0.8176	Intermediate Similarity	NPC292487
0.8176	Intermediate Similarity	NPC32630
0.8176	Intermediate Similarity	NPC183781
0.8176	Intermediate Similarity	NPC471388
0.817	Intermediate Similarity	NPC473876
0.8163	Intermediate Similarity	NPC230734
0.8163	Intermediate Similarity	NPC165482
0.8163	Intermediate Similarity	NPC3293
0.8163	Intermediate Similarity	NPC104167
0.8163	Intermediate Similarity	NPC474639
0.8163	Intermediate Similarity	NPC172818
0.8163	Intermediate Similarity	NPC203230
0.8163	Intermediate Similarity	NPC242028
0.8163	Intermediate Similarity	NPC197723
0.8163	Intermediate Similarity	NPC306441
0.8163	Intermediate Similarity	NPC472800
0.8163	Intermediate Similarity	NPC138350
0.8163	Intermediate Similarity	NPC25695
0.8163	Intermediate Similarity	NPC475628
0.8163	Intermediate Similarity	NPC16435
0.8163	Intermediate Similarity	NPC227503
0.8163	Intermediate Similarity	NPC40664
0.8158	Intermediate Similarity	NPC233980
0.8146	Intermediate Similarity	NPC473108
0.8146	Intermediate Similarity	NPC28440
0.8146	Intermediate Similarity	NPC171932
0.8146	Intermediate Similarity	NPC50250
0.8138	Intermediate Similarity	NPC126029
0.8138	Intermediate Similarity	NPC78770
0.8138	Intermediate Similarity	NPC15658
0.8138	Intermediate Similarity	NPC219876
0.8138	Intermediate Similarity	NPC185604
0.8138	Intermediate Similarity	NPC261619
0.8138	Intermediate Similarity	NPC61477
0.8133	Intermediate Similarity	NPC469559
0.8133	Intermediate Similarity	NPC186033
0.8133	Intermediate Similarity	NPC189115
0.8129	Intermediate Similarity	NPC473621
0.8129	Intermediate Similarity	NPC2745
0.8129	Intermediate Similarity	NPC302915
0.8117	Intermediate Similarity	NPC318373
0.8117	Intermediate Similarity	NPC321657
0.8112	Intermediate Similarity	NPC148366
0.8112	Intermediate Similarity	NPC87224
0.8112	Intermediate Similarity	NPC311293
0.8112	Intermediate Similarity	NPC40377
0.8112	Intermediate Similarity	NPC222572
0.8108	Intermediate Similarity	NPC103976
0.8108	Intermediate Similarity	NPC176051
0.8108	Intermediate Similarity	NPC59324
0.8108	Intermediate Similarity	NPC326797
0.8108	Intermediate Similarity	NPC211549
0.8108	Intermediate Similarity	NPC474282
0.8108	Intermediate Similarity	NPC65530
0.8108	Intermediate Similarity	NPC102904
0.8108	Intermediate Similarity	NPC107551
0.8105	Intermediate Similarity	NPC262911
0.8105	Intermediate Similarity	NPC294558
0.8105	Intermediate Similarity	NPC204770
0.8105	Intermediate Similarity	NPC170103
0.8105	Intermediate Similarity	NPC70409
0.8105	Intermediate Similarity	NPC236202
0.8105	Intermediate Similarity	NPC58190
0.8105	Intermediate Similarity	NPC99183
0.8105	Intermediate Similarity	NPC82917
0.8105	Intermediate Similarity	NPC202742
0.8105	Intermediate Similarity	NPC108811
0.8105	Intermediate Similarity	NPC18185
0.8105	Intermediate Similarity	NPC263940
0.8098	Intermediate Similarity	NPC103633
0.8095	Intermediate Similarity	NPC234333
0.8095	Intermediate Similarity	NPC94750
0.8095	Intermediate Similarity	NPC472337
0.8095	Intermediate Similarity	NPC260898
0.8095	Intermediate Similarity	NPC112939
0.8095	Intermediate Similarity	NPC47398
0.8095	Intermediate Similarity	NPC112246
0.8095	Intermediate Similarity	NPC474206
0.8095	Intermediate Similarity	NPC470356
0.8095	Intermediate Similarity	NPC121812
0.8092	Intermediate Similarity	NPC11422
0.8092	Intermediate Similarity	NPC307466
0.8092	Intermediate Similarity	NPC178014
0.8092	Intermediate Similarity	NPC221318
0.8092	Intermediate Similarity	NPC42716
0.8092	Intermediate Similarity	NPC472457
0.8092	Intermediate Similarity	NPC474749

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 NPC288531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	883
0.2-0.3	2032
0.3-0.4	2836
0.4-0.5	1583
0.5-0.6	946
0.6-0.7	430
0.7-0.8	23
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD3787	Discontinued
0.8671	High Similarity	NPD3751	Discontinued
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1091	Approved
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6674	Discontinued
0.7808	Intermediate Similarity	NPD4625	Phase 3
0.7793	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD3027	Phase 3
0.7671	Intermediate Similarity	NPD2861	Phase 2
0.7658	Intermediate Similarity	NPD1653	Approved
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7597	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD8455	Phase 2
0.7517	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4749	Approved
0.7515	Intermediate Similarity	NPD5844	Phase 1
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD37	Approved
0.7465	Intermediate Similarity	NPD1548	Phase 1
0.7456	Intermediate Similarity	NPD7228	Approved
0.7439	Intermediate Similarity	NPD4965	Approved
0.7439	Intermediate Similarity	NPD4966	Approved
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7074	Phase 3
0.7368	Intermediate Similarity	NPD7472	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7342	Intermediate Similarity	NPD5058	Phase 3
0.7333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6797	Phase 2
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7283	Intermediate Similarity	NPD7251	Discontinued
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2677	Approved
0.726	Intermediate Similarity	NPD3705	Approved
0.7244	Intermediate Similarity	NPD7266	Discontinued
0.7241	Intermediate Similarity	NPD7808	Phase 3
0.7241	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6166	Phase 2
0.7205	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7240	Approved
0.7169	Intermediate Similarity	NPD5402	Approved
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.7152	Intermediate Similarity	NPD1934	Approved
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5762	Approved
0.7134	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD6671	Approved
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5125	Phase 3
0.7123	Intermediate Similarity	NPD5126	Approved
0.7115	Intermediate Similarity	NPD5960	Phase 3
0.7114	Intermediate Similarity	NPD8651	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3892	Phase 2
0.7107	Intermediate Similarity	NPD3750	Approved
0.7102	Intermediate Similarity	NPD8313	Approved
0.7102	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD6559	Discontinued
0.7081	Intermediate Similarity	NPD7213	Phase 3
0.7081	Intermediate Similarity	NPD7212	Phase 2
0.7073	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6959	Discontinued
0.7051	Intermediate Similarity	NPD4538	Approved
0.7051	Intermediate Similarity	NPD4536	Approved
0.7051	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD290	Approved
0.7045	Intermediate Similarity	NPD7549	Discontinued
0.7037	Intermediate Similarity	NPD7447	Phase 1
0.7032	Intermediate Similarity	NPD5735	Approved
0.703	Intermediate Similarity	NPD4380	Phase 2
0.7029	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD2801	Approved
0.7006	Intermediate Similarity	NPD5588	Approved
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.6994	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7095	Approved
0.6974	Remote Similarity	NPD3018	Phase 2
0.6968	Remote Similarity	NPD2238	Phase 2
0.6962	Remote Similarity	NPD6099	Approved
0.6962	Remote Similarity	NPD6100	Approved
0.6951	Remote Similarity	NPD5403	Approved
0.6948	Remote Similarity	NPD6798	Discontinued
0.6927	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7819	Suspended
0.6899	Remote Similarity	NPD2155	Approved
0.6899	Remote Similarity	NPD7033	Discontinued
0.6899	Remote Similarity	NPD2154	Approved
0.6899	Remote Similarity	NPD3748	Approved
0.6899	Remote Similarity	NPD2156	Approved
0.6899	Remote Similarity	NPD4108	Discontinued
0.6897	Remote Similarity	NPD7157	Approved
0.6897	Remote Similarity	NPD709	Approved
0.6894	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6516	Phase 2
0.6892	Remote Similarity	NPD5846	Approved
0.6889	Remote Similarity	NPD4663	Approved
0.6887	Remote Similarity	NPD6696	Suspended
0.6882	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2684	Approved
0.6871	Remote Similarity	NPD1511	Approved
0.6864	Remote Similarity	NPD3817	Phase 2
0.6859	Remote Similarity	NPD4140	Approved
0.6859	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3620	Phase 2
0.6857	Remote Similarity	NPD968	Approved
0.6852	Remote Similarity	NPD6190	Approved
0.6846	Remote Similarity	NPD3496	Discontinued
0.6845	Remote Similarity	NPD6777	Approved
0.6845	Remote Similarity	NPD6779	Approved
0.6845	Remote Similarity	NPD6780	Approved
0.6845	Remote Similarity	NPD6776	Approved
0.6845	Remote Similarity	NPD6778	Approved
0.6845	Remote Similarity	NPD6782	Approved
0.6845	Remote Similarity	NPD6781	Approved
0.6836	Remote Similarity	NPD7007	Discovery
0.6829	Remote Similarity	NPD5401	Approved
0.6829	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1357	Approved
0.6821	Remote Similarity	NPD7229	Phase 3
0.6821	Remote Similarity	NPD6232	Discontinued
0.6821	Remote Similarity	NPD2982	Phase 2
0.6821	Remote Similarity	NPD2983	Phase 2
0.6821	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4578	Approved
0.6816	Remote Similarity	NPD7311	Approved
0.6816	Remote Similarity	NPD7310	Approved
0.6816	Remote Similarity	NPD4577	Approved
0.6816	Remote Similarity	NPD7312	Approved
0.6816	Remote Similarity	NPD7313	Approved
0.6815	Remote Similarity	NPD6355	Discontinued
0.6813	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7843	Approved
0.6805	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5494	Approved
0.68	Remote Similarity	NPD422	Phase 1
0.68	Remote Similarity	NPD1611	Approved
0.6798	Remote Similarity	NPD7685	Pre-registration
0.679	Remote Similarity	NPD4628	Phase 3
0.679	Remote Similarity	NPD7466	Approved
0.6788	Remote Similarity	NPD1512	Approved
0.6786	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3749	Approved
0.6784	Remote Similarity	NPD7075	Discontinued
0.6782	Remote Similarity	NPD2969	Approved
0.6782	Remote Similarity	NPD2970	Approved
0.6778	Remote Similarity	NPD7309	Approved
0.6778	Remote Similarity	NPD8053	Approved
0.6778	Remote Similarity	NPD8054	Approved
0.6776	Remote Similarity	NPD3225	Approved
0.6772	Remote Similarity	NPD6823	Phase 2
0.6772	Remote Similarity	NPD6653	Approved
0.677	Remote Similarity	NPD2424	Discontinued
0.677	Remote Similarity	NPD1549	Phase 2
0.6768	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5283	Phase 1
0.6759	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7906	Approved
0.6755	Remote Similarity	NPD2231	Phase 2
0.6755	Remote Similarity	NPD2981	Phase 2
0.6755	Remote Similarity	NPD2235	Phase 2
0.6753	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7783	Phase 2
0.6752	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7435	Discontinued
0.6728	Remote Similarity	NPD5177	Phase 3
0.6725	Remote Similarity	NPD7768	Phase 2
0.6725	Remote Similarity	NPD3882	Suspended
0.6724	Remote Similarity	NPD3051	Approved
0.6711	Remote Similarity	NPD5327	Phase 3
0.6709	Remote Similarity	NPD4340	Discontinued
0.6708	Remote Similarity	NPD1375	Discontinued
0.6706	Remote Similarity	NPD5929	Approved
0.6705	Remote Similarity	NPD7473	Discontinued
0.6702	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6584	Phase 3
0.6686	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD4005	Discontinued
0.6667	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD6353	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