NPASS Compound

Structure

NPC472155 OpenBabel07101718202D 28 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 -0.8398 2.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9395 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 -0.8398 2.4244 0.0000 C 0 0 1 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 1.9395 0.0000 C 0 0 2 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 -0.8398 0.4849 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 -0.8398 3.3942 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 0.8398 2.4244 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 -1.6797 0.0000 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 1 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 26 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 12 18 1 1 0 0 0 12 21 1 0 0 0 0 13 19 1 1 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 23 1 6 0 0 0 16 18 1 1 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 6 0 0 0 18 28 1 0 0 0 0 19 20 1 1 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.12
Volume:	360.277
LogP:	1.006
LogD:	0.486
LogS:	-3.909
# Rotatable Bonds:	0
TPSA:	132.14
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	5.316
Fsp3:	0.5
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:	-5.806
MDCK Permeability:	2.220439273514785e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.137
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.349
Plasma Protein Binding (PPB):	93.94939422607422%
Volume Distribution (VD):	0.453
Pgp-substrate:	3.1200881004333496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.262
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.081

ADMET: Excretion

Clearance (CL):	7.659
Half-life (T1/2):	0.504

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.988
Drug-inuced Liver Injury (DILI):	0.516
AMES Toxicity:	0.521
Rat Oral Acute Toxicity:	0.738
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.288
Carcinogencity:	0.972
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC472155

Natural Product ID:	NPC472155
*Common Name:**	GJOPRRHPJJXPBD-XJOGIRLRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GJOPRRHPJJXPBD-XJOGIRLRSA-N
Standard InCHI:	InChI=1S/C20H20O8/c21-12-7-8-13(22)19-18(12,28-19)16(24)15(23)17(25)20(19)26-10-5-1-3-9-4-2-6-11(27-20)14(9)10/h1-6,12-13,15-17,21-25H,7-8H2/t12-,13+,15-,16-,17+,18-,19-/m0/s1
SMILES:	C1CC(C23C(C1O)(O2)C(C(C(C34OC5=CC=CC6=C5C(=CC=C6)O4)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342635
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[534490]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[534490]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[534490]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[534490]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[534490]

☑ 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 NPC472155 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	510
0.1-0.2	1801
0.2-0.3	4438
0.3-0.4	10035
0.4-0.5	8628
0.5-0.6	5432
0.6-0.7	8738
0.7-0.8	2949
0.8-0.85	145
0.85-0.9	13
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC472154
0.9783	High Similarity	NPC173630
0.9571	High Similarity	NPC288531
0.9568	High Similarity	NPC151704
0.95	High Similarity	NPC271076
0.95	High Similarity	NPC23807
0.9281	High Similarity	NPC193920
0.8947	High Similarity	NPC472153
0.8936	High Similarity	NPC472151
0.8849	High Similarity	NPC138940
0.8831	High Similarity	NPC120677
0.8831	High Similarity	NPC74371
0.8774	High Similarity	NPC75944
0.8733	High Similarity	NPC306267
0.8733	High Similarity	NPC20050
0.8693	High Similarity	NPC472156
0.8667	High Similarity	NPC233467
0.8667	High Similarity	NPC21902
0.8599	High Similarity	NPC472150
0.8571	High Similarity	NPC284232
0.8543	High Similarity	NPC44192
0.8543	High Similarity	NPC469944
0.8543	High Similarity	NPC226108
0.8543	High Similarity	NPC272552
0.8543	High Similarity	NPC134911
0.8543	High Similarity	NPC46283
0.8543	High Similarity	NPC322899
0.8523	High Similarity	NPC175976
0.8516	High Similarity	NPC100936
0.8516	High Similarity	NPC1253
0.8514	High Similarity	NPC190714
0.8514	High Similarity	NPC248053
0.8514	High Similarity	NPC155564
0.8514	High Similarity	NPC99515
0.8514	High Similarity	NPC102280
0.8503	High Similarity	NPC469313
0.8503	High Similarity	NPC76176
0.8503	High Similarity	NPC138227
0.8503	High Similarity	NPC168579
0.8493	Intermediate Similarity	NPC472353
0.8487	Intermediate Similarity	NPC78809
0.8456	Intermediate Similarity	NPC473480
0.8456	Intermediate Similarity	NPC15538
0.8452	Intermediate Similarity	NPC183402
0.8435	Intermediate Similarity	NPC252169
0.8435	Intermediate Similarity	NPC473044
0.8435	Intermediate Similarity	NPC37793
0.8425	Intermediate Similarity	NPC76871
0.8425	Intermediate Similarity	NPC178054
0.8425	Intermediate Similarity	NPC108674
0.8425	Intermediate Similarity	NPC210192
0.8421	Intermediate Similarity	NPC474442
0.8421	Intermediate Similarity	NPC59692
0.8411	Intermediate Similarity	NPC238140
0.84	Intermediate Similarity	NPC280945
0.8392	Intermediate Similarity	NPC130496
0.8392	Intermediate Similarity	NPC188555
0.8389	Intermediate Similarity	NPC125755
0.838	Intermediate Similarity	NPC26080
0.838	Intermediate Similarity	NPC303422
0.838	Intermediate Similarity	NPC85799
0.838	Intermediate Similarity	NPC165686
0.8378	Intermediate Similarity	NPC28440
0.8378	Intermediate Similarity	NPC171932
0.8378	Intermediate Similarity	NPC473045
0.8378	Intermediate Similarity	NPC25292
0.8367	Intermediate Similarity	NPC60249
0.8367	Intermediate Similarity	NPC475084
0.8365	Intermediate Similarity	NPC175082
0.8345	Intermediate Similarity	NPC262328
0.8345	Intermediate Similarity	NPC134260
0.8345	Intermediate Similarity	NPC87777
0.8344	Intermediate Similarity	NPC321657
0.8344	Intermediate Similarity	NPC318373
0.8344	Intermediate Similarity	NPC44452
0.8333	Intermediate Similarity	NPC202742
0.8333	Intermediate Similarity	NPC263940
0.8333	Intermediate Similarity	NPC204770
0.8333	Intermediate Similarity	NPC164787
0.8333	Intermediate Similarity	NPC99183
0.8333	Intermediate Similarity	NPC170103
0.8333	Intermediate Similarity	NPC236202
0.8333	Intermediate Similarity	NPC82917
0.8333	Intermediate Similarity	NPC58190
0.8333	Intermediate Similarity	NPC262911
0.8333	Intermediate Similarity	NPC294558
0.8333	Intermediate Similarity	NPC70409
0.8333	Intermediate Similarity	NPC227902
0.8333	Intermediate Similarity	NPC193749
0.8333	Intermediate Similarity	NPC108811
0.8333	Intermediate Similarity	NPC79957
0.8333	Intermediate Similarity	NPC18185
0.8333	Intermediate Similarity	NPC238243
0.8322	Intermediate Similarity	NPC115022
0.8322	Intermediate Similarity	NPC263064
0.8322	Intermediate Similarity	NPC475096
0.8322	Intermediate Similarity	NPC161700
0.8322	Intermediate Similarity	NPC294166
0.8322	Intermediate Similarity	NPC277867
0.8313	Intermediate Similarity	NPC103633
0.8311	Intermediate Similarity	NPC81638
0.8311	Intermediate Similarity	NPC472451
0.831	Intermediate Similarity	NPC121376
0.831	Intermediate Similarity	NPC475067
0.8302	Intermediate Similarity	NPC11608
0.8302	Intermediate Similarity	NPC297404
0.8299	Intermediate Similarity	NPC277331
0.8299	Intermediate Similarity	NPC100482
0.8299	Intermediate Similarity	NPC469661
0.8298	Intermediate Similarity	NPC218003
0.8289	Intermediate Similarity	NPC469707
0.8289	Intermediate Similarity	NPC218041
0.8289	Intermediate Similarity	NPC145979
0.8289	Intermediate Similarity	NPC185955
0.8289	Intermediate Similarity	NPC469706
0.8289	Intermediate Similarity	NPC182368
0.8289	Intermediate Similarity	NPC214326
0.8289	Intermediate Similarity	NPC9933
0.8289	Intermediate Similarity	NPC225815
0.8289	Intermediate Similarity	NPC260781
0.8278	Intermediate Similarity	NPC270751
0.8278	Intermediate Similarity	NPC227516
0.8278	Intermediate Similarity	NPC20757
0.8276	Intermediate Similarity	NPC203230
0.8276	Intermediate Similarity	NPC302701
0.8276	Intermediate Similarity	NPC269091
0.8276	Intermediate Similarity	NPC234952
0.8276	Intermediate Similarity	NPC40664
0.8276	Intermediate Similarity	NPC92932
0.8276	Intermediate Similarity	NPC138350
0.8276	Intermediate Similarity	NPC165482
0.8276	Intermediate Similarity	NPC3293
0.8276	Intermediate Similarity	NPC104167
0.8276	Intermediate Similarity	NPC242028
0.8276	Intermediate Similarity	NPC197723
0.8269	Intermediate Similarity	NPC4809
0.8269	Intermediate Similarity	NPC147743
0.8269	Intermediate Similarity	NPC73517
0.8267	Intermediate Similarity	NPC274454
0.8267	Intermediate Similarity	NPC96576
0.8267	Intermediate Similarity	NPC162193
0.8267	Intermediate Similarity	NPC215678
0.8264	Intermediate Similarity	NPC187194
0.8264	Intermediate Similarity	NPC476411
0.8255	Intermediate Similarity	NPC304894
0.8255	Intermediate Similarity	NPC15659
0.8243	Intermediate Similarity	NPC189115
0.8243	Intermediate Similarity	NPC469559
0.8243	Intermediate Similarity	NPC186033
0.8235	Intermediate Similarity	NPC259707
0.8235	Intermediate Similarity	NPC471403
0.8235	Intermediate Similarity	NPC473621
0.8231	Intermediate Similarity	NPC109240
0.8231	Intermediate Similarity	NPC262189
0.8228	Intermediate Similarity	NPC48880
0.8227	Intermediate Similarity	NPC148366
0.8227	Intermediate Similarity	NPC311293
0.8227	Intermediate Similarity	NPC40377
0.8224	Intermediate Similarity	NPC476969
0.8224	Intermediate Similarity	NPC211561
0.8219	Intermediate Similarity	NPC65530
0.8219	Intermediate Similarity	NPC59324
0.8217	Intermediate Similarity	NPC185231
0.8217	Intermediate Similarity	NPC106601
0.8217	Intermediate Similarity	NPC86630
0.8217	Intermediate Similarity	NPC159526
0.8217	Intermediate Similarity	NPC205613
0.8217	Intermediate Similarity	NPC471404
0.8217	Intermediate Similarity	NPC212614
0.8217	Intermediate Similarity	NPC151474
0.8212	Intermediate Similarity	NPC174251
0.8212	Intermediate Similarity	NPC474397
0.8212	Intermediate Similarity	NPC153182
0.8207	Intermediate Similarity	NPC151224
0.8207	Intermediate Similarity	NPC61946
0.8194	Intermediate Similarity	NPC215037
0.8194	Intermediate Similarity	NPC69513
0.8194	Intermediate Similarity	NPC215833
0.8188	Intermediate Similarity	NPC163508
0.8188	Intermediate Similarity	NPC116922
0.8188	Intermediate Similarity	NPC173203
0.8182	Intermediate Similarity	NPC9912
0.8182	Intermediate Similarity	NPC215060
0.8182	Intermediate Similarity	NPC325860
0.8182	Intermediate Similarity	NPC476352
0.8176	Intermediate Similarity	NPC257095
0.8176	Intermediate Similarity	NPC89686
0.8176	Intermediate Similarity	NPC273932
0.8176	Intermediate Similarity	NPC471389
0.817	Intermediate Similarity	NPC477612
0.817	Intermediate Similarity	NPC158784
0.8169	Intermediate Similarity	NPC97326
0.8163	Intermediate Similarity	NPC98777
0.8163	Intermediate Similarity	NPC212770
0.8163	Intermediate Similarity	NPC471388
0.8163	Intermediate Similarity	NPC183781
0.8163	Intermediate Similarity	NPC292487
0.8163	Intermediate Similarity	NPC32630
0.8163	Intermediate Similarity	NPC22517
0.8158	Intermediate Similarity	NPC281549

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 NPC472155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	879
0.2-0.3	1906
0.3-0.4	2865
0.4-0.5	1682
0.5-0.6	964
0.6-0.7	409
0.7-0.8	43
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8766	High Similarity	NPD3787	Discontinued
0.8313	Intermediate Similarity	NPD3751	Discontinued
0.8125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1613	Approved
0.7986	Intermediate Similarity	NPD1091	Approved
0.7933	Intermediate Similarity	NPD6674	Discontinued
0.7848	Intermediate Similarity	NPD8455	Phase 2
0.7847	Intermediate Similarity	NPD4908	Phase 1
0.7847	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4625	Phase 3
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1653	Approved
0.774	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3027	Phase 3
0.7669	Intermediate Similarity	NPD7199	Phase 2
0.7655	Intermediate Similarity	NPD2861	Phase 2
0.7606	Intermediate Similarity	NPD1610	Phase 2
0.7562	Intermediate Similarity	NPD37	Approved
0.7545	Intermediate Similarity	NPD7228	Approved
0.7531	Intermediate Similarity	NPD4966	Approved
0.7531	Intermediate Similarity	NPD4965	Approved
0.7531	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7097	Phase 1
0.747	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD7074	Phase 3
0.7447	Intermediate Similarity	NPD1548	Phase 1
0.7439	Intermediate Similarity	NPD6234	Discontinued
0.7436	Intermediate Similarity	NPD5058	Phase 3
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.7383	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD4749	Approved
0.7372	Intermediate Similarity	NPD2677	Approved
0.7368	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7361	Intermediate Similarity	NPD3705	Approved
0.7342	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7266	Discontinued
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6166	Phase 2
0.7321	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4060	Phase 1
0.7283	Intermediate Similarity	NPD8312	Approved
0.7283	Intermediate Similarity	NPD8313	Approved
0.7256	Intermediate Similarity	NPD5402	Approved
0.7246	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD1652	Phase 2
0.7235	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD5762	Approved
0.7226	Intermediate Similarity	NPD5763	Approved
0.7222	Intermediate Similarity	NPD5126	Approved
0.7222	Intermediate Similarity	NPD5125	Phase 3
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD5960	Phase 3
0.7197	Intermediate Similarity	NPD3892	Phase 2
0.7193	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7153	Intermediate Similarity	NPD290	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4536	Approved
0.7143	Intermediate Similarity	NPD4538	Approved
0.7143	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1934	Approved
0.7124	Intermediate Similarity	NPD5735	Approved
0.7124	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD4380	Phase 2
0.7113	Intermediate Similarity	NPD6671	Approved
0.7113	Intermediate Similarity	NPD7157	Approved
0.7105	Intermediate Similarity	NPD6233	Phase 2
0.7097	Intermediate Similarity	NPD5588	Approved
0.7095	Intermediate Similarity	NPD8651	Approved
0.7091	Intermediate Similarity	NPD7819	Suspended
0.7091	Intermediate Similarity	NPD1465	Phase 2
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7095	Approved
0.7081	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7212	Phase 2
0.7063	Intermediate Similarity	NPD7213	Phase 3
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3817	Phase 2
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7037	Intermediate Similarity	NPD5403	Approved
0.7029	Intermediate Similarity	NPD7549	Discontinued
0.7027	Intermediate Similarity	NPD2983	Phase 2
0.7027	Intermediate Similarity	NPD2982	Phase 2
0.7021	Intermediate Similarity	NPD7843	Approved
0.7019	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5401	Approved
0.7019	Intermediate Similarity	NPD7447	Phase 1
0.7011	Intermediate Similarity	NPD6778	Approved
0.7011	Intermediate Similarity	NPD6782	Approved
0.7011	Intermediate Similarity	NPD6780	Approved
0.7011	Intermediate Similarity	NPD6776	Approved
0.7011	Intermediate Similarity	NPD6777	Approved
0.7011	Intermediate Similarity	NPD6779	Approved
0.7011	Intermediate Similarity	NPD6781	Approved
0.7006	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD709	Approved
0.6988	Remote Similarity	NPD2801	Approved
0.6987	Remote Similarity	NPD2156	Approved
0.6987	Remote Similarity	NPD2154	Approved
0.6987	Remote Similarity	NPD2155	Approved
0.6987	Remote Similarity	NPD4108	Discontinued
0.6986	Remote Similarity	NPD5846	Approved
0.6986	Remote Similarity	NPD6516	Phase 2
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3750	Approved
0.6978	Remote Similarity	NPD2684	Approved
0.6959	Remote Similarity	NPD2981	Phase 2
0.6948	Remote Similarity	NPD4140	Approved
0.6948	Remote Similarity	NPD2238	Phase 2
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6937	Remote Similarity	NPD6190	Approved
0.6935	Remote Similarity	NPD6823	Phase 2
0.6914	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6355	Discontinued
0.6901	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD6232	Discontinued
0.6899	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7435	Discontinued
0.6892	Remote Similarity	NPD1611	Approved
0.6886	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5494	Approved
0.6879	Remote Similarity	NPD7033	Discontinued
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD7685	Pre-registration
0.6875	Remote Similarity	NPD7466	Approved
0.6872	Remote Similarity	NPD4663	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.6864	Remote Similarity	NPD7075	Discontinued
0.6855	Remote Similarity	NPD2424	Discontinued
0.6854	Remote Similarity	NPD8054	Approved
0.6854	Remote Similarity	NPD8053	Approved
0.6853	Remote Similarity	NPD5283	Phase 1
0.6852	Remote Similarity	NPD1511	Approved
0.6845	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8127	Discontinued
0.6839	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3620	Phase 2
0.6835	Remote Similarity	NPD968	Approved
0.6833	Remote Similarity	NPD6843	Phase 3
0.6833	Remote Similarity	NPD6842	Approved
0.6833	Remote Similarity	NPD7906	Approved
0.6833	Remote Similarity	NPD6841	Approved
0.6824	Remote Similarity	NPD3496	Discontinued
0.6823	Remote Similarity	NPD7783	Phase 2
0.6823	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7007	Discovery
0.6809	Remote Similarity	NPD7696	Phase 3
0.6809	Remote Similarity	NPD7697	Approved
0.6809	Remote Similarity	NPD7698	Approved
0.6805	Remote Similarity	NPD7768	Phase 2
0.6803	Remote Similarity	NPD1357	Approved
0.6802	Remote Similarity	NPD3051	Approved
0.68	Remote Similarity	NPD8156	Discontinued
0.68	Remote Similarity	NPD5327	Phase 3
0.68	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4577	Approved
0.6798	Remote Similarity	NPD4578	Approved
0.6792	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1375	Discontinued
0.6792	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7473	Discontinued
0.6779	Remote Similarity	NPD422	Phase 1
0.6774	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7870	Phase 2
0.6772	Remote Similarity	NPD7871	Phase 2
0.677	Remote Similarity	NPD4628	Phase 3
0.677	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1512	Approved
0.6766	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7411	Suspended
0.6765	Remote Similarity	NPD3749	Approved
0.6755	Remote Similarity	NPD3225	Approved
0.6754	Remote Similarity	NPD7701	Phase 2
0.6752	Remote Similarity	NPD6353	Approved
0.6752	Remote Similarity	NPD6653	Approved
0.675	Remote Similarity	NPD1549	Phase 2
0.6748	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6799	Approved
0.6747	Remote Similarity	NPD4005	Discontinued
0.6743	Remote Similarity	NPD8251	Approved
0.6743	Remote Similarity	NPD8099	Discontinued
0.6743	Remote Similarity	NPD8252	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