NPASS Compound

Structure

NPC472154 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 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 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:	386.1
Volume:	357.64
LogP:	0.951
LogD:	0.309
LogS:	-3.874
# 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:	0.294
Synthetic Accessibility Score:	5.411
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:	-5.753
MDCK Permeability:	2.8734842999256216e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.21
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.309
Plasma Protein Binding (PPB):	93.5592041015625%
Volume Distribution (VD):	0.48
Pgp-substrate:	3.589897632598877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.337
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	5.477
Half-life (T1/2):	0.524

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.988
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.587
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.139
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC472154

Natural Product ID:	NPC472154
*Common Name:**	PKEIHANGEAWICI-XJOGIRLRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PKEIHANGEAWICI-XJOGIRLRSA-N
Standard InCHI:	InChI=1S/C20H18O8/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/h1-8,12-13,15-17,21-25H/t12-,13+,15-,16-,17+,18-,19-/m0/s1
SMILES:	O[C@@H]1[C@@H](O)C2(Oc3cccc4c3c(O2)ccc4)[C@]23[C@]([C@H]1O)(O2)[C@@H](O)C=C[C@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342634
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[493522]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[493522]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[493522]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[493522]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[493522]

☑ 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 NPC472154 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	499
0.1-0.2	1758
0.2-0.3	4415
0.3-0.4	10391
0.4-0.5	8141
0.5-0.6	5113
0.6-0.7	8903
0.7-0.8	3239
0.8-0.85	220
0.85-0.9	7
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC288531
0.9783	High Similarity	NPC472155
0.9571	High Similarity	NPC173630
0.95	High Similarity	NPC151704
0.9493	High Similarity	NPC193920
0.9433	High Similarity	NPC23807
0.9433	High Similarity	NPC271076
0.9143	High Similarity	NPC472151
0.8882	High Similarity	NPC472156
0.8786	High Similarity	NPC138940
0.8782	High Similarity	NPC472150
0.8777	High Similarity	NPC284232
0.8766	High Similarity	NPC472153
0.8733	High Similarity	NPC21902
0.8675	High Similarity	NPC306267
0.8675	High Similarity	NPC20050
0.8654	High Similarity	NPC120677
0.8654	High Similarity	NPC74371
0.8609	High Similarity	NPC233467
0.8599	High Similarity	NPC75944
0.8591	High Similarity	NPC175976
0.8581	High Similarity	NPC190714
0.8581	High Similarity	NPC99515
0.8571	High Similarity	NPC138227
0.8571	High Similarity	NPC469313
0.8571	High Similarity	NPC76176
0.8571	High Similarity	NPC168579
0.8562	High Similarity	NPC472353
0.8553	High Similarity	NPC78809
0.8544	High Similarity	NPC175082
0.8523	High Similarity	NPC473480
0.8523	High Similarity	NPC15538
0.8516	High Similarity	NPC193749
0.8503	High Similarity	NPC473044
0.8503	High Similarity	NPC37793
0.8503	High Similarity	NPC252169
0.8493	Intermediate Similarity	NPC210192
0.8493	Intermediate Similarity	NPC178054
0.8487	Intermediate Similarity	NPC474442
0.8487	Intermediate Similarity	NPC272552
0.8487	Intermediate Similarity	NPC469944
0.8487	Intermediate Similarity	NPC226108
0.8487	Intermediate Similarity	NPC46283
0.8487	Intermediate Similarity	NPC322899
0.8487	Intermediate Similarity	NPC134911
0.8487	Intermediate Similarity	NPC44192
0.8472	Intermediate Similarity	NPC92932
0.8467	Intermediate Similarity	NPC280945
0.8462	Intermediate Similarity	NPC130496
0.8462	Intermediate Similarity	NPC1253
0.8462	Intermediate Similarity	NPC188555
0.8462	Intermediate Similarity	NPC100936
0.8456	Intermediate Similarity	NPC155564
0.8456	Intermediate Similarity	NPC102280
0.8456	Intermediate Similarity	NPC248053
0.8456	Intermediate Similarity	NPC125755
0.8451	Intermediate Similarity	NPC26080
0.8451	Intermediate Similarity	NPC85799
0.8451	Intermediate Similarity	NPC165686
0.8451	Intermediate Similarity	NPC303422
0.8446	Intermediate Similarity	NPC25292
0.8446	Intermediate Similarity	NPC473045
0.8435	Intermediate Similarity	NPC475084
0.8435	Intermediate Similarity	NPC60249
0.8414	Intermediate Similarity	NPC134260
0.8414	Intermediate Similarity	NPC87777
0.8414	Intermediate Similarity	NPC262328
0.8411	Intermediate Similarity	NPC44452
0.8403	Intermediate Similarity	NPC79957
0.8403	Intermediate Similarity	NPC164787
0.8403	Intermediate Similarity	NPC238243
0.84	Intermediate Similarity	NPC227902
0.8397	Intermediate Similarity	NPC183402
0.8392	Intermediate Similarity	NPC294166
0.8392	Intermediate Similarity	NPC115022
0.8389	Intermediate Similarity	NPC277867
0.8389	Intermediate Similarity	NPC475096
0.8389	Intermediate Similarity	NPC161700
0.838	Intermediate Similarity	NPC121376
0.838	Intermediate Similarity	NPC475067
0.8378	Intermediate Similarity	NPC81638
0.8378	Intermediate Similarity	NPC472451
0.8369	Intermediate Similarity	NPC218003
0.8367	Intermediate Similarity	NPC76871
0.8367	Intermediate Similarity	NPC469661
0.8367	Intermediate Similarity	NPC108674
0.8366	Intermediate Similarity	NPC59692
0.8355	Intermediate Similarity	NPC238140
0.8355	Intermediate Similarity	NPC9933
0.8355	Intermediate Similarity	NPC218041
0.8355	Intermediate Similarity	NPC225815
0.8355	Intermediate Similarity	NPC260781
0.8355	Intermediate Similarity	NPC214326
0.8355	Intermediate Similarity	NPC182368
0.8355	Intermediate Similarity	NPC469706
0.8355	Intermediate Similarity	NPC185955
0.8355	Intermediate Similarity	NPC145979
0.8355	Intermediate Similarity	NPC469707
0.8345	Intermediate Similarity	NPC3293
0.8345	Intermediate Similarity	NPC104167
0.8345	Intermediate Similarity	NPC234952
0.8345	Intermediate Similarity	NPC242028
0.8345	Intermediate Similarity	NPC197723
0.8345	Intermediate Similarity	NPC165482
0.8345	Intermediate Similarity	NPC203230
0.8345	Intermediate Similarity	NPC138350
0.8345	Intermediate Similarity	NPC302701
0.8345	Intermediate Similarity	NPC269091
0.8345	Intermediate Similarity	NPC40664
0.8333	Intermediate Similarity	NPC162193
0.8322	Intermediate Similarity	NPC28440
0.8322	Intermediate Similarity	NPC171932
0.8311	Intermediate Similarity	NPC189115
0.8311	Intermediate Similarity	NPC469559
0.8301	Intermediate Similarity	NPC473621
0.8299	Intermediate Similarity	NPC109240
0.8298	Intermediate Similarity	NPC311293
0.8298	Intermediate Similarity	NPC40377
0.8298	Intermediate Similarity	NPC148366
0.8289	Intermediate Similarity	NPC318373
0.8289	Intermediate Similarity	NPC321657
0.8288	Intermediate Similarity	NPC65530
0.8288	Intermediate Similarity	NPC59324
0.8278	Intermediate Similarity	NPC70409
0.8278	Intermediate Similarity	NPC108811
0.8278	Intermediate Similarity	NPC204770
0.8278	Intermediate Similarity	NPC263940
0.8278	Intermediate Similarity	NPC262911
0.8278	Intermediate Similarity	NPC294558
0.8278	Intermediate Similarity	NPC58190
0.8278	Intermediate Similarity	NPC99183
0.8278	Intermediate Similarity	NPC236202
0.8278	Intermediate Similarity	NPC170103
0.8278	Intermediate Similarity	NPC18185
0.8278	Intermediate Similarity	NPC202742
0.8278	Intermediate Similarity	NPC474397
0.8278	Intermediate Similarity	NPC82917
0.8276	Intermediate Similarity	NPC61946
0.8276	Intermediate Similarity	NPC151224
0.8264	Intermediate Similarity	NPC215037
0.8264	Intermediate Similarity	NPC263064
0.8261	Intermediate Similarity	NPC103633
0.8255	Intermediate Similarity	NPC116922
0.8255	Intermediate Similarity	NPC197461
0.825	Intermediate Similarity	NPC297404
0.825	Intermediate Similarity	NPC11608
0.8247	Intermediate Similarity	NPC325860
0.8243	Intermediate Similarity	NPC277331
0.8243	Intermediate Similarity	NPC100482
0.8243	Intermediate Similarity	NPC89686
0.8243	Intermediate Similarity	NPC471389
0.8243	Intermediate Similarity	NPC273932
0.8243	Intermediate Similarity	NPC257095
0.8239	Intermediate Similarity	NPC97326
0.8235	Intermediate Similarity	NPC158784
0.8231	Intermediate Similarity	NPC292487
0.8231	Intermediate Similarity	NPC212770
0.8231	Intermediate Similarity	NPC22517
0.8231	Intermediate Similarity	NPC98777
0.8231	Intermediate Similarity	NPC183781
0.8231	Intermediate Similarity	NPC32630
0.8231	Intermediate Similarity	NPC471388
0.8224	Intermediate Similarity	NPC20757
0.8224	Intermediate Similarity	NPC270751
0.8224	Intermediate Similarity	NPC473876
0.8224	Intermediate Similarity	NPC227516
0.8219	Intermediate Similarity	NPC172818
0.8219	Intermediate Similarity	NPC474639
0.8219	Intermediate Similarity	NPC25695
0.8219	Intermediate Similarity	NPC16435
0.8219	Intermediate Similarity	NPC227503
0.8219	Intermediate Similarity	NPC475628
0.8219	Intermediate Similarity	NPC306441
0.8219	Intermediate Similarity	NPC230734
0.8219	Intermediate Similarity	NPC472800
0.8217	Intermediate Similarity	NPC73517
0.8217	Intermediate Similarity	NPC147743
0.8217	Intermediate Similarity	NPC4809
0.8212	Intermediate Similarity	NPC96576
0.8212	Intermediate Similarity	NPC215678
0.8212	Intermediate Similarity	NPC233980
0.8212	Intermediate Similarity	NPC274454
0.8207	Intermediate Similarity	NPC251981
0.8207	Intermediate Similarity	NPC476411
0.8207	Intermediate Similarity	NPC87696
0.8207	Intermediate Similarity	NPC187194
0.8207	Intermediate Similarity	NPC48863
0.8207	Intermediate Similarity	NPC13745
0.8207	Intermediate Similarity	NPC170694
0.82	Intermediate Similarity	NPC225445
0.82	Intermediate Similarity	NPC15659
0.82	Intermediate Similarity	NPC304894
0.82	Intermediate Similarity	NPC473108
0.82	Intermediate Similarity	NPC50250
0.82	Intermediate Similarity	NPC177597
0.8194	Intermediate Similarity	NPC61477
0.8194	Intermediate Similarity	NPC219876
0.8194	Intermediate Similarity	NPC15658
0.8194	Intermediate Similarity	NPC78770
0.8194	Intermediate Similarity	NPC185604

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 NPC472154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	866
0.2-0.3	1948
0.3-0.4	2817
0.4-0.5	1665
0.5-0.6	962
0.6-0.7	447
0.7-0.8	48
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD3787	Discontinued
0.8491	Intermediate Similarity	NPD3751	Discontinued
0.8194	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1613	Approved
0.8058	Intermediate Similarity	NPD1091	Approved
0.7917	Intermediate Similarity	NPD4908	Phase 1
0.7917	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6674	Discontinued
0.7862	Intermediate Similarity	NPD4625	Phase 3
0.7847	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1653	Approved
0.7808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3027	Phase 3
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7688	Intermediate Similarity	NPD8455	Phase 2
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.7647	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD37	Approved
0.7622	Intermediate Similarity	NPD7199	Phase 2
0.7605	Intermediate Similarity	NPD7228	Approved
0.7593	Intermediate Similarity	NPD4967	Phase 2
0.7593	Intermediate Similarity	NPD4966	Approved
0.7593	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD4749	Approved
0.7568	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5844	Phase 1
0.756	Intermediate Similarity	NPD7054	Approved
0.7546	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1548	Phase 1
0.7515	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7266	Discontinued
0.7389	Intermediate Similarity	NPD5058	Phase 3
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7384	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6166	Phase 2
0.7381	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4060	Phase 1
0.7326	Intermediate Similarity	NPD7240	Approved
0.7325	Intermediate Similarity	NPD2677	Approved
0.732	Intermediate Similarity	NPD7097	Phase 1
0.7317	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD3705	Approved
0.7294	Intermediate Similarity	NPD3818	Discontinued
0.7251	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7225	Intermediate Similarity	NPD6559	Discontinued
0.7202	Intermediate Similarity	NPD6959	Discontinued
0.7197	Intermediate Similarity	NPD1652	Phase 2
0.7195	Intermediate Similarity	NPD1934	Approved
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.7183	Intermediate Similarity	NPD6671	Approved
0.7181	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD5763	Approved
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.7168	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8651	Approved
0.7161	Intermediate Similarity	NPD5960	Phase 3
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD3892	Phase 2
0.7152	Intermediate Similarity	NPD1465	Phase 2
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3018	Phase 2
0.7125	Intermediate Similarity	NPD7212	Phase 2
0.7125	Intermediate Similarity	NPD7213	Phase 3
0.7117	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD290	Approved
0.7099	Intermediate Similarity	NPD5403	Approved
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7086	Intermediate Similarity	NPD7549	Discontinued
0.7081	Intermediate Similarity	NPD7447	Phase 1
0.7078	Intermediate Similarity	NPD5735	Approved
0.7063	Intermediate Similarity	NPD7157	Approved
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7051	Intermediate Similarity	NPD5588	Approved
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7048	Intermediate Similarity	NPD2801	Approved
0.7039	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2238	Phase 2
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD6190	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.698	Remote Similarity	NPD2982	Phase 2
0.698	Remote Similarity	NPD2983	Phase 2
0.6975	Remote Similarity	NPD5401	Approved
0.6973	Remote Similarity	NPD6778	Approved
0.6973	Remote Similarity	NPD6779	Approved
0.6973	Remote Similarity	NPD6776	Approved
0.6973	Remote Similarity	NPD6780	Approved
0.6973	Remote Similarity	NPD6782	Approved
0.6973	Remote Similarity	NPD6781	Approved
0.6973	Remote Similarity	NPD6777	Approved
0.6972	Remote Similarity	NPD7843	Approved
0.6962	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6232	Discontinued
0.6944	Remote Similarity	NPD709	Approved
0.6943	Remote Similarity	NPD2156	Approved
0.6943	Remote Similarity	NPD3748	Approved
0.6943	Remote Similarity	NPD2155	Approved
0.6943	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD4108	Discontinued
0.6943	Remote Similarity	NPD2154	Approved
0.6939	Remote Similarity	NPD5846	Approved
0.6939	Remote Similarity	NPD6516	Phase 2
0.6937	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6696	Suspended
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6929	Remote Similarity	NPD2684	Approved
0.6927	Remote Similarity	NPD4663	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6914	Remote Similarity	NPD1511	Approved
0.6913	Remote Similarity	NPD2981	Phase 2
0.6906	Remote Similarity	NPD968	Approved
0.6905	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4140	Approved
0.6903	Remote Similarity	NPD3620	Phase 2
0.6898	Remote Similarity	NPD6823	Phase 2
0.6892	Remote Similarity	NPD3496	Discontinued
0.6889	Remote Similarity	NPD7906	Approved
0.6875	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7007	Discovery
0.6875	Remote Similarity	NPD7783	Phase 2
0.6871	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1357	Approved
0.6871	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD7435	Discontinued
0.686	Remote Similarity	NPD7229	Phase 3
0.6859	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7310	Approved
0.6854	Remote Similarity	NPD7313	Approved
0.6854	Remote Similarity	NPD7311	Approved
0.6854	Remote Similarity	NPD4578	Approved
0.6854	Remote Similarity	NPD7312	Approved
0.6854	Remote Similarity	NPD4577	Approved
0.6846	Remote Similarity	NPD1611	Approved
0.6846	Remote Similarity	NPD422	Phase 1
0.6845	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5494	Approved
0.6839	Remote Similarity	NPD7473	Discontinued
0.6832	Remote Similarity	NPD4628	Phase 3
0.6832	Remote Similarity	NPD7466	Approved
0.6829	Remote Similarity	NPD1512	Approved
0.6828	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7411	Suspended
0.6826	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3749	Approved
0.6821	Remote Similarity	NPD2970	Approved
0.6821	Remote Similarity	NPD2969	Approved
0.6821	Remote Similarity	NPD3225	Approved
0.6816	Remote Similarity	NPD7309	Approved
0.6816	Remote Similarity	NPD8054	Approved
0.6816	Remote Similarity	NPD8053	Approved
0.6815	Remote Similarity	NPD6653	Approved
0.6813	Remote Similarity	NPD1549	Phase 2
0.6813	Remote Similarity	NPD2424	Discontinued
0.681	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5283	Phase 1
0.68	Remote Similarity	NPD2231	Phase 2
0.68	Remote Similarity	NPD2235	Phase 2
0.6796	Remote Similarity	NPD6842	Approved
0.6796	Remote Similarity	NPD6841	Approved
0.6796	Remote Similarity	NPD6843	Phase 3
0.6795	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6801	Discontinued
0.6782	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7698	Approved
0.6772	Remote Similarity	NPD7697	Approved
0.6772	Remote Similarity	NPD7680	Approved
0.6772	Remote Similarity	NPD7696	Phase 3
0.677	Remote Similarity	NPD5177	Phase 3
0.6765	Remote Similarity	NPD7768	Phase 2
0.6765	Remote Similarity	NPD3882	Suspended

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