NPASS Compound

Structure

NPC57141 OpenBabel07101718292D 24 28 0 0 0 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7359 -1.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0667 -2.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4268 -0.3715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0886 -1.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.9067 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 4.0960 0.3716 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4195 -2.6009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3554 1.6160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 10 1 0 0 0 0 4 10 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 2 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.07
Volume:	314.621
LogP:	3.622
LogD:	2.779
LogS:	-4.404
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.62
Synthetic Accessibility Score:	3.4
Fsp3:	0.105
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:	-4.887
MDCK Permeability:	2.1095307602081448e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.175

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	98.1315689086914%
Volume Distribution (VD):	0.506
Pgp-substrate:	1.2889347076416016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.921
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.827
CYP2D6-substrate:	0.312
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	7.584
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.953
Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.894
Carcinogencity:	0.933
Eye Corrosion:	0.004
Eye Irritation:	0.906
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC57141

Natural Product ID:	NPC57141
*Common Name:**	NLXZERAARWDGRG-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NLXZERAARWDGRG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O5/c20-11-7-8-12(21)18-17(11)13(22)9-19(18)23-14-5-1-3-10-4-2-6-15(24-19)16(10)14/h1-8,20-21H,9H2
SMILES:	c1cc2cccc3c2c(c1)OC1(CC(=O)c2c(ccc(c12)O)O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342644
PubChem CID:	10403707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes [CHEMONTID:0001151] Indanones

*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[553495]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[553495]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	=	124.5	ug.mL-1	PMID[553495]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[553495]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[553495]

☑ 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 NPC57141 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	473
0.1-0.2	2047
0.2-0.3	4698
0.3-0.4	11379
0.4-0.5	6509
0.5-0.6	4531
0.6-0.7	6185
0.7-0.8	6408
0.8-0.85	453
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9245	High Similarity	NPC472160
0.9195	High Similarity	NPC301949
0.9074	High Similarity	NPC472158
0.906	High Similarity	NPC306816
0.9006	High Similarity	NPC472159
0.9	High Similarity	NPC47152
0.8924	High Similarity	NPC73148
0.8874	High Similarity	NPC473951
0.859	High Similarity	NPC227122
0.8544	High Similarity	NPC280530
0.8544	High Similarity	NPC95842
0.8544	High Similarity	NPC178964
0.8497	Intermediate Similarity	NPC159855
0.8497	Intermediate Similarity	NPC169479
0.8481	Intermediate Similarity	NPC474843
0.8477	Intermediate Similarity	NPC18457
0.8462	Intermediate Similarity	NPC106328
0.8462	Intermediate Similarity	NPC216624
0.8462	Intermediate Similarity	NPC35150
0.8418	Intermediate Similarity	NPC115324
0.8418	Intermediate Similarity	NPC193976
0.8418	Intermediate Similarity	NPC23668
0.8415	Intermediate Similarity	NPC297404
0.8415	Intermediate Similarity	NPC11608
0.8385	Intermediate Similarity	NPC477833
0.8377	Intermediate Similarity	NPC310340
0.8375	Intermediate Similarity	NPC166054
0.8375	Intermediate Similarity	NPC55662
0.8375	Intermediate Similarity	NPC99199
0.8373	Intermediate Similarity	NPC137460
0.8366	Intermediate Similarity	NPC275734
0.8366	Intermediate Similarity	NPC145673
0.8365	Intermediate Similarity	NPC142308
0.8365	Intermediate Similarity	NPC207624
0.8365	Intermediate Similarity	NPC281272
0.8354	Intermediate Similarity	NPC120105
0.8354	Intermediate Similarity	NPC470107
0.8354	Intermediate Similarity	NPC295036
0.8354	Intermediate Similarity	NPC101957
0.8354	Intermediate Similarity	NPC325983
0.8344	Intermediate Similarity	NPC96031
0.8344	Intermediate Similarity	NPC186397
0.8344	Intermediate Similarity	NPC37135
0.8333	Intermediate Similarity	NPC85368
0.8323	Intermediate Similarity	NPC137100
0.8323	Intermediate Similarity	NPC13879
0.8313	Intermediate Similarity	NPC103633
0.8313	Intermediate Similarity	NPC235333
0.8313	Intermediate Similarity	NPC89474
0.8302	Intermediate Similarity	NPC106372
0.8302	Intermediate Similarity	NPC202157
0.8302	Intermediate Similarity	NPC58668
0.8293	Intermediate Similarity	NPC216752
0.8293	Intermediate Similarity	NPC469575
0.8291	Intermediate Similarity	NPC223988
0.8291	Intermediate Similarity	NPC266499
0.8282	Intermediate Similarity	NPC292863
0.8282	Intermediate Similarity	NPC139036
0.8282	Intermediate Similarity	NPC184326
0.828	Intermediate Similarity	NPC12305
0.8272	Intermediate Similarity	NPC268360
0.8272	Intermediate Similarity	NPC177742
0.8269	Intermediate Similarity	NPC97662
0.8269	Intermediate Similarity	NPC32470
0.8269	Intermediate Similarity	NPC131766
0.8269	Intermediate Similarity	NPC155144
0.8269	Intermediate Similarity	NPC98926
0.8263	Intermediate Similarity	NPC222455
0.8261	Intermediate Similarity	NPC254351
0.8261	Intermediate Similarity	NPC213936
0.8261	Intermediate Similarity	NPC297531
0.8261	Intermediate Similarity	NPC148938
0.8242	Intermediate Similarity	NPC470178
0.8239	Intermediate Similarity	NPC471984
0.8235	Intermediate Similarity	NPC102053
0.8232	Intermediate Similarity	NPC137232
0.8232	Intermediate Similarity	NPC162668
0.8232	Intermediate Similarity	NPC472157
0.8232	Intermediate Similarity	NPC18380
0.8228	Intermediate Similarity	NPC276930
0.8225	Intermediate Similarity	NPC24748
0.8225	Intermediate Similarity	NPC59491
0.8221	Intermediate Similarity	NPC193749
0.8221	Intermediate Similarity	NPC183402
0.8221	Intermediate Similarity	NPC195167
0.8217	Intermediate Similarity	NPC267509
0.821	Intermediate Similarity	NPC142339
0.821	Intermediate Similarity	NPC274730
0.8205	Intermediate Similarity	NPC113770
0.8199	Intermediate Similarity	NPC299761
0.8199	Intermediate Similarity	NPC92153
0.8199	Intermediate Similarity	NPC279281
0.8199	Intermediate Similarity	NPC230439
0.8199	Intermediate Similarity	NPC135522
0.8199	Intermediate Similarity	NPC329844
0.8194	Intermediate Similarity	NPC197461
0.8194	Intermediate Similarity	NPC133585
0.8194	Intermediate Similarity	NPC105648
0.8193	Intermediate Similarity	NPC474591
0.8188	Intermediate Similarity	NPC141549
0.8187	Intermediate Similarity	NPC258249
0.8187	Intermediate Similarity	NPC117579
0.8187	Intermediate Similarity	NPC39819
0.8182	Intermediate Similarity	NPC310603
0.8182	Intermediate Similarity	NPC472402
0.8182	Intermediate Similarity	NPC3448
0.8182	Intermediate Similarity	NPC101116
0.8182	Intermediate Similarity	NPC473499
0.8182	Intermediate Similarity	NPC229632
0.8182	Intermediate Similarity	NPC329760
0.8182	Intermediate Similarity	NPC212099
0.8182	Intermediate Similarity	NPC477239
0.8176	Intermediate Similarity	NPC473978
0.8176	Intermediate Similarity	NPC10027
0.8176	Intermediate Similarity	NPC65775
0.8176	Intermediate Similarity	NPC70764
0.8171	Intermediate Similarity	NPC235018
0.8171	Intermediate Similarity	NPC45146
0.8171	Intermediate Similarity	NPC200746
0.8171	Intermediate Similarity	NPC328093
0.8166	Intermediate Similarity	NPC223375
0.8166	Intermediate Similarity	NPC260263
0.8166	Intermediate Similarity	NPC475825
0.8165	Intermediate Similarity	NPC259632
0.8165	Intermediate Similarity	NPC239312
0.8165	Intermediate Similarity	NPC130230
0.8165	Intermediate Similarity	NPC71055
0.8165	Intermediate Similarity	NPC77903
0.8165	Intermediate Similarity	NPC275772
0.8165	Intermediate Similarity	NPC17816
0.8165	Intermediate Similarity	NPC17101
0.816	Intermediate Similarity	NPC300727
0.816	Intermediate Similarity	NPC212967
0.816	Intermediate Similarity	NPC165977
0.816	Intermediate Similarity	NPC241904
0.816	Intermediate Similarity	NPC217677
0.816	Intermediate Similarity	NPC236796
0.816	Intermediate Similarity	NPC246647
0.816	Intermediate Similarity	NPC164110
0.816	Intermediate Similarity	NPC96342
0.8153	Intermediate Similarity	NPC311144
0.8153	Intermediate Similarity	NPC303185
0.8153	Intermediate Similarity	NPC184649
0.8144	Intermediate Similarity	NPC30027
0.8144	Intermediate Similarity	NPC272560
0.8141	Intermediate Similarity	NPC73028
0.814	Intermediate Similarity	NPC114257
0.814	Intermediate Similarity	NPC58538
0.814	Intermediate Similarity	NPC277710
0.814	Intermediate Similarity	NPC299149
0.814	Intermediate Similarity	NPC153578
0.8137	Intermediate Similarity	NPC217447
0.8137	Intermediate Similarity	NPC175978
0.8137	Intermediate Similarity	NPC41326
0.8133	Intermediate Similarity	NPC207690
0.8133	Intermediate Similarity	NPC290160
0.8133	Intermediate Similarity	NPC159508
0.8133	Intermediate Similarity	NPC23298
0.8133	Intermediate Similarity	NPC110257
0.8133	Intermediate Similarity	NPC189473
0.8133	Intermediate Similarity	NPC476505
0.8129	Intermediate Similarity	NPC182421
0.8129	Intermediate Similarity	NPC101991
0.8129	Intermediate Similarity	NPC220106
0.8125	Intermediate Similarity	NPC306821
0.8125	Intermediate Similarity	NPC184136
0.8125	Intermediate Similarity	NPC202595
0.8125	Intermediate Similarity	NPC230713
0.8125	Intermediate Similarity	NPC61620
0.8125	Intermediate Similarity	NPC167576
0.8125	Intermediate Similarity	NPC294646
0.8125	Intermediate Similarity	NPC307780
0.8125	Intermediate Similarity	NPC62042
0.8125	Intermediate Similarity	NPC78335
0.8125	Intermediate Similarity	NPC309979
0.8121	Intermediate Similarity	NPC24761
0.8121	Intermediate Similarity	NPC32694
0.8121	Intermediate Similarity	NPC7569
0.8121	Intermediate Similarity	NPC474187
0.8121	Intermediate Similarity	NPC278787
0.8118	Intermediate Similarity	NPC203751
0.8113	Intermediate Similarity	NPC7025
0.8113	Intermediate Similarity	NPC12367
0.8113	Intermediate Similarity	NPC5537
0.8113	Intermediate Similarity	NPC194856
0.8113	Intermediate Similarity	NPC118726
0.8113	Intermediate Similarity	NPC27221
0.8113	Intermediate Similarity	NPC256672
0.811	Intermediate Similarity	NPC472877
0.811	Intermediate Similarity	NPC177650
0.811	Intermediate Similarity	NPC18699
0.811	Intermediate Similarity	NPC476242
0.811	Intermediate Similarity	NPC190487
0.811	Intermediate Similarity	NPC55443
0.811	Intermediate Similarity	NPC100123
0.811	Intermediate Similarity	NPC329091
0.811	Intermediate Similarity	NPC154304
0.811	Intermediate Similarity	NPC474290
0.811	Intermediate Similarity	NPC186113
0.811	Intermediate Similarity	NPC472156

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 NPC57141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	443
0.1-0.2	993
0.2-0.3	1692
0.3-0.4	2763
0.4-0.5	1887
0.5-0.6	948
0.6-0.7	280
0.7-0.8	140
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD3751	Discontinued
0.7975	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD1511	Approved
0.795	Intermediate Similarity	NPD3226	Approved
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3750	Approved
0.7885	Intermediate Similarity	NPD1549	Phase 2
0.7875	Intermediate Similarity	NPD1512	Approved
0.7866	Intermediate Similarity	NPD7819	Suspended
0.7861	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3787	Discontinued
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7771	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6232	Discontinued
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7733	Intermediate Similarity	NPD7054	Approved
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.7719	Intermediate Similarity	NPD7473	Discontinued
0.7714	Intermediate Similarity	NPD8312	Approved
0.7714	Intermediate Similarity	NPD8313	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7707	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD7472	Approved
0.7688	Intermediate Similarity	NPD7074	Phase 3
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6166	Phase 2
0.7661	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7644	Intermediate Similarity	NPD6797	Phase 2
0.7633	Intermediate Similarity	NPD5494	Approved
0.7611	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7251	Discontinued
0.76	Intermediate Similarity	NPD6559	Discontinued
0.758	Intermediate Similarity	NPD3748	Approved
0.7576	Intermediate Similarity	NPD4380	Phase 2
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7768	Phase 2
0.756	Intermediate Similarity	NPD3882	Suspended
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.755	Intermediate Similarity	NPD1203	Approved
0.7548	Intermediate Similarity	NPD1240	Approved
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2800	Approved
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7452	Intermediate Similarity	NPD1607	Approved
0.7434	Intermediate Similarity	NPD1470	Approved
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD2796	Approved
0.7419	Intermediate Similarity	NPD3764	Approved
0.7412	Intermediate Similarity	NPD7075	Discontinued
0.7403	Intermediate Similarity	NPD4287	Approved
0.74	Intermediate Similarity	NPD1201	Approved
0.7396	Intermediate Similarity	NPD3817	Phase 2
0.7391	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2798	Approved
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7317	Intermediate Similarity	NPD6799	Approved
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD5408	Approved
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5403	Approved
0.7278	Intermediate Similarity	NPD447	Suspended
0.7278	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD5401	Approved
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.7255	Intermediate Similarity	NPD3225	Approved
0.725	Intermediate Similarity	NPD2799	Discontinued
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7435	Discontinued
0.7211	Intermediate Similarity	NPD7697	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7197	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD920	Approved
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7171	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5761	Phase 2
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4625	Phase 3
0.7107	Intermediate Similarity	NPD943	Approved
0.7102	Intermediate Similarity	NPD3926	Phase 2
0.7097	Intermediate Similarity	NPD2797	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1247	Approved
0.7079	Intermediate Similarity	NPD7177	Discontinued
0.7076	Intermediate Similarity	NPD6801	Discontinued
0.707	Intermediate Similarity	NPD4908	Phase 1
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7059	Intermediate Similarity	NPD6535	Approved
0.7059	Intermediate Similarity	NPD6534	Approved
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7048	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5710	Approved
0.7045	Intermediate Similarity	NPD5711	Approved
0.7039	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7005	Intermediate Similarity	NPD6213	Phase 3
0.7005	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD2296	Approved
0.699	Remote Similarity	NPD7874	Approved
0.699	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3267	Approved
0.6987	Remote Similarity	NPD3266	Approved
0.6981	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD37	Approved
0.6971	Remote Similarity	NPD6234	Discontinued
0.6954	Remote Similarity	NPD4967	Phase 2
0.6954	Remote Similarity	NPD4966	Approved
0.6954	Remote Similarity	NPD4965	Approved
0.6954	Remote Similarity	NPD7801	Approved
0.6947	Remote Similarity	NPD7700	Phase 2
0.6947	Remote Similarity	NPD7699	Phase 2
0.6928	Remote Similarity	NPD4628	Phase 3
0.6928	Remote Similarity	NPD7003	Approved
0.6903	Remote Similarity	NPD1481	Phase 2
0.6901	Remote Similarity	NPD7458	Discontinued
0.6889	Remote Similarity	NPD7228	Approved
0.6885	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD919	Approved
0.6868	Remote Similarity	NPD5953	Discontinued
0.6855	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7286	Phase 2
0.6848	Remote Similarity	NPD6002	Phase 3
0.6848	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6005	Phase 3
0.6848	Remote Similarity	NPD6004	Phase 3
0.6848	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1535	Discovery
0.6839	Remote Similarity	NPD1610	Phase 2
0.6815	Remote Similarity	NPD1876	Approved
0.6792	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4307	Phase 2
0.6776	Remote Similarity	NPD9493	Approved
0.677	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4749	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