NPASS Compound

Structure

NPC472160 OpenBabel07101718322D 29 33 0 0 1 0 0 0 0 0999 V2000 0.9857 0.9103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -0.6615 1.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3166 1.6535 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 -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 -1.9487 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.4945 0.0000 C 0 0 1 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 0.6256 2.6045 0.0000 O 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 0.0076 0.7024 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 11 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 12 1 0 0 0 0 5 12 1 0 0 0 0 6 15 2 0 0 0 0 7 16 2 0 0 0 0 8 9 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 23 2 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 28 1 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.09
Volume:	381.453
LogP:	3.344
LogD:	2.473
LogS:	-3.821
# Rotatable Bonds:	2
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	4.108
Fsp3:	0.182
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:	-5.093
MDCK Permeability:	1.7522654161439277e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	97.70442199707031%
Volume Distribution (VD):	0.582
Pgp-substrate:	1.5312343835830688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.162
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.749
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.593

ADMET: Excretion

Clearance (CL):	3.511
Half-life (T1/2):	0.524

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.956
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.355
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.531
Respiratory Toxicity:	0.371

Download Data

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

Natural Product: NPC472160

Natural Product ID:	NPC472160
*Common Name:**	FNLORMFZWKRPDK-OAQYLSRUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FNLORMFZWKRPDK-OAQYLSRUSA-N
Standard InCHI:	InChI=1S/C22H16O7/c1-11(23)10-21(27)20(26)18-13(24)8-9-14(25)19(18)22(21)28-15-6-2-4-12-5-3-7-16(29-22)17(12)15/h2-9,24-25,27H,10H2,1H3/t21-/m1/s1
SMILES:	CC(=O)CC1(C(=O)C2=C(C=CC(=C2C13OC4=CC=CC5=C4C(=CC=C5)O3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342640
PubChem CID:	n.a.
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[475829]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[475829]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[475829]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[475829]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[475829]

☑ 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 NPC472160 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	432
0.1-0.2	1928
0.2-0.3	3949
0.3-0.4	10441
0.4-0.5	8292
0.5-0.6	4281
0.6-0.7	6470
0.7-0.8	6331
0.8-0.85	565
0.85-0.9	4
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC472158
0.9509	High Similarity	NPC472159
0.9245	High Similarity	NPC57141
0.8623	High Similarity	NPC73148
0.8512	High Similarity	NPC96031
0.8509	High Similarity	NPC301949
0.8497	Intermediate Similarity	NPC85368
0.84	Intermediate Similarity	NPC102053
0.8393	Intermediate Similarity	NPC311574
0.8393	Intermediate Similarity	NPC264932
0.8385	Intermediate Similarity	NPC306816
0.8373	Intermediate Similarity	NPC178964
0.8373	Intermediate Similarity	NPC95842
0.8373	Intermediate Similarity	NPC280530
0.8363	Intermediate Similarity	NPC88243
0.8353	Intermediate Similarity	NPC472402
0.8353	Intermediate Similarity	NPC216752
0.8343	Intermediate Similarity	NPC200746
0.8343	Intermediate Similarity	NPC172687
0.8343	Intermediate Similarity	NPC139036
0.8333	Intermediate Similarity	NPC161650
0.8333	Intermediate Similarity	NPC177742
0.8333	Intermediate Similarity	NPC210048
0.8333	Intermediate Similarity	NPC477833
0.8333	Intermediate Similarity	NPC47152
0.8324	Intermediate Similarity	NPC137460
0.8324	Intermediate Similarity	NPC222455
0.8314	Intermediate Similarity	NPC113093
0.8305	Intermediate Similarity	NPC153578
0.8305	Intermediate Similarity	NPC114257
0.8305	Intermediate Similarity	NPC299149
0.8305	Intermediate Similarity	NPC277710
0.8305	Intermediate Similarity	NPC58538
0.8304	Intermediate Similarity	NPC189473
0.8304	Intermediate Similarity	NPC23298
0.8303	Intermediate Similarity	NPC227122
0.8295	Intermediate Similarity	NPC475233
0.8295	Intermediate Similarity	NPC156635
0.8295	Intermediate Similarity	NPC272656
0.8286	Intermediate Similarity	NPC203751
0.8284	Intermediate Similarity	NPC474290
0.8284	Intermediate Similarity	NPC476242
0.8284	Intermediate Similarity	NPC472156
0.8284	Intermediate Similarity	NPC152904
0.8276	Intermediate Similarity	NPC287884
0.8276	Intermediate Similarity	NPC8704
0.8274	Intermediate Similarity	NPC274730
0.8266	Intermediate Similarity	NPC292233
0.8266	Intermediate Similarity	NPC103633
0.8263	Intermediate Similarity	NPC89474
0.8256	Intermediate Similarity	NPC224280
0.8256	Intermediate Similarity	NPC472450
0.8256	Intermediate Similarity	NPC234052
0.8256	Intermediate Similarity	NPC275780
0.8256	Intermediate Similarity	NPC239752
0.8253	Intermediate Similarity	NPC471229
0.8246	Intermediate Similarity	NPC101116
0.8246	Intermediate Similarity	NPC329760
0.8246	Intermediate Similarity	NPC278329
0.8246	Intermediate Similarity	NPC146837
0.8246	Intermediate Similarity	NPC25152
0.8246	Intermediate Similarity	NPC229632
0.8246	Intermediate Similarity	NPC212099
0.8242	Intermediate Similarity	NPC277032
0.8239	Intermediate Similarity	NPC470667
0.8239	Intermediate Similarity	NPC186800
0.8229	Intermediate Similarity	NPC76128
0.8229	Intermediate Similarity	NPC475825
0.8229	Intermediate Similarity	NPC30432
0.8229	Intermediate Similarity	NPC111536
0.8229	Intermediate Similarity	NPC223375
0.8229	Intermediate Similarity	NPC271385
0.8229	Intermediate Similarity	NPC5029
0.8225	Intermediate Similarity	NPC241904
0.8225	Intermediate Similarity	NPC300727
0.8221	Intermediate Similarity	NPC473951
0.8214	Intermediate Similarity	NPC476169
0.8214	Intermediate Similarity	NPC55662
0.8214	Intermediate Similarity	NPC99199
0.8214	Intermediate Similarity	NPC166054
0.8208	Intermediate Similarity	NPC39091
0.8208	Intermediate Similarity	NPC472150
0.8208	Intermediate Similarity	NPC37870
0.8208	Intermediate Similarity	NPC472449
0.8204	Intermediate Similarity	NPC474843
0.8204	Intermediate Similarity	NPC210597
0.8198	Intermediate Similarity	NPC248638
0.8198	Intermediate Similarity	NPC207690
0.8198	Intermediate Similarity	NPC236521
0.8198	Intermediate Similarity	NPC475985
0.8198	Intermediate Similarity	NPC152659
0.8193	Intermediate Similarity	NPC267117
0.8192	Intermediate Similarity	NPC475246
0.8192	Intermediate Similarity	NPC289876
0.8187	Intermediate Similarity	NPC61010
0.8187	Intermediate Similarity	NPC476929
0.8182	Intermediate Similarity	NPC473834
0.8182	Intermediate Similarity	NPC98776
0.8182	Intermediate Similarity	NPC216624
0.8176	Intermediate Similarity	NPC231475
0.8176	Intermediate Similarity	NPC100123
0.8176	Intermediate Similarity	NPC280680
0.8176	Intermediate Similarity	NPC57072
0.8167	Intermediate Similarity	NPC476170
0.8167	Intermediate Similarity	NPC224557
0.8167	Intermediate Similarity	NPC292706
0.8166	Intermediate Similarity	NPC142339
0.8166	Intermediate Similarity	NPC303255
0.8161	Intermediate Similarity	NPC476306
0.8161	Intermediate Similarity	NPC42892
0.8161	Intermediate Similarity	NPC150131
0.8161	Intermediate Similarity	NPC76482
0.8156	Intermediate Similarity	NPC97523
0.8155	Intermediate Similarity	NPC100134
0.8155	Intermediate Similarity	NPC209760
0.8155	Intermediate Similarity	NPC303950
0.8155	Intermediate Similarity	NPC203080
0.815	Intermediate Similarity	NPC297404
0.815	Intermediate Similarity	NPC11608
0.815	Intermediate Similarity	NPC26386
0.815	Intermediate Similarity	NPC178281
0.815	Intermediate Similarity	NPC280923
0.8146	Intermediate Similarity	NPC67302
0.8144	Intermediate Similarity	NPC23668
0.8144	Intermediate Similarity	NPC202157
0.8144	Intermediate Similarity	NPC193976
0.814	Intermediate Similarity	NPC61594
0.814	Intermediate Similarity	NPC469575
0.814	Intermediate Similarity	NPC56735
0.8136	Intermediate Similarity	NPC3718
0.8136	Intermediate Similarity	NPC108202
0.8136	Intermediate Similarity	NPC68381
0.8136	Intermediate Similarity	NPC470454
0.8136	Intermediate Similarity	NPC199533
0.8129	Intermediate Similarity	NPC45146
0.8129	Intermediate Similarity	NPC56085
0.8129	Intermediate Similarity	NPC470810
0.8129	Intermediate Similarity	NPC204290
0.8129	Intermediate Similarity	NPC328093
0.8129	Intermediate Similarity	NPC471973
0.8129	Intermediate Similarity	NPC14353
0.8129	Intermediate Similarity	NPC235018
0.8129	Intermediate Similarity	NPC320359
0.8129	Intermediate Similarity	NPC471976
0.8129	Intermediate Similarity	NPC228785
0.8129	Intermediate Similarity	NPC80375
0.8125	Intermediate Similarity	NPC476405
0.8125	Intermediate Similarity	NPC260263
0.8125	Intermediate Similarity	NPC117260
0.8122	Intermediate Similarity	NPC241847
0.8122	Intermediate Similarity	NPC87583
0.8121	Intermediate Similarity	NPC472918
0.8118	Intermediate Similarity	NPC6985
0.8118	Intermediate Similarity	NPC236796
0.8118	Intermediate Similarity	NPC217677
0.8118	Intermediate Similarity	NPC165977
0.8118	Intermediate Similarity	NPC268360
0.8118	Intermediate Similarity	NPC136674
0.8114	Intermediate Similarity	NPC472381
0.8114	Intermediate Similarity	NPC472383
0.8114	Intermediate Similarity	NPC246274
0.8114	Intermediate Similarity	NPC152477
0.8114	Intermediate Similarity	NPC259905
0.8114	Intermediate Similarity	NPC247136
0.8111	Intermediate Similarity	NPC478001
0.8107	Intermediate Similarity	NPC326910
0.8107	Intermediate Similarity	NPC471116
0.8103	Intermediate Similarity	NPC175082
0.8103	Intermediate Similarity	NPC70441
0.8103	Intermediate Similarity	NPC170245
0.8103	Intermediate Similarity	NPC477517
0.8103	Intermediate Similarity	NPC178851
0.8101	Intermediate Similarity	NPC476273
0.8095	Intermediate Similarity	NPC281272
0.8095	Intermediate Similarity	NPC207624
0.8095	Intermediate Similarity	NPC321363
0.8095	Intermediate Similarity	NPC253904
0.8095	Intermediate Similarity	NPC142308
0.8092	Intermediate Similarity	NPC146134
0.8092	Intermediate Similarity	NPC470178
0.8092	Intermediate Similarity	NPC220313
0.8092	Intermediate Similarity	NPC41301
0.8092	Intermediate Similarity	NPC183672
0.8092	Intermediate Similarity	NPC133065
0.8092	Intermediate Similarity	NPC147596
0.809	Intermediate Similarity	NPC46958
0.809	Intermediate Similarity	NPC472380
0.809	Intermediate Similarity	NPC472384
0.809	Intermediate Similarity	NPC472382
0.8087	Intermediate Similarity	NPC314672
0.8084	Intermediate Similarity	NPC471984
0.8084	Intermediate Similarity	NPC101957
0.8084	Intermediate Similarity	NPC470107
0.8084	Intermediate Similarity	NPC120105
0.8081	Intermediate Similarity	NPC29876
0.8081	Intermediate Similarity	NPC167678
0.8081	Intermediate Similarity	NPC278052
0.8081	Intermediate Similarity	NPC173137
0.8081	Intermediate Similarity	NPC472153
0.8081	Intermediate Similarity	NPC40491

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 NPC472160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	983
0.2-0.3	1750
0.3-0.4	2733
0.4-0.5	1923
0.5-0.6	924
0.6-0.7	288
0.7-0.8	143
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
0.8161	Intermediate Similarity	NPD3751	Discontinued
0.8077	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD3787	Discontinued
0.8012	Intermediate Similarity	NPD3749	Approved
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD2801	Approved
0.7933	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6232	Discontinued
0.7821	Intermediate Similarity	NPD6797	Phase 2
0.7809	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD5402	Approved
0.7784	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD6776	Approved
0.7778	Intermediate Similarity	NPD6777	Approved
0.7778	Intermediate Similarity	NPD1934	Approved
0.7778	Intermediate Similarity	NPD6779	Approved
0.7778	Intermediate Similarity	NPD6778	Approved
0.7778	Intermediate Similarity	NPD6781	Approved
0.7778	Intermediate Similarity	NPD6782	Approved
0.7778	Intermediate Similarity	NPD6780	Approved
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7753	Intermediate Similarity	NPD3818	Discontinued
0.7746	Intermediate Similarity	NPD3882	Suspended
0.7738	Intermediate Similarity	NPD1512	Approved
0.7735	Intermediate Similarity	NPD7808	Phase 3
0.7733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7054	Approved
0.7709	Intermediate Similarity	NPD5844	Phase 1
0.7706	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD7075	Discontinued
0.7692	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD8313	Approved
0.7684	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6559	Discontinued
0.7679	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7472	Approved
0.7656	Intermediate Similarity	NPD7435	Discontinued
0.7644	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7819	Suspended
0.763	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1511	Approved
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.7614	Intermediate Similarity	NPD5494	Approved
0.7609	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3817	Phase 2
0.7581	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7565	Intermediate Similarity	NPD7698	Approved
0.7565	Intermediate Similarity	NPD7697	Approved
0.7565	Intermediate Similarity	NPD7696	Phase 3
0.7558	Intermediate Similarity	NPD4380	Phase 2
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD7411	Suspended
0.7513	Intermediate Similarity	NPD6535	Approved
0.7513	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7475	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD7783	Phase 2
0.7471	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2346	Discontinued
0.747	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2344	Approved
0.7457	Intermediate Similarity	NPD6599	Discontinued
0.7444	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1549	Phase 2
0.7424	Intermediate Similarity	NPD7874	Approved
0.7424	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7700	Phase 2
0.7396	Intermediate Similarity	NPD7699	Phase 2
0.7389	Intermediate Similarity	NPD3926	Phase 2
0.7387	Intermediate Similarity	NPD7801	Approved
0.7384	Intermediate Similarity	NPD5403	Approved
0.738	Intermediate Similarity	NPD8150	Discontinued
0.7371	Intermediate Similarity	NPD6801	Discontinued
0.7345	Intermediate Similarity	NPD7768	Phase 2
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD2309	Approved
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD5401	Approved
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD1510	Phase 2
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1240	Approved
0.7209	Intermediate Similarity	NPD7390	Discontinued
0.7209	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2796	Approved
0.72	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6213	Phase 3
0.7188	Intermediate Similarity	NPD6212	Phase 3
0.7184	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD1247	Approved
0.7176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2800	Approved
0.716	Intermediate Similarity	NPD2798	Approved
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3748	Approved
0.7135	Intermediate Similarity	NPD5761	Phase 2
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD1607	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.7099	Intermediate Similarity	NPD1470	Approved
0.7091	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7085	Intermediate Similarity	NPD8319	Approved
0.7085	Intermediate Similarity	NPD8320	Phase 1
0.7072	Intermediate Similarity	NPD6234	Discontinued
0.7066	Intermediate Similarity	NPD1933	Approved
0.7066	Intermediate Similarity	NPD447	Suspended
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD5762	Approved
0.705	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2799	Discontinued
0.7041	Intermediate Similarity	NPD7033	Discontinued
0.7039	Intermediate Similarity	NPD8455	Phase 2
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4628	Phase 3
0.703	Intermediate Similarity	NPD4625	Phase 3
0.7029	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD1551	Phase 2
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6994	Remote Similarity	NPD1203	Approved
0.6989	Remote Similarity	NPD7228	Approved
0.6988	Remote Similarity	NPD3268	Approved
0.6983	Remote Similarity	NPD37	Approved
0.6978	Remote Similarity	NPD919	Approved
0.6961	Remote Similarity	NPD4965	Approved
0.6961	Remote Similarity	NPD4967	Phase 2
0.6961	Remote Similarity	NPD4966	Approved
0.6957	Remote Similarity	NPD7229	Phase 3
0.6957	Remote Similarity	NPD1201	Approved
0.6954	Remote Similarity	NPD3300	Phase 2
0.6946	Remote Similarity	NPD6233	Phase 2
0.6941	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1608	Approved
0.691	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD2861	Phase 2
0.6905	Remote Similarity	NPD943	Approved
0.6898	Remote Similarity	NPD7799	Discontinued
0.6898	Remote Similarity	NPD7177	Discontinued
0.6893	Remote Similarity	NPD920	Approved
0.689	Remote Similarity	NPD2797	Approved
0.6889	Remote Similarity	NPD6844	Discontinued
0.6886	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD1243	Approved
0.6872	Remote Similarity	NPD7028	Phase 2
0.6867	Remote Similarity	NPD4908	Phase 1
0.6865	Remote Similarity	NPD5711	Approved
0.6865	Remote Similarity	NPD5710	Approved
0.6864	Remote Similarity	NPD6355	Discontinued
0.686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7930	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6826	Remote Similarity	NPD7095	Approved
0.6822	Remote Similarity	NPD8059	Phase 3
0.6822	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2296	Approved
0.681	Remote Similarity	NPD9717	Approved
0.6805	Remote Similarity	NPD4060	Phase 1
0.68	Remote Similarity	NPD6190	Approved
0.6793	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5953	Discontinued
0.6786	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.678	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6832	Phase 2
0.6766	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7584	Approved
0.6765	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6764	Approved
0.6754	Remote Similarity	NPD6765	Approved
0.675	Remote Similarity	NPD8285	Discontinued
0.6748	Remote Similarity	NPD1547	Clinical (unspecified phase)

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