NPASS Compound

Structure

NPC73148 OpenBabel07101719152D 26 30 0 0 1 0 0 0 0 0999 V2000 0.7366 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 2.7272 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 -3.2350 1.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 -1.0658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2350 0.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 1.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 -0.5658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 -0.5658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7366 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3689 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 0.9342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1010 0.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6369 2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2350 -1.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2291 -1.0658 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 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 16 1 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 23 2 0 0 0 0 14 17 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 6 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	340.707
LogP:	3.211
LogD:	2.833
LogS:	-3.86
# Rotatable Bonds:	0
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	3.871
Fsp3:	0.15
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:	-5.238
MDCK Permeability:	1.632787643757183e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.758
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	97.69795227050781%
Volume Distribution (VD):	0.51
Pgp-substrate:	1.4984911680221558%

ADMET: Metabolism

CYP1A2-inhibitor:	0.509
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.816
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	7.254
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.282
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.947
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.204
Skin Sensitization:	0.898
Carcinogencity:	0.955
Eye Corrosion:	0.003
Eye Irritation:	0.76
Respiratory Toxicity:	0.892

Download Data

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

Natural Product: NPC73148

Natural Product ID:	NPC73148
*Common Name:**	IDLZGEAPEUPIGD-MRXNPFEDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IDLZGEAPEUPIGD-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C20H14O6/c21-11-7-8-12(22)19-18(11)13(23)9-16(24)20(19)25-14-5-1-3-10-4-2-6-15(26-20)17(10)14/h1-8,16,21-22,24H,9H2/t16-/m1/s1
SMILES:	O[C@@H]1CC(=O)c2c(C31Oc1cccc4c1c(O3)ccc4)c(O)ccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342630
PubChem CID:	10521808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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[504554]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[504554]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	37.5	ug.mL-1	PMID[504554]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	=	37.5	ug.mL-1	PMID[504554]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	=	50.0	ug.mL-1	PMID[504554]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	37.5	ug.mL-1	PMID[504554]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	37.5	ug.mL-1	PMID[504554]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	=	50.0	ug.mL-1	PMID[504554]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	=	64.8	ug.mL-1	PMID[504554]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[504554]

☑ 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 NPC73148 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	418
0.1-0.2	1713
0.2-0.3	3897
0.3-0.4	9688
0.4-0.5	8752
0.5-0.6	3748
0.6-0.7	5963
0.7-0.8	5988
0.8-0.85	2366
0.85-0.9	154
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9308	High Similarity	NPC297404
0.9308	High Similarity	NPC11608
0.9255	High Similarity	NPC137460
0.9193	High Similarity	NPC103633
0.9145	High Similarity	NPC301949
0.9114	High Similarity	NPC183402
0.9013	High Similarity	NPC306816
0.8994	High Similarity	NPC193749
0.897	High Similarity	NPC85368
0.8924	High Similarity	NPC57141
0.8875	High Similarity	NPC472156
0.8869	High Similarity	NPC114257
0.8869	High Similarity	NPC277710
0.8869	High Similarity	NPC153578
0.8869	High Similarity	NPC299149
0.8862	High Similarity	NPC102053
0.8831	High Similarity	NPC47152
0.8824	High Similarity	NPC231254
0.8812	High Similarity	NPC177742
0.8788	High Similarity	NPC222455
0.878	High Similarity	NPC472150
0.878	High Similarity	NPC175082
0.8772	High Similarity	NPC261623
0.8772	High Similarity	NPC111490
0.8765	High Similarity	NPC472153
0.8757	High Similarity	NPC58538
0.875	High Similarity	NPC472991
0.875	High Similarity	NPC472992
0.8743	High Similarity	NPC203751
0.8727	High Similarity	NPC58716
0.8727	High Similarity	NPC146792
0.8727	High Similarity	NPC45618
0.8721	High Similarity	NPC65489
0.8721	High Similarity	NPC179947
0.8712	High Similarity	NPC61594
0.8712	High Similarity	NPC56735
0.8712	High Similarity	NPC216752
0.871	High Similarity	NPC473951
0.8704	High Similarity	NPC328093
0.8698	High Similarity	NPC476620
0.8698	High Similarity	NPC476621
0.8698	High Similarity	NPC476622
0.8698	High Similarity	NPC476623
0.8698	High Similarity	NPC472387
0.8698	High Similarity	NPC476618
0.8698	High Similarity	NPC476619
0.8696	High Similarity	NPC477833
0.869	High Similarity	NPC3718
0.8683	High Similarity	NPC260263
0.8683	High Similarity	NPC3583
0.8683	High Similarity	NPC301683
0.8683	High Similarity	NPC259152
0.8683	High Similarity	NPC267254
0.8679	High Similarity	NPC474843
0.8675	High Similarity	NPC226294
0.8675	High Similarity	NPC170675
0.8675	High Similarity	NPC201292
0.8675	High Similarity	NPC58053
0.8675	High Similarity	NPC93337
0.8675	High Similarity	NPC105025
0.8675	High Similarity	NPC472383
0.8675	High Similarity	NPC475942
0.8675	High Similarity	NPC186807
0.8675	High Similarity	NPC469931
0.8675	High Similarity	NPC45638
0.8675	High Similarity	NPC472381
0.8675	High Similarity	NPC112755
0.8675	High Similarity	NPC471457
0.8671	High Similarity	NPC473618
0.8667	High Similarity	NPC70441
0.8663	High Similarity	NPC87583
0.8663	High Similarity	NPC241847
0.8663	High Similarity	NPC469650
0.8659	High Similarity	NPC147596
0.8659	High Similarity	NPC470178
0.8659	High Similarity	NPC120677
0.8659	High Similarity	NPC74371
0.8655	High Similarity	NPC476203
0.8642	High Similarity	NPC329091
0.8639	High Similarity	NPC475246
0.8639	High Similarity	NPC289876
0.8634	High Similarity	NPC261866
0.8631	High Similarity	NPC239549
0.8631	High Similarity	NPC51774
0.8631	High Similarity	NPC204693
0.8631	High Similarity	NPC236191
0.8631	High Similarity	NPC470438
0.8625	High Similarity	NPC230439
0.8625	High Similarity	NPC279281
0.8625	High Similarity	NPC185103
0.8625	High Similarity	NPC299761
0.8625	High Similarity	NPC92153
0.8623	High Similarity	NPC183357
0.8623	High Similarity	NPC21190
0.8623	High Similarity	NPC282987
0.8623	High Similarity	NPC105511
0.8623	High Similarity	NPC44558
0.8623	High Similarity	NPC471416
0.8623	High Similarity	NPC34287
0.8623	High Similarity	NPC22195
0.8623	High Similarity	NPC149011
0.8623	High Similarity	NPC204937
0.8623	High Similarity	NPC472160
0.8623	High Similarity	NPC245014
0.8623	High Similarity	NPC84265
0.8621	High Similarity	NPC472724
0.8621	High Similarity	NPC31208
0.8621	High Similarity	NPC469652
0.8621	High Similarity	NPC472721
0.8621	High Similarity	NPC472720
0.8621	High Similarity	NPC160543
0.8621	High Similarity	NPC93065
0.8614	High Similarity	NPC42892
0.8614	High Similarity	NPC243877
0.8614	High Similarity	NPC93099
0.8614	High Similarity	NPC295082
0.8614	High Similarity	NPC14662
0.8613	High Similarity	NPC105591
0.8613	High Similarity	NPC260521
0.8613	High Similarity	NPC469649
0.8606	High Similarity	NPC99216
0.8606	High Similarity	NPC75944
0.8605	High Similarity	NPC292706
0.8605	High Similarity	NPC224557
0.8605	High Similarity	NPC49690
0.8598	High Similarity	NPC77660
0.8598	High Similarity	NPC189142
0.8598	High Similarity	NPC101116
0.8598	High Similarity	NPC212099
0.8596	High Similarity	NPC8940
0.859	High Similarity	NPC97662
0.8589	High Similarity	NPC292863
0.8589	High Similarity	NPC184326
0.858	High Similarity	NPC60966
0.858	High Similarity	NPC470667
0.858	High Similarity	NPC470454
0.858	High Similarity	NPC472158
0.858	High Similarity	NPC102028
0.858	High Similarity	NPC199533
0.8571	High Similarity	NPC117260
0.8571	High Similarity	NPC67134
0.8571	High Similarity	NPC47140
0.8571	High Similarity	NPC30432
0.8571	High Similarity	NPC476405
0.8571	High Similarity	NPC472386
0.8571	High Similarity	NPC271385
0.8571	High Similarity	NPC5029
0.8571	High Similarity	NPC271848
0.8571	High Similarity	NPC81332
0.8571	High Similarity	NPC262580
0.8571	High Similarity	NPC254540
0.8571	High Similarity	NPC205076
0.8571	High Similarity	NPC4200
0.8571	High Similarity	NPC111536
0.8571	High Similarity	NPC289396
0.8571	High Similarity	NPC264302
0.8571	High Similarity	NPC76128
0.8571	High Similarity	NPC172807
0.8571	High Similarity	NPC156977
0.8571	High Similarity	NPC211594
0.8571	High Similarity	NPC307518
0.8571	High Similarity	NPC212038
0.8571	High Similarity	NPC48773
0.8563	High Similarity	NPC158214
0.8563	High Similarity	NPC240200
0.8563	High Similarity	NPC210042
0.8563	High Similarity	NPC95855
0.8563	High Similarity	NPC477083
0.8563	High Similarity	NPC477081
0.8563	High Similarity	NPC259905
0.8563	High Similarity	NPC223534
0.8563	High Similarity	NPC290289
0.8563	High Similarity	NPC300307
0.8554	High Similarity	NPC272560
0.8554	High Similarity	NPC178851
0.8554	High Similarity	NPC210073
0.8554	High Similarity	NPC115674
0.8554	High Similarity	NPC8856
0.8547	High Similarity	NPC36138
0.8547	High Similarity	NPC132111
0.8545	High Similarity	NPC168822
0.8545	High Similarity	NPC29830
0.8545	High Similarity	NPC290160
0.8545	High Similarity	NPC243930
0.8545	High Similarity	NPC191306
0.8545	High Similarity	NPC19709
0.8545	High Similarity	NPC88043
0.8545	High Similarity	NPC88023
0.8545	High Similarity	NPC270335
0.8545	High Similarity	NPC309025
0.8545	High Similarity	NPC127415
0.8544	High Similarity	NPC106328
0.8544	High Similarity	NPC35150
0.8538	High Similarity	NPC84494
0.8538	High Similarity	NPC245059
0.8538	High Similarity	NPC324742
0.8537	High Similarity	NPC288131
0.8537	High Similarity	NPC84324
0.8537	High Similarity	NPC270675
0.8537	High Similarity	NPC18380

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 NPC73148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	906
0.2-0.3	1793
0.3-0.4	2656
0.4-0.5	1805
0.5-0.6	1025
0.6-0.7	393
0.7-0.8	138
0.8-0.85	35
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD3751	Discontinued
0.8712	High Similarity	NPD3787	Discontinued
0.8471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7054	Approved
0.8402	Intermediate Similarity	NPD7074	Phase 3
0.8402	Intermediate Similarity	NPD7472	Approved
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD1934	Approved
0.8314	Intermediate Similarity	NPD8312	Approved
0.8314	Intermediate Similarity	NPD8313	Approved
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8304	Intermediate Similarity	NPD7251	Discontinued
0.8295	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD2801	Approved
0.8256	Intermediate Similarity	NPD7808	Phase 3
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5402	Approved
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8063	Intermediate Similarity	NPD1511	Approved
0.8035	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD3749	Approved
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7978	Intermediate Similarity	NPD6776	Approved
0.7978	Intermediate Similarity	NPD6778	Approved
0.7978	Intermediate Similarity	NPD6781	Approved
0.7978	Intermediate Similarity	NPD6782	Approved
0.7978	Intermediate Similarity	NPD6779	Approved
0.7978	Intermediate Similarity	NPD6780	Approved
0.7978	Intermediate Similarity	NPD6777	Approved
0.7975	Intermediate Similarity	NPD1549	Phase 2
0.7963	Intermediate Similarity	NPD1512	Approved
0.7941	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD5494	Approved
0.7907	Intermediate Similarity	NPD7473	Discontinued
0.7904	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3882	Suspended
0.7849	Intermediate Similarity	NPD7435	Discontinued
0.7849	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD1465	Phase 2
0.7844	Intermediate Similarity	NPD7819	Suspended
0.7842	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD7783	Phase 2
0.7811	Intermediate Similarity	NPD7075	Discontinued
0.7807	Intermediate Similarity	NPD7870	Phase 2
0.7807	Intermediate Similarity	NPD7871	Phase 2
0.7798	Intermediate Similarity	NPD3817	Phase 2
0.7754	Intermediate Similarity	NPD7697	Approved
0.7754	Intermediate Similarity	NPD7698	Approved
0.7754	Intermediate Similarity	NPD7696	Phase 3
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD8455	Phase 2
0.7737	Intermediate Similarity	NPD8151	Discontinued
0.7725	Intermediate Similarity	NPD7411	Suspended
0.7711	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6534	Approved
0.7705	Intermediate Similarity	NPD6535	Approved
0.7701	Intermediate Similarity	NPD6823	Phase 2
0.7697	Intermediate Similarity	NPD5403	Approved
0.7684	Intermediate Similarity	NPD7701	Phase 2
0.7683	Intermediate Similarity	NPD5401	Approved
0.7683	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1510	Phase 2
0.7654	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6799	Approved
0.7605	Intermediate Similarity	NPD3226	Approved
0.7604	Intermediate Similarity	NPD7874	Approved
0.7604	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7700	Phase 2
0.7581	Intermediate Similarity	NPD7699	Phase 2
0.7578	Intermediate Similarity	NPD2346	Discontinued
0.7576	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6801	Discontinued
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7569	Intermediate Similarity	NPD8150	Discontinued
0.7565	Intermediate Similarity	NPD7801	Approved
0.7554	Intermediate Similarity	NPD6212	Phase 3
0.7554	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6213	Phase 3
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD1933	Approved
0.7469	Intermediate Similarity	NPD2344	Approved
0.7458	Intermediate Similarity	NPD7228	Approved
0.7456	Intermediate Similarity	NPD6599	Discontinued
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7421	Intermediate Similarity	NPD1240	Approved
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1551	Phase 2
0.7396	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7368	Intermediate Similarity	NPD37	Approved
0.7365	Intermediate Similarity	NPD2533	Approved
0.7365	Intermediate Similarity	NPD2534	Approved
0.7365	Intermediate Similarity	NPD2532	Approved
0.7356	Intermediate Similarity	NPD6234	Discontinued
0.7346	Intermediate Similarity	NPD3748	Approved
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4966	Approved
0.7337	Intermediate Similarity	NPD1653	Approved
0.7329	Intermediate Similarity	NPD1607	Approved
0.7313	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1613	Approved
0.7312	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5405	Approved
0.7301	Intermediate Similarity	NPD5404	Approved
0.7301	Intermediate Similarity	NPD5406	Approved
0.7301	Intermediate Similarity	NPD5408	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7289	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1247	Approved
0.7262	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8320	Phase 1
0.7254	Intermediate Similarity	NPD8319	Approved
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1470	Approved
0.7191	Intermediate Similarity	NPD3926	Phase 2
0.7189	Intermediate Similarity	NPD8434	Phase 2
0.7186	Intermediate Similarity	NPD6190	Approved
0.7169	Intermediate Similarity	NPD2800	Approved
0.7161	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2798	Approved
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7128	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7003	Approved
0.7118	Intermediate Similarity	NPD6273	Approved
0.7112	Intermediate Similarity	NPD4287	Approved
0.7104	Intermediate Similarity	NPD7240	Approved
0.7091	Intermediate Similarity	NPD6100	Approved
0.7091	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD3764	Approved
0.7076	Intermediate Similarity	NPD920	Approved
0.7072	Intermediate Similarity	NPD7177	Discontinued
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD4908	Phase 1
0.7063	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD919	Approved
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7053	Intermediate Similarity	NPD8059	Phase 3
0.7053	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1091	Approved
0.7047	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7229	Phase 3
0.703	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD9717	Approved
0.7005	Intermediate Similarity	NPD7584	Approved
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3268	Approved
0.697	Remote Similarity	NPD7097	Phase 1
0.6964	Remote Similarity	NPD6674	Discontinued
0.6946	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7266	Discontinued
0.6944	Remote Similarity	NPD5711	Approved
0.6944	Remote Similarity	NPD5710	Approved
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3225	Approved
0.6899	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD2651	Approved
0.6897	Remote Similarity	NPD2649	Approved
0.6894	Remote Similarity	NPD9494	Approved
0.689	Remote Similarity	NPD4060	Phase 1
0.6889	Remote Similarity	NPD8127	Discontinued
0.6882	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4363	Phase 3
0.6875	Remote Similarity	NPD2797	Approved
0.6875	Remote Similarity	NPD4360	Phase 2

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