NPASS Compound

Structure

NPC472158 OpenBabel07101718182D 29 33 0 0 1 0 0 0 0 0999 V2000 -0.6256 2.6045 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 -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 0.6615 1.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 0.4945 0.0000 C 0 0 2 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 1.3307 2.1887 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 -0.3166 1.6535 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 27 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 10 1 0 0 0 0 5 10 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.07
Volume:	372.947
LogP:	3.567
LogD:	2.333
LogS:	-3.636
# Rotatable Bonds:	2
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	4.088
Fsp3:	0.143
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:	-5.229
MDCK Permeability:	1.8861950593418442e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.668

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	97.1479263305664%
Volume Distribution (VD):	0.527
Pgp-substrate:	2.0434486865997314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.442
CYP2C19-inhibitor:	0.816
CYP2C19-substrate:	0.144
CYP2C9-inhibitor:	0.828
CYP2C9-substrate:	0.71
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.8
CYP3A4-substrate:	0.742

ADMET: Excretion

Clearance (CL):	2.506
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.422
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.27
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.424
Respiratory Toxicity:	0.208

Download Data

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

Natural Product: NPC472158

Natural Product ID:	NPC472158
*Common Name:**	ANFJVULUYFHQLL-FQEVSTJZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ANFJVULUYFHQLL-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C21H14O8/c1-27-19(25)20(26)18(24)16-11(22)8-9-12(23)17(16)21(20)28-13-6-2-4-10-5-3-7-14(29-21)15(10)13/h2-9,22-23,26H,1H3/t20-/m0/s1
SMILES:	COC(=O)C1(C(=O)C2=C(C=CC(=C2C13OC4=CC=CC5=C4C(=CC=C5)O3)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342638
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[505407]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[505407]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT1477	Organism	Staphylococcus haemolyticus	Staphylococcus haemolyticus	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT4150	Organism	Xanthomonas vesicatoria	Xanthomonas vesicatoria	MIC	>	250.0	ug.mL-1	PMID[505407]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	200.0	ug.mL-1	PMID[505407]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[505407]

☑ 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 NPC472158 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	395
0.1-0.2	1826
0.2-0.3	3843
0.3-0.4	9385
0.4-0.5	9269
0.5-0.6	4308
0.6-0.7	6440
0.7-0.8	6469
0.8-0.85	755
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC472159
0.9573	High Similarity	NPC472160
0.9074	High Similarity	NPC57141
0.858	High Similarity	NPC73148
0.843	Intermediate Similarity	NPC88243
0.8409	Intermediate Similarity	NPC470667
0.8391	Intermediate Similarity	NPC137460
0.8363	Intermediate Similarity	NPC96031
0.8354	Intermediate Similarity	NPC301949
0.8352	Intermediate Similarity	NPC85368
0.8314	Intermediate Similarity	NPC216752
0.8305	Intermediate Similarity	NPC470454
0.8305	Intermediate Similarity	NPC199533
0.8305	Intermediate Similarity	NPC186800
0.8304	Intermediate Similarity	NPC328093
0.8294	Intermediate Similarity	NPC474441
0.8294	Intermediate Similarity	NPC474401
0.8294	Intermediate Similarity	NPC474398
0.8294	Intermediate Similarity	NPC476026
0.8294	Intermediate Similarity	NPC177742
0.8294	Intermediate Similarity	NPC477833
0.8287	Intermediate Similarity	NPC241847
0.8276	Intermediate Similarity	NPC113093
0.8266	Intermediate Similarity	NPC475183
0.8258	Intermediate Similarity	NPC472380
0.8258	Intermediate Similarity	NPC472382
0.8258	Intermediate Similarity	NPC272656
0.8258	Intermediate Similarity	NPC102053
0.8258	Intermediate Similarity	NPC472384
0.8251	Intermediate Similarity	NPC314672
0.8246	Intermediate Similarity	NPC231475
0.8246	Intermediate Similarity	NPC57072
0.8246	Intermediate Similarity	NPC472156
0.8239	Intermediate Similarity	NPC313304
0.8239	Intermediate Similarity	NPC287884
0.8239	Intermediate Similarity	NPC8704
0.8239	Intermediate Similarity	NPC298778
0.8232	Intermediate Similarity	NPC306816
0.8229	Intermediate Similarity	NPC103633
0.8225	Intermediate Similarity	NPC230439
0.8225	Intermediate Similarity	NPC279281
0.8225	Intermediate Similarity	NPC299761
0.8225	Intermediate Similarity	NPC92153
0.8222	Intermediate Similarity	NPC97523
0.8218	Intermediate Similarity	NPC99216
0.8218	Intermediate Similarity	NPC297404
0.8218	Intermediate Similarity	NPC11608
0.8218	Intermediate Similarity	NPC178281
0.8218	Intermediate Similarity	NPC280923
0.8212	Intermediate Similarity	NPC472387
0.8208	Intermediate Similarity	NPC472402
0.8204	Intermediate Similarity	NPC277032
0.8202	Intermediate Similarity	NPC477848
0.8202	Intermediate Similarity	NPC68381
0.8202	Intermediate Similarity	NPC264735
0.8198	Intermediate Similarity	NPC139036
0.8192	Intermediate Similarity	NPC472386
0.8182	Intermediate Similarity	NPC222455
0.8182	Intermediate Similarity	NPC280493
0.8182	Intermediate Similarity	NPC47152
0.8177	Intermediate Similarity	NPC36138
0.8172	Intermediate Similarity	NPC314687
0.8171	Intermediate Similarity	NPC475174
0.8171	Intermediate Similarity	NPC472150
0.8171	Intermediate Similarity	NPC30027
0.8167	Intermediate Similarity	NPC58538
0.8167	Intermediate Similarity	NPC299149
0.8167	Intermediate Similarity	NPC245059
0.8167	Intermediate Similarity	NPC153578
0.8167	Intermediate Similarity	NPC277710
0.8167	Intermediate Similarity	NPC114257
0.8167	Intermediate Similarity	NPC84494
0.8166	Intermediate Similarity	NPC281272
0.8161	Intermediate Similarity	NPC17432
0.8161	Intermediate Similarity	NPC474350
0.8156	Intermediate Similarity	NPC324220
0.8156	Intermediate Similarity	NPC233994
0.8156	Intermediate Similarity	NPC156635
0.8156	Intermediate Similarity	NPC475233
0.8156	Intermediate Similarity	NPC211532
0.8156	Intermediate Similarity	NPC312630
0.8156	Intermediate Similarity	NPC472385
0.8156	Intermediate Similarity	NPC268533
0.8156	Intermediate Similarity	NPC198324
0.8155	Intermediate Similarity	NPC267117
0.8155	Intermediate Similarity	NPC470107
0.8146	Intermediate Similarity	NPC470438
0.8146	Intermediate Similarity	NPC203751
0.8144	Intermediate Similarity	NPC216624
0.8142	Intermediate Similarity	NPC174486
0.814	Intermediate Similarity	NPC476242
0.814	Intermediate Similarity	NPC264932
0.814	Intermediate Similarity	NPC152904
0.814	Intermediate Similarity	NPC311574
0.8136	Intermediate Similarity	NPC199079
0.8136	Intermediate Similarity	NPC210808
0.8132	Intermediate Similarity	NPC231254
0.8132	Intermediate Similarity	NPC470416
0.8125	Intermediate Similarity	NPC473094
0.8125	Intermediate Similarity	NPC42892
0.8125	Intermediate Similarity	NPC298847
0.8125	Intermediate Similarity	NPC86477
0.8125	Intermediate Similarity	NPC292233
0.8125	Intermediate Similarity	NPC76647
0.8125	Intermediate Similarity	NPC249977
0.8125	Intermediate Similarity	NPC76482
0.8122	Intermediate Similarity	NPC477860
0.8122	Intermediate Similarity	NPC470448
0.8122	Intermediate Similarity	NPC470452
0.8122	Intermediate Similarity	NPC470453
0.8122	Intermediate Similarity	NPC208069
0.8122	Intermediate Similarity	NPC475161
0.8122	Intermediate Similarity	NPC265795
0.8122	Intermediate Similarity	NPC164047
0.8118	Intermediate Similarity	NPC280530
0.8118	Intermediate Similarity	NPC178964
0.8118	Intermediate Similarity	NPC95842
0.8118	Intermediate Similarity	NPC299435
0.8118	Intermediate Similarity	NPC185103
0.8118	Intermediate Similarity	NPC260604
0.8118	Intermediate Similarity	NPC203080
0.8114	Intermediate Similarity	NPC239752
0.8114	Intermediate Similarity	NPC7752
0.8114	Intermediate Similarity	NPC234052
0.8114	Intermediate Similarity	NPC224280
0.8114	Intermediate Similarity	NPC139060
0.8114	Intermediate Similarity	NPC472450
0.8114	Intermediate Similarity	NPC72016
0.8114	Intermediate Similarity	NPC275780
0.8111	Intermediate Similarity	NPC476621
0.8111	Intermediate Similarity	NPC29587
0.8111	Intermediate Similarity	NPC476623
0.8111	Intermediate Similarity	NPC35167
0.8111	Intermediate Similarity	NPC476619
0.8111	Intermediate Similarity	NPC476622
0.8111	Intermediate Similarity	NPC476618
0.8111	Intermediate Similarity	NPC297807
0.8111	Intermediate Similarity	NPC476620
0.8111	Intermediate Similarity	NPC98546
0.8107	Intermediate Similarity	NPC471229
0.8103	Intermediate Similarity	NPC101116
0.8103	Intermediate Similarity	NPC146837
0.8103	Intermediate Similarity	NPC27942
0.8103	Intermediate Similarity	NPC229632
0.8103	Intermediate Similarity	NPC278329
0.8103	Intermediate Similarity	NPC61594
0.8103	Intermediate Similarity	NPC212099
0.8103	Intermediate Similarity	NPC56735
0.8103	Intermediate Similarity	NPC469575
0.8103	Intermediate Similarity	NPC164937
0.8101	Intermediate Similarity	NPC101191
0.8101	Intermediate Similarity	NPC49344
0.8101	Intermediate Similarity	NPC474345
0.8101	Intermediate Similarity	NPC210094
0.8101	Intermediate Similarity	NPC135277
0.8101	Intermediate Similarity	NPC43211
0.8101	Intermediate Similarity	NPC237435
0.8101	Intermediate Similarity	NPC115760
0.8101	Intermediate Similarity	NPC108202
0.8098	Intermediate Similarity	NPC205721
0.8092	Intermediate Similarity	NPC471744
0.8092	Intermediate Similarity	NPC172687
0.8092	Intermediate Similarity	NPC200746
0.809	Intermediate Similarity	NPC76128
0.809	Intermediate Similarity	NPC260263
0.809	Intermediate Similarity	NPC111536
0.809	Intermediate Similarity	NPC30432
0.809	Intermediate Similarity	NPC476405
0.809	Intermediate Similarity	NPC211594
0.809	Intermediate Similarity	NPC475825
0.809	Intermediate Similarity	NPC222665
0.809	Intermediate Similarity	NPC175107
0.809	Intermediate Similarity	NPC149502
0.809	Intermediate Similarity	NPC223375
0.809	Intermediate Similarity	NPC137871
0.809	Intermediate Similarity	NPC254540
0.809	Intermediate Similarity	NPC257011
0.809	Intermediate Similarity	NPC190003
0.809	Intermediate Similarity	NPC271385
0.809	Intermediate Similarity	NPC5029
0.809	Intermediate Similarity	NPC288152
0.809	Intermediate Similarity	NPC172807
0.809	Intermediate Similarity	NPC9002
0.809	Intermediate Similarity	NPC254071
0.809	Intermediate Similarity	NPC117260
0.809	Intermediate Similarity	NPC271755
0.8087	Intermediate Similarity	NPC111490
0.8087	Intermediate Similarity	NPC261623
0.8081	Intermediate Similarity	NPC300727
0.8081	Intermediate Similarity	NPC210048
0.8081	Intermediate Similarity	NPC208651
0.8081	Intermediate Similarity	NPC473395
0.8081	Intermediate Similarity	NPC206641
0.8081	Intermediate Similarity	NPC241904
0.8081	Intermediate Similarity	NPC6985
0.8081	Intermediate Similarity	NPC161650
0.8079	Intermediate Similarity	NPC472383
0.8079	Intermediate Similarity	NPC473096
0.8079	Intermediate Similarity	NPC259905
0.8079	Intermediate Similarity	NPC473095

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 NPC472158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	965
0.2-0.3	1840
0.3-0.4	2650
0.4-0.5	1938
0.5-0.6	927
0.6-0.7	311
0.7-0.8	149
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
0.8142	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD5402	Approved
0.791	Intermediate Similarity	NPD6166	Phase 2
0.791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7898	Intermediate Similarity	NPD3787	Discontinued
0.7874	Intermediate Similarity	NPD7075	Discontinued
0.7874	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7473	Discontinued
0.7857	Intermediate Similarity	NPD8312	Approved
0.7857	Intermediate Similarity	NPD8313	Approved
0.7853	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7819	Suspended
0.7803	Intermediate Similarity	NPD2801	Approved
0.779	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD3226	Approved
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3817	Phase 2
0.7747	Intermediate Similarity	NPD6559	Discontinued
0.7747	Intermediate Similarity	NPD7251	Discontinued
0.7746	Intermediate Similarity	NPD1934	Approved
0.7742	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6959	Discontinued
0.774	Intermediate Similarity	NPD7199	Phase 2
0.7735	Intermediate Similarity	NPD7074	Phase 3
0.7722	Intermediate Similarity	NPD3818	Discontinued
0.772	Intermediate Similarity	NPD7435	Discontinued
0.7705	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD7411	Suspended
0.768	Intermediate Similarity	NPD7054	Approved
0.7656	Intermediate Similarity	NPD6776	Approved
0.7656	Intermediate Similarity	NPD6781	Approved
0.7656	Intermediate Similarity	NPD6782	Approved
0.7656	Intermediate Similarity	NPD6777	Approved
0.7656	Intermediate Similarity	NPD6780	Approved
0.7656	Intermediate Similarity	NPD6778	Approved
0.7656	Intermediate Similarity	NPD6779	Approved
0.765	Intermediate Similarity	NPD7685	Pre-registration
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD7472	Approved
0.7626	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7783	Phase 2
0.7614	Intermediate Similarity	NPD3882	Suspended
0.7611	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6799	Approved
0.7558	Intermediate Similarity	NPD5403	Approved
0.7557	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2346	Discontinued
0.7544	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5401	Approved
0.7543	Intermediate Similarity	NPD6801	Discontinued
0.754	Intermediate Similarity	NPD8150	Discontinued
0.7529	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD4380	Phase 2
0.7515	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7871	Phase 2
0.7487	Intermediate Similarity	NPD7874	Approved
0.7487	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5494	Approved
0.7485	Intermediate Similarity	NPD1511	Approved
0.7449	Intermediate Similarity	NPD7696	Phase 3
0.7449	Intermediate Similarity	NPD7697	Approved
0.7449	Intermediate Similarity	NPD7698	Approved
0.744	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7768	Phase 2
0.7396	Intermediate Similarity	NPD1549	Phase 2
0.7396	Intermediate Similarity	NPD6535	Approved
0.7396	Intermediate Similarity	NPD6534	Approved
0.7387	Intermediate Similarity	NPD7701	Phase 2
0.7381	Intermediate Similarity	NPD2935	Discontinued
0.7363	Intermediate Similarity	NPD3926	Phase 2
0.7356	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2534	Approved
0.7341	Intermediate Similarity	NPD2532	Approved
0.7341	Intermediate Similarity	NPD2533	Approved
0.7337	Intermediate Similarity	NPD2344	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7700	Phase 2
0.7282	Intermediate Similarity	NPD7699	Phase 2
0.7277	Intermediate Similarity	NPD7801	Approved
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1933	Approved
0.7238	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD6823	Phase 2
0.7219	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD1510	Phase 2
0.7212	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8455	Phase 2
0.7188	Intermediate Similarity	NPD4287	Approved
0.7186	Intermediate Similarity	NPD1240	Approved
0.7176	Intermediate Similarity	NPD1551	Phase 2
0.7169	Intermediate Similarity	NPD3764	Approved
0.7169	Intermediate Similarity	NPD2313	Discontinued
0.7168	Intermediate Similarity	NPD2309	Approved
0.7158	Intermediate Similarity	NPD1247	Approved
0.7151	Intermediate Similarity	NPD7228	Approved
0.7151	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD2800	Approved
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD5762	Approved
0.7135	Intermediate Similarity	NPD5763	Approved
0.7127	Intermediate Similarity	NPD4965	Approved
0.7127	Intermediate Similarity	NPD4967	Phase 2
0.7127	Intermediate Similarity	NPD4966	Approved
0.7118	Intermediate Similarity	NPD7033	Discontinued
0.711	Intermediate Similarity	NPD4628	Phase 3
0.7102	Intermediate Similarity	NPD6273	Approved
0.7101	Intermediate Similarity	NPD1607	Approved
0.7086	Intermediate Similarity	NPD7390	Discontinued
0.7077	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6212	Phase 3
0.7077	Intermediate Similarity	NPD6213	Phase 3
0.7076	Intermediate Similarity	NPD2796	Approved
0.7076	Intermediate Similarity	NPD6100	Approved
0.7076	Intermediate Similarity	NPD6099	Approved
0.7073	Intermediate Similarity	NPD1203	Approved
0.7062	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD7799	Discontinued
0.7027	Intermediate Similarity	NPD7229	Phase 3
0.7024	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD2799	Discontinued
0.7017	Intermediate Similarity	NPD5760	Phase 2
0.7017	Intermediate Similarity	NPD5761	Phase 2
0.7011	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7930	Approved
0.6994	Remote Similarity	NPD1608	Approved
0.6983	Remote Similarity	NPD7458	Discontinued
0.6977	Remote Similarity	NPD5408	Approved
0.6977	Remote Similarity	NPD5406	Approved
0.6977	Remote Similarity	NPD5404	Approved
0.6977	Remote Similarity	NPD5405	Approved
0.6971	Remote Similarity	NPD6190	Approved
0.697	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7177	Discontinued
0.6964	Remote Similarity	NPD3268	Approved
0.6964	Remote Similarity	NPD6798	Discontinued
0.6957	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1243	Approved
0.6949	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6832	Phase 2
0.6946	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6355	Discontinued
0.6941	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1471	Phase 3
0.6936	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5710	Approved
0.6935	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD2798	Approved
0.6919	Remote Similarity	NPD4308	Phase 3
0.6919	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.689	Remote Similarity	NPD9717	Approved
0.6882	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD1470	Approved
0.6864	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5953	Discontinued
0.6836	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1653	Approved
0.6829	Remote Similarity	NPD1201	Approved
0.6826	Remote Similarity	NPD5647	Approved
0.6823	Remote Similarity	NPD6765	Approved
0.6823	Remote Similarity	NPD7240	Approved
0.6823	Remote Similarity	NPD6764	Approved
0.6821	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7003	Approved
0.6816	Remote Similarity	NPD8285	Discontinued
0.681	Remote Similarity	NPD17	Approved
0.6807	Remote Similarity	NPD3225	Approved
0.6805	Remote Similarity	NPD7095	Approved
0.6805	Remote Similarity	NPD4625	Phase 3
0.6791	Remote Similarity	NPD8127	Discontinued
0.6786	Remote Similarity	NPD2861	Phase 2
0.6784	Remote Similarity	NPD943	Approved
0.678	Remote Similarity	NPD2354	Approved
0.6776	Remote Similarity	NPD6844	Discontinued
0.6766	Remote Similarity	NPD3267	Approved
0.6766	Remote Similarity	NPD3266	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