NPASS Compound

Structure

CID99381 OpenBabel06191715442D 27 29 0 0 1 0 0 0 0 0999 V2000 -0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 -4.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -4.0489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -4.0489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1405 -2.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 -4.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 -3.0245 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 0.9309 -4.4143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 1 1 6 0 0 0 9 26 1 0 0 0 0 10 25 1 0 0 0 0 11 16 2 0 0 0 0 12 17 1 0 0 0 0 12 20 2 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 6 0 0 0 18 11 1 1 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.13
Volume:	366.014
LogP:	2.101
LogD:	1.755
LogS:	-3.957
# Rotatable Bonds:	1
TPSA:	122.66
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.492
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	5.28954406036064e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.735

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287
Plasma Protein Binding (PPB):	78.99707794189453%
Volume Distribution (VD):	0.235
Pgp-substrate:	10.486059188842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.342
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	10.544
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.691
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.208
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.083
Respiratory Toxicity:	0.349

Download Data

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

Natural Product: NPC99381

Natural Product ID:	NPC99381
*Common Name:**	Hypothemycin
IUPAC Name:	n.a.
Synonyms:	Hypothemycin
Standard InCHIKey:	SSNQAUBBJYCSMY-KNTMUCJRSA-N
Standard InCHI:	InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1
SMILES:	COc1cc2[C@H]3O[C@@H]3C[C@H](O)[C@H](O)C(=O)/C=CC[C@@H](OC(=O)c2c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471474
PubChem CID:	9929643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues [CHEMONTID:0001788] Zearalenones

*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
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067161]
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20118535]
NPO33691	Paecilomyces sp. SC0930	Species		Eukaryota	n.a.	Dinghu Mountain Biosphere Reserve, Guangdong, China	2003-MAR	PMID[28749671]
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	15
Others	5

Activity Type	# Activity
Cell Line	12
Individual Protein	5
ORGANISM	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	70.0	nM	PMID[484551]
NPT1915	Cell Line	COLO-829	Homo sapiens	IC50	=	150.0	nM	PMID[484551]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5900.0	nM	PMID[484551]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16300.0	nM	PMID[484552]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	4300.0	nM	PMID[484552]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	12700.0	nM	PMID[484552]
NPT3442	Individual Protein	Mitogen-activated protein kinase kinase kinase 7	Homo sapiens	IC50	=	33.0	nM	PMID[484554]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1000.0	nM	PMID[484555]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1000.0	nM	PMID[484555]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3300.0	nM	PMID[484555]
NPT1649	Cell Line	MV4-11	Homo sapiens	IC50	=	15.0	nM	PMID[484556]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	Inhibition	=	92.0	%	PMID[484556]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	Inhibition	=	85.0	%	PMID[484556]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	1000.0	nM	PMID[484556]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	1000.0	nM	PMID[484556]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	Inhibition	=	52.0	%	PMID[484556]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	Inhibition	=	91.0	%	PMID[484556]
NPT2	Others	Unspecified		INH	=	17.0	nM	PMID[484553]
NPT25805	ORGANISM	Phytophthora litchii	Phytophthora litchii	IC50	=	1900.0	nM	PMID[484555]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	IC50	=	1100.0	nM	PMID[484555]

☑ 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 NPC99381 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	369
0.1-0.2	1445
0.2-0.3	3804
0.3-0.4	7973
0.4-0.5	9826
0.5-0.6	4471
0.6-0.7	5848
0.7-0.8	7030
0.8-0.85	1721
0.85-0.9	184
0.9-0.95	22
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC469670
0.9728	High Similarity	NPC56204
0.9728	High Similarity	NPC469619
0.9592	High Similarity	NPC215711
0.9592	High Similarity	NPC73411
0.9524	High Similarity	NPC210320
0.9456	High Similarity	NPC107625
0.94	High Similarity	NPC240768
0.94	High Similarity	NPC200773
0.94	High Similarity	NPC70016
0.94	High Similarity	NPC215921
0.9388	High Similarity	NPC83272
0.932	High Similarity	NPC277426
0.932	High Similarity	NPC280404
0.932	High Similarity	NPC210425
0.932	High Similarity	NPC86373
0.9262	High Similarity	NPC472036
0.9252	High Similarity	NPC51106
0.9252	High Similarity	NPC472006
0.9195	High Similarity	NPC472033
0.9184	High Similarity	NPC474385
0.9128	High Similarity	NPC257558
0.9128	High Similarity	NPC472034
0.9116	High Similarity	NPC67650
0.9116	High Similarity	NPC1704
0.906	High Similarity	NPC126882
0.906	High Similarity	NPC478203
0.906	High Similarity	NPC210966
0.9048	High Similarity	NPC158472
0.9013	High Similarity	NPC270160
0.9013	High Similarity	NPC77325
0.9013	High Similarity	NPC4423
0.9013	High Similarity	NPC237440
0.8994	High Similarity	NPC472049
0.8993	High Similarity	NPC469542
0.8986	High Similarity	NPC244923
0.8986	High Similarity	NPC475730
0.8981	High Similarity	NPC472055
0.8974	High Similarity	NPC472889
0.8974	High Similarity	NPC246466
0.8974	High Similarity	NPC473395
0.8968	High Similarity	NPC16082
0.8968	High Similarity	NPC472890
0.8968	High Similarity	NPC478230
0.8968	High Similarity	NPC69043
0.8968	High Similarity	NPC79998
0.8968	High Similarity	NPC82592
0.8961	High Similarity	NPC478224
0.8954	High Similarity	NPC179178
0.8947	High Similarity	NPC153417
0.8926	High Similarity	NPC469579
0.8924	High Similarity	NPC117985
0.8917	High Similarity	NPC470339
0.8912	High Similarity	NPC212693
0.8912	High Similarity	NPC478200
0.8912	High Similarity	NPC33144
0.8912	High Similarity	NPC94248
0.8912	High Similarity	NPC191835
0.891	High Similarity	NPC472050
0.8903	High Similarity	NPC137301
0.8903	High Similarity	NPC478231
0.8903	High Similarity	NPC155686
0.8903	High Similarity	NPC281477
0.8889	High Similarity	NPC476684
0.8882	High Similarity	NPC283041
0.8882	High Similarity	NPC14098
0.8882	High Similarity	NPC52106
0.8875	High Similarity	NPC191930
0.8868	High Similarity	NPC48860
0.8867	High Similarity	NPC354984
0.8859	High Similarity	NPC472035
0.8859	High Similarity	NPC313123
0.8859	High Similarity	NPC158634
0.8859	High Similarity	NPC478201
0.8859	High Similarity	NPC90411
0.8859	High Similarity	NPC478217
0.8854	High Similarity	NPC77679
0.8854	High Similarity	NPC478225
0.8854	High Similarity	NPC84935
0.8854	High Similarity	NPC190020
0.8851	High Similarity	NPC52358
0.8846	High Similarity	NPC170189
0.8846	High Similarity	NPC317585
0.8846	High Similarity	NPC208173
0.8846	High Similarity	NPC478221
0.8844	High Similarity	NPC70380
0.8844	High Similarity	NPC135837
0.8839	High Similarity	NPC115249
0.8839	High Similarity	NPC470340
0.8839	High Similarity	NPC184284
0.8839	High Similarity	NPC76041
0.8839	High Similarity	NPC167903
0.8831	High Similarity	NPC472891
0.8824	High Similarity	NPC471642
0.8824	High Similarity	NPC240253
0.8824	High Similarity	NPC172329
0.8824	High Similarity	NPC240622
0.8824	High Similarity	NPC471641
0.8824	High Similarity	NPC2569
0.882	High Similarity	NPC20237
0.8812	High Similarity	NPC249181
0.8808	High Similarity	NPC184702
0.8805	High Similarity	NPC201560
0.88	High Similarity	NPC49108
0.88	High Similarity	NPC250755
0.879	High Similarity	NPC150227
0.8774	High Similarity	NPC91809
0.8774	High Similarity	NPC132990
0.8774	High Similarity	NPC46882
0.8758	High Similarity	NPC137296
0.8758	High Similarity	NPC8817
0.8743	High Similarity	NPC208069
0.8742	High Similarity	NPC478202
0.8726	High Similarity	NPC68727
0.8726	High Similarity	NPC199926
0.8726	High Similarity	NPC473241
0.8725	High Similarity	NPC139634
0.8725	High Similarity	NPC268052
0.8725	High Similarity	NPC32360
0.8725	High Similarity	NPC105456
0.8718	High Similarity	NPC113608
0.8718	High Similarity	NPC470338
0.8718	High Similarity	NPC180944
0.8718	High Similarity	NPC51824
0.8718	High Similarity	NPC470337
0.8718	High Similarity	NPC268992
0.8718	High Similarity	NPC474843
0.8716	High Similarity	NPC71256
0.871	High Similarity	NPC164762
0.871	High Similarity	NPC96501
0.871	High Similarity	NPC295036
0.871	High Similarity	NPC470107
0.8707	High Similarity	NPC182496
0.8707	High Similarity	NPC180905
0.8701	High Similarity	NPC470359
0.8693	High Similarity	NPC473023
0.8693	High Similarity	NPC260946
0.8693	High Similarity	NPC470357
0.8688	High Similarity	NPC112418
0.8688	High Similarity	NPC96031
0.8688	High Similarity	NPC317544
0.8684	High Similarity	NPC470932
0.8684	High Similarity	NPC301751
0.8684	High Similarity	NPC245482
0.8679	High Similarity	NPC477410
0.8675	High Similarity	NPC297985
0.8675	High Similarity	NPC96692
0.8671	High Similarity	NPC227062
0.8671	High Similarity	NPC471787
0.8662	High Similarity	NPC144801
0.8662	High Similarity	NPC197188
0.8662	High Similarity	NPC238672
0.8662	High Similarity	NPC43872
0.8662	High Similarity	NPC301233
0.8662	High Similarity	NPC291510
0.8662	High Similarity	NPC116850
0.8658	High Similarity	NPC475974
0.8658	High Similarity	NPC472602
0.8658	High Similarity	NPC9121
0.8658	High Similarity	NPC177307
0.8654	High Similarity	NPC228662
0.8654	High Similarity	NPC471229
0.865	High Similarity	NPC473094
0.8645	High Similarity	NPC89442
0.8645	High Similarity	NPC84142
0.8645	High Similarity	NPC198927
0.8642	High Similarity	NPC471788
0.8636	High Similarity	NPC81835
0.8636	High Similarity	NPC166583
0.8636	High Similarity	NPC53362
0.8634	High Similarity	NPC191360
0.8634	High Similarity	NPC471745
0.8627	High Similarity	NPC75694
0.8627	High Similarity	NPC312789
0.8627	High Similarity	NPC134621
0.8625	High Similarity	NPC24627
0.8625	High Similarity	NPC471744
0.8618	High Similarity	NPC148545
0.8616	High Similarity	NPC478226
0.8616	High Similarity	NPC263483
0.8609	High Similarity	NPC472605
0.8609	High Similarity	NPC472603
0.8609	High Similarity	NPC472604
0.8609	High Similarity	NPC53649
0.8608	High Similarity	NPC67396
0.8608	High Similarity	NPC38898
0.86	High Similarity	NPC247409
0.8599	High Similarity	NPC273483
0.8599	High Similarity	NPC243171
0.8599	High Similarity	NPC35567
0.8599	High Similarity	NPC171651
0.8599	High Similarity	NPC256141
0.8598	High Similarity	NPC473096
0.8598	High Similarity	NPC473095
0.8591	High Similarity	NPC149372
0.8591	High Similarity	NPC240147
0.8591	High Similarity	NPC474849
0.8591	High Similarity	NPC121243
0.8591	High Similarity	NPC178467
0.8591	High Similarity	NPC65837

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 NPC99381 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	958
0.2-0.3	1913
0.3-0.4	2538
0.4-0.5	1851
0.5-0.6	1004
0.6-0.7	405
0.7-0.8	154
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD2532	Approved
0.8627	High Similarity	NPD2534	Approved
0.8627	High Similarity	NPD2533	Approved
0.8616	High Similarity	NPD7075	Discontinued
0.86	High Similarity	NPD970	Clinical (unspecified phase)
0.8544	High Similarity	NPD7819	Suspended
0.8481	Intermediate Similarity	NPD6801	Discontinued
0.8471	Intermediate Similarity	NPD4380	Phase 2
0.8442	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5402	Approved
0.8375	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8313	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD6166	Phase 2
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.825	Intermediate Similarity	NPD1934	Approved
0.821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5403	Approved
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8133	Intermediate Similarity	NPD1240	Approved
0.8129	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1549	Phase 2
0.8114	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD1512	Approved
0.8086	Intermediate Similarity	NPD2801	Approved
0.8079	Intermediate Similarity	NPD230	Phase 1
0.8075	Intermediate Similarity	NPD7411	Suspended
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6797	Phase 2
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5401	Approved
0.8026	Intermediate Similarity	NPD1607	Approved
0.8013	Intermediate Similarity	NPD3750	Approved
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD1511	Approved
0.7965	Intermediate Similarity	NPD7808	Phase 3
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7941	Intermediate Similarity	NPD7054	Approved
0.7939	Intermediate Similarity	NPD3749	Approved
0.7927	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD7472	Approved
0.7882	Intermediate Similarity	NPD3751	Discontinued
0.787	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7857	Intermediate Similarity	NPD5711	Approved
0.7857	Intermediate Similarity	NPD5710	Approved
0.784	Intermediate Similarity	NPD3226	Approved
0.7812	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7751	Intermediate Similarity	NPD3787	Discontinued
0.7738	Intermediate Similarity	NPD5494	Approved
0.7722	Intermediate Similarity	NPD2800	Approved
0.7716	Intermediate Similarity	NPD920	Approved
0.7692	Intermediate Similarity	NPD3748	Approved
0.7684	Intermediate Similarity	NPD8150	Discontinued
0.7679	Intermediate Similarity	NPD919	Approved
0.7676	Intermediate Similarity	NPD7435	Discontinued
0.7662	Intermediate Similarity	NPD943	Approved
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD6190	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD447	Suspended
0.761	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6777	Approved
0.7609	Intermediate Similarity	NPD6778	Approved
0.7609	Intermediate Similarity	NPD6779	Approved
0.7609	Intermediate Similarity	NPD6780	Approved
0.7609	Intermediate Similarity	NPD6776	Approved
0.7609	Intermediate Similarity	NPD6782	Approved
0.7609	Intermediate Similarity	NPD6781	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2346	Discontinued
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD37	Approved
0.7584	Intermediate Similarity	NPD8434	Phase 2
0.758	Intermediate Similarity	NPD2799	Discontinued
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7564	Intermediate Similarity	NPD6651	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD1247	Approved
0.7483	Intermediate Similarity	NPD9545	Approved
0.7474	Intermediate Similarity	NPD8151	Discontinued
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD9717	Approved
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7874	Approved
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD7698	Approved
0.7394	Intermediate Similarity	NPD7696	Phase 3
0.7394	Intermediate Similarity	NPD7697	Approved
0.7375	Intermediate Similarity	NPD2344	Approved
0.7371	Intermediate Similarity	NPD7228	Approved
0.7354	Intermediate Similarity	NPD7870	Phase 2
0.7354	Intermediate Similarity	NPD7871	Phase 2
0.7351	Intermediate Similarity	NPD9269	Phase 2
0.7347	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD6535	Approved
0.733	Intermediate Similarity	NPD7701	Phase 2
0.7325	Intermediate Similarity	NPD4060	Phase 1
0.732	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7308	Intermediate Similarity	NPD411	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7305	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8319	Approved
0.7263	Intermediate Similarity	NPD8320	Phase 1
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD1653	Approved
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7226	Intermediate Similarity	NPD9494	Approved
0.7219	Intermediate Similarity	NPD7700	Phase 2
0.7219	Intermediate Similarity	NPD7699	Phase 2
0.7216	Intermediate Similarity	NPD7801	Approved
0.7205	Intermediate Similarity	NPD5406	Approved
0.7205	Intermediate Similarity	NPD5408	Approved
0.7205	Intermediate Similarity	NPD5405	Approved
0.7205	Intermediate Similarity	NPD5404	Approved
0.72	Intermediate Similarity	NPD9268	Approved
0.72	Intermediate Similarity	NPD5242	Approved
0.7197	Intermediate Similarity	NPD6798	Discontinued
0.7195	Intermediate Similarity	NPD2309	Approved
0.7193	Intermediate Similarity	NPD5353	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1019	Discontinued
0.7161	Intermediate Similarity	NPD2798	Approved
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7152	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7126	Intermediate Similarity	NPD6273	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1613	Approved
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD1470	Approved
0.7093	Intermediate Similarity	NPD4288	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5691	Approved
0.7073	Intermediate Similarity	NPD1652	Phase 2
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD1471	Phase 3

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