NPASS Compound

Structure

NPC472891 OpenBabel07101719162D 28 30 0 0 1 0 0 0 0 0999 V2000 5.1962 -3.0000 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -3.4641 -1.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1 4 1 0 0 0 0 2 11 1 0 0 0 0 4 5 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 27 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 6 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 3 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	383.906
LogP:	3.148
LogD:	2.499
LogS:	-3.526
# Rotatable Bonds:	4
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.42
Fsp3:	0.238
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:	-5.053
MDCK Permeability:	2.0256362404325046e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.174
Human Intestinal Absorption (HIA):	0.347
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	90.54779815673828%
Volume Distribution (VD):	1.246
Pgp-substrate:	7.153619289398193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.646
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.253

ADMET: Excretion

Clearance (CL):	4.779
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.966
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.921
Carcinogencity:	0.922
Eye Corrosion:	0.005
Eye Irritation:	0.741
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC472891

Natural Product ID:	NPC472891
*Common Name:**	[(7S,8S)-7-Hydroxy-7-Methyl-6-Oxo-3-[(E)-Prop-1-Enyl]-8H-Isochromen-8-Yl] 2,4-Dihydroxy-6-Methylbenzoate
IUPAC Name:	[(7S,8S)-7-hydroxy-7-methyl-6-oxo-3-[(E)-prop-1-enyl]-8H-isochromen-8-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	SYFXCPIQIAFGIJ-PXODQFSGSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-4-5-14-7-12-8-17(24)21(3,26)19(15(12)10-27-14)28-20(25)18-11(2)6-13(22)9-16(18)23/h4-10,19,22-23,26H,1-3H3/b5-4+/t19-,21+/m0/s1
SMILES:	C/C=C/C1=CC2=CC(=O)[C@@]([C@H](C2=CO1)OC(=O)c1c(C)cc(cc1O)O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593566
PubChem CID:	44225039
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	=	16600.0	nM	PMID[523015]

☑ 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 NPC472891 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	338
0.1-0.2	1408
0.2-0.3	3463
0.3-0.4	7594
0.4-0.5	10464
0.5-0.6	4391
0.6-0.7	6274
0.7-0.8	7136
0.8-0.85	1397
0.85-0.9	181
0.9-0.95	35
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC115249
0.9862	High Similarity	NPC184284
0.9862	High Similarity	NPC478224
0.9862	High Similarity	NPC76041
0.9795	High Similarity	NPC137301
0.9728	High Similarity	NPC472890
0.9728	High Similarity	NPC69043
0.9728	High Similarity	NPC208173
0.9728	High Similarity	NPC478230
0.9728	High Similarity	NPC170189
0.966	High Similarity	NPC478231
0.9597	High Similarity	NPC472889
0.9597	High Similarity	NPC478225
0.9595	High Similarity	NPC478221
0.9595	High Similarity	NPC317585
0.9521	High Similarity	NPC84142
0.9467	High Similarity	NPC246466
0.9467	High Similarity	NPC478226
0.9456	High Similarity	NPC164762
0.9392	High Similarity	NPC91809
0.9281	High Similarity	NPC317544
0.9252	High Similarity	NPC210320
0.9236	High Similarity	NPC158634
0.9226	High Similarity	NPC191930
0.9189	High Similarity	NPC215711
0.9189	High Similarity	NPC73411
0.9167	High Similarity	NPC158472
0.9161	High Similarity	NPC249181
0.9161	High Similarity	NPC478200
0.9161	High Similarity	NPC33144
0.9145	High Similarity	NPC472050
0.9139	High Similarity	NPC471695
0.911	High Similarity	NPC478202
0.9108	High Similarity	NPC283041
0.9097	High Similarity	NPC268052
0.9097	High Similarity	NPC32360
0.9097	High Similarity	NPC247409
0.9048	High Similarity	NPC280404
0.9048	High Similarity	NPC210425
0.9048	High Similarity	NPC277426
0.9048	High Similarity	NPC86373
0.9045	High Similarity	NPC20237
0.9028	High Similarity	NPC191835
0.9	High Similarity	NPC4423
0.9	High Similarity	NPC237440
0.9	High Similarity	NPC77325
0.9	High Similarity	NPC270160
0.8973	High Similarity	NPC472035
0.8973	High Similarity	NPC313123
0.8973	High Similarity	NPC478201
0.8973	High Similarity	NPC478217
0.8973	High Similarity	NPC53649
0.8973	High Similarity	NPC244923
0.8966	High Similarity	NPC52358
0.8958	High Similarity	NPC70380
0.894	High Similarity	NPC56204
0.8931	High Similarity	NPC328321
0.8926	High Similarity	NPC473023
0.8919	High Similarity	NPC42540
0.8919	High Similarity	NPC151607
0.8912	High Similarity	NPC474385
0.8912	High Similarity	NPC82913
0.891	High Similarity	NPC117985
0.8903	High Similarity	NPC470339
0.8897	High Similarity	NPC94248
0.8897	High Similarity	NPC472602
0.8897	High Similarity	NPC212693
0.8889	High Similarity	NPC235115
0.8882	High Similarity	NPC70016
0.8882	High Similarity	NPC215921
0.8881	High Similarity	NPC175943
0.8859	High Similarity	NPC472034
0.8859	High Similarity	NPC83272
0.8851	High Similarity	NPC159721
0.8851	High Similarity	NPC472006
0.8846	High Similarity	NPC472055
0.8844	High Similarity	NPC67650
0.8844	High Similarity	NPC475730
0.8844	High Similarity	NPC1704
0.8844	High Similarity	NPC472603
0.8836	High Similarity	NPC92655
0.8831	High Similarity	NPC99381
0.8828	High Similarity	NPC71256
0.8811	High Similarity	NPC153783
0.8808	High Similarity	NPC240253
0.8808	High Similarity	NPC471641
0.8808	High Similarity	NPC471642
0.8808	High Similarity	NPC240622
0.88	High Similarity	NPC472033
0.8792	High Similarity	NPC210966
0.8792	High Similarity	NPC478203
0.8792	High Similarity	NPC126882
0.8776	High Similarity	NPC472601
0.8776	High Similarity	NPC155205
0.8776	High Similarity	NPC156872
0.8776	High Similarity	NPC472600
0.8767	High Similarity	NPC9121
0.8767	High Similarity	NPC177307
0.8758	High Similarity	NPC200773
0.8758	High Similarity	NPC240768
0.8758	High Similarity	NPC46882
0.8758	High Similarity	NPC132990
0.8742	High Similarity	NPC472036
0.8733	High Similarity	NPC257558
0.8733	High Similarity	NPC312789
0.8725	High Similarity	NPC469542
0.8725	High Similarity	NPC471731
0.8725	High Similarity	NPC51106
0.8716	High Similarity	NPC472604
0.8716	High Similarity	NPC472605
0.871	High Similarity	NPC471456
0.8707	High Similarity	NPC139634
0.8707	High Similarity	NPC105456
0.8701	High Similarity	NPC470340
0.8701	High Similarity	NPC167903
0.8699	High Similarity	NPC474849
0.8699	High Similarity	NPC178467
0.8699	High Similarity	NPC474771
0.8699	High Similarity	NPC135837
0.8699	High Similarity	NPC149372
0.8699	High Similarity	NPC65837
0.8693	High Similarity	NPC469619
0.8693	High Similarity	NPC158866
0.8693	High Similarity	NPC469670
0.869	High Similarity	NPC27407
0.8684	High Similarity	NPC37139
0.8684	High Similarity	NPC94781
0.8675	High Similarity	NPC107625
0.8671	High Similarity	NPC219892
0.8671	High Similarity	NPC189823
0.8667	High Similarity	NPC475201
0.8667	High Similarity	NPC103910
0.8667	High Similarity	NPC257025
0.8658	High Similarity	NPC471733
0.8658	High Similarity	NPC250755
0.8658	High Similarity	NPC469579
0.8658	High Similarity	NPC322112
0.8654	High Similarity	NPC227062
0.8645	High Similarity	NPC472799
0.8645	High Similarity	NPC155686
0.8645	High Similarity	NPC192189
0.8639	High Similarity	NPC475974
0.8639	High Similarity	NPC197666
0.8639	High Similarity	NPC126739
0.8639	High Similarity	NPC472403
0.8636	High Similarity	NPC205918
0.8634	High Similarity	NPC473094
0.863	High Similarity	NPC50455
0.8627	High Similarity	NPC280753
0.8627	High Similarity	NPC476684
0.8627	High Similarity	NPC44378
0.8618	High Similarity	NPC166583
0.8618	High Similarity	NPC81835
0.8618	High Similarity	NPC259632
0.8618	High Similarity	NPC476463
0.8618	High Similarity	NPC53362
0.86	High Similarity	NPC354984
0.86	High Similarity	NPC472610
0.86	High Similarity	NPC21873
0.8599	High Similarity	NPC473395
0.8591	High Similarity	NPC130485
0.859	High Similarity	NPC56786
0.859	High Similarity	NPC79998
0.859	High Similarity	NPC16082
0.859	High Similarity	NPC80534
0.859	High Similarity	NPC237560
0.859	High Similarity	NPC82592
0.859	High Similarity	NPC473241
0.8581	High Similarity	NPC88269
0.8581	High Similarity	NPC113608
0.8581	High Similarity	NPC268992
0.8581	High Similarity	NPC256141
0.8581	High Similarity	NPC51824
0.8581	High Similarity	NPC470337
0.8581	High Similarity	NPC295339
0.8581	High Similarity	NPC470338
0.858	High Similarity	NPC473096
0.858	High Similarity	NPC472619
0.858	High Similarity	NPC473095
0.8571	High Similarity	NPC261292
0.8571	High Similarity	NPC150928
0.8571	High Similarity	NPC179178
0.8571	High Similarity	NPC194579
0.8571	High Similarity	NPC301915
0.8571	High Similarity	NPC295036
0.8571	High Similarity	NPC85131
0.8571	High Similarity	NPC180351
0.8562	High Similarity	NPC180905
0.8562	High Similarity	NPC221352
0.8562	High Similarity	NPC182496
0.8562	High Similarity	NPC142027
0.8553	High Similarity	NPC51513
0.8553	High Similarity	NPC163846
0.8553	High Similarity	NPC260946
0.8553	High Similarity	NPC202112
0.8553	High Similarity	NPC112418
0.8553	High Similarity	NPC225173
0.8544	High Similarity	NPC280680
0.8544	High Similarity	NPC477410
0.8543	High Similarity	NPC95123

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 NPC472891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	875
0.2-0.3	1780
0.3-0.4	2618
0.4-0.5	1923
0.5-0.6	1074
0.6-0.7	426
0.7-0.8	141
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD970	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7075	Discontinued
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8421	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD2534	Approved
0.8247	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2533	Approved
0.8228	Intermediate Similarity	NPD1934	Approved
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD3882	Suspended
0.8176	Intermediate Similarity	NPD2801	Approved
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8141	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD1510	Phase 2
0.8125	Intermediate Similarity	NPD5402	Approved
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8105	Intermediate Similarity	NPD3750	Approved
0.8065	Intermediate Similarity	NPD1511	Approved
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6797	Phase 2
0.8026	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5401	Approved
0.7988	Intermediate Similarity	NPD7251	Discontinued
0.7974	Intermediate Similarity	NPD1549	Phase 2
0.7961	Intermediate Similarity	NPD2796	Approved
0.7941	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7917	Intermediate Similarity	NPD7054	Approved
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1607	Approved
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7472	Approved
0.7867	Intermediate Similarity	NPD1240	Approved
0.7861	Intermediate Similarity	NPD8150	Discontinued
0.7857	Intermediate Similarity	NPD3818	Discontinued
0.7853	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7811	Intermediate Similarity	NPD5844	Phase 1
0.7805	Intermediate Similarity	NPD3749	Approved
0.7791	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3748	Approved
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7727	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD6190	Approved
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7768	Phase 2
0.7633	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD5710	Approved
0.7619	Intermediate Similarity	NPD5711	Approved
0.7616	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD2935	Discontinued
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7569	Intermediate Similarity	NPD9545	Approved
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7485	Intermediate Similarity	NPD3226	Approved
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2800	Approved
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.7458	Intermediate Similarity	NPD8434	Phase 2
0.744	Intermediate Similarity	NPD6234	Discontinued
0.7431	Intermediate Similarity	NPD9493	Approved
0.7419	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD6535	Approved
0.7403	Intermediate Similarity	NPD6534	Approved
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6776	Approved
0.7391	Intermediate Similarity	NPD6779	Approved
0.7391	Intermediate Similarity	NPD6777	Approved
0.7391	Intermediate Similarity	NPD6780	Approved
0.7391	Intermediate Similarity	NPD6781	Approved
0.7391	Intermediate Similarity	NPD6778	Approved
0.7391	Intermediate Similarity	NPD6782	Approved
0.7365	Intermediate Similarity	NPD1201	Approved
0.7362	Intermediate Similarity	NPD920	Approved
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1243	Approved
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7349	Intermediate Similarity	NPD37	Approved
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD3300	Phase 2
0.7329	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8320	Phase 1
0.7326	Intermediate Similarity	NPD8319	Approved
0.7325	Intermediate Similarity	NPD7033	Discontinued
0.7322	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7288	Intermediate Similarity	NPD8313	Approved
0.7288	Intermediate Similarity	NPD8312	Approved
0.7285	Intermediate Similarity	NPD1470	Approved
0.7283	Intermediate Similarity	NPD7700	Phase 2
0.7283	Intermediate Similarity	NPD7699	Phase 2
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7251	Intermediate Similarity	NPD1247	Approved
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD447	Suspended
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7216	Intermediate Similarity	NPD5953	Discontinued
0.7215	Intermediate Similarity	NPD2799	Discontinued
0.7205	Intermediate Similarity	NPD8166	Discontinued
0.72	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD9269	Phase 2
0.7192	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7178	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8151	Discontinued
0.7171	Intermediate Similarity	NPD1203	Approved
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7169	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7126	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD7701	Phase 2
0.7115	Intermediate Similarity	NPD6233	Phase 2
0.7108	Intermediate Similarity	NPD1653	Approved
0.7107	Intermediate Similarity	NPD4308	Phase 3
0.7102	Intermediate Similarity	NPD7286	Phase 2
0.7079	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD2797	Approved
0.7051	Intermediate Similarity	NPD2313	Discontinued
0.7047	Intermediate Similarity	NPD9268	Approved
0.7039	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD2654	Approved
0.703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2403	Approved
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5762	Approved
0.7019	Intermediate Similarity	NPD2344	Approved
0.7019	Intermediate Similarity	NPD5763	Approved
0.7012	Intermediate Similarity	NPD7236	Approved
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD4626	Approved
0.6994	Remote Similarity	NPD7003	Approved
0.6988	Remote Similarity	NPD6273	Approved
0.6987	Remote Similarity	NPD7095	Approved
0.6987	Remote Similarity	NPD4625	Phase 3
0.6987	Remote Similarity	NPD3027	Phase 3
0.6974	Remote Similarity	NPD1608	Approved
0.6968	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD1613	Approved
0.6962	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5353	Approved
0.6957	Remote Similarity	NPD2438	Suspended
0.6951	Remote Similarity	NPD3887	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